NO332574B1 - Preparat omfattende etylendicystein-ligander konjugert til en malrettende ligand, metode for syntetisering av en etylendicystein-ligand, anvendelse og sett - Google Patents
Preparat omfattende etylendicystein-ligander konjugert til en malrettende ligand, metode for syntetisering av en etylendicystein-ligand, anvendelse og sett Download PDFInfo
- Publication number
- NO332574B1 NO332574B1 NO20025729A NO20025729A NO332574B1 NO 332574 B1 NO332574 B1 NO 332574B1 NO 20025729 A NO20025729 A NO 20025729A NO 20025729 A NO20025729 A NO 20025729A NO 332574 B1 NO332574 B1 NO 332574B1
- Authority
- NO
- Norway
- Prior art keywords
- ligand
- 99mtc
- tumor
- ethylenedicysteine
- targeting ligand
- Prior art date
Links
- 239000003446 ligand Substances 0.000 title claims abstract description 132
- BQHFYSWNHZMMDO-WDSKDSINSA-N (2r)-2-[2-[[(1r)-1-carboxy-2-sulfanylethyl]amino]ethylamino]-3-sulfanylpropanoic acid Chemical compound OC(=O)[C@H](CS)NCCN[C@@H](CS)C(O)=O BQHFYSWNHZMMDO-WDSKDSINSA-N 0.000 title claims abstract description 110
- 238000002360 preparation method Methods 0.000 title claims description 54
- 238000000034 method Methods 0.000 title claims description 40
- 230000008685 targeting Effects 0.000 title claims description 39
- 230000002194 synthesizing effect Effects 0.000 title claims description 5
- 238000003384 imaging method Methods 0.000 claims abstract description 75
- 206010028980 Neoplasm Diseases 0.000 claims description 177
- 229960004927 neomycin Drugs 0.000 claims description 51
- 239000011724 folic acid Substances 0.000 claims description 42
- -1 paromycin Chemical compound 0.000 claims description 38
- 229940014144 folate Drugs 0.000 claims description 36
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 35
- 239000008103 glucose Substances 0.000 claims description 35
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
- 229960002442 glucosamine Drugs 0.000 claims description 31
- 206010006187 Breast cancer Diseases 0.000 claims description 29
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims description 27
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims description 27
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 25
- 239000003638 chemical reducing agent Substances 0.000 claims description 24
- 201000011510 cancer Diseases 0.000 claims description 22
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 claims description 21
- 229960001592 paclitaxel Drugs 0.000 claims description 20
- 229930012538 Paclitaxel Natural products 0.000 claims description 19
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 19
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 18
- 235000019152 folic acid Nutrition 0.000 claims description 18
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 18
- 229930193140 Neomycin Natural products 0.000 claims description 17
- 229960000318 kanamycin Drugs 0.000 claims description 15
- 229960000707 tobramycin Drugs 0.000 claims description 15
- 230000002285 radioactive effect Effects 0.000 claims description 14
- 229940126575 aminoglycoside Drugs 0.000 claims description 13
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 12
- 229960005070 ascorbic acid Drugs 0.000 claims description 12
- 239000004220 glutamic acid Substances 0.000 claims description 12
- 229930027917 kanamycin Natural products 0.000 claims description 12
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 claims description 12
- 229930182823 kanamycin A Natural products 0.000 claims description 12
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 claims description 12
- VRYALKFFQXWPIH-PBXRRBTRSA-N (3r,4s,5r)-3,4,5,6-tetrahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)CC=O VRYALKFFQXWPIH-PBXRRBTRSA-N 0.000 claims description 11
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 11
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 11
- 235000013922 glutamic acid Nutrition 0.000 claims description 11
- 208000026310 Breast neoplasm Diseases 0.000 claims description 10
- 229930182566 Gentamicin Natural products 0.000 claims description 10
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 claims description 10
- DNYGXMICFMACRA-XHEDQWPISA-N Gentamicin C2b Chemical compound O1[C@H](CNC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N DNYGXMICFMACRA-XHEDQWPISA-N 0.000 claims description 10
- 229930183998 Lividomycin Natural products 0.000 claims description 10
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 claims description 10
- URWAJWIAIPFPJE-UHFFFAOYSA-N Rickamicin Natural products O1CC(O)(C)C(NC)C(O)C1OC1C(O)C(OC2C(CC=C(CN)O2)N)C(N)CC1N URWAJWIAIPFPJE-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 229960004821 amikacin Drugs 0.000 claims description 10
- LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 claims description 10
- 239000003963 antioxidant agent Substances 0.000 claims description 10
- 235000006708 antioxidants Nutrition 0.000 claims description 10
- 235000010323 ascorbic acid Nutrition 0.000 claims description 10
- 239000011668 ascorbic acid Substances 0.000 claims description 10
- 239000013522 chelant Substances 0.000 claims description 10
- 229960000798 isepamicin Drugs 0.000 claims description 10
- UDIIBEDMEYAVNG-ZKFPOVNWSA-N isepamicin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O2)O)[C@@H](N)C[C@H]1NC(=O)[C@@H](O)CN UDIIBEDMEYAVNG-ZKFPOVNWSA-N 0.000 claims description 10
- 229950003076 lividomycin Drugs 0.000 claims description 10
- DBLVDAUGBTYDFR-SWMBIRFSSA-N lividomycin A Chemical compound O([C@@H]1[C@@H](N)C[C@@H](N)[C@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@H]([C@H]1O)O[C@H]1O[C@H]([C@H]([C@H](O)[C@H]1N)O[C@@H]1[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CN)[C@H]1O[C@H](CO)[C@@H](O)C[C@H]1N DBLVDAUGBTYDFR-SWMBIRFSSA-N 0.000 claims description 10
- 229960000808 netilmicin Drugs 0.000 claims description 10
- ZBGPYVZLYBDXKO-HILBYHGXSA-N netilmycin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@]([C@H](NC)[C@@H](O)CO1)(C)O)NCC)[C@H]1OC(CN)=CC[C@H]1N ZBGPYVZLYBDXKO-HILBYHGXSA-N 0.000 claims description 10
- 229930190553 ribostamycin Natural products 0.000 claims description 10
- 229960003485 ribostamycin Drugs 0.000 claims description 10
- NSKGQURZWSPSBC-NLZFXWNVSA-N ribostamycin Chemical compound N[C@H]1[C@H](O)[C@@H](O)[C@H](CN)O[C@@H]1O[C@@H]1[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](CO)O2)O)[C@H](O)[C@@H](N)C[C@H]1N NSKGQURZWSPSBC-NLZFXWNVSA-N 0.000 claims description 10
- NSKGQURZWSPSBC-UHFFFAOYSA-N ribostamycin A Natural products NC1C(O)C(O)C(CN)OC1OC1C(OC2C(C(O)C(CO)O2)O)C(O)C(N)CC1N NSKGQURZWSPSBC-UHFFFAOYSA-N 0.000 claims description 10
- URWAJWIAIPFPJE-YFMIWBNJSA-N sisomycin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC=C(CN)O2)N)[C@@H](N)C[C@H]1N URWAJWIAIPFPJE-YFMIWBNJSA-N 0.000 claims description 10
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 9
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 9
- 108010020346 Polyglutamic Acid Proteins 0.000 claims description 9
- 235000003704 aspartic acid Nutrition 0.000 claims description 9
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 9
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 8
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 8
- 239000004472 Lysine Substances 0.000 claims description 8
- 229950004074 astromicin Drugs 0.000 claims description 8
- BIDUPMYXGFNAEJ-APGVDKLISA-N astromicin Chemical compound O[C@@H]1[C@H](N(C)C(=O)CN)[C@@H](OC)[C@@H](O)[C@H](N)[C@H]1O[C@@H]1[C@H](N)CC[C@@H]([C@H](C)N)O1 BIDUPMYXGFNAEJ-APGVDKLISA-N 0.000 claims description 8
- 229960001031 glucose Drugs 0.000 claims description 8
- 108010003205 Vasoactive Intestinal Peptide Proteins 0.000 claims description 7
- 230000003078 antioxidant effect Effects 0.000 claims description 7
- VBUWHHLIZKOSMS-RIWXPGAOSA-N invicorp Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)C(C)C)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=C(O)C=C1 VBUWHHLIZKOSMS-RIWXPGAOSA-N 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- 108010079518 technetium 99m ethylenedicysteine deoxyglucose Proteins 0.000 claims description 7
- 229920000805 Polyaspartic acid Polymers 0.000 claims description 6
- 150000001413 amino acids Chemical class 0.000 claims description 6
- 208000015181 infectious disease Diseases 0.000 claims description 6
- 210000004072 lung Anatomy 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 108010064470 polyaspartate Proteins 0.000 claims description 6
- 229920002643 polyglutamic acid Polymers 0.000 claims description 6
- 206010033128 Ovarian cancer Diseases 0.000 claims description 5
- 235000001014 amino acid Nutrition 0.000 claims description 5
- 229960004857 mitomycin Drugs 0.000 claims description 5
- DEQANNDTNATYII-OULOTJBUSA-N (4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-19-[[(2r)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-n-[(2r,3r)-1,3-dihydroxybutan-2-yl]-7-[(1r)-1-hydroxyethyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxa Chemical compound C([C@@H](N)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@H](CO)[C@H](O)C)C1=CC=CC=C1 DEQANNDTNATYII-OULOTJBUSA-N 0.000 claims description 4
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims description 4
- 108010079505 Endostatins Proteins 0.000 claims description 4
- GYHNNYVSQQEPJS-YPZZEJLDSA-N Gallium-68 Chemical compound [68Ga] GYHNNYVSQQEPJS-YPZZEJLDSA-N 0.000 claims description 4
- 101000904173 Homo sapiens Progonadoliberin-1 Proteins 0.000 claims description 4
- 108010016076 Octreotide Proteins 0.000 claims description 4
- 102100024028 Progonadoliberin-1 Human genes 0.000 claims description 4
- 101000996723 Sus scrofa Gonadotropin-releasing hormone receptor Proteins 0.000 claims description 4
- NHYXMAKLBXBVEO-UHFFFAOYSA-N bromomethyl acetate Chemical compound CC(=O)OCBr NHYXMAKLBXBVEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000000872 buffer Substances 0.000 claims description 4
- 239000012459 cleaning agent Substances 0.000 claims description 4
- 229960005309 estradiol Drugs 0.000 claims description 4
- 229930182833 estradiol Natural products 0.000 claims description 4
- 229960005420 etoposide Drugs 0.000 claims description 4
- XLXSAKCOAKORKW-UHFFFAOYSA-N gonadorelin Chemical compound C1CCC(C(=O)NCC(N)=O)N1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 XLXSAKCOAKORKW-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229960002700 octreotide Drugs 0.000 claims description 4
- 239000003755 preservative agent Substances 0.000 claims description 4
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 claims description 4
- 229960000303 topotecan Drugs 0.000 claims description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 3
- 206010060862 Prostate cancer Diseases 0.000 claims description 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
- 210000004556 brain Anatomy 0.000 claims description 3
- 229960003807 dibekacin Drugs 0.000 claims description 3
- JJCQSGDBDPYCEO-XVZSLQNASA-N dibekacin Chemical compound O1[C@H](CN)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N JJCQSGDBDPYCEO-XVZSLQNASA-N 0.000 claims description 3
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims description 3
- 210000000936 intestine Anatomy 0.000 claims description 3
- 210000004185 liver Anatomy 0.000 claims description 3
- 239000008177 pharmaceutical agent Substances 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 210000004696 endometrium Anatomy 0.000 claims description 2
- 210000002216 heart Anatomy 0.000 claims description 2
- 210000000496 pancreas Anatomy 0.000 claims description 2
- 230000002335 preservative effect Effects 0.000 claims description 2
- GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 claims description 2
- 229960004622 raloxifene Drugs 0.000 claims description 2
- 210000000952 spleen Anatomy 0.000 claims description 2
- 102100031162 Collagen alpha-1(XVIII) chain Human genes 0.000 claims 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 46
- 229940079593 drug Drugs 0.000 abstract description 43
- 238000002372 labelling Methods 0.000 abstract description 11
- 239000012216 imaging agent Substances 0.000 abstract description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 6
- 201000010099 disease Diseases 0.000 abstract description 5
- 229940124597 therapeutic agent Drugs 0.000 abstract description 2
- 210000001519 tissue Anatomy 0.000 description 70
- 241000700159 Rattus Species 0.000 description 69
- 210000004027 cell Anatomy 0.000 description 58
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- 230000015572 biosynthetic process Effects 0.000 description 41
- 238000003786 synthesis reaction Methods 0.000 description 41
- 206010021143 Hypoxia Diseases 0.000 description 32
- 239000000047 product Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 24
- 210000002966 serum Anatomy 0.000 description 24
- 238000004809 thin layer chromatography Methods 0.000 description 24
- 210000004881 tumor cell Anatomy 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 22
- 238000002347 injection Methods 0.000 description 22
- 239000007924 injection Substances 0.000 description 22
- 239000000203 mixture Substances 0.000 description 22
- 238000005160 1H NMR spectroscopy Methods 0.000 description 21
- 230000000694 effects Effects 0.000 description 20
- 230000007954 hypoxia Effects 0.000 description 20
- 208000020816 lung neoplasm Diseases 0.000 description 19
- 239000008280 blood Substances 0.000 description 18
- 238000001727 in vivo Methods 0.000 description 18
- 241001465754 Metazoa Species 0.000 description 17
- 238000002603 single-photon emission computed tomography Methods 0.000 description 17
- 208000006011 Stroke Diseases 0.000 description 16
- 239000000700 radioactive tracer Substances 0.000 description 16
- 238000001228 spectrum Methods 0.000 description 16
- 238000011282 treatment Methods 0.000 description 16
- 210000004369 blood Anatomy 0.000 description 15
- 229960001338 colchicine Drugs 0.000 description 14
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 13
- 230000004700 cellular uptake Effects 0.000 description 13
- 238000009826 distribution Methods 0.000 description 13
- 230000003902 lesion Effects 0.000 description 13
- 201000005202 lung cancer Diseases 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 102000006815 folate receptor Human genes 0.000 description 12
- 108020005243 folate receptor Proteins 0.000 description 12
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 239000001301 oxygen Substances 0.000 description 12
- HIIJZYSUEJYLMX-UHFFFAOYSA-N 1-fluoro-3-(2-nitroimidazol-1-yl)propan-2-ol Chemical compound FCC(O)CN1C=CN=C1[N+]([O-])=O HIIJZYSUEJYLMX-UHFFFAOYSA-N 0.000 description 11
- 102000005548 Hexokinase Human genes 0.000 description 11
- 108700040460 Hexokinases Proteins 0.000 description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
- 230000001146 hypoxic effect Effects 0.000 description 11
- 229960000282 metronidazole Drugs 0.000 description 11
- 238000000163 radioactive labelling Methods 0.000 description 11
- 238000002512 chemotherapy Methods 0.000 description 10
- 238000010253 intravenous injection Methods 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- 210000003205 muscle Anatomy 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000003556 assay Methods 0.000 description 9
- 210000000481 breast Anatomy 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 238000002595 magnetic resonance imaging Methods 0.000 description 9
- 239000012528 membrane Substances 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- 108090000672 Annexin A5 Proteins 0.000 description 8
- 102000004121 Annexin A5 Human genes 0.000 description 8
- 102000029749 Microtubule Human genes 0.000 description 8
- 108091022875 Microtubule Proteins 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 8
- 230000001640 apoptogenic effect Effects 0.000 description 8
- 230000027455 binding Effects 0.000 description 8
- 238000001514 detection method Methods 0.000 description 8
- 238000000502 dialysis Methods 0.000 description 8
- 238000004108 freeze drying Methods 0.000 description 8
- 238000000338 in vitro Methods 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- RPENMORRBUTCPR-UHFFFAOYSA-M sodium;1-hydroxy-2,5-dioxopyrrolidine-3-sulfonate Chemical compound [Na+].ON1C(=O)CC(S([O-])(=O)=O)C1=O RPENMORRBUTCPR-UHFFFAOYSA-M 0.000 description 8
- 238000013112 stability test Methods 0.000 description 8
- 229910052713 technetium Inorganic materials 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- GZCGUPFRVQAUEE-VANKVMQKSA-N aldehydo-L-glucose Chemical compound OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)C=O GZCGUPFRVQAUEE-VANKVMQKSA-N 0.000 description 7
- 230000002927 anti-mitotic effect Effects 0.000 description 7
- 230000001413 cellular effect Effects 0.000 description 7
- 230000006870 function Effects 0.000 description 7
- 230000005855 radiation Effects 0.000 description 7
- 239000012217 radiopharmaceutical Substances 0.000 description 7
- 229940121896 radiopharmaceutical Drugs 0.000 description 7
- 230000002799 radiopharmaceutical effect Effects 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 description 6
- 102000004877 Insulin Human genes 0.000 description 6
- 108090001061 Insulin Proteins 0.000 description 6
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 6
- 206010039491 Sarcoma Diseases 0.000 description 6
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 102400000015 Vasoactive intestinal peptide Human genes 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000002246 antineoplastic agent Substances 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 6
- 238000002513 implantation Methods 0.000 description 6
- 229940125396 insulin Drugs 0.000 description 6
- 208000037841 lung tumor Diseases 0.000 description 6
- 238000004949 mass spectrometry Methods 0.000 description 6
- 230000001404 mediated effect Effects 0.000 description 6
- 229960000485 methotrexate Drugs 0.000 description 6
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 6
- 210000004688 microtubule Anatomy 0.000 description 6
- OBBCSXFCDPPXOL-UHFFFAOYSA-N misonidazole Chemical compound COCC(O)CN1C=CN=C1[N+]([O-])=O OBBCSXFCDPPXOL-UHFFFAOYSA-N 0.000 description 6
- 229950010514 misonidazole Drugs 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- 235000011150 stannous chloride Nutrition 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 6
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 5
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 5
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 102000004243 Tubulin Human genes 0.000 description 5
- 108090000704 Tubulin Proteins 0.000 description 5
- 229940024606 amino acid Drugs 0.000 description 5
- 238000010171 animal model Methods 0.000 description 5
- 238000000211 autoradiogram Methods 0.000 description 5
- 239000007857 degradation product Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000010265 fast atom bombardment Methods 0.000 description 5
- 229960000304 folic acid Drugs 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 229960003299 ketamine Drugs 0.000 description 5
- 235000018977 lysine Nutrition 0.000 description 5
- 230000007246 mechanism Effects 0.000 description 5
- 210000002381 plasma Anatomy 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 238000012453 sprague-dawley rat model Methods 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 238000012800 visualization Methods 0.000 description 5
- PMHQXRGRBMOZDU-UHFFFAOYSA-N 1,1-diaminoethanethiol Chemical compound CC(N)(N)S PMHQXRGRBMOZDU-UHFFFAOYSA-N 0.000 description 4
- YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 description 4
- VPYQMEOYEWOVKO-UHFFFAOYSA-N 3h-dithiole-3,5-diamine Chemical class NC1SSC(N)=C1 VPYQMEOYEWOVKO-UHFFFAOYSA-N 0.000 description 4
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
- 239000005695 Ammonium acetate Substances 0.000 description 4
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 102000004142 Trypsin Human genes 0.000 description 4
- 108090000631 Trypsin Proteins 0.000 description 4
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 229940043376 ammonium acetate Drugs 0.000 description 4
- 235000019257 ammonium acetate Nutrition 0.000 description 4
- 206010002224 anaplastic astrocytoma Diseases 0.000 description 4
- 229940041181 antineoplastic drug Drugs 0.000 description 4
- 230000006907 apoptotic process Effects 0.000 description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 230000032823 cell division Effects 0.000 description 4
- 230000003915 cell function Effects 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 229940044683 chemotherapy drug Drugs 0.000 description 4
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 4
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 4
- 229910000397 disodium phosphate Inorganic materials 0.000 description 4
- 235000019800 disodium phosphate Nutrition 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000011503 in vivo imaging Methods 0.000 description 4
- 238000011534 incubation Methods 0.000 description 4
- 208000030883 malignant astrocytoma Diseases 0.000 description 4
- 206010027191 meningioma Diseases 0.000 description 4
- 230000002503 metabolic effect Effects 0.000 description 4
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 4
- 230000001575 pathological effect Effects 0.000 description 4
- 239000002953 phosphate buffered saline Substances 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 239000012588 trypsin Substances 0.000 description 4
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 3
- DZLNHFMRPBPULJ-GSVOUGTGSA-N D-thioproline Chemical compound OC(=O)[C@H]1CSCN1 DZLNHFMRPBPULJ-GSVOUGTGSA-N 0.000 description 3
- 102400001047 Endostatin Human genes 0.000 description 3
- 229910052688 Gadolinium Inorganic materials 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 238000000692 Student's t-test Methods 0.000 description 3
- GKLVYJBZJHMRIY-OUBTZVSYSA-N Technetium-99 Chemical compound [99Tc] GKLVYJBZJHMRIY-OUBTZVSYSA-N 0.000 description 3
- 238000000376 autoradiography Methods 0.000 description 3
- 230000003851 biochemical process Effects 0.000 description 3
- 238000004820 blood count Methods 0.000 description 3
- FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical compound [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000002738 chelating agent Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000001684 chronic effect Effects 0.000 description 3
- 229920000370 gamma-poly(glutamate) polymer Polymers 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 210000003734 kidney Anatomy 0.000 description 3
- 238000012423 maintenance Methods 0.000 description 3
- 229910052748 manganese Inorganic materials 0.000 description 3
- 239000011572 manganese Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 210000003657 middle cerebral artery Anatomy 0.000 description 3
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 3
- 208000010125 myocardial infarction Diseases 0.000 description 3
- BWUXDKMMCZJFAB-UHFFFAOYSA-N oxotechnetium Chemical group [Tc]=O BWUXDKMMCZJFAB-UHFFFAOYSA-N 0.000 description 3
- 230000026731 phosphorylation Effects 0.000 description 3
- 238000006366 phosphorylation reaction Methods 0.000 description 3
- 238000001959 radiotherapy Methods 0.000 description 3
- 229960004432 raltitrexed Drugs 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229940056501 technetium 99m Drugs 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- 210000001685 thyroid gland Anatomy 0.000 description 3
- 230000005747 tumor angiogenesis Effects 0.000 description 3
- 230000004614 tumor growth Effects 0.000 description 3
- LJJFNFYPZOHRHM-UHFFFAOYSA-N 1-isocyano-2-methoxy-2-methylpropane Chemical compound COC(C)(C)C[N+]#[C-] LJJFNFYPZOHRHM-UHFFFAOYSA-N 0.000 description 2
- BQHFYSWNHZMMDO-UHFFFAOYSA-N 2-[2-[(1-carboxy-2-sulfanylethyl)amino]ethylamino]-3-sulfanylpropanoic acid Chemical compound OC(=O)C(CS)NCCNC(CS)C(O)=O BQHFYSWNHZMMDO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 102100025064 Cellular tumor antigen p53 Human genes 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 206010061818 Disease progression Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 108010031792 IGF Type 2 Receptor Proteins 0.000 description 2
- SHGAZHPCJJPHSC-NUEINMDLSA-N Isotretinoin Chemical compound OC(=O)C=C(C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-NUEINMDLSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- 208000027007 Meningioma benign Diseases 0.000 description 2
- 206010027476 Metastases Diseases 0.000 description 2
- ZOKXTWBITQBERF-AKLPVKDBSA-N Molybdenum Mo-99 Chemical compound [99Mo] ZOKXTWBITQBERF-AKLPVKDBSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 101150050048 SNCB gene Proteins 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 231100000632 Spindle poison Toxicity 0.000 description 2
- 241000862969 Stella Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 230000000735 allogeneic effect Effects 0.000 description 2
- 230000033115 angiogenesis Effects 0.000 description 2
- 230000001772 anti-angiogenic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 201000009467 benign meningioma Diseases 0.000 description 2
- 210000001185 bone marrow Anatomy 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 230000022131 cell cycle Effects 0.000 description 2
- 230000009087 cell motility Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000001886 ciliary effect Effects 0.000 description 2
- 238000011260 co-administration Methods 0.000 description 2
- 238000013170 computed tomography imaging Methods 0.000 description 2
- 238000003745 diagnosis Methods 0.000 description 2
- 230000005750 disease progression Effects 0.000 description 2
- 229960004679 doxorubicin Drugs 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000013439 flagellum movement Effects 0.000 description 2
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 2
- 229930195712 glutamate Natural products 0.000 description 2
- 230000034659 glycolysis Effects 0.000 description 2
- 208000014829 head and neck neoplasm Diseases 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000002163 immunogen Effects 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000010189 intracellular transport Effects 0.000 description 2
- 230000002601 intratumoral effect Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229960005280 isotretinoin Drugs 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 230000009401 metastasis Effects 0.000 description 2
- 231100000782 microtubule inhibitor Toxicity 0.000 description 2
- 230000036456 mitotic arrest Effects 0.000 description 2
- 230000000394 mitotic effect Effects 0.000 description 2
- 229950009740 molybdenum mo-99 Drugs 0.000 description 2
- 150000002772 monosaccharides Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000009206 nuclear medicine Methods 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 230000003204 osmotic effect Effects 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 230000002062 proliferating effect Effects 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 2
- 230000006335 response to radiation Effects 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 108010093847 technetium Tc 99m ethylenedicysteine annexin V Proteins 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 230000032258 transport Effects 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- AKDIWSYVVMNJHG-BPIFLZNUSA-N (2S)-2-[[4-[(2-amino-4-oxo-3H-pteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid (2R)-2-[2-[[(1R)-1-carboxy-2-sulfanylethyl]amino]ethylamino]-3-sulfanylpropanoic acid Chemical compound OC(=O)[C@H](CS)NCCN[C@@H](CS)C(O)=O.N1=C2C(=O)NC(N)=NC2=NC=C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 AKDIWSYVVMNJHG-BPIFLZNUSA-N 0.000 description 1
- MBBVEKGDFGDLGO-HDKDAPSGSA-N (2S)-2-aminopentanedioic acid (2R)-2-[2-[[(1R)-1-carboxy-2-sulfanylethyl]amino]ethylamino]-3-sulfanylpropanoic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O.OC(=O)[C@@H](N)CCC(O)=O.OC(=O)[C@@H](N)CCC(O)=O.OC(=O)[C@@H](N)CCC(O)=O.OC(=O)[C@@H](N)CCC(O)=O.OC(=O)[C@H](CS)NCCN[C@@H](CS)C(O)=O MBBVEKGDFGDLGO-HDKDAPSGSA-N 0.000 description 1
- HJSYLUZWEHYRDR-GEMLJDPKSA-N (2r)-2-[2-[[(1r)-1-carboxy-2-sulfanylethyl]amino]ethylamino]-3-sulfanylpropanoic acid;2-nitro-1h-imidazole Chemical compound [O-][N+](=O)C1=NC=CN1.OC(=O)[C@H](CS)NCCN[C@@H](CS)C(O)=O HJSYLUZWEHYRDR-GEMLJDPKSA-N 0.000 description 1
- CBOJBBMQJBVCMW-BTVCFUMJSA-N (2r,3r,4s,5r)-2-amino-3,4,5,6-tetrahydroxyhexanal;hydrochloride Chemical compound Cl.O=C[C@H](N)[C@@H](O)[C@H](O)[C@H](O)CO CBOJBBMQJBVCMW-BTVCFUMJSA-N 0.000 description 1
- KWBUARAINLGYMG-JGMIRXPNSA-N (2r,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(1r,2r,3s,4r,6s)-4,6-diamino-2-[(2s,3r,4s,5r)-4-[(2r,3r,4r,5s,6s)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol;sulfuric acid Chemical class OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O2)N)O[C@@H]1CO KWBUARAINLGYMG-JGMIRXPNSA-N 0.000 description 1
- ODYNNYOEHBJUQP-LTCKWSDVSA-N (2s)-2-[[4-[(2-amino-4-oxo-1h-pteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid;dihydrate Chemical compound O.O.C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 ODYNNYOEHBJUQP-LTCKWSDVSA-N 0.000 description 1
- QKPLRMLTKYXDST-NSEZLWDYSA-N (3r,4r,5s,6r)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol;hydrochloride Chemical compound Cl.N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O QKPLRMLTKYXDST-NSEZLWDYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 1
- HIIJZYSUEJYLMX-JZRMKITLSA-N 1-fluoranyl-3-(2-nitroimidazol-1-yl)propan-2-ol Chemical compound [18F]CC(O)CN1C=CN=C1[N+]([O-])=O HIIJZYSUEJYLMX-JZRMKITLSA-N 0.000 description 1
- CLTWZERGIYDXHV-UHFFFAOYSA-N 1-methyl-4-[3-(4-methylphenyl)sulfonylpropylsulfonyl]benzene Chemical compound C1=CC(C)=CC=C1S(=O)(=O)CCCS(=O)(=O)C1=CC=C(C)C=C1 CLTWZERGIYDXHV-UHFFFAOYSA-N 0.000 description 1
- CNLWNYCFDMAZCB-HUVROIHYSA-N 2-[2-[[2-[[(2r)-1-[[(4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-16-benzyl-4-[[(2r,3r)-1,3-dihydroxybutan-2-yl]carbamoyl]-7-[(1r)-1-hydroxyethyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicos-19-yl]amino]-1-oxo-3-phe Chemical compound C([C@H](C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@H](CO)[C@H](O)C)NC(=O)CN(CCN(CCN(CC(O)=O)CC(O)=O)CC(O)=O)CC(O)=O)C1=CC=CC=C1 CNLWNYCFDMAZCB-HUVROIHYSA-N 0.000 description 1
- RXACEEPNTRHYBQ-UHFFFAOYSA-N 2-[[2-[[2-[(2-sulfanylacetyl)amino]acetyl]amino]acetyl]amino]acetic acid Chemical compound OC(=O)CNC(=O)CNC(=O)CNC(=O)CS RXACEEPNTRHYBQ-UHFFFAOYSA-N 0.000 description 1
- IVTVGDXNLFLDRM-UHFFFAOYSA-N 2-[[5-[methyl-[(2-methyl-4-oxo-1h-quinazolin-6-yl)methyl]amino]thiophene-2-carbonyl]amino]pentanedioic acid Chemical compound C=1C=C2NC(C)=NC(=O)C2=CC=1CN(C)C1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)S1 IVTVGDXNLFLDRM-UHFFFAOYSA-N 0.000 description 1
- RGHQKFQZGLKBCF-UHFFFAOYSA-N 2-bromoethyl acetate Chemical compound CC(=O)OCCBr RGHQKFQZGLKBCF-UHFFFAOYSA-N 0.000 description 1
- AOYNUTHNTBLRMT-SLPGGIOYSA-N 2-deoxy-2-fluoro-aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](F)C=O AOYNUTHNTBLRMT-SLPGGIOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- SWPKSKUWMXUSCH-UHFFFAOYSA-N 5-[3-(4-methylphenyl)sulfonylpropyl]-2-nitro-1h-imidazole Chemical compound C1=CC(C)=CC=C1S(=O)(=O)CCCC1=CN=C([N+]([O-])=O)N1 SWPKSKUWMXUSCH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 206010002660 Anoxia Diseases 0.000 description 1
- 241000976983 Anoxia Species 0.000 description 1
- 108020000948 Antisense Oligonucleotides Proteins 0.000 description 1
- 206010003571 Astrocytoma Diseases 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 description 1
- 201000006474 Brain Ischemia Diseases 0.000 description 1
- 208000003174 Brain Neoplasms Diseases 0.000 description 1
- 101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 description 1
- 206010008111 Cerebral haemorrhage Diseases 0.000 description 1
- 208000031404 Chromosome Aberrations Diseases 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- 208000000059 Dyspnea Diseases 0.000 description 1
- 206010013975 Dyspnoeas Diseases 0.000 description 1
- 208000001976 Endocrine Gland Neoplasms Diseases 0.000 description 1
- 201000009273 Endometriosis Diseases 0.000 description 1
- 102000018711 Facilitative Glucose Transport Proteins Human genes 0.000 description 1
- 206010018341 Gliosis Diseases 0.000 description 1
- 108091052347 Glucose transporter family Proteins 0.000 description 1
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 102100025947 Insulin-like growth factor II Human genes 0.000 description 1
- 206010051925 Intestinal adenocarcinoma Diseases 0.000 description 1
- 208000019693 Lung disease Diseases 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 102000019218 Mannose-6-phosphate receptors Human genes 0.000 description 1
- 206010027193 Meningioma malignant Diseases 0.000 description 1
- 206010048723 Multiple-drug resistance Diseases 0.000 description 1
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 1
- 208000009525 Myocarditis Diseases 0.000 description 1
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical group OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 108010029485 Protein Isoforms Proteins 0.000 description 1
- 102000001708 Protein Isoforms Human genes 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 206010067362 Radiation necrosis Diseases 0.000 description 1
- 101001039269 Rattus norvegicus Glycine N-methyltransferase Proteins 0.000 description 1
- 208000015634 Rectal Neoplasms Diseases 0.000 description 1
- 102000002114 Reduced Folate Carrier Human genes 0.000 description 1
- 108050009454 Reduced Folate Carrier Proteins 0.000 description 1
- 208000006265 Renal cell carcinoma Diseases 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 108050001286 Somatostatin Receptor Proteins 0.000 description 1
- 102000011096 Somatostatin receptor Human genes 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 1
- IVTVGDXNLFLDRM-HNNXBMFYSA-N Tomudex Chemical compound C=1C=C2NC(C)=NC(=O)C2=CC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)S1 IVTVGDXNLFLDRM-HNNXBMFYSA-N 0.000 description 1
- 102000044209 Tumor Suppressor Genes Human genes 0.000 description 1
- 108700025716 Tumor Suppressor Genes Proteins 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009098 adjuvant therapy Methods 0.000 description 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 208000014534 anaplastic ependymoma Diseases 0.000 description 1
- 239000004037 angiogenesis inhibitor Substances 0.000 description 1
- 230000007953 anoxia Effects 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 230000003432 anti-folate effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000001946 anti-microtubular Effects 0.000 description 1
- 229940127074 antifolate Drugs 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 239000000074 antisense oligonucleotide Substances 0.000 description 1
- 238000012230 antisense oligonucleotides Methods 0.000 description 1
- 238000003782 apoptosis assay Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000011717 athymic nude mouse Methods 0.000 description 1
- 210000004227 basal ganglia Anatomy 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 238000010322 bone marrow transplantation Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003727 cerebral blood flow Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 210000002987 choroid plexus Anatomy 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 230000001268 conjugating effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- 230000002559 cytogenic effect Effects 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- JADUPRVJUTYLMN-VRGTWVFCSA-D decasodium (2S)-2-aminopentanedioate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[O-]C(=O)[C@@H](N)CCC([O-])=O.[O-]C(=O)[C@@H](N)CCC([O-])=O.[O-]C(=O)[C@@H](N)CCC([O-])=O.[O-]C(=O)[C@@H](N)CCC([O-])=O.[O-]C(=O)[C@@H](N)CCC([O-])=O JADUPRVJUTYLMN-VRGTWVFCSA-D 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000012470 diluted sample Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 229940075933 dithionate Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 201000011523 endocrine gland cancer Diseases 0.000 description 1
- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000004052 folic acid antagonist Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 230000007387 gliosis Effects 0.000 description 1
- 229960001911 glucosamine hydrochloride Drugs 0.000 description 1
- 230000004153 glucose metabolism Effects 0.000 description 1
- 230000006377 glucose transport Effects 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-L glutamate group Chemical group N[C@@H](CCC(=O)[O-])C(=O)[O-] WHUUTDBJXJRKMK-VKHMYHEASA-L 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 229930004094 glycosylphosphatidylinositol Natural products 0.000 description 1
- 208000030316 grade III meningioma Diseases 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- 201000010536 head and neck cancer Diseases 0.000 description 1
- 230000002008 hemorrhagic effect Effects 0.000 description 1
- 208000027671 high grade ependymoma Diseases 0.000 description 1
- 229940125697 hormonal agent Drugs 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000009169 immunotherapy Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 229960001786 megestrol Drugs 0.000 description 1
- RQZAXGRLVPAYTJ-GQFGMJRRSA-N megestrol acetate Chemical compound C1=C(C)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 RQZAXGRLVPAYTJ-GQFGMJRRSA-N 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 230000031864 metaphase Effects 0.000 description 1
- 230000001394 metastastic effect Effects 0.000 description 1
- 206010061289 metastatic neoplasm Diseases 0.000 description 1
- 230000029115 microtubule polymerization Effects 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 229960001156 mitoxantrone Drugs 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- QLILWZWHWVIQDS-UHFFFAOYSA-N n'-aminopyridine-3-carbohydrazide Chemical class NNNC(=O)C1=CC=CN=C1 QLILWZWHWVIQDS-UHFFFAOYSA-N 0.000 description 1
- 210000005170 neoplastic cell Anatomy 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 230000005298 paramagnetic effect Effects 0.000 description 1
- 229960003465 pentetreotide Drugs 0.000 description 1
- 108700023050 pentetreotide Proteins 0.000 description 1
- 102000014187 peptide receptors Human genes 0.000 description 1
- 108010011903 peptide receptors Proteins 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 210000002826 placenta Anatomy 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000010837 poor prognosis Methods 0.000 description 1
- 238000002600 positron emission tomography Methods 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 238000012910 preclinical development Methods 0.000 description 1
- 230000001855 preneoplastic effect Effects 0.000 description 1
- 230000005522 programmed cell death Effects 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- 231100000654 protein toxin Toxicity 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000001107 pteroylglutamyl group Chemical group 0.000 description 1
- 235000008160 pyridoxine Nutrition 0.000 description 1
- 239000011677 pyridoxine Substances 0.000 description 1
- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000011362 radionuclide therapy Methods 0.000 description 1
- 206010038038 rectal cancer Diseases 0.000 description 1
- 201000001275 rectum cancer Diseases 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000002271 resection Methods 0.000 description 1
- 235000005493 rutin Nutrition 0.000 description 1
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 description 1
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 description 1
- 229960004555 rutoside Drugs 0.000 description 1
- 208000013220 shortness of breath Diseases 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical class C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 229960001603 tamoxifen Drugs 0.000 description 1
- CVKJXWOUXWRRJT-UHFFFAOYSA-N technetium dioxide Chemical compound O=[Tc]=O CVKJXWOUXWRRJT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- 239000011721 thiamine Substances 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 229950002376 tirapazamine Drugs 0.000 description 1
- QVMPZNRFXAKISM-UHFFFAOYSA-N tirapazamine Chemical compound C1=CC=C2[N+]([O-])=NC(=N)N(O)C2=C1 QVMPZNRFXAKISM-UHFFFAOYSA-N 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 238000003325 tomography Methods 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 150000002266 vitamin A derivatives Chemical class 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 229940011671 vitamin b6 Drugs 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0453—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0459—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having six-membered rings with two nitrogen atoms as the only ring hetero atoms, e.g. piperazine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0491—Sugars, nucleosides, nucleotides, oligonucleotides, nucleic acids, e.g. DNA, RNA, nucleic acid aptamers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0497—Organic compounds conjugates with a carrier being an organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
- A61K51/087—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins the peptide being an annexin, e.g. annexin V
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
- A61K51/088—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins conjugates with carriers being peptides, polyamino acids or proteins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Optics & Photonics (AREA)
- Epidemiology (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58758300A | 2000-06-02 | 2000-06-02 | |
| US09/599,152 US7067111B1 (en) | 1999-10-25 | 2000-06-21 | Ethylenedicysteine (EC)-drug conjugates, compositions and methods for tissue specific disease imaging |
| PCT/US2001/018060 WO2001091807A2 (en) | 2000-06-02 | 2001-06-01 | Ethylenedicysteine (ec)-drug conjugates |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20025729D0 NO20025729D0 (no) | 2002-11-28 |
| NO20025729L NO20025729L (no) | 2003-01-29 |
| NO332574B1 true NO332574B1 (no) | 2012-11-05 |
Family
ID=27080078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20025729A NO332574B1 (no) | 2000-06-02 | 2002-11-28 | Preparat omfattende etylendicystein-ligander konjugert til en malrettende ligand, metode for syntetisering av en etylendicystein-ligand, anvendelse og sett |
Country Status (16)
| Country | Link |
|---|---|
| US (4) | US7615208B2 (hu) |
| EP (2) | EP2316494A1 (hu) |
| JP (3) | JP5448284B2 (hu) |
| KR (1) | KR100784120B1 (hu) |
| CN (1) | CN1292798C (hu) |
| AU (2) | AU7521001A (hu) |
| BR (1) | BRPI0111220B8 (hu) |
| CA (1) | CA2410906C (hu) |
| DK (1) | DK1286704T3 (hu) |
| ES (1) | ES2518926T3 (hu) |
| HK (1) | HK1056682A1 (hu) |
| HU (1) | HU230437B1 (hu) |
| IL (2) | IL153218A0 (hu) |
| NO (1) | NO332574B1 (hu) |
| PL (1) | PL212211B1 (hu) |
| WO (1) | WO2001091807A2 (hu) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7067111B1 (en) | 1999-10-25 | 2006-06-27 | Board Of Regents, University Of Texas System | Ethylenedicysteine (EC)-drug conjugates, compositions and methods for tissue specific disease imaging |
| BRPI0111220B8 (pt) * | 2000-06-02 | 2021-07-27 | Univ Texas | conjugados de fármacos com etilenodicisteína (ec) |
| US6726895B2 (en) * | 2001-04-03 | 2004-04-27 | Board Of Trustees Of The Leland Stanford Junior University | Method of imaging cell death in vivo |
| US7740854B2 (en) | 2001-05-02 | 2010-06-22 | Purdue Research Foundation | Treatment of macrophage mediated disease |
| US7261875B2 (en) | 2001-12-21 | 2007-08-28 | Board Of Regents, The University Of Texas System | Dendritic poly (amino acid) carriers and methods of use |
| US8043602B2 (en) | 2002-02-07 | 2011-10-25 | Endocyte, Inc. | Folate targeted enhanced tumor and folate receptor positive tissue optical imaging technology |
| US8043603B2 (en) | 2002-02-07 | 2011-10-25 | Endocyte, Inc. | Folate targeted enhanced tumor and folate receptor positive tissue optical imaging technology |
| EP1486216A4 (en) * | 2002-02-26 | 2006-08-23 | Amato Pharm Prod Ltd | PROCESS FOR ENCAPSULATING METAL COMPLEXES IN LIPOSOMES |
| US7824661B2 (en) | 2002-03-11 | 2010-11-02 | Molecular Insight Pharmaceuticals, Inc. | Technetium- and rhenium-bis(heteroaryl) complexes, and methods of use thereof |
| US7381399B2 (en) | 2002-03-11 | 2008-06-03 | Molecular Insight Pharmaceuticals, Inc. | Technetium-dipyridine complexes, and methods of use thereof |
| EP2258401B1 (en) | 2002-05-06 | 2014-07-09 | Endocyte, Inc. | Folate-receptor targeted imaging agents |
| EP2316493A3 (en) * | 2002-11-07 | 2011-08-10 | Board of Regents, The University of Texas System | Ethylenedicysteine (EC)-drug conjugates, compositions and methods for tissue specific disease imaging |
| SI1592457T1 (sl) * | 2003-01-27 | 2012-12-31 | Endocyte, Inc. | Konjugat folat-vinblastin kot zdravilo |
| US9050378B2 (en) | 2003-12-10 | 2015-06-09 | Board Of Regents, The University Of Texas System | N2S2 chelate-targeting ligand conjugates |
| WO2005079866A1 (en) | 2004-02-12 | 2005-09-01 | Molecular Insight Pharmaceuticals | Technetium-and rhenium-bis(heteroaryl) complexes, and methods of use thereof |
| WO2005087275A2 (en) * | 2004-03-11 | 2005-09-22 | Board Of Regents, The University Of Texas System | Metal radiolabeled pet imaging agents |
| EP1827239B1 (en) * | 2004-12-23 | 2019-04-17 | Purdue Research Foundation | Positron emission tomography imaging method |
| KR20080009682A (ko) * | 2005-04-01 | 2008-01-29 | 더 보드 오브 리전츠 오브 더 유니버시티 오브 텍사스 시스템 | 킬레이트제인 폴리(펩티드): 제조 방법과 용도 |
| EP1904183B1 (en) | 2005-07-05 | 2014-10-15 | Purdue Research Foundation | Pharmaceutical composition for the treatment of osteoarthritis |
| US10925977B2 (en) | 2006-10-05 | 2021-02-23 | Ceil>Point, LLC | Efficient synthesis of chelators for nuclear imaging and radiotherapy: compositions and applications |
| EP2087337A4 (en) | 2006-11-03 | 2010-09-08 | Purdue Research Foundation | METHOD AND DEVICE FOR EX-VIVO FLOW CYTOMETRY |
| US20100104511A1 (en) * | 2006-11-22 | 2010-04-29 | The Board Of Regents Of The University Of Texas System | Methods and compositions using chelator-antibody conjugates |
| WO2008098112A2 (en) | 2007-02-07 | 2008-08-14 | Purdue Research Foundation | Positron emission tomography imaging method |
| CA2682064C (en) * | 2007-03-27 | 2013-09-24 | Radiomedix Inc. | Compositions for targeted imaging and therapy |
| WO2008148001A2 (en) | 2007-05-25 | 2008-12-04 | Purdue Research Foundation | Method of imaging localized infections |
| EP2268320A4 (en) * | 2008-03-24 | 2014-10-01 | Univ Texas | IMAGING THERAPY OF MYOKARD DISEASE: COMPOSITION, MANUFACTURE AND APPLICATIONS |
| CN101721720B (zh) | 2008-10-29 | 2011-08-24 | 阮建评 | 硝咪唑-氨基酸化合型核素乏氧造影剂及其前体 |
| US20110085969A1 (en) * | 2009-10-09 | 2011-04-14 | Rollo F David | Chelator-targeting ligand conjugates for cardiovascular imaging |
| US20110280770A1 (en) * | 2010-05-12 | 2011-11-17 | Jeffrey Lacy | Nanogenerator |
| EP2721045B1 (en) | 2011-06-20 | 2017-04-12 | Radiomedix Inc. | Compositions, methods of synthesis and use of carbohydrate targeted agents |
| US9549995B2 (en) * | 2012-03-26 | 2017-01-24 | Board Of Regents, The University Of Texas System | Efficient synthesis of ethylenedicysteine-sugar conjugates for imaging and therapy |
| US9886546B2 (en) | 2012-11-20 | 2018-02-06 | General Electric Company | Methods and apparatus to label radiology images |
| CA2930581A1 (en) * | 2013-11-14 | 2015-05-21 | Endocyte, Inc. | Compounds for positron emission tomography |
| WO2017030893A1 (en) | 2015-08-14 | 2017-02-23 | Endocyte, Inc. | Method of imaging with a chelating compound |
| WO2017090047A1 (en) | 2015-11-27 | 2017-06-01 | Technology Innovation Momentum Fund (Israel) Limited Partnership | Glucosamine and derivatives thereof in imaging |
| CN111372940A (zh) * | 2017-09-19 | 2020-07-03 | 阿尔伯塔大学理事会 | 生物还原活化的化合物、其前药、放射性药物、组合物及其在包括癌症在内的低氧疾病的多模式治疗控制中的应用 |
| RU2692451C2 (ru) * | 2017-10-02 | 2019-06-24 | Федеральное государственное бюджетное научное учреждение "Томский национальный исследовательский медицинский центр" Российской академии наук ("Томский НИМЦ") | Способ радионуклидной диагностики опухолей головного мозга |
| WO2019123409A1 (en) | 2017-12-21 | 2019-06-27 | University Of The Free State | Multinuclear complexes and their preparation |
| EP3826681A4 (en) * | 2018-07-26 | 2022-08-17 | Purdue Research Foundation | ANTI-LIGAND-TARGETED SMALL MOLECULE DRUG CONJUGATES FOR ANTI-INFLUENZA CHEMOTHERAPY AND IMMUNOTHERAPY |
| CN113041366A (zh) * | 2021-03-12 | 2021-06-29 | 青岛大学附属医院 | 一种新型肿瘤乏氧正电子显像剂及其制备方法 |
Family Cites Families (106)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4141654A (en) | 1977-05-23 | 1979-02-27 | James V. Massey, III | Standard for calibrating and/or verifying instrument accuracy |
| US4279992A (en) | 1978-03-13 | 1981-07-21 | Miles Laboratories, Inc. | Specific binding assay employing an enzyme-cleavable substrate as label |
| US4181654A (en) | 1978-07-24 | 1980-01-01 | The United States Of America As Represented By The United States Department Of Energy | 2,3-Dihydroxybenzoic acid amides of tetraazaalkanes and tetaaza cycloalkanes |
| US4418068A (en) | 1981-04-03 | 1983-11-29 | Eli Lilly And Company | Antiestrogenic and antiandrugenic benzothiophenes |
| US5648063A (en) | 1981-07-24 | 1997-07-15 | Schering Aktiengesellschaft | Sterile composition comprising a chelate complex for magnetic resonance imaging |
| US4558120A (en) | 1983-01-07 | 1985-12-10 | The Dow Chemical Company | Dense star polymer |
| US4631337A (en) | 1983-01-07 | 1986-12-23 | The Dow Chemical Company | Hydrolytically-stable dense star polyamine |
| US4737550A (en) | 1983-01-07 | 1988-04-12 | The Dow Chemical Company | Bridged dense star polymers |
| US4507466A (en) | 1983-01-07 | 1985-03-26 | The Dow Chemical Corporation | Dense star polymers having core, core branches, terminal groups |
| US4568737A (en) | 1983-01-07 | 1986-02-04 | The Dow Chemical Company | Dense star polymers and dendrimers |
| US4587329A (en) | 1984-08-17 | 1986-05-06 | The Dow Chemical Company | Dense star polymers having two dimensional molecular diameter |
| US4732863A (en) | 1984-12-31 | 1988-03-22 | University Of New Mexico | PEG-modified antibody with reduced affinity for cell surface Fc receptors |
| US5242679A (en) | 1985-01-14 | 1993-09-07 | Neorx Corporation | Metal radionuclide labeled proteins for diagnosis and therapy |
| US4824659A (en) | 1985-06-07 | 1989-04-25 | Immunomedics, Inc. | Antibody conjugates |
| GB8525974D0 (en) | 1985-10-22 | 1985-11-27 | Nyegaard & Co As | Chemical substance |
| US4871779A (en) | 1985-12-23 | 1989-10-03 | The Dow Chemical Company | Ion exchange/chelation resins containing dense star polymers having ion exchange or chelate capabilities |
| MX174467B (es) | 1986-01-23 | 1994-05-17 | Squibb & Sons Inc | 1,4,7-triscarboximetil-1,4,7,10-tetraazaciclodo decano substituido en 1 y compuestos analogos |
| US4694064A (en) | 1986-02-28 | 1987-09-15 | The Dow Chemical Company | Rod-shaped dendrimer |
| US4789542A (en) | 1986-04-29 | 1988-12-06 | The United States Of America As Represented By The United States Department Of Energy | Radioiodinated glucose analogues for use as imaging agents |
| US4861869A (en) | 1986-05-29 | 1989-08-29 | Mallinckrodt, Inc. | Coupling agents for joining radionuclide metal ions with biologically useful proteins |
| US4713975A (en) | 1986-05-30 | 1987-12-22 | The Dow Chemical Company | Dense star polymers for calibrating/characterizing sub-micron apertures |
| IN165717B (hu) | 1986-08-07 | 1989-12-23 | Battelle Memorial Institute | |
| US4730968A (en) | 1986-09-08 | 1988-03-15 | David Diperstein | Self-tapping, self-aligning thread repair insert |
| US5279811A (en) | 1987-02-18 | 1994-01-18 | The Du Pont Merck Pharmaceutical Company | Ester-substituted diaminedithiols and radiolabeled complexes thereof |
| US4965392A (en) | 1987-03-26 | 1990-10-23 | Neorx Corporation | Chelating compounds for metal-radionuclide labeled proteins |
| US4857599A (en) | 1988-02-08 | 1989-08-15 | The Dow Chemical Company | Modified dense star polymers |
| US5164294A (en) | 1988-05-17 | 1992-11-17 | Syntex (U.S.A.) Inc. | Method for immunochromatographic analysis |
| US4988496A (en) | 1988-05-31 | 1991-01-29 | Neorx Corporation | Metal radionuclide chelating compounds for improved chelation kinetics |
| US5071965A (en) | 1988-07-19 | 1991-12-10 | Mallinckrodt Medical, Inc. | Novel tc-99m complexes |
| US4925650A (en) | 1988-11-16 | 1990-05-15 | Mallinckrodt, Inc. | Technetium -99m complex for examining the renal function |
| US4960790A (en) | 1989-03-09 | 1990-10-02 | University Of Kansas | Derivatives of taxol, pharmaceutical compositions thereof and methods for the preparation thereof |
| US5688488A (en) | 1989-04-03 | 1997-11-18 | Purdue Research Foundation | Composition and method for tumor imaging |
| US5108921A (en) | 1989-04-03 | 1992-04-28 | Purdue Research Foundation | Method for enhanced transmembrane transport of exogenous molecules |
| US5364613A (en) | 1989-04-07 | 1994-11-15 | Sieving Paul F | Polychelants containing macrocyclic chelant moieties |
| JP2517760B2 (ja) | 1989-05-11 | 1996-07-24 | 新技術事業団 | 水溶性高分子化医薬製剤 |
| US5013556A (en) | 1989-10-20 | 1991-05-07 | Liposome Technology, Inc. | Liposomes with enhanced circulation time |
| US5356793A (en) | 1990-03-15 | 1994-10-18 | Nitta Gelatin Inc. | Method for testing the sensitivity of anticancer drug |
| ATE170757T1 (de) | 1990-04-17 | 1998-09-15 | Mallinckrodt Medical Inc | Methode und reagentien um technetium-99m-komplexe herzustellen |
| JPH05508162A (ja) * | 1990-06-18 | 1993-11-18 | マリンクロッド・メディカル・インコーポレイテッド | イソニトリルリガンド含有金属―放射性核種錯化合物 |
| US5385719A (en) | 1991-09-24 | 1995-01-31 | Unger; Evan C. | Copolymers and their use as contrast agents in magnetic resonance imaging and in other applications |
| US5808091A (en) | 1991-10-29 | 1998-09-15 | Bracco International B.V. | Rhenium and technetium complexes containing a hypoxia localizing moiety |
| EP0662001A4 (en) | 1991-11-08 | 1995-11-22 | Univ Missouri | Multifunctional ligands for potential use in the design of therapeutic or diagnostic radiopharmaceutical imaging agents. |
| US5310536A (en) | 1992-02-06 | 1994-05-10 | Mallinckrodt Medical, Inc. | Ligands for improving metal chelate formation kinetics |
| US5877289A (en) | 1992-03-05 | 1999-03-02 | The Scripps Research Institute | Tissue factor compositions and ligands for the specific coagulation of vasculature |
| US6033884A (en) | 1992-03-20 | 2000-03-07 | Baylor College Of Medicine | Nucleic acid transporter systems and methods of use |
| US6113946A (en) | 1992-04-03 | 2000-09-05 | The Regents Of The University Of California | Self-assembling polynucleotide delivery system comprising dendrimer polycations |
| US5541287A (en) | 1992-06-09 | 1996-07-30 | Neorx Corporation | Pretargeting methods and compounds |
| EP1138334A3 (en) | 1992-06-09 | 2002-04-03 | Neorx Corporation | Pretargeting methods and compounds |
| US5716596A (en) | 1992-06-23 | 1998-02-10 | Diatide, Inc. | Radioactively labeled somatostatin-derived peptides for imaging and therapeutic uses |
| US5620675A (en) | 1992-06-23 | 1997-04-15 | Diatech, Inc. | Radioactive peptides |
| US5496533A (en) * | 1992-07-31 | 1996-03-05 | Australian Nuclear Science & Technology Organisation | Rhenium complexes |
| US5605671A (en) | 1992-10-05 | 1997-02-25 | The Regents Of The University Of Michigan | Radiolabeled neutrophil activating peptides for imaging |
| US5834266A (en) | 1993-02-12 | 1998-11-10 | President & Fellows Of Harvard College | Regulated apoptosis |
| US5951964A (en) | 1993-06-04 | 1999-09-14 | Diatide, Inc. | Technetium-99m labeled peptides for imaging |
| US5605672A (en) | 1993-06-09 | 1997-02-25 | The General Hospital Corporation | Blood pool imaging composition and method of its use |
| US5534241A (en) | 1993-07-23 | 1996-07-09 | Torchilin; Vladimir P. | Amphipathic polychelating compounds and methods of use |
| US5449761A (en) | 1993-09-28 | 1995-09-12 | Cytogen Corporation | Metal-binding targeted polypeptide constructs |
| JPH07126165A (ja) * | 1993-10-29 | 1995-05-16 | Masao Oguro | 腫瘍治療剤 |
| US5443953A (en) | 1993-12-08 | 1995-08-22 | Immunomedics, Inc. | Preparation and use of immunoconjugates |
| AU2194695A (en) | 1994-03-28 | 1995-10-17 | Regents Of The University Of California, The | Method for preparing radionuclide-labeled chelating agent-ligand complexes |
| US5730968A (en) | 1994-03-31 | 1998-03-24 | Sterling Winthrop Inc. | Segmented chelating polymers as imaging and therapeutic agents |
| US5670132A (en) | 1994-09-20 | 1997-09-23 | Immunomedics, Inc. | Modified radioantibody fragments for reduced renal uptake |
| US6232295B1 (en) | 1994-10-12 | 2001-05-15 | Jon Faiz Kayyem | Cell-specific contrast agent and gene delivery vehicles |
| US6083741A (en) | 1994-11-17 | 2000-07-04 | Imperial College Of Science Technology And Medicine | Internalisation of DNA, using conjugates of poly-l-lysine and an integrin receptor ligand |
| US5643883A (en) | 1995-01-19 | 1997-07-01 | Uab Research Foundation | Glucose-6-phosphate uptake inhibitors and novel uses thereof |
| US5955605A (en) | 1995-02-21 | 1999-09-21 | Neorx Corporation | Biotinidase resistant biotin-DOTA conjugates |
| US5830431A (en) | 1995-06-07 | 1998-11-03 | Mallinckrodt Medical, Inc. | Radiolabeled peptide compositions for site-specific targeting |
| US5908777A (en) | 1995-06-23 | 1999-06-01 | University Of Pittsburgh | Lipidic vector for nucleic acid delivery |
| JP3543201B2 (ja) * | 1995-10-03 | 2004-07-14 | 日本ペイント株式会社 | 熱硬化性樹脂粒子の製造方法 |
| US5739313A (en) | 1995-11-13 | 1998-04-14 | Regents Of The University Of Minnesota | Radionuclide labeling of vitamin B12 and coenzymes thereof |
| US6441025B2 (en) | 1996-03-12 | 2002-08-27 | Pg-Txl Company, L.P. | Water soluble paclitaxel derivatives |
| ATE314843T1 (de) | 1996-03-12 | 2006-02-15 | Pg Txl Co Lp | Wasserlösliche paclitaxel-prodrogen |
| JP3963996B2 (ja) * | 1996-03-28 | 2007-08-22 | 日本メジフィジックス株式会社 | 糖代謝機能診断剤 |
| US5986074A (en) | 1996-05-06 | 1999-11-16 | Emory University | Metal chelates as pharmaceutical imaging agents, processes of making such and uses thereof |
| US5955053A (en) | 1996-05-06 | 1999-09-21 | Emory University | Metal chelates as pharmaceutical imaging agents, processes of making such and uses thereof |
| IT1284046B1 (it) | 1996-06-21 | 1998-05-08 | Bracco Spa | Processo per la preparazione di tetraazamacrocicli |
| US5900228A (en) | 1996-07-31 | 1999-05-04 | California Institute Of Technology | Bifunctional detection agents having a polymer covalently linked to an MRI agent and an optical dye |
| TW520297B (en) | 1996-10-11 | 2003-02-11 | Sequus Pharm Inc | Fusogenic liposome composition and method |
| GB9708265D0 (en) | 1997-04-24 | 1997-06-18 | Nycomed Imaging As | Contrast agents |
| ES2392246T3 (es) | 1996-11-12 | 2012-12-07 | The Regents Of The University Of California | Preparación de formulaciones estables de complejos de lípido-ácido nucleico para el suministro eficaz in vivo |
| WO1998026912A1 (fr) * | 1996-12-18 | 1998-06-25 | Toray Industries, Inc. | Pre-impregne de fibres de carbone |
| US6187286B1 (en) | 1996-12-27 | 2001-02-13 | The General Hospital Corporation | Tumor imaging agents, methods and kits |
| US6005083A (en) | 1997-03-28 | 1999-12-21 | Neorx Corporation | Bridged aromatic substituted amine ligands with donor atoms |
| EP0879606A1 (en) * | 1997-04-25 | 1998-11-25 | Paul Scherrer Institut | Method for the preparation of facial metal tricarbonyl compounds and their use in the labelling of biologically active substrates |
| CA2288131A1 (en) | 1997-04-30 | 1998-11-05 | The Board Of Trustees Of The Leland Stanford Junior University | Method of imaging cell death in vivo |
| JP3794517B2 (ja) * | 1997-05-08 | 2006-07-05 | 日本メジフィジックス株式会社 | 腫瘍診断剤 |
| US6251866B1 (en) | 1997-08-05 | 2001-06-26 | Watson Laboratories, Inc. | Conjugates targeted to the interleukin-2 receptor |
| US20030013772A1 (en) | 2000-02-23 | 2003-01-16 | Murphy Michael A. | Composition, synthesis and therapeutic applications of polyamines |
| US6713046B1 (en) | 1997-10-27 | 2004-03-30 | Research Corporation Technologies | Magnetic resonance imaging agents for the delivery of therapeutic agents |
| CA2309783C (en) * | 1997-11-25 | 2011-06-28 | Genentech, Inc. | Fibroblast growth factor-19 |
| US6071490A (en) | 1998-05-07 | 2000-06-06 | Immunomedics, Inc. | Position emission tomography using gallium-68 chelates |
| CA2333392A1 (en) | 1998-05-28 | 1999-12-02 | Parker Hughes Institute | Quinazolines for treating brain tumor |
| IT1302125B1 (it) | 1998-08-03 | 2000-07-31 | Sigma Tau Healthscience Spa | Composizione ad attivita' antiossidante ed antiproliferativacomprendente una carnitina ed un carotenoide |
| US20010041189A1 (en) | 1999-04-13 | 2001-11-15 | Jingya Xu | Poly(dipeptide) as a drug carrier |
| US7067111B1 (en) * | 1999-10-25 | 2006-06-27 | Board Of Regents, University Of Texas System | Ethylenedicysteine (EC)-drug conjugates, compositions and methods for tissue specific disease imaging |
| US6692724B1 (en) | 1999-10-25 | 2004-02-17 | Board Of Regents, The University Of Texas System | Ethylenedicysteine (EC)-drug conjugates, compositions and methods for tissue specific disease imaging |
| DE10024874A1 (de) | 2000-05-16 | 2001-11-29 | Siemens Ag | Polierflüssigkeit und Verfahren zur Strukturierung von Metallen und Metalloxiden |
| BRPI0111220B8 (pt) * | 2000-06-02 | 2021-07-27 | Univ Texas | conjugados de fármacos com etilenodicisteína (ec) |
| US6656450B2 (en) | 2000-07-17 | 2003-12-02 | California Institute Of Technology, Inc. | Macrocyclic magnetic resonance imaging contrast agents |
| US6440389B1 (en) | 2000-07-19 | 2002-08-27 | The General Hospital Corporation | Fluorescent agents for real-time measurement of organ function |
| AU2002220082A1 (en) | 2000-10-19 | 2002-04-29 | The General Hospital Corporation | Imaging of enzymatic activity |
| JP2002241307A (ja) | 2001-02-19 | 2002-08-28 | Yasuhiko Tabata | 光増感剤を含有する超音波治療用活性酸素発生剤 |
| DE10135355C1 (de) | 2001-07-20 | 2003-04-17 | Schering Ag | Konjugate makrocyclischer Metallkomplexe mit Biomolekülen und deren Verwendung zur Herstellung von Mitteln für die NMR- und Radiodiagnostik sowie die Radiotherapie |
| US20030152512A1 (en) | 2001-11-13 | 2003-08-14 | Milind Rajopadhye | Imaging thrombus with glycoprotein llb/llla antagonists |
| US7261875B2 (en) | 2001-12-21 | 2007-08-28 | Board Of Regents, The University Of Texas System | Dendritic poly (amino acid) carriers and methods of use |
| US7121926B2 (en) | 2001-12-21 | 2006-10-17 | Micron Technology, Inc. | Methods for planarization of group VIII metal-containing surfaces using a fixed abrasive article |
-
2001
- 2001-06-01 BR BRPI0111220A patent/BRPI0111220B8/pt not_active IP Right Cessation
- 2001-06-01 AU AU7521001A patent/AU7521001A/xx active Pending
- 2001-06-01 IL IL15321801A patent/IL153218A0/xx unknown
- 2001-06-01 HU HU0300951A patent/HU230437B1/hu unknown
- 2001-06-01 PL PL359337A patent/PL212211B1/pl not_active IP Right Cessation
- 2001-06-01 EP EP10181884A patent/EP2316494A1/en not_active Withdrawn
- 2001-06-01 EP EP01941895.3A patent/EP1286704B1/en not_active Expired - Lifetime
- 2001-06-01 WO PCT/US2001/018060 patent/WO2001091807A2/en active Application Filing
- 2001-06-01 JP JP2001587819A patent/JP5448284B2/ja not_active Expired - Lifetime
- 2001-06-01 ES ES01941895.3T patent/ES2518926T3/es not_active Expired - Lifetime
- 2001-06-01 DK DK01941895.3T patent/DK1286704T3/da active
- 2001-06-01 CA CA2410906A patent/CA2410906C/en not_active Expired - Lifetime
- 2001-06-01 CN CNB018116051A patent/CN1292798C/zh not_active Expired - Lifetime
- 2001-06-01 KR KR1020027016455A patent/KR100784120B1/ko active IP Right Grant
- 2001-06-01 AU AU2001275210A patent/AU2001275210B2/en not_active Expired
-
2002
- 2002-11-28 NO NO20025729A patent/NO332574B1/no not_active IP Right Cessation
- 2002-12-02 IL IL153218A patent/IL153218A/en active IP Right Grant
-
2003
- 2003-12-11 HK HK03109030A patent/HK1056682A1/xx not_active IP Right Cessation
-
2007
- 2007-06-08 US US11/760,456 patent/US7615208B2/en not_active Expired - Fee Related
-
2008
- 2008-05-09 JP JP2008123946A patent/JP2008208138A/ja not_active Withdrawn
-
2009
- 2009-09-21 US US12/563,724 patent/US8236279B2/en not_active Expired - Lifetime
-
2012
- 2012-07-11 JP JP2012155112A patent/JP5781026B2/ja not_active Expired - Lifetime
- 2012-07-18 US US13/552,414 patent/US20130165631A1/en not_active Abandoned
-
2014
- 2014-01-24 US US14/163,434 patent/US20140200329A1/en not_active Abandoned
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7582281B2 (en) | Ethylenedicysteine (EC)-drug conjugates compositions and methods for tissue specific disease imaging | |
| JP5781026B2 (ja) | エチレンジシステイン（ｅｃ）−薬物結合体 | |
| US6692724B1 (en) | Ethylenedicysteine (EC)-drug conjugates, compositions and methods for tissue specific disease imaging | |
| AU2001275210A1 (en) | Ethylenedicysteine (EC)-drug conjugates | |
| AU2009200201B2 (en) | Ethylenedicysteine (EC)-drug conjugates, compositions and methods for tissue specific disease imaging | |
| CA2682064C (en) | Compositions for targeted imaging and therapy | |
| US20060246005A1 (en) | Poly(peptide) as a chelator: methods of manufacture and uses | |
| JP2009534381A (ja) | 細胞画像化および治療のための組成物および方法 | |
| Müller et al. | Folate Receptor-Targeted Radionuclide Imaging Agents | |
| Yang et al. | Targeted Imaging: Overview | |
| Yang et al. | Radiopharmaceuticals for Tumor-Targeted Imaging: Overview |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |