JP2001503748A - 分子薬の光活性における選択性改善と検出のための方法 - Google Patents
分子薬の光活性における選択性改善と検出のための方法Info
- Publication number
- JP2001503748A JP2001503748A JP52060498A JP52060498A JP2001503748A JP 2001503748 A JP2001503748 A JP 2001503748A JP 52060498 A JP52060498 A JP 52060498A JP 52060498 A JP52060498 A JP 52060498A JP 2001503748 A JP2001503748 A JP 2001503748A
- Authority
- JP
- Japan
- Prior art keywords
- coumarin
- light
- tissue
- photoactive
- drug
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims abstract description 225
- 239000003814 drug Substances 0.000 title claims abstract description 182
- 229940079593 drug Drugs 0.000 title claims abstract description 181
- 238000001514 detection method Methods 0.000 title abstract description 55
- 230000005284 excitation Effects 0.000 claims abstract description 281
- 241001465754 Metazoa Species 0.000 claims abstract description 63
- 238000003384 imaging method Methods 0.000 claims abstract description 49
- 239000000126 substance Substances 0.000 claims abstract description 20
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 94
- 230000003287 optical effect Effects 0.000 claims description 55
- 239000000463 material Substances 0.000 claims description 49
- 229960000956 coumarin Drugs 0.000 claims description 47
- 235000001671 coumarin Nutrition 0.000 claims description 47
- 230000008569 process Effects 0.000 claims description 38
- 230000005855 radiation Effects 0.000 claims description 33
- -1 4-tert - butylphenyl Chemical group 0.000 claims description 28
- 239000000975 dye Substances 0.000 claims description 25
- SQBBOVROCFXYBN-UHFFFAOYSA-N methoxypsoralen Natural products C1=C2OC(=O)C(OC)=CC2=CC2=C1OC=C2 SQBBOVROCFXYBN-UHFFFAOYSA-N 0.000 claims description 22
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 22
- BGEBZHIAGXMEMV-UHFFFAOYSA-N 5-methoxypsoralen Chemical compound O1C(=O)C=CC2=C1C=C1OC=CC1=C2OC BGEBZHIAGXMEMV-UHFFFAOYSA-N 0.000 claims description 20
- HUVXQFBFIFIDDU-UHFFFAOYSA-N aluminum phthalocyanine Chemical compound [Al+3].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 HUVXQFBFIFIDDU-UHFFFAOYSA-N 0.000 claims description 18
- 238000002059 diagnostic imaging Methods 0.000 claims description 18
- 229960004469 methoxsalen Drugs 0.000 claims description 18
- 230000000694 effects Effects 0.000 claims description 17
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 16
- XHXMPURWMSJENN-UHFFFAOYSA-N coumarin 480 Chemical compound C12=C3CCCN2CCCC1=CC1=C3OC(=O)C=C1C XHXMPURWMSJENN-UHFFFAOYSA-N 0.000 claims description 15
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims description 15
- OYINILBBZAQBEV-UWJYYQICSA-N (17s,18s)-18-(2-carboxyethyl)-20-(carboxymethyl)-12-ethenyl-7-ethyl-3,8,13,17-tetramethyl-17,18,22,23-tetrahydroporphyrin-2-carboxylic acid Chemical compound N1C2=C(C)C(C=C)=C1C=C(N1)C(C)=C(CC)C1=CC(C(C)=C1C(O)=O)=NC1=C(CC(O)=O)C([C@@H](CCC(O)=O)[C@@H]1C)=NC1=C2 OYINILBBZAQBEV-UWJYYQICSA-N 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- UJKPHYRXOLRVJJ-MLSVHJFASA-N CC(O)C1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4C(C)O)/C(CCC(O)=O)=C3C Chemical class CC(O)C1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4C(C)O)/C(CCC(O)=O)=C3C UJKPHYRXOLRVJJ-MLSVHJFASA-N 0.000 claims description 13
- ZCCUUQDIBDJBTK-UHFFFAOYSA-N psoralen Chemical compound C1=C2OC(=O)C=CC2=CC2=C1OC=C2 ZCCUUQDIBDJBTK-UHFFFAOYSA-N 0.000 claims description 13
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical compound C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 claims description 13
- ZTKQHJHANLVEBM-UHFFFAOYSA-N 2-[3-(ethylamino)-6-ethylimino-2,7-dimethylxanthen-9-yl]benzoic acid Chemical compound C1=2C=C(C)C(NCC)=CC=2OC2=CC(=NCC)C(C)=CC2=C1C1=CC=CC=C1C(O)=O ZTKQHJHANLVEBM-UHFFFAOYSA-N 0.000 claims description 12
- BUNGCZLFHHXKBX-UHFFFAOYSA-N 8-methoxypsoralen Natural products C1=CC(=O)OC2=C1C=C1CCOC1=C2OC BUNGCZLFHHXKBX-UHFFFAOYSA-N 0.000 claims description 12
- QXKHYNVANLEOEG-UHFFFAOYSA-N Methoxsalen Chemical compound C1=CC(=O)OC2=C1C=C1C=COC1=C2OC QXKHYNVANLEOEG-UHFFFAOYSA-N 0.000 claims description 12
- LBGCRGLFTKVXDZ-UHFFFAOYSA-M ac1mc2aw Chemical compound [Al+3].[Cl-].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 LBGCRGLFTKVXDZ-UHFFFAOYSA-M 0.000 claims description 12
- 230000008859 change Effects 0.000 claims description 12
- VYXSBFYARXAAKO-WTKGSRSZSA-N chembl402140 Chemical compound Cl.C1=2C=C(C)C(NCC)=CC=2OC2=C\C(=N/CC)C(C)=CC2=C1C1=CC=CC=C1C(=O)OCC VYXSBFYARXAAKO-WTKGSRSZSA-N 0.000 claims description 12
- 239000003446 ligand Substances 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- AFYCEAFSNDLKSX-UHFFFAOYSA-N coumarin 460 Chemical compound CC1=CC(=O)OC2=CC(N(CC)CC)=CC=C21 AFYCEAFSNDLKSX-UHFFFAOYSA-N 0.000 claims description 11
- MUSLHCJRTRQOSP-UHFFFAOYSA-N rhodamine 101 Chemical compound [O-]C(=O)C1=CC=CC=C1C(C1=CC=2CCCN3CCCC(C=23)=C1O1)=C2C1=C(CCC1)C3=[N+]1CCCC3=C2 MUSLHCJRTRQOSP-UHFFFAOYSA-N 0.000 claims description 11
- 229940043267 rhodamine b Drugs 0.000 claims description 11
- COIVODZMVVUETJ-UHFFFAOYSA-N sulforhodamine 101 Chemical compound OS(=O)(=O)C1=CC(S([O-])(=O)=O)=CC=C1C1=C(C=C2C3=C4CCCN3CCC2)C4=[O+]C2=C1C=C1CCCN3CCCC2=C13 COIVODZMVVUETJ-UHFFFAOYSA-N 0.000 claims description 11
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 10
- 229960002045 bergapten Drugs 0.000 claims description 10
- KGZDKFWCIPZMRK-UHFFFAOYSA-N bergapten Natural products COC1C2=C(Cc3ccoc13)C=CC(=O)O2 KGZDKFWCIPZMRK-UHFFFAOYSA-N 0.000 claims description 10
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 claims description 10
- LLSRPENMALNOFW-UHFFFAOYSA-N coumarin 106 Chemical compound C12=C3CCCN2CCCC1=CC1=C3OC(=O)C2=C1CCC2 LLSRPENMALNOFW-UHFFFAOYSA-N 0.000 claims description 10
- GLNDAGDHSLMOKX-UHFFFAOYSA-N coumarin 120 Chemical compound C1=C(N)C=CC2=C1OC(=O)C=C2C GLNDAGDHSLMOKX-UHFFFAOYSA-N 0.000 claims description 10
- 229920001296 polysiloxane Polymers 0.000 claims description 10
- 108090000623 proteins and genes Proteins 0.000 claims description 10
- 235000021286 stilbenes Nutrition 0.000 claims description 10
- QZXAEJGHNXJTSE-UHFFFAOYSA-N 7-(ethylamino)-4,6-dimethylchromen-2-one Chemical compound O1C(=O)C=C(C)C2=C1C=C(NCC)C(C)=C2 QZXAEJGHNXJTSE-UHFFFAOYSA-N 0.000 claims description 9
- VSSSHNJONFTXHS-UHFFFAOYSA-N coumarin 153 Chemical compound C12=C3CCCN2CCCC1=CC1=C3OC(=O)C=C1C(F)(F)F VSSSHNJONFTXHS-UHFFFAOYSA-N 0.000 claims description 9
- VMJKUPWQKZFFCX-UHFFFAOYSA-N coumarin 504 Chemical compound C1CCC2=C(OC(C(C(=O)OCC)=C3)=O)C3=CC3=C2N1CCC3 VMJKUPWQKZFFCX-UHFFFAOYSA-N 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- JBNOVHJXQSHGRL-UHFFFAOYSA-N 7-amino-4-(trifluoromethyl)coumarin Chemical compound FC(F)(F)C1=CC(=O)OC2=CC(N)=CC=C21 JBNOVHJXQSHGRL-UHFFFAOYSA-N 0.000 claims description 8
- JBPCDMSEJVCNGV-UHFFFAOYSA-N coumarin 334 Chemical compound C1CCC2=C(OC(C(C(=O)C)=C3)=O)C3=CC3=C2N1CCC3 JBPCDMSEJVCNGV-UHFFFAOYSA-N 0.000 claims description 8
- LGDDFMCJIHJNMK-UHFFFAOYSA-N coumarin 337 Chemical compound C12=C3CCCN2CCCC1=CC1=C3OC(=O)C(C#N)=C1 LGDDFMCJIHJNMK-UHFFFAOYSA-N 0.000 claims description 8
- UIMOXRDVWDLOHW-UHFFFAOYSA-N coumarin 481 Chemical compound FC(F)(F)C1=CC(=O)OC2=CC(N(CC)CC)=CC=C21 UIMOXRDVWDLOHW-UHFFFAOYSA-N 0.000 claims description 8
- VBVAVBCYMYWNOU-UHFFFAOYSA-N coumarin 6 Chemical compound C1=CC=C2SC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 VBVAVBCYMYWNOU-UHFFFAOYSA-N 0.000 claims description 8
- 229960003569 hematoporphyrin Drugs 0.000 claims description 8
- 150000004032 porphyrins Chemical class 0.000 claims description 8
- 102000004169 proteins and genes Human genes 0.000 claims description 8
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 8
- FMHHVULEAZTJMA-UHFFFAOYSA-N trioxsalen Chemical compound CC1=CC(=O)OC2=C1C=C1C=C(C)OC1=C2C FMHHVULEAZTJMA-UHFFFAOYSA-N 0.000 claims description 8
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 claims description 7
- HSHNITRMYYLLCV-UHFFFAOYSA-N 4-methylumbelliferone Chemical compound C1=C(O)C=CC2=C1OC(=O)C=C2C HSHNITRMYYLLCV-UHFFFAOYSA-N 0.000 claims description 7
- GZEYLLPOQRZUDF-UHFFFAOYSA-N 7-(dimethylamino)-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(N(C)C)=CC=C21 GZEYLLPOQRZUDF-UHFFFAOYSA-N 0.000 claims description 7
- NRZJOTSUPLCYDJ-UHFFFAOYSA-N 7-(ethylamino)-6-methyl-4-(trifluoromethyl)chromen-2-one Chemical compound O1C(=O)C=C(C(F)(F)F)C2=C1C=C(NCC)C(C)=C2 NRZJOTSUPLCYDJ-UHFFFAOYSA-N 0.000 claims description 7
- SXQRATTWLJENLK-UHFFFAOYSA-N [9-(diethylamino)benzo[a]phenoxazin-5-ylidene]-ethylazanium;chloride Chemical compound [Cl-].C12=CC=CC=C2C(=[NH+]CC)C=C2C1=NC1=CC=C(N(CC)CC)C=C1O2 SXQRATTWLJENLK-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- KCDCNGXPPGQERR-UHFFFAOYSA-N coumarin 343 Chemical compound C1CCC2=C(OC(C(C(=O)O)=C3)=O)C3=CC3=C2N1CCC3 KCDCNGXPPGQERR-UHFFFAOYSA-N 0.000 claims description 7
- VYXSBFYARXAAKO-UHFFFAOYSA-N ethyl 2-[3-(ethylamino)-6-ethylimino-2,7-dimethylxanthen-9-yl]benzoate;hydron;chloride Chemical compound [Cl-].C1=2C=C(C)C(NCC)=CC=2OC2=CC(=[NH+]CC)C(C)=CC2=C1C1=CC=CC=C1C(=O)OCC VYXSBFYARXAAKO-UHFFFAOYSA-N 0.000 claims description 7
- MHIITNFQDPFSES-UHFFFAOYSA-N 25,26,27,28-tetrazahexacyclo[16.6.1.13,6.18,11.113,16.019,24]octacosa-1(25),2,4,6,8(27),9,11,13,15,17,19,21,23-tridecaene Chemical class N1C(C=C2C3=CC=CC=C3C(C=C3NC(=C4)C=C3)=N2)=CC=C1C=C1C=CC4=N1 MHIITNFQDPFSES-UHFFFAOYSA-N 0.000 claims description 6
- WBIICVGYYRRURR-UHFFFAOYSA-N 3-(aminomethyl)-2,5,9-trimethylfuro[3,2-g]chromen-7-one Chemical compound O1C(=O)C=C(C)C2=C1C(C)=C1OC(C)=C(CN)C1=C2 WBIICVGYYRRURR-UHFFFAOYSA-N 0.000 claims description 6
- VXGRJERITKFWPL-UHFFFAOYSA-N 4',5'-Dihydropsoralen Natural products C1=C2OC(=O)C=CC2=CC2=C1OCC2 VXGRJERITKFWPL-UHFFFAOYSA-N 0.000 claims description 6
- ZGXJTSGNIOSYLO-UHFFFAOYSA-N 88755TAZ87 Chemical compound NCC(=O)CCC(O)=O ZGXJTSGNIOSYLO-UHFFFAOYSA-N 0.000 claims description 6
- 229930003316 Vitamin D Natural products 0.000 claims description 6
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 claims description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- UPZKDDJKJWYWHQ-UHFFFAOYSA-O [6-amino-9-(2-carboxyphenyl)xanthen-3-ylidene]azanium Chemical compound C=12C=CC(=[NH2+])C=C2OC2=CC(N)=CC=C2C=1C1=CC=CC=C1C(O)=O UPZKDDJKJWYWHQ-UHFFFAOYSA-O 0.000 claims description 6
- HACOCUMLBPNDIN-UHFFFAOYSA-M ac1l2skh Chemical compound [O-]Cl(=O)(=O)=O.C1CCN2CCCC3=C2C1=C1OC2=C(CCC4)C5=[N+]4CCCC5=CC2=C(C#N)C1=C3 HACOCUMLBPNDIN-UHFFFAOYSA-M 0.000 claims description 6
- 229960002749 aminolevulinic acid Drugs 0.000 claims description 6
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical class C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 claims description 6
- 229910052732 germanium Inorganic materials 0.000 claims description 6
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 6
- 229950003776 protoporphyrin Drugs 0.000 claims description 6
- TUFFYSFVSYUHPA-UHFFFAOYSA-M rhodamine 123 Chemical compound [Cl-].COC(=O)C1=CC=CC=C1C1=C(C=CC(N)=C2)C2=[O+]C2=C1C=CC(N)=C2 TUFFYSFVSYUHPA-UHFFFAOYSA-M 0.000 claims description 6
- HTNRBNPBWAFIKA-UHFFFAOYSA-M rhodamine 700 perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C1CCN2CCCC3=C2C1=C1OC2=C(CCC4)C5=[N+]4CCCC5=CC2=C(C(F)(F)F)C1=C3 HTNRBNPBWAFIKA-UHFFFAOYSA-M 0.000 claims description 6
- CVAVMIODJQHEEH-UHFFFAOYSA-O rhodamine B(1+) Chemical compound C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O CVAVMIODJQHEEH-UHFFFAOYSA-O 0.000 claims description 6
- 235000019166 vitamin D Nutrition 0.000 claims description 6
- 239000011710 vitamin D Substances 0.000 claims description 6
- 150000003710 vitamin D derivatives Chemical class 0.000 claims description 6
- 229940046008 vitamin d Drugs 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- KFNLIWIAIPMECU-UHFFFAOYSA-N 1-(1-methyl-2H-pyridin-2-yl)-21,23-dihydro-2H-porphyrin Chemical compound CN1C=CC=CC1C1(C=C2N=C(C=C2)C=C2C=CC(N2)=CC=2C=CC(N=2)=C2)NC2=CC1 KFNLIWIAIPMECU-UHFFFAOYSA-N 0.000 claims description 5
- IOOMXAQUNPWDLL-UHFFFAOYSA-N 2-[6-(diethylamino)-3-(diethyliminiumyl)-3h-xanthen-9-yl]-5-sulfobenzene-1-sulfonate Chemical compound C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S(O)(=O)=O)C=C1S([O-])(=O)=O IOOMXAQUNPWDLL-UHFFFAOYSA-N 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 claims description 5
- ZUELZXZJXUXJCH-UHFFFAOYSA-N 3-[10,15,20-tris(3-hydroxyphenyl)-21,23-dihydroporphyrin-5-yl]phenol Chemical compound Oc1cccc(c1)-c1c2ccc(n2)c(-c2cccc(O)c2)c2ccc([nH]2)c(-c2cccc(O)c2)c2ccc(n2)c(-c2cccc(O)c2)c2ccc1[nH]2 ZUELZXZJXUXJCH-UHFFFAOYSA-N 0.000 claims description 5
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- 239000002738 chelating agent Substances 0.000 claims description 5
- KDTAEYOYAZPLIC-UHFFFAOYSA-N coumarin 152 Chemical compound FC(F)(F)C1=CC(=O)OC2=CC(N(C)C)=CC=C21 KDTAEYOYAZPLIC-UHFFFAOYSA-N 0.000 claims description 5
- GZTMNDOZYLMFQE-UHFFFAOYSA-N coumarin 500 Chemical compound FC(F)(F)C1=CC(=O)OC2=CC(NCC)=CC=C21 GZTMNDOZYLMFQE-UHFFFAOYSA-N 0.000 claims description 5
- IMVPLRZGEHZIEM-UHFFFAOYSA-N coumarin 522 Chemical compound FC(F)(F)C1=CC(=O)OC2=C1C=C1CCCN(C)C1=C2 IMVPLRZGEHZIEM-UHFFFAOYSA-N 0.000 claims description 5
- MZSOXGPKUOAXNY-UHFFFAOYSA-N coumarin 6h Chemical compound C1CCC2=C(OC(=O)C=C3)C3=CC3=C2N1CCC3 MZSOXGPKUOAXNY-UHFFFAOYSA-N 0.000 claims description 5
- 229940015493 dihematoporphyrin ether Drugs 0.000 claims description 5
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- KAAFBHHNXFTWGY-UHFFFAOYSA-N 5-n,9-n,9-n-triethyl-12h-benzo[a]phenoselenazine-5,9-diamine Chemical compound C12=CC=CC=C2C(NCC)=CC2=C1NC1=CC=C(N(CC)CC)C=C1[Se]2 KAAFBHHNXFTWGY-UHFFFAOYSA-N 0.000 claims description 4
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- A61K49/0021—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules the fluorescent group being a small organic molecule
- A61K49/0041—Xanthene dyes, used in vivo, e.g. administered to a mice, e.g. rhodamines, rose Bengal
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- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
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- B82Y15/00—Nanotechnology for interacting, sensing or actuating, e.g. quantum dots as markers in protein assays or molecular motors
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- Medicines Containing Plant Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/741,370 US5832931A (en) | 1996-10-30 | 1996-10-30 | Method for improved selectivity in photo-activation and detection of molecular diagnostic agents |
| US08/741,370 | 1996-10-30 | ||
| PCT/US1997/019249 WO1998018398A1 (en) | 1996-10-30 | 1997-10-27 | Method for improved selectivity in photo-activation and detection of molecular diagnostic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2001503748A true JP2001503748A (ja) | 2001-03-21 |
Family
ID=24980452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP52060498A Ceased JP2001503748A (ja) | 1996-10-30 | 1997-10-27 | 分子薬の光活性における選択性改善と検出のための方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US5832931A (en:Method) |
| EP (1) | EP1032321A4 (en:Method) |
| JP (1) | JP2001503748A (en:Method) |
| KR (1) | KR20000035894A (en:Method) |
| CN (1) | CN1226147A (en:Method) |
| AU (1) | AU716504B2 (en:Method) |
| BR (1) | BR9713979A (en:Method) |
| CA (1) | CA2252782A1 (en:Method) |
| IL (1) | IL128356A (en:Method) |
| IN (1) | IN185849B (en:Method) |
| IS (1) | IS5007A (en:Method) |
| NO (1) | NO991493L (en:Method) |
| NZ (1) | NZ334191A (en:Method) |
| WO (1) | WO1998018398A1 (en:Method) |
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| JP2013054175A (ja) * | 2011-09-02 | 2013-03-21 | Olympus Corp | 非線形光学顕微鏡 |
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| CN107375929B (zh) * | 2017-08-04 | 2020-10-30 | 大连理工大学 | 一类光敏剂及其衍生物和应用 |
| US20220370373A1 (en) * | 2019-10-21 | 2022-11-24 | The Trustees Of Princeton University | Sequential multi-step flash nanoprecipitation for the formation of nanoparticles with high core loadings |
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| CN116029185B (zh) * | 2023-03-27 | 2023-06-16 | 季华实验室 | 电子自旋禁阻激发偶极确定方法、装置、设备及存储介质 |
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| JPS63111886A (ja) * | 1986-10-29 | 1988-05-17 | 呉羽化学工業株式会社 | 光ダイオ−ドを用いた癌治療装置 |
| DE69020638T2 (de) * | 1989-04-18 | 1996-01-25 | Nippon Telegraph & Telephone | Optisches Speichermedium und Speicherungsprozess. |
| US4973848A (en) * | 1989-07-28 | 1990-11-27 | J. Mccaughan | Laser apparatus for concurrent analysis and treatment |
| US5034613A (en) * | 1989-11-14 | 1991-07-23 | Cornell Research Foundation, Inc. | Two-photon laser microscopy |
| EP0505355A4 (en) * | 1989-12-11 | 1992-12-30 | Lasb Laser, Corp. | Laser therapeutic apparatus and method |
| GB9014263D0 (en) * | 1990-06-27 | 1990-08-15 | Dixon Arthur E | Apparatus and method for spatially- and spectrally- resolvedmeasurements |
| US5558666A (en) * | 1994-01-14 | 1996-09-24 | Coherent, Inc. | Handpiece for producing highly collimated laser beam for dermatological procedures |
| US5483338A (en) * | 1994-05-26 | 1996-01-09 | Martin Marietta Energy Systems, Inc. | Method and apparatus for evaluating structural weakness in polymer matrix composites |
| US5522868A (en) * | 1994-08-23 | 1996-06-04 | Sisters Of Providence In Oregon | Method and apparatus for determination of psoralen concentrations in biological tissues |
| US5586981A (en) * | 1994-08-25 | 1996-12-24 | Xin-Hua Hu | Treatment of cutaneous vascular and pigmented lesions |
| WO1996038410A1 (en) * | 1995-06-02 | 1996-12-05 | Forskningscenter Risø | Novel physically functional materials |
| CA2231114A1 (en) * | 1995-09-06 | 1997-03-13 | The Research Foundation Of State University Of New York | Two-photon upconverting dyes and applications |
| AUPN673995A0 (en) * | 1995-11-22 | 1995-12-14 | Down Hole Technologies Pty Ltd | A sleeve for orientating a tool |
| US6111641A (en) * | 1998-03-23 | 2000-08-29 | The United States Of America As Represented By The Secretary Of The Air Force | Nonlinear spectrophotometer |
-
1996
- 1996-10-30 US US08/741,370 patent/US5832931A/en not_active Expired - Lifetime
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1997
- 1997-10-24 IN IN2409MA1997 patent/IN185849B/en unknown
- 1997-10-27 JP JP52060498A patent/JP2001503748A/ja not_active Ceased
- 1997-10-27 IL IL12835697A patent/IL128356A/en not_active IP Right Cessation
- 1997-10-27 BR BR9713979-3A patent/BR9713979A/pt unknown
- 1997-10-27 CN CN97196813A patent/CN1226147A/zh active Pending
- 1997-10-27 KR KR1019997001606A patent/KR20000035894A/ko not_active Ceased
- 1997-10-27 CA CA002252782A patent/CA2252782A1/en not_active Abandoned
- 1997-10-27 EP EP97948121A patent/EP1032321A4/en not_active Withdrawn
- 1997-10-27 NZ NZ334191A patent/NZ334191A/xx unknown
- 1997-10-27 AU AU54254/98A patent/AU716504B2/en not_active Ceased
- 1997-10-27 WO PCT/US1997/019249 patent/WO1998018398A1/en not_active Application Discontinuation
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1998
- 1998-05-05 US US09/072,963 patent/US7346387B1/en not_active Expired - Fee Related
-
1999
- 1999-03-19 IS IS5007A patent/IS5007A/is unknown
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006511473A (ja) * | 2002-09-23 | 2006-04-06 | ゼネラル・エレクトリック・カンパニイ | 蛍光染料及びｍｒｉ造影剤を含む二元機能造影剤 |
| JP2007132794A (ja) * | 2005-11-10 | 2007-05-31 | Olympus Corp | 多光子励起型観察装置および多光子励起型観察用光源装置 |
| JP2016135316A (ja) * | 2009-05-05 | 2016-07-28 | ルミト・アーベー | 散乱媒体の拡散ルミネセンスイメージングまたは断層撮影の改善のためのシステム、方法、およびルミネセンスマーカー |
| JP2018128470A (ja) * | 2009-05-05 | 2018-08-16 | ルミト・アーベー | 散乱媒体の拡散ルミネセンスイメージングまたは断層撮影の改善のためのシステム、方法、およびルミネセンスマーカー |
| JP2013054175A (ja) * | 2011-09-02 | 2013-03-21 | Olympus Corp | 非線形光学顕微鏡 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU5425498A (en) | 1998-05-22 |
| IS5007A (is) | 1999-03-19 |
| IL128356A0 (en) | 2000-01-31 |
| KR20000035894A (ko) | 2000-06-26 |
| IL128356A (en) | 2001-11-25 |
| NO991493L (no) | 1999-05-27 |
| EP1032321A1 (en) | 2000-09-06 |
| US5832931A (en) | 1998-11-10 |
| NO991493D0 (no) | 1999-03-26 |
| CA2252782A1 (en) | 1998-05-07 |
| US7346387B1 (en) | 2008-03-18 |
| IN185849B (en:Method) | 2001-05-12 |
| CN1226147A (zh) | 1999-08-18 |
| NZ334191A (en) | 2000-01-28 |
| AU716504B2 (en) | 2000-02-24 |
| EP1032321A4 (en) | 2000-09-06 |
| BR9713979A (pt) | 2000-05-02 |
| WO1998018398A1 (en) | 1998-05-07 |
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