JP5972171B2 - 光力学的療法のためのヒト血清アルブミンをベースにしたナノ粒子キャリアシステム - Google Patents
光力学的療法のためのヒト血清アルブミンをベースにしたナノ粒子キャリアシステム Download PDFInfo
- Publication number
- JP5972171B2 JP5972171B2 JP2012543221A JP2012543221A JP5972171B2 JP 5972171 B2 JP5972171 B2 JP 5972171B2 JP 2012543221 A JP2012543221 A JP 2012543221A JP 2012543221 A JP2012543221 A JP 2012543221A JP 5972171 B2 JP5972171 B2 JP 5972171B2
- Authority
- JP
- Japan
- Prior art keywords
- hsa
- nanoparticles
- photosensitizer
- photodynamic therapy
- pharmaceutical formulation
- 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.)
- Expired - Fee Related
Links
- 239000002105 nanoparticle Substances 0.000 title claims description 171
- 102000008100 Human Serum Albumin Human genes 0.000 title claims description 116
- 108091006905 Human Serum Albumin Proteins 0.000 title claims description 116
- 238000002428 photodynamic therapy Methods 0.000 title claims description 37
- 239000003504 photosensitizing agent Substances 0.000 claims description 91
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 35
- 238000002360 preparation method Methods 0.000 claims description 30
- 239000002245 particle Substances 0.000 claims description 27
- 239000000243 solution Substances 0.000 claims description 24
- 102000004169 proteins and genes Human genes 0.000 claims description 20
- 108090000623 proteins and genes Proteins 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 230000002209 hydrophobic effect Effects 0.000 claims description 17
- SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 238000004807 desolvation Methods 0.000 claims description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 12
- 239000003381 stabilizer Substances 0.000 claims description 12
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims description 11
- 206010028980 Neoplasm Diseases 0.000 claims description 11
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 11
- 239000002202 Polyethylene glycol Substances 0.000 claims description 10
- 229920001223 polyethylene glycol Polymers 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 230000000274 adsorptive effect Effects 0.000 claims description 6
- 150000004036 bacteriochlorins Chemical class 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000011780 sodium chloride Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- 230000000087 stabilizing effect Effects 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 3
- 108010038807 Oligopeptides Proteins 0.000 claims description 3
- 102000015636 Oligopeptides Human genes 0.000 claims description 3
- 208000012931 Urologic disease Diseases 0.000 claims description 3
- 206010003246 arthritis Diseases 0.000 claims description 3
- 125000000837 carbohydrate group Chemical group 0.000 claims description 3
- 125000003827 glycol group Chemical group 0.000 claims description 3
- 238000010253 intravenous injection Methods 0.000 claims description 3
- 230000001613 neoplastic effect Effects 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 3
- 208000017520 skin disease Diseases 0.000 claims description 3
- 208000014001 urinary system disease Diseases 0.000 claims description 3
- 239000007900 aqueous suspension Substances 0.000 claims description 2
- 210000004027 cell Anatomy 0.000 description 41
- 239000000203 mixture Substances 0.000 description 30
- 238000009472 formulation Methods 0.000 description 23
- 239000003814 drug Substances 0.000 description 19
- 229940079593 drug Drugs 0.000 description 18
- 230000000694 effects Effects 0.000 description 14
- 238000011534 incubation Methods 0.000 description 14
- 230000004700 cellular uptake Effects 0.000 description 13
- 206010034972 Photosensitivity reaction Diseases 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- BHPNXACHQYJJJS-UHFFFAOYSA-N bacteriochlorin Chemical compound N1C(C=C2N=C(C=C3NC(=C4)C=C3)CC2)=CC=C1C=C1CCC4=N1 BHPNXACHQYJJJS-UHFFFAOYSA-N 0.000 description 9
- 208000007578 phototoxic dermatitis Diseases 0.000 description 9
- 231100000018 phototoxicity Toxicity 0.000 description 9
- 238000004108 freeze drying Methods 0.000 description 7
- 238000007911 parenteral administration Methods 0.000 description 7
- 230000001954 sterilising effect Effects 0.000 description 7
- 238000004659 sterilization and disinfection Methods 0.000 description 7
- UDNKWMCZJWRQNR-UHFFFAOYSA-N OC1=CC=CC(C=2C3=CC4=CC=C([N]4)C=C4C=CC(N4)=CC4=CC=C([N]4)C=C(N3)C=2)=C1 Chemical compound OC1=CC=CC(C=2C3=CC4=CC=C([N]4)C=C4C=CC(N4)=CC4=CC=C([N]4)C=C(N3)C=2)=C1 UDNKWMCZJWRQNR-UHFFFAOYSA-N 0.000 description 6
- -1 for example Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 150000004032 porphyrins Chemical class 0.000 description 6
- 238000001179 sorption measurement Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical group C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 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 description 5
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
- 230000001640 apoptogenic effect Effects 0.000 description 4
- 239000006285 cell suspension Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 238000012377 drug delivery Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 229930014626 natural product Natural products 0.000 description 4
- 238000011002 quantification Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000006257 total synthesis reaction Methods 0.000 description 4
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 3
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- LYPFDBRUNKHDGX-SOGSVHMOSA-N N1C2=CC=C1\C(=C1\C=CC(=N1)\C(=C1\C=C/C(/N1)=C(/C1=N/C(/CC1)=C2/C1=CC(O)=CC=C1)C1=CC(O)=CC=C1)\C1=CC(O)=CC=C1)C1=CC(O)=CC=C1 Chemical compound N1C2=CC=C1\C(=C1\C=CC(=N1)\C(=C1\C=C/C(/N1)=C(/C1=N/C(/CC1)=C2/C1=CC(O)=CC=C1)C1=CC(O)=CC=C1)\C1=CC(O)=CC=C1)C1=CC(O)=CC=C1 LYPFDBRUNKHDGX-SOGSVHMOSA-N 0.000 description 3
- 229930012538 Paclitaxel Natural products 0.000 description 3
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 3
- 239000002246 antineoplastic agent Substances 0.000 description 3
- 229940041181 antineoplastic drug Drugs 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 238000001218 confocal laser scanning microscopy Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 230000005486 microgravity Effects 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 229960001592 paclitaxel Drugs 0.000 description 3
- 230000002688 persistence Effects 0.000 description 3
- 231100000760 phototoxic Toxicity 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 238000006862 quantum yield reaction Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 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 description 3
- 229960002197 temoporfin Drugs 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 102000009027 Albumins Human genes 0.000 description 2
- 108010088751 Albumins Proteins 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- 102000057297 Pepsin A Human genes 0.000 description 2
- 108090000284 Pepsin A Proteins 0.000 description 2
- 239000012980 RPMI-1640 medium Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- GLNADSQYFUSGOU-GPTZEZBUSA-J Trypan blue Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(/N=N/C3=CC=C(C=C3C)C=3C=C(C(=CC=3)\N=N\C=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)C)=C(O)C2=C1N GLNADSQYFUSGOU-GPTZEZBUSA-J 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000006907 apoptotic process Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 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 description 2
- 208000002352 blister Diseases 0.000 description 2
- 230000030833 cell death Effects 0.000 description 2
- 238000010382 chemical cross-linking Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 206010020718 hyperplasia Diseases 0.000 description 2
- 230000036512 infertility Effects 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000017074 necrotic cell death Effects 0.000 description 2
- 230000001338 necrotic effect Effects 0.000 description 2
- 230000009826 neoplastic cell growth Effects 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 238000011275 oncology therapy Methods 0.000 description 2
- 229940111202 pepsin Drugs 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000004033 porphyrin derivatives Chemical class 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 230000009424 thromboembolic effect Effects 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 238000004627 transmission electron microscopy Methods 0.000 description 2
- RZFDLDWSAAUYFW-UHFFFAOYSA-N 1,2,3,4,21,23-hexahydroporphyrin Chemical compound N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)CCC1C=C1C=CC4=N1 RZFDLDWSAAUYFW-UHFFFAOYSA-N 0.000 description 1
- IICCLYANAQEHCI-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 IICCLYANAQEHCI-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 108010003118 Bacteriochlorophylls Proteins 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- 241000122205 Chamaeleonidae Species 0.000 description 1
- 108010062580 Concanavalin A Proteins 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- 101150050192 PIGM gene Proteins 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 229920001030 Polyethylene Glycol 4000 Polymers 0.000 description 1
- 208000010378 Pulmonary Embolism Diseases 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000000246 agarose gel electrophoresis Methods 0.000 description 1
- 230000000890 antigenic effect Effects 0.000 description 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- DSJXIQQMORJERS-AGGZHOMASA-M bacteriochlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC([C@H](CC)[C@H]3C)=[N+]4C3=CC3=C(C(C)=O)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 DSJXIQQMORJERS-AGGZHOMASA-M 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000000560 biocompatible material Substances 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- KSXLETNRCMCRAQ-UHFFFAOYSA-N chembl383675 Chemical compound OC1=CC=CC(C=2C=3C=CC(N=3)=C(C=3C=C(O)C=CC=3)C3=CC=C(N3)C(C=3C=C(O)C=CC=3)=C3C=CC(N3)=C(C=3C=C(O)C=CC=3)C=3CCC=2N=3)=C1 KSXLETNRCMCRAQ-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000004035 chlorins Chemical class 0.000 description 1
- 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 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940039227 diagnostic agent Drugs 0.000 description 1
- 239000000032 diagnostic agent Substances 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000005906 dihydroxylation reaction Methods 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 230000000547 effect on apoptosis Effects 0.000 description 1
- 230000000438 effect on necrosis Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002481 ethanol extraction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000000899 immune system response Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 238000012792 lyophilization process Methods 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 238000007431 microscopic evaluation Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012120 mounting media Substances 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229930188006 polyphyllin Natural products 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000002096 quantum dot Substances 0.000 description 1
- 239000003642 reactive oxygen metabolite Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229930187593 rose bengal Natural products 0.000 description 1
- 229940081623 rose bengal Drugs 0.000 description 1
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/409—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having four such rings, e.g. porphine derivatives, bilirubin, biliverdine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/0057—Photodynamic therapy with a photosensitizer, i.e. agent able to produce reactive oxygen species upon exposure to light or radiation, e.g. UV or visible light; photocleavage of nucleic acids with an agent
- A61K41/0071—PDT with porphyrins having exactly 20 ring atoms, i.e. based on the non-expanded tetrapyrrolic ring system, e.g. bacteriochlorin, chlorin-e6, or phthalocyanines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/51—Nanocapsules; Nanoparticles
- A61K9/5107—Excipients; Inactive ingredients
- A61K9/513—Organic macromolecular compounds; Dendrimers
- A61K9/5169—Proteins, e.g. albumin, gelatin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Gastroenterology & Hepatology (AREA)
- Biomedical Technology (AREA)
- Optics & Photonics (AREA)
- Nanotechnology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Physics & Mathematics (AREA)
- Rheumatology (AREA)
- Ophthalmology & Optometry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28590209P | 2009-12-11 | 2009-12-11 | |
| US61/285,902 | 2009-12-11 | ||
| US12/941,350 | 2010-11-08 | ||
| US12/941,350 US9211283B2 (en) | 2009-12-11 | 2010-11-08 | Nanoparticle carrier systems based on human serum albumin for photodynamic therapy |
| PCT/US2010/059364 WO2011071968A2 (en) | 2009-12-11 | 2010-12-08 | Nanoparticle carrier systems based on human serum albumin for photodynamic therapy |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013513609A JP2013513609A (ja) | 2013-04-22 |
| JP2013513609A5 JP2013513609A5 (enExample) | 2014-08-14 |
| JP5972171B2 true JP5972171B2 (ja) | 2016-08-17 |
Family
ID=44143223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012543221A Expired - Fee Related JP5972171B2 (ja) | 2009-12-11 | 2010-12-08 | 光力学的療法のためのヒト血清アルブミンをベースにしたナノ粒子キャリアシステム |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9211283B2 (enExample) |
| EP (1) | EP2509620A4 (enExample) |
| JP (1) | JP5972171B2 (enExample) |
| CN (1) | CN102740875A (enExample) |
| BR (1) | BR112012013952A2 (enExample) |
| CA (1) | CA2784001C (enExample) |
| WO (1) | WO2011071968A2 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2591803A1 (de) * | 2011-11-09 | 2013-05-15 | APOCARE Pharma GmbH | Zusammensetzung für die photodynamische Diagnostik und Therapie von Tumoren |
| CN103169968B (zh) * | 2013-03-12 | 2014-11-26 | 中国科学院理化技术研究所 | 一种基于白蛋白的疏水二氢卟吩光敏剂纳米药物制剂、制备方法及其应用 |
| KR101329646B1 (ko) | 2013-05-02 | 2013-11-14 | 주식회사 지니스 | 표적지향증폭형 항암나노입자 및 이의 제조방법 |
| US10456375B2 (en) | 2014-09-30 | 2019-10-29 | Biolitec Unternehmensbeteiligungs Ii Ag | Specifically meso-substituted porphyrins and chlorins for photodynamic therapy |
| CN104587466B (zh) * | 2014-12-15 | 2017-11-21 | 苏州大学 | 蛋白‑聚吡咯复合物及蛋白‑聚吡咯复合物衍生物的制备方法与应用 |
| EP3210626B1 (en) | 2016-02-26 | 2024-11-27 | biolitec Holding GmbH & Co KG | Conjugates of porphyrinoid photosensitizers and glycerol-based polymers for photodynamic therapy |
| DE102016125666A1 (de) * | 2016-12-23 | 2018-06-28 | Michael Denck | HSA-Galenik |
| EP3694322B1 (en) | 2017-10-09 | 2024-07-03 | Terumo BCT Biotechnologies, LLC | Lyophilization container and method of using same |
| WO2020120474A1 (en) | 2018-12-10 | 2020-06-18 | Universität Hamburg | Specifically glyco-substituted porphyrins and chlorins for photodynamic therapy |
| JP7471316B2 (ja) | 2019-03-14 | 2024-04-19 | テルモ ビーシーティー バイオテクノロジーズ，エルエルシー | マルチパート凍結乾燥容器 |
| CN110251672B (zh) * | 2019-06-18 | 2022-04-01 | 深圳大学 | 一种纳米诊疗剂及其制备方法与应用 |
| CN111110861B (zh) * | 2020-02-23 | 2023-08-25 | 上海交通大学医学院附属瑞金医院 | 一种基于人血清白蛋白的载药颗粒及其制备方法 |
| CN112972676B (zh) * | 2020-08-17 | 2024-09-24 | 滨州医学院 | HSA-Biotin-DDA-TCPP分子的合成及其作为光动力治疗剂及纳米药的应用 |
| CN113855645B (zh) * | 2021-09-13 | 2024-02-02 | 苏州大学 | 一种基于功能化蛋白质纳米粒的核壳型组装体及其制备方法与应用 |
| WO2023039691A1 (zh) * | 2021-09-17 | 2023-03-23 | 苏州大学 | 一种基于功能化蛋白质纳米粒的核壳型组装体及其制备方法与应用 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8805849D0 (en) | 1988-03-11 | 1988-04-13 | Efamol Holdings | Porphyrins & cancer treatment |
| US5916596A (en) | 1993-02-22 | 1999-06-29 | Vivorx Pharmaceuticals, Inc. | Protein stabilized pharmacologically active agents, methods for the preparation thereof and methods for the use thereof |
| GB9420355D0 (en) * | 1994-10-10 | 1994-11-23 | Univ Nottingham | Preparation of protein microspheres, films and coatings |
| US5648485A (en) | 1994-10-26 | 1997-07-15 | University Of British Columbia | β, β-dihydroxy meso-substituted chlorins, isobacteriochlorins, and bacteriochlorins |
| US6649192B2 (en) * | 1996-07-29 | 2003-11-18 | Universidade De Santiago De Compostela | Application of nanoparticles based on hydrophilic polymers as pharmaceutical forms |
| AU4278400A (en) | 1999-04-14 | 2000-11-14 | University Of British Columbia, The | Improved beta,beta,-dihydroxy meso-substituted chlorins, isobacteriochlorins, and bacteriochlorins |
| AU7599900A (en) | 1999-09-23 | 2001-04-24 | Dabur Research Foundation | Formulations of paclitaxel entrapped into nanoparticles of polymeric micelles |
| US20030103995A1 (en) * | 2001-06-04 | 2003-06-05 | Hamblin Michael R. | Detection and therapy of vulnerable plaque with photodynamic compounds |
| US7455858B2 (en) | 2002-05-16 | 2008-11-25 | Qlt Inc. | Compositions and methods for delivery of photosensitive drugs |
| US8709449B2 (en) * | 2004-02-12 | 2014-04-29 | Biolitec Pharma Marketing Ltd | Methods and compositions for improving photodynamic therapy through administration of lipids |
| DE102004011776A1 (de) * | 2004-03-09 | 2005-11-03 | Lts Lohmann Therapie-Systeme Ag | Trägersystem in Form von Nanopartikeln auf Proteinbasis zur zellspezifischen Anreicherung von pharmazeutisch aktiven Wirkstoffen |
| JP2006056807A (ja) * | 2004-08-18 | 2006-03-02 | Konica Minolta Medical & Graphic Inc | 光線力学療法製剤 |
| US20070218049A1 (en) * | 2006-02-02 | 2007-09-20 | Wei Chen | Nanoparticle based photodynamic therapy and methods of making and using same |
| WO2006133271A2 (en) * | 2005-06-06 | 2006-12-14 | The General Hospital Corporation | Compositions and methods relating to target-specific photodynamic therapy |
| CN101485629B (zh) * | 2008-01-16 | 2013-01-23 | 沈阳药科大学 | 一种给药系统及其制备方法 |
| KR20150136137A (ko) * | 2008-04-10 | 2015-12-04 | 아브락시스 바이오사이언스, 엘엘씨 | 소수성 탁산 유도체의 조성물 및 그의 용도 |
| US8815931B2 (en) * | 2009-04-28 | 2014-08-26 | Biolitec Pharma Marketing Ltd | Oral formulations for tetrapyrrole derivatives |
| CN102414556B (zh) * | 2009-04-30 | 2015-09-02 | 赛默科技便携式分析仪器有限公司 | 利用具有不同检验体积的xrf分析对关注元素定位 |
| US20110275686A1 (en) * | 2009-12-11 | 2011-11-10 | Biolitec, Inc. | Nanoparticle carrier systems based on poly(dl-lactic-co-glycolic acid) (plga) for photodynamic therapy (pdt) |
-
2010
- 2010-11-08 US US12/941,350 patent/US9211283B2/en active Active
- 2010-12-08 CN CN2010800629189A patent/CN102740875A/zh active Pending
- 2010-12-08 JP JP2012543221A patent/JP5972171B2/ja not_active Expired - Fee Related
- 2010-12-08 CA CA2784001A patent/CA2784001C/en not_active Expired - Fee Related
- 2010-12-08 EP EP10836582.6A patent/EP2509620A4/en active Pending
- 2010-12-08 BR BR112012013952A patent/BR112012013952A2/pt not_active IP Right Cessation
- 2010-12-08 WO PCT/US2010/059364 patent/WO2011071968A2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| CN102740875A (zh) | 2012-10-17 |
| CA2784001C (en) | 2018-04-10 |
| EP2509620A4 (en) | 2015-10-21 |
| EP2509620A2 (en) | 2012-10-17 |
| JP2013513609A (ja) | 2013-04-22 |
| WO2011071968A2 (en) | 2011-06-16 |
| CA2784001A1 (en) | 2011-06-16 |
| US20110142948A1 (en) | 2011-06-16 |
| WO2011071968A3 (en) | 2011-11-17 |
| BR112012013952A2 (pt) | 2018-06-05 |
| US9211283B2 (en) | 2015-12-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5972171B2 (ja) | 光力学的療法のためのヒト血清アルブミンをベースにしたナノ粒子キャリアシステム | |
| JP5868869B2 (ja) | 光力学的療法のための乳酸・グリコール酸共重合体をベースにしたナノ粒子キャリアシステム | |
| Sztandera et al. | Nanocarriers in photodynamic therapy—in vitro and in vivo studies | |
| Li et al. | Cancer cell membrane camouflaged cascade bioreactor for cancer targeted starvation and photodynamic therapy | |
| Konan et al. | Enhanced photodynamic activity of meso-tetra (4-hydroxyphenyl) porphyrin by incorporation into sub-200 nm nanoparticles | |
| US8916205B2 (en) | Polymeric nanoparticles for photosensitizers | |
| KR102081666B1 (ko) | 암 치료용 약학 조성물 | |
| CN112076319B (zh) | 青蒿素及其衍生物在制备热动力治疗敏化剂中的应用 | |
| KR20080095182A (ko) | 고분자 유도체-광감작제 복합체를 이용한 새로운 광역학치료제 | |
| KR101188979B1 (ko) | 광역학 진단 또는 치료를 위한 생체 적합성 고분자와 광감작제의 결합체 및 이의 제조방법 | |
| CN112546025A (zh) | 一种Ce6@CMCS-DSP-IPI549抗肿瘤纳米传递系统的制备方法 | |
| CN109806394B (zh) | 一种介孔二氧化硅药物递送系统及其应用 | |
| KR101608122B1 (ko) | 효소 민감성 폴리아미노산과 접합된 광응답제 또는 소광제 및 광역학 치료를 위한 소수성 약물 봉입 나노입자 | |
| Wang et al. | Progress of porphyrin-based nanoassemblies for cancer theranostics | |
| da Silva et al. | In vitro photodynamic activity of chloro (5, 10, 15, 20-tetraphenylporphyrinato) indium (III) loaded-poly (lactide-co-glycolide) nanoparticles in LNCaP prostate tumour cells | |
| Huang et al. | Nanogenerator with L-Arginine loading: new choices as cascaded and synergistic nitric oxide/photodynamic antitumor agents | |
| Fong et al. | Photodynamic therapy | |
| Shabbirahmed et al. | Recent advancements in nanomaterials for photodynamic therapy of cancers | |
| CN113827553B (zh) | 用于肿瘤光动力学治疗的瘤内注射给药的酞菁锌在位凝胶及其制备方法 | |
| CN101249075B (zh) | 基于竹红菌素纳米晶体的水溶性竹红菌素二氧化硅纳米粒的制备方法 | |
| JP2006137682A (ja) | 新規光感受性薬剤及びその製造方法 | |
| CN120693180A (zh) | 水溶性叶绿素蛋白作为有效的光敏剂用于癌症光动力治疗 | |
| WO2004110438A1 (en) | Agent for photodynamic diagnosis and therapy of oncological diseases | |
| Morozova et al. | Selenium-containing Nanosystems based on the Amphiphilic Molecular Brushes and Fotoditazin for Photodynamic Therapy | |
| Leung | In Vitro and in Vivo Photodynamic Activities for BAM-SiPc, an Unsymmetrical Bisamino Silicon (IV) Phthalocyanine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20131206 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140626 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20141202 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20150227 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20150401 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20150501 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20150528 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20151110 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20160209 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20160310 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20160408 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20160509 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20160705 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20160712 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5972171 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313111 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| LAPS | Cancellation because of no payment of annual fees |