ES2682762T3 - Conjugado de un fotosensibilizador y quitosano y usos del mismo - Google Patents
Conjugado de un fotosensibilizador y quitosano y usos del mismo Download PDFInfo
- Publication number
- ES2682762T3 ES2682762T3 ES13725109.6T ES13725109T ES2682762T3 ES 2682762 T3 ES2682762 T3 ES 2682762T3 ES 13725109 T ES13725109 T ES 13725109T ES 2682762 T3 ES2682762 T3 ES 2682762T3
- Authority
- ES
- Spain
- Prior art keywords
- compound
- group
- cell
- molecule
- cells
- 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.)
- Active
Links
- 239000003504 photosensitizing agent Substances 0.000 title claims abstract description 29
- 229920001661 Chitosan Polymers 0.000 title claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 210000004027 cell Anatomy 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- 239000003642 reactive oxygen metabolite Substances 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 6
- 210000000172 cytosol Anatomy 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 231100000433 cytotoxic Toxicity 0.000 claims description 4
- 230000001472 cytotoxic effect Effects 0.000 claims description 4
- 238000000338 in vitro Methods 0.000 claims description 4
- 239000002539 nanocarrier Substances 0.000 claims description 4
- 108090000623 proteins and genes Proteins 0.000 claims description 4
- 108010006654 Bleomycin Proteins 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 229960001561 bleomycin Drugs 0.000 claims description 2
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 claims description 2
- 238000002255 vaccination Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 230000000890 antigenic effect Effects 0.000 claims 6
- 230000028993 immune response Effects 0.000 claims 6
- 230000001678 irradiating effect Effects 0.000 claims 6
- 238000002560 therapeutic procedure Methods 0.000 claims 6
- 239000008186 active pharmaceutical agent Substances 0.000 claims 5
- 230000002265 prevention Effects 0.000 claims 5
- 239000000427 antigen Substances 0.000 claims 3
- 108091007433 antigens Proteins 0.000 claims 3
- 102000036639 antigens Human genes 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 230000002068 genetic effect Effects 0.000 claims 3
- 208000015181 infectious disease Diseases 0.000 claims 3
- 238000011275 oncology therapy Methods 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 230000004083 survival effect Effects 0.000 claims 3
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 claims 3
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 claims 2
- 108010002350 Interleukin-2 Proteins 0.000 claims 2
- 230000002159 abnormal effect Effects 0.000 claims 2
- 229940125807 compound 37 Drugs 0.000 claims 2
- 229940127573 compound 38 Drugs 0.000 claims 2
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 claims 2
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 claims 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 claims 1
- ZJMSXVSGTCVBQK-UHFFFAOYSA-N I.I.I.I.I.I.I Chemical compound I.I.I.I.I.I.I ZJMSXVSGTCVBQK-UHFFFAOYSA-N 0.000 claims 1
- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 claims 1
- OLZICYAYCSRSEL-UHFFFAOYSA-N [Si](=O)=O.[Si]=O Chemical compound [Si](=O)=O.[Si]=O OLZICYAYCSRSEL-UHFFFAOYSA-N 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 230000010261 cell growth Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000011550 stock solution Substances 0.000 claims 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims 1
- 238000002834 transmittance Methods 0.000 claims 1
- 238000002428 photodynamic therapy Methods 0.000 description 10
- 229920002101 Chitin Polymers 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 150000004032 porphyrins Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 235000017168 chlorine Nutrition 0.000 description 4
- 239000002105 nanoparticle Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 125000001309 chloro group Chemical class Cl* 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 150000004676 glycans Chemical class 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002086 nanomaterial Substances 0.000 description 3
- 229920001282 polysaccharide Polymers 0.000 description 3
- 239000005017 polysaccharide Substances 0.000 description 3
- 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 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 230000030833 cell death Effects 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000002502 liposome Substances 0.000 description 2
- 208000017983 photosensitivity disease Diseases 0.000 description 2
- 231100000434 photosensitization Toxicity 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 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 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- WUIABRMSWOKTOF-OYALTWQYSA-O 3-[[2-[2-[2-[[(2s,3r)-2-[[(2s,3s,4r)-4-[[(2s,3r)-2-[[6-amino-2-[(1s)-3-amino-1-[[(2s)-2,3-diamino-3-oxopropyl]amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[(2r,3s,4s,5s,6s)-3-[(2r,3s,4s,5r,6r)-4-carbamoyloxy-3,5-dihydroxy-6-(hydroxymethyl)ox Chemical compound OS(O)(=O)=O.N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C WUIABRMSWOKTOF-OYALTWQYSA-O 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- ZJVHUBRPWHTDAZ-UHFFFAOYSA-N C1=CC=CC=C1Cl(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound C1=CC=CC=C1Cl(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ZJVHUBRPWHTDAZ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 102000014914 Carrier Proteins Human genes 0.000 description 1
- 108010078791 Carrier Proteins Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- NHYCGSASNAIGLD-UHFFFAOYSA-N Chlorine monoxide Chemical class Cl[O] NHYCGSASNAIGLD-UHFFFAOYSA-N 0.000 description 1
- 241000238424 Crustacea Species 0.000 description 1
- 241000238557 Decapoda Species 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 239000004098 Tetracycline Substances 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-QZABAPFNSA-N beta-D-glucosamine Chemical group N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-QZABAPFNSA-N 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 231100000050 cytotoxic potential Toxicity 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- -1 dendnomers Substances 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 229960004679 doxorubicin Drugs 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000012202 endocytosis Effects 0.000 description 1
- 210000001163 endosome Anatomy 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 150000003278 haem Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000005847 immunogenicity Effects 0.000 description 1
- 229940051026 immunotoxin Drugs 0.000 description 1
- 230000002637 immunotoxin Effects 0.000 description 1
- 239000002596 immunotoxin Substances 0.000 description 1
- 231100000608 immunotoxin Toxicity 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000002132 lysosomal effect Effects 0.000 description 1
- 210000003712 lysosome Anatomy 0.000 description 1
- 230000001868 lysosomic effect Effects 0.000 description 1
- 230000002080 lysosomotropic effect Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 229950006780 n-acetylglucosamine Drugs 0.000 description 1
- 239000007908 nanoemulsion Substances 0.000 description 1
- 229940031182 nanoparticles iron oxide Drugs 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000000886 photobiology Effects 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 210000003705 ribosome Anatomy 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 238000002626 targeted therapy Methods 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000513 vascular toxicity Toxicity 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
- A61K31/722—Chitin, chitosan
-
- 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
-
- 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
-
- 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
- A61K41/0076—PDT with expanded (metallo)porphyrins, i.e. having more than 20 ring atoms, e.g. texaphyrins, sapphyrins, hexaphyrins, pentaphyrins, porphocyanines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/61—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule the organic macromolecular compound being a polysaccharide or a derivative thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Immunology (AREA)
- Materials Engineering (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1208548.6A GB201208548D0 (en) | 2012-05-15 | 2012-05-15 | Compound and method |
| GB201208548 | 2012-05-15 | ||
| PCT/EP2013/059968 WO2013189663A1 (en) | 2012-05-15 | 2013-05-14 | Conjugate of a photosensitiser and chitosan and uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2682762T3 true ES2682762T3 (es) | 2018-09-21 |
Family
ID=46458880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13725109.6T Active ES2682762T3 (es) | 2012-05-15 | 2013-05-14 | Conjugado de un fotosensibilizador y quitosano y usos del mismo |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US9901636B2 (enExample) |
| EP (1) | EP2849791B1 (enExample) |
| JP (1) | JP6456284B2 (enExample) |
| KR (2) | KR102269861B1 (enExample) |
| CN (1) | CN104780941B (enExample) |
| AU (1) | AU2013279748B2 (enExample) |
| BR (1) | BR112014028315B1 (enExample) |
| CA (1) | CA2873259C (enExample) |
| DK (1) | DK2849791T3 (enExample) |
| ES (1) | ES2682762T3 (enExample) |
| GB (1) | GB201208548D0 (enExample) |
| HR (1) | HRP20181276T1 (enExample) |
| HU (1) | HUE039725T2 (enExample) |
| IN (1) | IN2014DN09418A (enExample) |
| MX (1) | MX362237B (enExample) |
| NZ (1) | NZ630582A (enExample) |
| PL (1) | PL2849791T3 (enExample) |
| PT (1) | PT2849791T (enExample) |
| RU (1) | RU2675830C2 (enExample) |
| SG (1) | SG11201407603YA (enExample) |
| SI (1) | SI2849791T1 (enExample) |
| WO (1) | WO2013189663A1 (enExample) |
| ZA (1) | ZA201408406B (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9905911D0 (en) | 1999-03-15 | 1999-05-05 | Photocure As | Method |
| EP3129045B1 (en) | 2014-04-11 | 2022-03-02 | PCI Biotech AS | Method of treating melanoma |
| NZ729408A (en) * | 2014-08-28 | 2021-12-24 | Pci Biotech As | A method of photochemical internalization (pci) utilizing a antigenic molecule, a photosensitizing agent, and a cytokine |
| CN104650259A (zh) * | 2015-01-23 | 2015-05-27 | 广西大学 | 一种纳米孔壳聚糖四(4-磺酸基苯基)金属卟啉微球及其制备方法和使用方法 |
| GB201503776D0 (en) | 2015-03-05 | 2015-04-22 | Pci Biotech As | Compound and method |
| GB201511159D0 (en) | 2015-06-24 | 2015-08-05 | Univ Nottingham | Controlled cell delivery vehicle and treatment of tumours |
| JP6776364B2 (ja) * | 2016-03-22 | 2020-10-28 | オーボ アカデミー ユニヴァーシティー | 蛍光増白剤としての多糖誘導体 |
| KR20190013289A (ko) * | 2017-08-01 | 2019-02-11 | 순천대학교 산학협력단 | 수용성 키토산을 포함하는 나노광증감제 |
| GB201801169D0 (en) * | 2018-01-24 | 2018-03-07 | Pci Biotech As | Method |
| CN108892743A (zh) * | 2018-05-28 | 2018-11-27 | 南京工业大学 | 用于光动力抗菌的纳米光敏剂，其制备方法及应用 |
| GB202101726D0 (en) | 2021-02-08 | 2021-03-24 | Pci Biotech As | Method |
| CN115399328B (zh) * | 2021-05-27 | 2024-03-22 | 中国科学院化学研究所 | 一种多糖基杀菌材料及其制备方法和应用 |
| GB202115451D0 (en) | 2021-10-27 | 2021-12-08 | Pci Biotech As | Method |
| CN117285662A (zh) * | 2022-06-15 | 2023-12-26 | 南京仁为医药科技有限公司 | 一种壳聚糖双吡啶季铵盐及其制备方法 |
| GB202301312D0 (en) | 2023-01-30 | 2023-03-15 | Pci Biotech As | Method and product |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO180167C (no) | 1994-09-08 | 1997-02-26 | Photocure As | Fotokjemisk fremgangsmåte til å innföre molekyler i cellers cytosol |
| GB9905911D0 (en) * | 1999-03-15 | 1999-05-05 | Photocure As | Method |
| US20020022032A1 (en) | 1999-04-23 | 2002-02-21 | Curry Patrick Mark | Immuno-adjuvant PDT treatment of metastatic tumors |
| GB0018527D0 (en) * | 2000-07-27 | 2000-09-13 | Photocure Asa | Composition |
| 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 |
| GB0121023D0 (en) | 2001-08-30 | 2001-10-24 | Norwegian Radium Hospital Res | Compound |
| GB0415663D0 (en) | 2004-07-13 | 2004-08-18 | Psimei Pharmaceuticals Plc | Compound |
| WO2007023398A2 (en) | 2005-05-16 | 2007-03-01 | Universite De Geneve | Compounds for photochemotherapy |
| JP4287411B2 (ja) * | 2005-07-01 | 2009-07-01 | 株式会社東芝 | 仮想メモリシステムおよび仮想記憶方法 |
| CN101024087A (zh) * | 2007-03-28 | 2007-08-29 | 长沙理工大学 | 壳聚糖－多肽－卟啉纳米药物载体及其制备和应用 |
| KR101035269B1 (ko) * | 2007-04-23 | 2011-05-26 | 한국과학기술연구원 | 고분자 유도체-광감작제 복합체를 이용한 새로운 광역학치료제 |
| KR20090047872A (ko) | 2007-11-08 | 2009-05-13 | 인제대학교 산학협력단 | 신규 카보하이드레이트 복합 클로린 화합물 및 이의제조방법 |
| WO2009077908A1 (en) | 2007-12-14 | 2009-06-25 | University Of Lausanne | Colloidal particle comprising multivalent cyclic anions |
| KR101076717B1 (ko) | 2008-11-07 | 2011-10-26 | 재단법인대구경북과학기술원 | 광역학 치료용 나노구조체 및 그 제조방법 |
| US20100129432A1 (en) | 2008-11-25 | 2010-05-27 | Taipei Medical University | Microorganism-killing combination |
| US20120035180A1 (en) | 2009-04-29 | 2012-02-09 | Diatech Korea Co., Ltd. | Pharmaceutical composition for treating cancer comprising chlorin e6-folic acid conjugate compound and chitosan |
| KR100918811B1 (ko) | 2009-04-29 | 2009-09-25 | 다이아텍코리아 주식회사 | 클로린 ｅ６-엽산 결합 화합물 및 키토산을 함유하는 암 치료용 약학적 조성물 |
| US20120184495A1 (en) * | 2009-06-12 | 2012-07-19 | Amrita Vishwa Vidyapeetham University Kerala | Targeted nano-photomedicines for photodynamic therapy of cancer |
| GB0914287D0 (en) | 2009-08-14 | 2009-09-30 | Pci Biotech As | Compositions |
| KR101228106B1 (ko) | 2010-01-21 | 2013-02-01 | 광주과학기술원 | 피부투과도, 세포유입 및 종양전달성이 증가된 나노운반체 |
| KR101250150B1 (ko) * | 2010-10-29 | 2013-04-04 | 가톨릭대학교 산학협력단 | 광역학치료를 위한 고분자-광응답제 접합체 및 이의 제조방법 |
-
2012
- 2012-05-15 GB GBGB1208548.6A patent/GB201208548D0/en not_active Ceased
-
2013
- 2013-05-14 CA CA2873259A patent/CA2873259C/en active Active
- 2013-05-14 EP EP13725109.6A patent/EP2849791B1/en active Active
- 2013-05-14 AU AU2013279748A patent/AU2013279748B2/en not_active Ceased
- 2013-05-14 PT PT13725109T patent/PT2849791T/pt unknown
- 2013-05-14 BR BR112014028315-0A patent/BR112014028315B1/pt not_active IP Right Cessation
- 2013-05-14 KR KR1020207019532A patent/KR102269861B1/ko active Active
- 2013-05-14 ES ES13725109.6T patent/ES2682762T3/es active Active
- 2013-05-14 WO PCT/EP2013/059968 patent/WO2013189663A1/en not_active Ceased
- 2013-05-14 CN CN201380037602.8A patent/CN104780941B/zh active Active
- 2013-05-14 NZ NZ630582A patent/NZ630582A/en not_active IP Right Cessation
- 2013-05-14 SG SG11201407603YA patent/SG11201407603YA/en unknown
- 2013-05-14 MX MX2014013516A patent/MX362237B/es active IP Right Grant
- 2013-05-14 HR HRP20181276TT patent/HRP20181276T1/hr unknown
- 2013-05-14 IN IN9418DEN2014 patent/IN2014DN09418A/en unknown
- 2013-05-14 JP JP2015512042A patent/JP6456284B2/ja not_active Expired - Fee Related
- 2013-05-14 RU RU2014150569A patent/RU2675830C2/ru active
- 2013-05-14 PL PL13725109T patent/PL2849791T3/pl unknown
- 2013-05-14 HU HUE13725109A patent/HUE039725T2/hu unknown
- 2013-05-14 US US14/401,215 patent/US9901636B2/en active Active
- 2013-05-14 SI SI201331125T patent/SI2849791T1/sl unknown
- 2013-05-14 KR KR1020147035218A patent/KR20150013803A/ko not_active Ceased
- 2013-05-14 DK DK13725109.6T patent/DK2849791T3/en active
-
2014
- 2014-11-17 ZA ZA2014/08406A patent/ZA201408406B/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2682762T3 (es) | Conjugado de un fotosensibilizador y quitosano y usos del mismo | |
| García‐Fernández et al. | New advances in in vivo applications of gated mesoporous silica as drug delivery nanocarriers | |
| Zhang et al. | Transferrin-mediated fullerenes nanoparticles as Fe2+-dependent drug vehicles for synergistic anti-tumor efficacy | |
| Xu et al. | Near-infrared light-triggered degradable hyaluronic acid hydrogel for on-demand drug release and combined chemo-photodynamic therapy | |
| Liu et al. | Photocleavage‐based photoresponsive drug delivery | |
| Sztandera et al. | Nanocarriers in photodynamic therapy—in vitro and in vivo studies | |
| Li et al. | Co‐delivery of drugs and genes using polymeric nanoparticles for synergistic cancer therapeutic effects | |
| Basu et al. | Polysaccharide-based conjugates for biomedical applications | |
| Deng et al. | Reduction-sensitive polymeric nanocarriers in cancer therapy: a comprehensive review | |
| Debele et al. | Drug carrier for photodynamic cancer therapy | |
| Bouramtane et al. | Porphyrin-xylan-coated silica nanoparticles for anticancer photodynamic therapy | |
| Deda et al. | Nanotechnology, Light and chemical action: an effective combination to kill cancer cells | |
| Della Sala et al. | Advances in hyaluronic‐acid‐based (nano) devices for cancer therapy | |
| Li et al. | Acetylated hyaluronic acid/photosensitizer conjugate for the preparation of nanogels with controllable phototoxicity: synthesis, characterization, autophotoquenching properties, and in vitro phototoxicity against HeLa cells | |
| CN105749280A (zh) | 一种协同化疗与光动力治疗的肿瘤靶向纳米给药系统的制备及应用 | |
| KR101444274B1 (ko) | 약제복합체용 블록 공중합체 및 의약조성물 | |
| Fan et al. | Recent progress of crosslinking strategies for polymeric micelles with enhanced drug delivery in cancer therapy | |
| Xia et al. | Enhanced fluorescence emission and singlet oxygen generation of photosensitizers embedded in injectable hydrogels for imaging-guided photodynamic cancer therapy | |
| Casas et al. | Sustained and efficient porphyrin generation in vivo using dendrimer conjugates of 5-ALA for photodynamic therapy | |
| Dag et al. | Phthalocyanine-conjugated glyconanoparticles for chemo-photodynamic combination therapy | |
| Sun et al. | Role of cholesterol conjugation in the antibacterial photodynamic therapy of branched polyethylenimine-containing nanoagents | |
| Fang et al. | Light-controllable charge-reversal nanoparticles with polyinosinic-polycytidylic acid for enhancing immunotherapy of triple negative breast cancer | |
| CN113663079B (zh) | 一种无载体自组装纳米粒子及其制备方法和应用 | |
| Orlova et al. | Perspectives of fullerene derivatives in PDT and radiotherapy of cancers | |
| Kano et al. | Tumor delivery of Photofrin® by PLL-g-PEG for photodynamic therapy |