CN104758255A - 一种姜黄素胶束载药系统及其制备方法 - Google Patents
一种姜黄素胶束载药系统及其制备方法 Download PDFInfo
- Publication number
- CN104758255A CN104758255A CN201410008487.8A CN201410008487A CN104758255A CN 104758255 A CN104758255 A CN 104758255A CN 201410008487 A CN201410008487 A CN 201410008487A CN 104758255 A CN104758255 A CN 104758255A
- Authority
- CN
- China
- Prior art keywords
- curcumin
- preparation
- carrying system
- micelle
- chain segment
- 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.)
- Pending
Links
- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 title claims abstract description 184
- 235000012754 curcumin Nutrition 0.000 title claims abstract description 93
- 229940109262 curcumin Drugs 0.000 title claims abstract description 92
- 239000004148 curcumin Substances 0.000 title claims abstract description 92
- VFLDPWHFBUODDF-UHFFFAOYSA-N diferuloylmethane Natural products C1=C(O)C(OC)=CC(C=CC(=O)CC(=O)C=CC=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-UHFFFAOYSA-N 0.000 title claims abstract description 92
- 239000003814 drug Substances 0.000 title claims abstract description 59
- 238000002360 preparation method Methods 0.000 title claims description 35
- 229940079593 drug Drugs 0.000 title abstract description 30
- 239000000693 micelle Substances 0.000 claims abstract description 77
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 19
- 125000001165 hydrophobic group Chemical group 0.000 claims abstract description 16
- 229920001400 block copolymer Polymers 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 229920001610 polycaprolactone Polymers 0.000 claims abstract description 3
- 239000004632 polycaprolactone Substances 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
- 229920000642 polymer Polymers 0.000 claims description 29
- 206010028980 Neoplasm Diseases 0.000 claims description 26
- 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 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- -1 tertbutyloxycarbonyl phenylalanine Chemical compound 0.000 claims description 10
- 239000002246 antineoplastic agent Substances 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- 238000004108 freeze drying Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims description 5
- 229920000151 polyglycol Polymers 0.000 claims description 5
- 239000010695 polyglycol Substances 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 230000004224 protection Effects 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 229940127089 cytotoxic agent Drugs 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 238000001291 vacuum drying Methods 0.000 claims description 4
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- 238000004062 sedimentation Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 2
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 claims description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 claims description 2
- HAWSQZCWOQZXHI-FQEVSTJZSA-N 10-Hydroxycamptothecin Chemical compound C1=C(O)C=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 HAWSQZCWOQZXHI-FQEVSTJZSA-N 0.000 claims description 2
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin 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-VTZDEGQISA-N 0.000 claims description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 2
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims 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 claims description 2
- HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 claims description 2
- 229930091371 Fructose Natural products 0.000 claims description 2
- 239000005715 Fructose Substances 0.000 claims description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 2
- 108010010803 Gelatin Proteins 0.000 claims 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 claims description 2
- XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 claims description 2
- XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 claims description 2
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 2
- 229930195725 Mannitol Natural products 0.000 claims description 2
- 229930192392 Mitomycin Natural products 0.000 claims description 2
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 claims description 2
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 2
- 229930012538 Paclitaxel Natural products 0.000 claims description 2
- KMSKQZKKOZQFFG-HSUXVGOQSA-N Pirarubicin Chemical compound O([C@H]1[C@@H](N)C[C@@H](O[C@H]1C)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]1CCCCO1 KMSKQZKKOZQFFG-HSUXVGOQSA-N 0.000 claims description 2
- 229930006000 Sucrose Natural products 0.000 claims 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 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 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 claims description 2
- 235000001014 amino acid Nutrition 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 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 claims description 2
- BMQGVNUXMIRLCK-OAGWZNDDSA-N cabazitaxel Chemical compound O([C@H]1[C@@H]2[C@]3(OC(C)=O)CO[C@@H]3C[C@@H]([C@]2(C(=O)[C@H](OC)C2=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=3C=CC=CC=3)C[C@]1(O)C2(C)C)C)OC)C(=O)C1=CC=CC=C1 BMQGVNUXMIRLCK-OAGWZNDDSA-N 0.000 claims description 2
- 229960001573 cabazitaxel Drugs 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 2
- 229960004316 cisplatin Drugs 0.000 claims description 2
- 229960003901 dacarbazine Drugs 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 239000012153 distilled water Substances 0.000 claims description 2
- 229960003668 docetaxel Drugs 0.000 claims description 2
- 229960004679 doxorubicin Drugs 0.000 claims description 2
- 229960001904 epirubicin Drugs 0.000 claims description 2
- 229930013356 epothilone Natural products 0.000 claims description 2
- HESCAJZNRMSMJG-KKQRBIROSA-N epothilone A Chemical class C/C([C@@H]1C[C@@H]2O[C@@H]2CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(C)=N1 HESCAJZNRMSMJG-KKQRBIROSA-N 0.000 claims description 2
- 239000008273 gelatin Substances 0.000 claims description 2
- 229920000159 gelatin Polymers 0.000 claims description 2
- 235000019322 gelatine Nutrition 0.000 claims description 2
- 235000011852 gelatine desserts Nutrition 0.000 claims description 2
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims description 2
- 229960005277 gemcitabine Drugs 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- 235000001727 glucose Nutrition 0.000 claims description 2
- 229960000908 idarubicin Drugs 0.000 claims description 2
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims description 2
- 229960001101 ifosfamide Drugs 0.000 claims description 2
- 229960004768 irinotecan Drugs 0.000 claims description 2
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims description 2
- 239000008101 lactose Substances 0.000 claims description 2
- 239000000594 mannitol Substances 0.000 claims description 2
- 235000010355 mannitol Nutrition 0.000 claims description 2
- 229960000485 methotrexate Drugs 0.000 claims description 2
- 229960004857 mitomycin Drugs 0.000 claims description 2
- 229960001156 mitoxantrone Drugs 0.000 claims description 2
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 claims description 2
- 125000005474 octanoate group Chemical group 0.000 claims description 2
- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 claims description 2
- 229960001756 oxaliplatin Drugs 0.000 claims description 2
- 229960001592 paclitaxel Drugs 0.000 claims description 2
- 229960001221 pirarubicin Drugs 0.000 claims description 2
- 235000010413 sodium alginate Nutrition 0.000 claims description 2
- 239000000661 sodium alginate Substances 0.000 claims description 2
- 229940005550 sodium alginate Drugs 0.000 claims description 2
- 239000005720 sucrose Substances 0.000 claims description 2
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 2
- WFWLQNSHRPWKFK-ZCFIWIBFSA-N tegafur Chemical compound O=C1NC(=O)C(F)=CN1[C@@H]1OCCC1 WFWLQNSHRPWKFK-ZCFIWIBFSA-N 0.000 claims description 2
- 229960001674 tegafur Drugs 0.000 claims description 2
- 229960000303 topotecan Drugs 0.000 claims description 2
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 claims description 2
- GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 claims description 2
- 229960002066 vinorelbine Drugs 0.000 claims description 2
- FJHBVJOVLFPMQE-QFIPXVFZSA-N 7-Ethyl-10-Hydroxy-Camptothecin Chemical compound C1=C(O)C=C2C(CC)=C(CN3C(C4=C([C@@](C(=O)OC4)(O)CC)C=C33)=O)C3=NC2=C1 FJHBVJOVLFPMQE-QFIPXVFZSA-N 0.000 claims 1
- 229920000469 amphiphilic block copolymer Polymers 0.000 abstract 2
- 150000002334 glycols Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 238000002347 injection Methods 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- 210000002381 plasma Anatomy 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 241000700159 Rattus Species 0.000 description 8
- 239000002671 adjuvant Substances 0.000 description 8
- 210000004369 blood Anatomy 0.000 description 8
- 239000008280 blood Substances 0.000 description 8
- 238000002390 rotary evaporation Methods 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 7
- 238000001727 in vivo Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- DYUQAZSOFZSPHD-UHFFFAOYSA-N Phenylpropyl alcohol Natural products CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229940009456 adriamycin Drugs 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 201000011510 cancer Diseases 0.000 description 5
- NWXMGUDVXFXRIG-WESIUVDSSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O NWXMGUDVXFXRIG-WESIUVDSSA-N 0.000 description 4
- 229930195573 Amycin Natural products 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000011580 nude mouse model Methods 0.000 description 4
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 3
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 229940041181 antineoplastic drug Drugs 0.000 description 3
- 239000012627 chemopreventive agent Substances 0.000 description 3
- 229940124443 chemopreventive agent Drugs 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000008014 freezing Effects 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- 239000003292 glue Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000011725 BALB/c mouse Methods 0.000 description 2
- 241000407170 Curcuma Species 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 208000034578 Multiple myelomas Diseases 0.000 description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 2
- 206010035226 Plasma cell myeloma Diseases 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000000890 drug combination Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 210000000865 mononuclear phagocyte system Anatomy 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000009520 phase I clinical trial Methods 0.000 description 2
- 201000001514 prostate carcinoma Diseases 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 108010052945 thanamycin Proteins 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
- 230000004614 tumor growth Effects 0.000 description 2
- 230000005760 tumorsuppression Effects 0.000 description 2
- 229910021642 ultra pure water Inorganic materials 0.000 description 2
- 239000012498 ultrapure water Substances 0.000 description 2
- 238000002255 vaccination Methods 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- SJVFAHZPLIXNDH-QFIPXVFZSA-N (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 SJVFAHZPLIXNDH-QFIPXVFZSA-N 0.000 description 1
- OFQCQIGMURIECL-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-2',6'-dimethylspiro[isoquinoline-4,4'-oxane]-1,3-dione;phosphoric acid Chemical compound OP(O)(O)=O.O=C1N(CCN(CC)CC)C(=O)C2=CC=CC=C2C21CC(C)OC(C)C2 OFQCQIGMURIECL-UHFFFAOYSA-N 0.000 description 1
- 239000001842 Brominated vegetable oil Substances 0.000 description 1
- 208000002177 Cataract Diseases 0.000 description 1
- 235000014375 Curcuma Nutrition 0.000 description 1
- 244000163122 Curcuma domestica Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- 206010019668 Hepatic fibrosis Diseases 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- 208000029549 Muscle injury Diseases 0.000 description 1
- 208000034530 PLAA-associated neurodevelopmental disease Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000000090 biomarker Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 230000002113 chemopreventative effect Effects 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 235000003373 curcuma longa Nutrition 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010579 first pass effect Methods 0.000 description 1
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 235000021472 generally recognized as safe Nutrition 0.000 description 1
- 229940074076 glycerol formal Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 210000003494 hepatocyte Anatomy 0.000 description 1
- 238000000703 high-speed centrifugation Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 229920001427 mPEG Polymers 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000007709 nanocrystallization Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 230000000590 parasiticidal effect Effects 0.000 description 1
- 239000002297 parasiticide Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 231100000683 possible toxicity Toxicity 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 208000005069 pulmonary fibrosis Diseases 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 238000004885 tandem mass spectrometry Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
Landscapes
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410008487.8A CN104758255A (zh) | 2014-01-08 | 2014-01-08 | 一种姜黄素胶束载药系统及其制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410008487.8A CN104758255A (zh) | 2014-01-08 | 2014-01-08 | 一种姜黄素胶束载药系统及其制备方法 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN104758255A true CN104758255A (zh) | 2015-07-08 |
Family
ID=53640591
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201410008487.8A Pending CN104758255A (zh) | 2014-01-08 | 2014-01-08 | 一种姜黄素胶束载药系统及其制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN104758255A (zh) |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105367804A (zh) * | 2015-10-16 | 2016-03-02 | 姚俊华 | 一种载药的两亲性嵌段聚合物及其制备方法和应用 |
CN105395481A (zh) * | 2015-10-16 | 2016-03-16 | 姚俊华 | 一种含有姜黄素的聚合物胶束载药系统及其制备方法和应用 |
EP3144006A1 (en) * | 2015-09-18 | 2017-03-22 | Signpath Pharma Inc. | Use of a combination of a curcuminoid and a chemotherapeutic agent for use in treatment of glioblastoma |
CN106619507A (zh) * | 2016-11-30 | 2017-05-10 | 陕西师范大学 | 一种包载难溶性抗肿瘤药物姜黄素聚合物胶束及其制备方法和应用 |
CN107913249A (zh) * | 2017-11-23 | 2018-04-17 | 广东医科大学 | 一种组合物及含有该组合物的纳米胶束与应用 |
US10117881B2 (en) | 2011-06-03 | 2018-11-06 | Signpath Pharma, Inc. | Protective effect of DMPC, DMPG, DMPC/DMPG, LYSOPG and LYSOPC against drugs that cause channelopathies |
US10238602B2 (en) | 2011-06-03 | 2019-03-26 | Signpath Pharma, Inc. | Protective effect of DMPC, DMPG, DMPC/DMPG, LysoPG and LysoPC against drugs that cause channelopathies |
US10258691B2 (en) | 2014-06-03 | 2019-04-16 | Signpath Pharma, Inc. | Protective effect of DMPC, DMPG, DMPC/DMPG, EGPG, LysoPG and LysoPC against drugs that cause channelopathies |
US10349884B2 (en) | 2011-06-03 | 2019-07-16 | Sighpath Pharma Inc. | Liposomal mitigation of drug-induced inhibition of the cardiac ikr channel |
US10357458B2 (en) | 2011-06-03 | 2019-07-23 | Signpath Pharma Inc. | Liposomal mitigation of drug-induced long QT syndrome and potassium delayed-rectifier current |
US10449193B2 (en) | 2011-06-03 | 2019-10-22 | Signpath Pharma Inc. | Protective effect of DMPC, DMPG, DMPC/DMPG, lysoPG and lysoPC against drugs that cause channelopathies |
US10532045B2 (en) | 2013-12-18 | 2020-01-14 | Signpath Pharma, Inc. | Liposomal mitigation of drug-induced inhibition of the cardiac IKr channel |
CN111956611A (zh) * | 2020-09-10 | 2020-11-20 | 西南医科大学附属医院 | 一种负载姜黄素的纳米胶束及其制备方法和应用 |
CN114425085A (zh) * | 2022-01-20 | 2022-05-03 | 西安交通大学医学院第一附属医院 | 一种7-乙基-10-羟基喜树碱和姜黄素配位聚合物纳米药物及其制备方法 |
US11806401B2 (en) | 2016-04-27 | 2023-11-07 | Signpath Pharma, Inc. | Prevention of drug-induced atrio-ventricular block |
US12004868B2 (en) | 2011-06-03 | 2024-06-11 | Signpath Pharma Inc. | Liposomal mitigation of drug-induced inhibition of the cardiac IKr channel |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1429120A (zh) * | 2000-05-17 | 2003-07-09 | 株式会社三养社 | 稳定的聚合胶束型药物组合物和制备它的方法 |
CN102641246A (zh) * | 2012-03-19 | 2012-08-22 | 南京维赛医药科技有限公司 | 一种抗肿瘤的双药纳米载药微球及其制备方法 |
-
2014
- 2014-01-08 CN CN201410008487.8A patent/CN104758255A/zh active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1429120A (zh) * | 2000-05-17 | 2003-07-09 | 株式会社三养社 | 稳定的聚合胶束型药物组合物和制备它的方法 |
CN102641246A (zh) * | 2012-03-19 | 2012-08-22 | 南京维赛医药科技有限公司 | 一种抗肿瘤的双药纳米载药微球及其制备方法 |
Non-Patent Citations (1)
Title |
---|
吴丽莎等: ""姜黄素mPEG114 -PCL36纳米胶束的制备及体外释药考察"", 《中国实验方剂学杂志》 * |
Cited By (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10449193B2 (en) | 2011-06-03 | 2019-10-22 | Signpath Pharma Inc. | Protective effect of DMPC, DMPG, DMPC/DMPG, lysoPG and lysoPC against drugs that cause channelopathies |
US10357458B2 (en) | 2011-06-03 | 2019-07-23 | Signpath Pharma Inc. | Liposomal mitigation of drug-induced long QT syndrome and potassium delayed-rectifier current |
US10617639B2 (en) | 2011-06-03 | 2020-04-14 | Signpath Pharma, Inc. | Liposomal mitigation of drug-induced long QT syndrome and potassium delayed-rectifier current |
US10349884B2 (en) | 2011-06-03 | 2019-07-16 | Sighpath Pharma Inc. | Liposomal mitigation of drug-induced inhibition of the cardiac ikr channel |
US12004868B2 (en) | 2011-06-03 | 2024-06-11 | Signpath Pharma Inc. | Liposomal mitigation of drug-induced inhibition of the cardiac IKr channel |
US10117881B2 (en) | 2011-06-03 | 2018-11-06 | Signpath Pharma, Inc. | Protective effect of DMPC, DMPG, DMPC/DMPG, LYSOPG and LYSOPC against drugs that cause channelopathies |
US10238602B2 (en) | 2011-06-03 | 2019-03-26 | Signpath Pharma, Inc. | Protective effect of DMPC, DMPG, DMPC/DMPG, LysoPG and LysoPC against drugs that cause channelopathies |
US10532045B2 (en) | 2013-12-18 | 2020-01-14 | Signpath Pharma, Inc. | Liposomal mitigation of drug-induced inhibition of the cardiac IKr channel |
US10258691B2 (en) | 2014-06-03 | 2019-04-16 | Signpath Pharma, Inc. | Protective effect of DMPC, DMPG, DMPC/DMPG, EGPG, LysoPG and LysoPC against drugs that cause channelopathies |
EP3144006A1 (en) * | 2015-09-18 | 2017-03-22 | Signpath Pharma Inc. | Use of a combination of a curcuminoid and a chemotherapeutic agent for use in treatment of glioblastoma |
US10485768B2 (en) | 2015-09-18 | 2019-11-26 | Signpath Pharma, Inc. | Treatment for glioblastoma |
EP3711770A1 (en) * | 2015-09-18 | 2020-09-23 | Signpath Pharma Inc. | A combination of a curcuminoid, an empty liposome and a chemotherapeutic agent for use in treatment of glioblastoma |
CN105395481A (zh) * | 2015-10-16 | 2016-03-16 | 姚俊华 | 一种含有姜黄素的聚合物胶束载药系统及其制备方法和应用 |
CN105367804A (zh) * | 2015-10-16 | 2016-03-02 | 姚俊华 | 一种载药的两亲性嵌段聚合物及其制备方法和应用 |
US11806401B2 (en) | 2016-04-27 | 2023-11-07 | Signpath Pharma, Inc. | Prevention of drug-induced atrio-ventricular block |
CN106619507A (zh) * | 2016-11-30 | 2017-05-10 | 陕西师范大学 | 一种包载难溶性抗肿瘤药物姜黄素聚合物胶束及其制备方法和应用 |
CN106619507B (zh) * | 2016-11-30 | 2020-08-04 | 陕西师范大学 | 一种包载难溶性抗肿瘤药物姜黄素聚合物胶束及其制备方法和应用 |
CN107913249A (zh) * | 2017-11-23 | 2018-04-17 | 广东医科大学 | 一种组合物及含有该组合物的纳米胶束与应用 |
CN107913249B (zh) * | 2017-11-23 | 2020-03-24 | 广东医科大学 | 一种组合物及含有该组合物的纳米胶束与应用 |
CN111956611A (zh) * | 2020-09-10 | 2020-11-20 | 西南医科大学附属医院 | 一种负载姜黄素的纳米胶束及其制备方法和应用 |
CN114425085A (zh) * | 2022-01-20 | 2022-05-03 | 西安交通大学医学院第一附属医院 | 一种7-乙基-10-羟基喜树碱和姜黄素配位聚合物纳米药物及其制备方法 |
CN114425085B (zh) * | 2022-01-20 | 2024-05-03 | 西安交通大学医学院第一附属医院 | 一种7-乙基-10-羟基喜树碱和姜黄素配位聚合物纳米药物及其制备方法 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104758255A (zh) | 一种姜黄素胶束载药系统及其制备方法 | |
Xiong et al. | A NIR light triggered disintegratable nanoplatform for enhanced penetration and chemotherapy in deep tumor tissues | |
US9393312B2 (en) | Amphiphilic block copolymer and preparation method thereof and micellar drug-loading system formed by same with antitumor drug | |
EP2515946B1 (en) | Nanoconjugates and nanoconjugate formulations | |
CN105816427A (zh) | 一种姜黄素胶束载药系统及其制备方法 | |
CN103006539B (zh) | 一种聚合物胶束药物组合物及其制备方法 | |
CN101422615B (zh) | 一种冬凌草甲素聚合物胶束给药制剂及制备方法 | |
CN104056275A (zh) | 多功能主动靶向透明质酸-聚乳酸载体合成及其抗肿瘤药物胶束制备方法 | |
CN108175860B (zh) | 一种酯酶响应型的多聚姜黄素硫代二丙酸共聚物前药纳米胶束及其制备方法和应用 | |
CN112076159B (zh) | 具有不对称膜结构的载药聚合物囊泡及制备方法与在制备治疗急性髓系白血病药物中的应用 | |
CN104116710A (zh) | 靶向肿瘤的pH敏感聚合物胶束组合物 | |
CN104856950A (zh) | 一种紫杉醇胶束载药系统及其制备方法 | |
CN104116709A (zh) | 靶向肿瘤的抗肿瘤耐药的pH敏感聚合物胶束组合物 | |
CN104856949A (zh) | 一种多西他赛胶束载药系统及其制备方法 | |
Wu et al. | Synergistic action of doxorubicin and 7-Ethyl-10-hydroxycamptothecin polyphosphorylcholine polymer prodrug | |
CN105287377A (zh) | 一种紫杉醇聚合物胶束载药系统及其制备方法和应用 | |
CN104116711A (zh) | 抗肿瘤耐药的pH敏感聚合物胶束组合物 | |
CN105399938B (zh) | 一种两亲性嵌段共聚物及其胶束的制备方法和应用 | |
CN104415029A (zh) | 一种穿心莲内酯聚合物胶束及其制备方法与医药用途 | |
CN103446040A (zh) | 一种包载多西紫杉醇的聚合物胶束及其制备方法 | |
CN104096237A (zh) | 一种Pluronics-紫杉醇两亲性大分子前药及其胶束制剂 | |
CN108451906A (zh) | 一种用于抗肿瘤和抗转移治疗的胆固醇-低分子量肝素的纳米制剂及制备方法 | |
CN105399931B (zh) | 一种两亲性嵌段共聚物及其制备方法和应用 | |
CN103933016A (zh) | 一种辣椒碱三元纳米胶束及其制法和用途 | |
CN105310981A (zh) | 一种多西他赛胶束载药系统及其制备方法和应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C41 | Transfer of patent application or patent right or utility model | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20151218 Address after: Suzhou City, Jiangsu Province, Suzhou Industrial Park 215123 Xinghu Street No. 218 BioBAY building A3 room 318 Applicant after: Suzhou Leina Pharmaceutical Research Development Co., Ltd. Applicant after: CHANGZHOU BADIAN MEDICINE TECHNOLOGY CO., LTD. Address before: Suzhou City, Jiangsu Province, Suzhou Industrial Park 215123 Xinghu Street No. 218 BioBAY building A3 room 318 Applicant before: Suzhou Leina Pharmaceutical Research Development Co., Ltd. |
|
C41 | Transfer of patent application or patent right or utility model | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20161111 Address after: 213000 Jiangsu city of Changzhou province's new No. 7 North Road Applicant after: CHANGZHOU BADIAN MEDICINE TECHNOLOGY CO., LTD. Address before: Suzhou City, Jiangsu Province, Suzhou Industrial Park 215123 Xinghu Street No. 218 BioBAY building A3 room 318 Applicant before: Suzhou Leina Pharmaceutical Research Development Co., Ltd. Applicant before: CHANGZHOU BADIAN MEDICINE TECHNOLOGY CO., LTD. |
|
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20150708 |
|
WD01 | Invention patent application deemed withdrawn after publication |