CN103724618A - Preparation method for light sensitivity gamma-polyglutamic acid grafted copolymer micelle - Google Patents
Preparation method for light sensitivity gamma-polyglutamic acid grafted copolymer micelle Download PDFInfo
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- CN103724618A CN103724618A CN201310643581.6A CN201310643581A CN103724618A CN 103724618 A CN103724618 A CN 103724618A CN 201310643581 A CN201310643581 A CN 201310643581A CN 103724618 A CN103724618 A CN 103724618A
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- Prior art keywords
- gamma
- polyglutamic acid
- photosensitivity
- graft copolymer
- preparation
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- 238000002360 preparation method Methods 0.000 title claims abstract description 31
- 229920001577 copolymer Polymers 0.000 title claims abstract description 6
- 239000000693 micelle Substances 0.000 title abstract description 7
- 229920002643 polyglutamic acid Polymers 0.000 title abstract 4
- 206010034960 Photophobia Diseases 0.000 title abstract 3
- 208000013469 light sensitivity Diseases 0.000 title abstract 3
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 5
- 206010034972 Photosensitivity reaction Diseases 0.000 claims description 50
- 230000036211 photosensitivity Effects 0.000 claims description 50
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 41
- 229920000578 graft copolymer Polymers 0.000 claims description 41
- 238000000502 dialysis Methods 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- GLNDAGDHSLMOKX-UHFFFAOYSA-N coumarin 120 Chemical compound C1=C(N)C=CC2=C1OC(=O)C=C2C GLNDAGDHSLMOKX-UHFFFAOYSA-N 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 8
- 239000008367 deionised water Substances 0.000 claims description 8
- 229910021641 deionized water Inorganic materials 0.000 claims description 8
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 7
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 7
- 150000007942 carboxylates Chemical group 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 230000009471 action Effects 0.000 claims description 5
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 5
- 238000001556 precipitation Methods 0.000 claims description 5
- 229960004756 ethanol Drugs 0.000 claims description 4
- 229940059260 amidate Drugs 0.000 claims description 3
- NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 claims description 3
- 238000005119 centrifugation Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000012512 characterization method Methods 0.000 claims 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 abstract description 13
- 238000001338 self-assembly Methods 0.000 abstract description 6
- 238000000576 coating method Methods 0.000 abstract description 5
- 239000003995 emulsifying agent Substances 0.000 abstract description 5
- 239000002245 particle Substances 0.000 abstract description 5
- 239000012620 biological material Substances 0.000 abstract description 2
- 229920002521 macromolecule Polymers 0.000 abstract description 2
- PQMOXTJVIYEOQL-UHFFFAOYSA-N Cumarin Natural products CC(C)=CCC1=C(O)C(C(=O)C(C)CC)=C(O)C2=C1OC(=O)C=C2CCC PQMOXTJVIYEOQL-UHFFFAOYSA-N 0.000 abstract 1
- FSOGIJPGPZWNGO-UHFFFAOYSA-N Meomammein Natural products CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C2=C1OC(=O)C=C2CCC FSOGIJPGPZWNGO-UHFFFAOYSA-N 0.000 abstract 1
- 238000007112 amidation reaction Methods 0.000 abstract 1
- 239000002861 polymer material Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 description 6
- 230000000975 bioactive effect Effects 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 229960000956 coumarin Drugs 0.000 description 3
- 235000001671 coumarin Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- 208000001132 Osteoporosis Diseases 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 230000002155 anti-virotic effect Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 210000000748 cardiovascular system Anatomy 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 208000017983 photosensitivity disease Diseases 0.000 description 2
- 231100000434 photosensitization Toxicity 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000004224 protection Effects 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000004043 responsiveness Effects 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- WHUUTDBJXJRKMK-GSVOUGTGSA-N D-glutamic acid Chemical compound OC(=O)[C@H](N)CCC(O)=O WHUUTDBJXJRKMK-GSVOUGTGSA-N 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- PMOWTIHVNWZYFI-WAYWQWQTSA-N cis-2-coumaric acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1O PMOWTIHVNWZYFI-WAYWQWQTSA-N 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- PMOWTIHVNWZYFI-UHFFFAOYSA-N o-Coumaric acid Natural products OC(=O)C=CC1=CC=CC=C1O PMOWTIHVNWZYFI-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
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- Polyamides (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
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Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201310643581.6A CN103724618B (en) | 2013-12-03 | 2013-12-03 | A kind of preparation method of heliosensitivity gamma-polyglutamic acid-graft copolymer micelle |
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CN201310643581.6A CN103724618B (en) | 2013-12-03 | 2013-12-03 | A kind of preparation method of heliosensitivity gamma-polyglutamic acid-graft copolymer micelle |
Publications (2)
Publication Number | Publication Date |
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CN103724618A true CN103724618A (en) | 2014-04-16 |
CN103724618B CN103724618B (en) | 2016-10-26 |
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CN201310643581.6A Active CN103724618B (en) | 2013-12-03 | 2013-12-03 | A kind of preparation method of heliosensitivity gamma-polyglutamic acid-graft copolymer micelle |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104195618A (en) * | 2014-07-31 | 2014-12-10 | 江南大学 | Electro-deposition preparation method of magnesium-based biological nano coating material |
CN106178116A (en) * | 2016-07-20 | 2016-12-07 | 江南大学 | A kind of preparation method of photosensitive n-trimethyl chitosan chloride antimicrobial coating |
CN107569716A (en) * | 2017-04-26 | 2018-01-12 | 温州医科大学附属口腔医院 | A kind of preparation method of titanium implant surface pH response medicine controlled releasing coatings |
CN109485845A (en) * | 2018-09-13 | 2019-03-19 | 天津大学 | A kind of preparation method of hydrophobically modified polyglutamic acid and its trehalose is promoted to be loaded into the application of cell |
CN110215411A (en) * | 2019-06-03 | 2019-09-10 | 江南大学 | A kind of composite nanoparticle and preparation method thereof that wide spectrum is sun-proof |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4237047A (en) * | 1978-08-10 | 1980-12-02 | Ajinomoto Company, Incorporated | Peptide derivative |
JPH11228597A (en) * | 1998-02-19 | 1999-08-24 | Taiho Yakuhin Kogyo Kk | Peptide-substituted coumarin derivative |
CN101321806A (en) * | 2005-12-05 | 2008-12-10 | 日东电工株式会社 | Polyglutamate-amino acid conjugates and methods |
CN102660032A (en) * | 2012-05-16 | 2012-09-12 | 上海大学 | Aliphatic polyester grafted polyamino acid copolymer and preparation method thereof |
-
2013
- 2013-12-03 CN CN201310643581.6A patent/CN103724618B/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4237047A (en) * | 1978-08-10 | 1980-12-02 | Ajinomoto Company, Incorporated | Peptide derivative |
JPH11228597A (en) * | 1998-02-19 | 1999-08-24 | Taiho Yakuhin Kogyo Kk | Peptide-substituted coumarin derivative |
CN101321806A (en) * | 2005-12-05 | 2008-12-10 | 日东电工株式会社 | Polyglutamate-amino acid conjugates and methods |
CN102660032A (en) * | 2012-05-16 | 2012-09-12 | 上海大学 | Aliphatic polyester grafted polyamino acid copolymer and preparation method thereof |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104195618A (en) * | 2014-07-31 | 2014-12-10 | 江南大学 | Electro-deposition preparation method of magnesium-based biological nano coating material |
CN106178116A (en) * | 2016-07-20 | 2016-12-07 | 江南大学 | A kind of preparation method of photosensitive n-trimethyl chitosan chloride antimicrobial coating |
CN107569716A (en) * | 2017-04-26 | 2018-01-12 | 温州医科大学附属口腔医院 | A kind of preparation method of titanium implant surface pH response medicine controlled releasing coatings |
CN107569716B (en) * | 2017-04-26 | 2020-10-20 | 温州医科大学附属口腔医院 | Preparation method of pH-responsive drug controlled-release coating on surface of titanium implant |
CN109485845A (en) * | 2018-09-13 | 2019-03-19 | 天津大学 | A kind of preparation method of hydrophobically modified polyglutamic acid and its trehalose is promoted to be loaded into the application of cell |
CN109485845B (en) * | 2018-09-13 | 2021-04-20 | 天津大学 | Preparation method of hydrophobically modified polyglutamic acid and application of hydrophobically modified polyglutamic acid in promoting loading of trehalose into cells |
CN110215411A (en) * | 2019-06-03 | 2019-09-10 | 江南大学 | A kind of composite nanoparticle and preparation method thereof that wide spectrum is sun-proof |
CN110215411B (en) * | 2019-06-03 | 2022-06-10 | 江南大学 | Broad-spectrum sunscreen composite nanoparticle and preparation method thereof |
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Publication number | Publication date |
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CN103724618B (en) | 2016-10-26 |
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Effective date of registration: 20240207 Address after: 101200 room 205-211526, No. 40, Fuqian West Street, Pinggu town, Pinggu District, Beijing (cluster registration) Patentee after: BEIJING YONGBO TECHNOLOGY CO.,LTD. Country or region after: China Address before: 1800 No. 214122 Jiangsu city of Wuxi Province Li Lake Avenue Patentee before: Jiangnan University Country or region before: China |
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Effective date of registration: 20240812 Address after: Building 1, No. 159 Keji Road, Sanshui Street, Jiangyan District, Taizhou City, Jiangsu Province, China 225500 Patentee after: Jiangsu Zhenxuan Biotechnology Co.,Ltd. Country or region after: China Address before: 101200 room 205-211526, No. 40, Fuqian West Street, Pinggu town, Pinggu District, Beijing (cluster registration) Patentee before: BEIJING YONGBO TECHNOLOGY CO.,LTD. Country or region before: China |