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Hyaluronic acid-cystamine-polylactic acid-glycollic acid graft polymer and preparation method thereof

A graft polymer, glycolic acid technology, applied in the field of hyaluronic acid-cystamine-polylactic acid-glycolic acid graft polymer and its preparation, can solve the problems of strong hydrophobicity of aliphatic polyester and the like

Active Publication Date: 2015-01-07
THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The graft polymer provided by the present invention overcomes the shortcomings that hyaluronic acid cannot form micelles alone, and aliphatic polyester has strong hydrophobicity.

Method used

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  • Hyaluronic acid-cystamine-polylactic acid-glycollic acid graft polymer and preparation method thereof
  • Hyaluronic acid-cystamine-polylactic acid-glycollic acid graft polymer and preparation method thereof
  • Hyaluronic acid-cystamine-polylactic acid-glycollic acid graft polymer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0092] (a) Combine 5g of polylactic acid-glycolic acid (molar ratio of lactic acid to glycolic acid 75 / 25, molecular weight: 20,000, Jinan Daigang), 0.144g of 1-ethyl-(3-dimethylaminopropyl ) Carbodiimide (Alfar Aesar, 98%) and 0.086g of N-hydroxysuccinimide (Alfar Aesar, 98%) were placed in a three-necked flask. After vacuuming for 1 hour, 15 mL of dichloromethane was added Dissolve, at a temperature of 20 DEG C, and react for 2 hours under nitrogen protection to obtain a crude product of N-hydroxysuccinimide activated polylactic acid-glycolic acid. The crude product solution was rotary evaporated at 25°C to remove dichloromethane, and then precipitated with 200mL ether, washed with a methanol / ether (3:7) mixed solution (100mL×3 times), and dried in a vacuum oven at 25°C for 36 hours To obtain 4.245 g of N-hydroxysuccinimide polylactic acid-glycolic acid as a solid product.

[0093] (b) Add 4.245 g of polylactic acid-glycolic acid activated by N-hydroxysuccinimide to 20 mL of d...

Embodiment 2

[0107] (a) Combine 5g of polylactic acid-glycolic acid (mole ratio of lactic acid to glycolic acid 75 / 25, molecular weight: 50,000, Jinan Daigang), 0.115g of 1-ethyl-(3-dimethylaminopropyl ) Carbodiimide (Alfar Aesar Company, 98%) and 0.081g of 1-hydroxybenzotriazole (Aladdin Reagent Shanghai Co., Ltd., 99%) were placed in a three-necked flask. After vacuuming for 1 hour, 10 mL of The chloroform is dissolved, the temperature is 40 DEG C, and the reaction is carried out for 4 hours under the protection of nitrogen to obtain the crude product of 1-hydroxybenzotriazole activated polylactic acid-glycolic acid. The crude product solution was rotary evaporated at 25°C to remove chloroform, and then precipitated with 200mL ether, washed with a methanol / ether (5:5) mixed solution (100mL×3 times), dried in a vacuum oven at 25°C for 36 hours to obtain The solid product 1-hydroxybenzotriazole activated polylactic acid-glycolic acid 4.461g.

[0108] (b) Add 4.461 g of 1-hydroxybenzotriazole...

Embodiment 3

[0114] (a) 5g of polylactic acid-glycolic acid (mole ratio of lactic acid to glycolic acid is 50 / 50, molecular weight: 20,000, Jinan Daigang), 0.309g of N,N-dicyclohexylcarbodiimide (Sinopharm Group Chemical Reagent Co., Ltd., 99%) and 0.173g of N-hydroxysuccinimide (Alfar Aesar, 98%) were placed in a three-necked flask. After vacuuming for 1 hour, add 50mL of dichloromethane to dissolve at a temperature of 25 It was reacted for 4 hours under the protection of nitrogen at ℃ to obtain the crude product of N-hydroxysuccinimide activated polylactic acid-glycolic acid. Then it was precipitated with 200mL ether, washed with methanol / ether (3:7) mixed solution (100mL×3 times), dried in a vacuum oven at 25°C for 36 hours to obtain a solid product of N-hydroxysuccinimide polylactic acid- Glycolic acid 4.845g.

[0115] (b) Add 4.845 g of N-hydroxysuccinimated polylactic acid-glycolic acid to 30 mL of dimethyl sulfoxide to prepare an N-hydroxysuccinimated polylactic acid-glycolic acid dim...

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Abstract

The invention relates to a hyaluronic acid-cystamine-polylactic acid-glycollic acid graft polymer and a preparation method thereof. The structural formula of the hyaluronic acid-cystamine-polylactic acid-glycollic acid graft polymer is disclosed as Formula (1), wherein n is a whole number ranging from 16 to 30, the Y:X ratio is (1-3):1, Y is a whole number ranging from 153 to 549, and X is a whole number ranging from 73 to 385; and the hyaluronic acid and the polylactic acid-glycollic acid are connected through a micromolecule (2) cystamine. The hyaluronic acid-cystamine-polylactic acid-glycollic acid graft polymer has the advantages of favorable biocompatibility effect and low toxicity, has the tumor tissue targeting action when being used as a drug carrier material, can be decomposed in a redox environment in the tumors, and has the function of controlled release of drugs.

Description

Technical field [0001] The invention belongs to the field of high molecular polymers, and particularly relates to a hyaluronic acid-cystamine-polylactic acid-glycolic acid graft polymer and a preparation method thereof. Background technique [0002] Hyaluronic acid is a natural macromolecule that exists in large quantities in vertebrates and bacteria, such as the extracellular matrix of human joint tissues, joint synovial fluid, skin dermis and the vitreous body of the eye (Fraser J, Laurent T, Laurent UJIntern. Med. 1997; 242: 27-33.; Laurent TC, Fraser J. FASEB J. 1992; 6: 2397-404.; Robert L, Robert AM, Renard G. Pathol. Biol. 2010; 58: 187-98. ). Hyaluronic acid is also a linear polysaccharide molecule. The monomer is composed of (1-β-4)D-glucuronic acid and (1-β-3)N-acetyl-D-glucosamine linked by glycosidic bonds. The disaccharide unit, the molecular weight is basically 1×10 5 ~-5×10 6 Between Dalton. Under physiological conditions, hyaluronic acid exists in the form of a...

Claims

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Application Information

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IPC IPC(8): C08G81/00C08G63/91C08B37/08A61K47/36A61P35/00
Inventor 吴雁陈春英胡克磊周会鸽
Owner THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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