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Polymethacrylamide cationic polymer cooperatively modified by side groups natural arginine and lactobionic acid, preparation method and application

A technology of polymethacrylamide cation and polymethacrylamide, which is applied in the field of biological functional materials, can solve the problems of reducing cell membrane damage ability and cationic charge density, and achieves reduced interaction and surface adsorption, low cytotoxicity, Effect of increasing surface osmotic pressure

Inactive Publication Date: 2014-10-08
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, studies have found that some small molecular sugars (such as sorbitol, mannose, gluconic acid, lactobionic acid, etc.) are used as structural building blocks, coupled with linear or branched PEI molecules, and used as gene carriers to transport DNA or siRNA can further improve the biocompatibility of the carrier, which may be due to the reduction of the cationic charge density on the surface of the carrier due to the introduction of polyhydroxy sugar molecular building blocks, thereby reducing the ability to damage the cell membrane

Method used

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  • Polymethacrylamide cationic polymer cooperatively modified by side groups natural arginine and lactobionic acid, preparation method and application
  • Polymethacrylamide cationic polymer cooperatively modified by side groups natural arginine and lactobionic acid, preparation method and application
  • Polymethacrylamide cationic polymer cooperatively modified by side groups natural arginine and lactobionic acid, preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The first step: the RAFT reagent 4-cyano-4-(dodecyltrithiocarbonic acid) valeric acid (35 mg), the hexamethylenediaminomethacrylamide functional monomer protected by the terminal amino Boc Azobisisobutyronitrile AIBN (2.8 mg) free radical initiator and 6 mL of dry tetrahydrofuran solvent were added to the Schlenk reaction tube. After 3 cycles of freezing-vacuumizing-thawing and nitrogen circulation to remove residual oxygen in the reaction solution, keep the reaction tube under a nitrogen atmosphere, move it into an oil bath preheated to 70°C and stir for 6 hours. Then the reaction was rapidly quenched with liquid nitrogen, and the reaction solution was concentrated by rotary evaporation under reduced pressure. The concentrated solution was precipitated in glacial ether to obtain a light yellow solid, which was filtered and dried in a vacuum oven for 24 hours to prepare hexamethylenediamine-terminated amino-protected Boc The methacrylamide polymer, conversion rate is 6...

Embodiment 2

[0033] The first step: the RAFT reagent 4-cyano-4-(dodecyltrithiocarbonic acid) valeric acid (70mg), the hexamethylenediaminomethacrylamide functional monomer protected by the terminal amino Boc Azobisisobutyronitrile AIBN (5.6 mg) free radical initiator and 15 mL of dry toluene solvent were added to the Schlenk reaction tube. After 3 cycles of freezing-vacuumizing-thawing and nitrogen circulation to remove residual oxygen in the reaction solution, keep the reaction tube under a nitrogen atmosphere, move it into an oil bath preheated to 70°C and stir for 6 hours. Then the reaction was rapidly quenched with liquid nitrogen, and the reaction solution was concentrated by rotary evaporation under reduced pressure. The concentrated solution was precipitated in glacial ether to obtain a light yellow solid, which was filtered and dried in a vacuum oven for 24 hours to prepare hexamethylenediamine-terminated amino-protected Boc The methacrylamide polymer, the conversion rate is 68%. ...

Embodiment 3

[0040] The first step: the RAFT reagent 4-cyano-4-(dodecyltrithiocarbonic acid) valeric acid (35 mg), the hexamethylenediaminomethacrylamide functional monomer protected by the terminal amino Boc Azobisisobutyronitrile AIBN (2.8 mg) free radical initiator and 6 mL of dry tetrahydrofuran solvent were added to the Schlenk reaction tube. After 3 cycles of freezing-vacuumizing-thawing and nitrogen circulation to remove residual oxygen in the reaction solution, keep the reaction tube under a nitrogen atmosphere, move it into an oil bath preheated to 70°C and stir for 6 hours. Then the reaction was rapidly quenched with liquid nitrogen, and the reaction solution was concentrated by rotary evaporation under reduced pressure. The concentrated solution was precipitated in glacial ether to obtain a light yellow solid, which was filtered and dried in a vacuum oven for 24 hours to prepare hexamethylenediamine-terminated amino-protected Boc The methacrylamide polymer, conversion rate is 6...

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Abstract

The invention discloses a polymethacrylamide cationic polymer cooperatively modified by side groups natural arginine and lactobionic acid, a preparation method and application thereof as a gene carrier. A methacrylamide cation functional polymer with amino as a side group is synthesized through reversible addition-fragmentation chain transfer (RAFT) polymerization and subsequent deprotection reaction, then arginine containing a protective group and a lactobionic acid building block are linked to a polymethacrylamide molecule, and finally the protective group is removed for obtaining the target polymer. The preparation method of the polymethacrylamide cationic polymer is simple and mild in reaction conditions. Cell evaluation results show that the prepared polymethacrylamide cationic polymer cooperatively modified by side groups natural arginine and lactobionic acid has high biological compatibility, low cytotoxicity, high gene transfection efficiency and good serum stability, and is an effective novel glycosyl-modified non-virogene carrier, and is applicable as an efficient gene transfection reagent.

Description

technical field [0001] The invention relates to the field of biofunctional materials. It specifically relates to a polymethacrylamide cationic polymer synergistically modified by side group natural arginine and lactobionic acid, a preparation method and its application as a biological function carrier material. Background technique [0002] The development of new cationic polymer carrier materials with high efficiency and low toxicity has become one of the main research directions in the field of biofunctional materials and transfection reagents. Recently, it has been found that the relatively low transfection efficiency of many cationic polymers as gene carriers is due to the fact that they need to cross some membranous organelles (such as cell membranes and nuclear membranes) during intracellular transport, and the transmembrane ability is low, thus enhancing The transmembrane ability of cationic polymer gene carrier will be one of the possible methods to improve its gene...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F120/60C08F8/30C08F8/00C12N15/63
Inventor 曹阿民李慧盛瑞隆罗挺孙景景
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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