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An Antimicrobial Activity Invoking Switch Based on Thermally Induced Conformational Reversible Transformation of Poly(n-isopropylacrylamide)

The technology of isopropyl acrylamide and antibacterial agent is applied in the field of antibacterial agent activity calling switch, which can solve the problems of difficult separation and purification, few expression products, high cost, etc., and achieves the effect of wide antibacterial spectrum, strong antibacterial activity and realizing shielding effect.

Inactive Publication Date: 2018-05-08
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reality is that the content of natural antimicrobial peptides in organisms is very small, the direct extraction process is cumbersome, the yield is low, and the cost is high. Artificial synthesis through genetic engineering also faces shortage of donors, high suicide rate of host cells, few expression products, and separation and purification. Many bottlenecks, such as difficulties, greatly limit the large-scale commercial use of such materials

Method used

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  • An Antimicrobial Activity Invoking Switch Based on Thermally Induced Conformational Reversible Transformation of Poly(n-isopropylacrylamide)
  • An Antimicrobial Activity Invoking Switch Based on Thermally Induced Conformational Reversible Transformation of Poly(n-isopropylacrylamide)

Examples

Experimental program
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Effect test

Embodiment 1

[0025] (1) Vinylation of ciprofloxacin: Mix 10 parts of ciprofloxacin, 4 parts of triethylamine and 300 parts of dichloromethane evenly, stir at 0°C for 30 minutes, then add dropwise under continuous stirring and nitrogen protection 4 parts of acryloyl chloride, after the dropwise addition, the temperature was raised to 20°C for 1 hour reaction; after the reaction, the above mixture was poured into n-hexane, and the precipitate was repeatedly washed with water and dried to obtain vinylated ciprofloxacin;

[0026] (2) N -Reversible addition-fragmentation chain transfer polymerization of isopropylacrylamide: 1 part of 2-phenyl-2-propylbenzodisulfide, N - Mix 90 parts of isopropylacrylamide, 0.07 parts of azobisisobutyronitrile and 120 parts of tetrahydrofuran evenly, seal, cycle freezing-thawing to remove oxygen, then raise the temperature to 55°C for 4 hours under continuous stirring and nitrogen protection, After the reaction was completed, the above mixture was poured into e...

Embodiment 2

[0032] (1) Gatifloxacin vinylation: Mix 15 parts of gatifloxacin, 6 parts of pyridine and 400 parts of tetrahydrofuran evenly, stir at 2°C for 45 minutes, then add 4-pentene dropwise under continuous stirring and nitrogen protection 6 parts of acid chloride, after the dropwise addition, the temperature was raised to 30°C and reacted for 1.5 hours; after the reaction was completed, the above mixture was poured into cyclohexane, and the precipitate was repeatedly washed with water and dried to obtain vinylated gatifloxacin;

[0033] (2) N -Reversible addition-fragmentation chain transfer polymerization of isopropylacrylamide: 2 parts of 2-cyanopropyl-2-ylbenzodisulfide, N - Mix 140 parts of isopropylacrylamide, 0.14 parts of azobisisoheptanonitrile and 180 parts of 1,4-dioxane evenly, seal, cycle freezing-thawing and deoxygenation, and then raise the temperature to React at 60°C for 6 hours, when the reaction is over, pour the above mixture into n-hexane, and dry the precipitat...

Embodiment 3

[0039] (1) Norfloxacin vinylation: 20 parts of norfloxacin, N,N - Mix 8 parts of diisopropylethylamine and 500 parts of chloroform evenly, stir at 5°C for 60 minutes, then add 8 parts of hex-5-enoyl chloride dropwise under continuous stirring and nitrogen protection, and raise the temperature to 35°C after the dropwise addition React for 2.5 hours; after the reaction is completed, pour the above mixture into n-heptane, and the precipitate is repeatedly washed with water and dried to obtain vinylated norfloxacin;

[0040] (2) N -Reversible addition-fragmentation chain transfer polymerization of isopropylacrylamide: 4 parts of 2-cyano-2-propyl dodecyl trithiocarbonate, N - Mix 300 parts of isopropylacrylamide, 0.24 parts of azobicyclohexanenitrile and 400 parts of pyridine evenly, seal, cycle freezing-thawing and deoxygenation, then raise the temperature to 65°C for 12 hours under continuous stirring and nitrogen protection, After the reaction, the above mixture is poured into...

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Abstract

The invention discloses an antibacterial agent activity calling switch based on poly(N-isopropylacrylamide)thermotropic conformation reversible transition. Reversible addition-fragmentation chain transfer free radical polymerization is employed to prepare a poly(N-isopropylacrylamide) macromolecule with one end containing an fluoroquinolone antibacterial group. At a lower critical solution temperature of poly(N-isopropylacrylamide), the macromolecule is completely dissolved in water, and presents a stretched conformation in the aqueous solution, the fluoroquinolone antibacterial end group can move freely, and its antibacterial activity can be fully reflected; when the ambient temperature rises to a temperature above the lower critical solution temperature of poly(N-isopropylacrylamide), the macromolecule collapses in the aqueous solution to form microspheres to hinder free motion of the fluoroquinolone antibacterial end group, so that the antibacterial end group can be difficult to diffuse and approach an action target, thereby shielding its antibacterial activity. The switch provided by the invention utilizes poly(N-isopropylacrylamide)thermotropic conformation reversible transition to realize controllable calling and shielding of the fluoroquinolone antibacterial end group activity so as to avoid the toxicity of antibacterial agent itself and alleviate drug resistance, thus having wide application prospect.

Description

technical field [0001] The present invention relates to a poly( N -Isopropylacrylamide) is an antimicrobial agent activity call switch with reversible thermally induced conformational change, which belongs to the field of antibacterial materials. Background technique [0002] For a long time, it has been proved to be an effective method to significantly improve the antibacterial and antiseptic properties of products by externally adding small molecule antibacterial agents. However, many traditional small-molecule antibacterial agents (such as fluoroquinolones) have a low selectivity between prokaryotic cells and eukaryotic cells. While effectively killing harmful microorganisms such as bacteria, they also have toxic effects on normal human tissue cells. Threat to consumer health and safety. Secondly, under the long-term and continuous stress of antibacterial agents, the ability of bacterial DNA replication and error correction is inactivated, and bacterial protein expressi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F293/00C08F220/54C08F220/60A01N43/60A01P1/00
CPCA01N43/60C08F220/54C08F220/60C08F220/606C08F293/00C08F2438/03
Inventor 陈意常金明范浩军曾琦王忠辉
Owner SICHUAN UNIV
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