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氟化季铵壳聚糖衍生物:合成、表征、抗菌活性及杀菌动力学

Fluorinated Quaternary Chitosan Derivatives: Synthesis, Characterization, Antibacterial Activity, and Killing Kinetics.

作者信息

Cele Zamani E D, Somboro Anou M, Amoako Daniel G, Ndlandla Lindokuhle F, Balogun Mohammed O

机构信息

Biopolymer Modification & Therapeutics Laboratory, Chemicals Cluster, Council for Scientific and Industrial Research, Meiring Naude Road, Brummeria, Pretoria 0001, South Africa.

Biomedical Resource Unit, College of Health Sciences, University of KwaZulu-Natal, Westville Campus, Durban 4000, South Africa.

出版信息

ACS Omega. 2020 Nov 13;5(46):29657-29666. doi: 10.1021/acsomega.0c01355. eCollection 2020 Nov 24.

Abstract

Chitosan has become an established platform biopolymer with applications in biomedical engineering, nanomedicine, and the development of new materials with improved solubility, antimicrobial activity, and low toxicity. In this study, a series of chitosan derivatives were synthesized by conjugating various perfluorocarbon chains to chitosan via Schiff base formation or nucleophilic substitution, followed by quaternization with glycidyl trimethylammonium chloride to confer non-pH-dependent permanent positive charges. Synthesized fluorinated -(2-hydroxypropyl)-3-trimethylammonium chitosan chloride polymers were characterized and investigated for their antibacterial efficacies against multidrug-resistant bacteria including clinical isolates. The polymers showed activity against both Gram-positive and Gram-negative bacteria (MIC = 64-512 μg/mL) but with greater potency against the former. They displayed rapid bactericidal properties, based on the MBC/MIC ratio, which were further confirmed by the time-kill kinetic assays. Given the properties presented here, fluorinated quaternary chitosan derivatives can serve as great candidates to be investigated as environmentally more benign, nontherapeutic antimicrobial agents that could serve as alternatives to the heavy reliance on antibiotics, which are currently in a very precarious state due to increasing occurrence of drug resistance.

摘要

壳聚糖已成为一种成熟的平台生物聚合物,应用于生物医学工程、纳米医学以及开发具有改善溶解性、抗菌活性和低毒性的新材料。在本研究中,通过席夫碱形成或亲核取代将各种全氟碳链与壳聚糖共轭,然后用缩水甘油基三甲基氯化铵进行季铵化,以赋予非pH依赖性的永久正电荷,从而合成了一系列壳聚糖衍生物。对合成的氟化-(2-羟丙基)-3-三甲基氯化铵壳聚糖聚合物进行了表征,并研究了它们对包括临床分离株在内的多重耐药细菌的抗菌效果。这些聚合物对革兰氏阳性菌和革兰氏阴性菌均有活性(MIC = 64-512 μg/mL),但对前者的效力更强。基于MBC/MIC比值,它们表现出快速杀菌特性,时间-杀菌动力学试验进一步证实了这一点。鉴于此处呈现的特性,氟化季铵化壳聚糖衍生物可作为极具潜力的候选物进行研究,有望成为环境更友好的非治疗性抗菌剂,以替代目前因耐药性日益增加而处于岌岌可危状态的对抗生素的严重依赖。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4e99/7689678/2f09f747449b/ao0c01355_0008.jpg

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