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季铵硅烷化合物的合成及抗菌活性测试。

Synthesis and antimicrobial activity testing of quaternary ammonium silane compounds.

机构信息

Science Faculty of Akdeniz University, 07058 Antalya, Türkiye.

Science Faculty of Akdeniz University, 07058 Antalya, Türkiye.

出版信息

Bioorg Chem. 2024 Oct;151:107614. doi: 10.1016/j.bioorg.2024.107614. Epub 2024 Jul 3.

Abstract

With increasing health awareness of the pathogenic effects of disease-causing microorganisms, interest in and use (of medical textiles, disinfectants in medical devices, etc.) of antimicrobial substances have increased in various applications, such as medical textiles and disinfectants (alcohol-based and nonalcoholic), in medical devices There are several concerns with alcohol-based disinfectants, such as surface deformation of medical devices due to high alcohol content and damage to skin tissue caused by lipid and protein denaturation of cell membranes. Quaternary ammonium compounds (quats) were preferred because they have the potential to prepare water-based disinfectants. In this study, novel (3-chloropropyl)triethoxysilane (CPTMO) and (3-chloropropyl)triethoxysilane (CPTEO) based quaternary ammonium silane compounds (silane-quats) were developed using quats with carbon chain lengths of C12, C14, C16 and C18. Titration (ASTM D2074) was used to calculate the yield of the synthesis and the structures of the products were characterised by Fourier transform infrared spectroscopy (FTIR), nuclear magnetic resonance spectroscopy (C NMR, H NMR) and gas chromatography-mass spectrometry (GC-MS).The in vitro antimicrobial activity of the synthesized samples was evaluated against Gram-positive (Staphylococcus aureus (S. aureus), Enterococcus hirae (E. hirae)) and Gram-negative (Escherichia coli (E. coli), Pseudomonas aeruginosa (P. aeruginosa)) bacteria and fungi (Candida albicans (C. albicans), Aspergillus brasiliensis (A. brasiliensis)) using the minimum inhibitory concentration (MIC) test. According to MIC tests, the silane-quats with the highest antimicrobial effects were dimethylhexadecyl[3-(trimethoxysilyl)propyl]ammonium chloride (SQ3), which had an MIC of < 16 μg/ml (ppm) against E. coli, S. aureus, E. hirae, C. albicans, and A. brasiliensis and 32 μg/ml against P. aeruginosa. The MIC test results also showed antimicrobial activity at least 2 times greater than that of the commercially available disinfectant benzalkonium chloride (BAC). Findings suggest that SQ3 (C16) holds promise as an effective medical disinfectant, presenting a novel approach to combating microbial infections in healthcare settings.

摘要

随着人们对致病微生物的致病性的健康意识不断提高,对抗菌物质的兴趣和应用(例如,医疗器械中的医用纺织品、消毒剂等)在各种应用中不断增加,例如医用纺织品和消毒剂(含酒精和不含酒精)、医疗器械。含酒精的消毒剂存在一些问题,例如由于高酒精含量而导致医疗器械表面变形以及细胞膜中脂质和蛋白质变性导致的皮肤组织损伤。季铵化合物(quats)因其有可能制备水性消毒剂而受到青睐。在这项研究中,使用碳链长度为 C12、C14、C16 和 C18 的 quats 开发了新型(3-氯丙基)三乙氧基硅烷(CPTMO)和(3-氯丙基)三乙氧基硅烷(CPTEO)基季铵硅烷化合物(硅烷-季铵盐)。通过滴定(ASTM D2074)来计算合成的产率,并且通过傅里叶变换红外光谱(FTIR)、核磁共振光谱(C NMR、H NMR)和气相色谱-质谱联用(GC-MS)对产物的结构进行了表征。使用最低抑菌浓度(MIC)试验评估了合成样品对革兰氏阳性(金黄色葡萄球菌(S. aureus)、屎肠球菌(E. hirae))和革兰氏阴性(大肠杆菌(E. coli)、铜绿假单胞菌(P. aeruginosa))细菌和真菌(白色念珠菌(C. albicans)、黄曲霉(A. brasiliensis))的体外抗菌活性。根据 MIC 试验,抗菌效果最高的硅烷-季铵盐是二甲基十六烷基[3-(三甲氧基硅基)丙基]氯化铵(SQ3),对大肠杆菌、金黄色葡萄球菌、屎肠球菌、白色念珠菌和黄曲霉的 MIC 均小于 16μg/ml(ppm),对铜绿假单胞菌的 MIC 为 32μg/ml。MIC 试验结果还表明,其抗菌活性至少是市售消毒剂苯扎氯铵(BAC)的 2 倍。研究结果表明,SQ3(C16)有望成为一种有效的医用消毒剂,为在医疗保健环境中对抗微生物感染提供了一种新方法。

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