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3-氨基-5-（吲哚-3-基）亚甲基-4-氧代-2-硫代噻唑烷衍生物作为抗菌剂：合成、计算及生物学评价

3-Amino-5-(indol-3-yl)methylene-4-oxo-2-thioxothiazolidine Derivatives as Antimicrobial Agents: Synthesis, Computational and Biological Evaluation.

作者信息

Horishny Volodymyr, Kartsev Victor, Matiychuk Vasyl, Geronikaki Athina, Anthi Petrou, Pogodin Pavel, Poroikov Vladimir, Ivanov Marija, Kostic Marina, Soković Marina D, Eleftheriou Phaedra

机构信息

Department of Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, Ukraine.

InterBioScreen, 142432 Chernogolovka, Moscow Region, Russia.

出版信息

Pharmaceuticals (Basel). 2020 Sep 1;13(9):229. doi: 10.3390/ph13090229.

DOI:10.3390/ph13090229
PMID:32883028
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7559366/
Abstract

Herein we report the design, synthesis, computational, and experimental evaluation of the antimicrobial activity of fourteen new 3-amino-5-(indol-3-yl) methylene-4-oxo-2-thioxothiazolidine derivatives. The structures were designed, and their antimicrobial activity and toxicity were predicted in silico. All synthesized compounds exhibited antibacterial activity against eight Gram-positive and Gram-negative bacteria. Their activity exceeded those of ampicillin and (for the majority of compounds) streptomycin. The most sensitive bacterium was (American Type Culture Collection ATCC 6538), while (NCTC 7973) was the most resistant. The best antibacterial activity was observed for compound (Z)-N-(5-((1H-indol-3-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)-4-hydroxybenzamide (Minimal inhibitory concentration, MIC at 37.9-113.8 μM, and Minimal bactericidal concentration MBC at 57.8-118.3 μM). Three most active compounds and being evaluated against three resistant strains, Methicillin resistant (MRSA), and , were more potent against MRSA than ampicillin (MIC at 248-372 μM, MBC at 372-1240 μM). At the same time, streptomycin (MIC at 43-172 μM, MBC at 86-344 μM) did not show bactericidal activity at all. The compound was also more active than ampicillin towards resistant strain. Antifungal activity of all compounds exceeded those of the reference antifungal agents bifonazole (MIC at 480-640 μM, and MFC at 640-800 μM) and ketoconazole (MIC 285-475 μM and MFC 380-950 μM). The best activity was exhibited by compound . The most sensitive fungal was (IAM 5061), while (human isolate was the most resistant. Low cytotoxicity against HEK-293 human embryonic kidney cell line and reasonable selectivity indices were shown for the most active compounds , , , using thiazolyl blue tetrazolium bromide MTT assay. The docking studies indicated a probable involvement of Mur B inhibition in the antibacterial action, while CYP51 inhibition is likely responsible for the antifungal activity of the tested compounds.

摘要

在此，我们报告了14种新型3-氨基-5-(吲哚-3-基)亚甲基-4-氧代-2-硫代噻唑烷衍生物的抗菌活性的设计、合成、计算和实验评估。设计了这些化合物的结构，并通过计算机模拟预测了它们的抗菌活性和毒性。所有合成化合物均对8种革兰氏阳性菌和革兰氏阴性菌表现出抗菌活性。它们的活性超过了氨苄西林以及（对于大多数化合物而言）链霉素。最敏感的细菌是 （美国典型培养物保藏中心ATCC 6538），而 （国家典型菌种保藏中心NCTC 7973）是最具抗性的。化合物 （Z）-N-（5-（（1H-吲哚-3-基）亚甲基）-4-氧代-2-硫代噻唑烷-3-基）-4-羟基苯甲酰胺表现出最佳抗菌活性（最低抑菌浓度，MIC为37.9 - 113.8 μM，最低杀菌浓度MBC为57.8 - 118.3 μM）。对三种最具活性的化合物 、 和 针对三种耐药菌株，即耐甲氧西林金黄色葡萄球菌（MRSA）、 和 进行了评估，它们对MRSA的活性比氨苄西林更强（MIC为248 - 372 μM，MBC为372 - 1240 μM）。同时，链霉素（MIC为43 - 172 μM，MBC为86 - 344 μM）根本没有表现出杀菌活性。化合物 对耐药 菌株的活性也比氨苄西林更强。所有化合物的抗真菌活性均超过了参考抗真菌剂联苯苄唑（MIC为480 - 640 μM，MFC为640 - 800 μM）和酮康唑（MIC为285 - 475 μM，MFC为380 - 950 μM）。化合物 表现出最佳活性。最敏感的真菌是 （IAM 5061），而 （人分离株）是最具抗性的。使用噻唑蓝四氮唑溴盐MTT法对最具活性的化合物 、 、 、 进行检测，结果显示它们对HEK - 293人胚肾细胞系的细胞毒性较低且具有合理的选择性指数。对接研究表明，Mur B抑制可能参与了抗菌作用，而CYP51抑制可能是受试化合物抗真菌活性的原因。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f18/7559366/fbcb68ff7b74/pharmaceuticals-13-00229-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f18/7559366/39b6fa14de74/pharmaceuticals-13-00229-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f18/7559366/44192f409035/pharmaceuticals-13-00229-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f18/7559366/fd53def9931f/pharmaceuticals-13-00229-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f18/7559366/46ae36a45a28/pharmaceuticals-13-00229-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f18/7559366/3c8a99ce194e/pharmaceuticals-13-00229-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f18/7559366/06e22988ecd9/pharmaceuticals-13-00229-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f18/7559366/a18a0ade352b/pharmaceuticals-13-00229-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f18/7559366/b41e4dc593ed/pharmaceuticals-13-00229-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f18/7559366/fbcb68ff7b74/pharmaceuticals-13-00229-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f18/7559366/39b6fa14de74/pharmaceuticals-13-00229-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f18/7559366/44192f409035/pharmaceuticals-13-00229-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f18/7559366/fd53def9931f/pharmaceuticals-13-00229-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f18/7559366/46ae36a45a28/pharmaceuticals-13-00229-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f18/7559366/3c8a99ce194e/pharmaceuticals-13-00229-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f18/7559366/06e22988ecd9/pharmaceuticals-13-00229-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f18/7559366/a18a0ade352b/pharmaceuticals-13-00229-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f18/7559366/b41e4dc593ed/pharmaceuticals-13-00229-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f18/7559366/fbcb68ff7b74/pharmaceuticals-13-00229-g007.jpg

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