Synthesis, characterization, in silico and in vitro studies of novel glycoconjugates as potential antibacterial, antifungal, and antileishmanial agents

IF 2.1 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY
Sher Wali Khan, Saira Nayab, Muhammad Naveed Umar, Momin Khan, Anila Iqbal, Nasir Ahmad, Haroon ur Rashid, Muhammad Ishaq Ali Shah, Naila Gulfam, Muhammad Zahoor, Riaz Ullah, Essam A. Ali
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Abstract

In the present work, several new glycoconjugates (8a–e) were generated from glycopyranosyl-α-trichloroacetimidates (sugar-OTCA) as glycosyl donors and dimethyl-l-tartrate as an aglycone acceptor in good to excellent yields. In the synthetic protocol, various monosaccharides were transformed into pentaacetylated derivatives and then into glycopyranosyl-α-trichloroacetimidates. Afterward, the sugar-OTCA was reacted with dimethyl-l-tartrate using Schmidt’s trichloroacetimidate protocol to give the desired products. The newly synthesized glycoconjugates were characterized by FT-IR, 1H, and 13C-NMR spectroscopic analytical methods. All the target compounds (8a–e) were tested in vitro against various strains of bacteria and fungi at different concentrations. The results revealed that the target compounds had encouraging antibacterial and antifungal potential. The antileishmanial activity of the target compounds against Leishmania tropica promastigotes was also investigated. The in vitro results were further supported by the in silico docking study that indicated minimum values of the docking scores and binding energies for the resulting complexes obtained by the favorable interactions between the target compounds (8a–e) and the selected strains of bacteria and fungi. The docking results proposed promising antibacterial and antifungal activities of the target compounds (8a–e) against the selected bacterial and fungal species.
作为潜在抗菌剂、抗真菌剂和抗利什曼病剂的新型糖共轭物的合成、表征、硅学和体外研究
在本研究中,以吡喃糖基-α-三氯乙酰亚氨酸(糖-OTCA)为糖基供体,以酒石酸二甲酯为苷元受体,生成了几种新的糖轭合物(8a-e),收率良好甚至极佳。在合成过程中,先将各种单糖转化为五乙酰化衍生物,然后再转化为糖吡喃糖基-α-三氯乙酰亚氨酸。之后,利用施密特三氯乙酰亚氨酸协议将糖-OTCA 与二甲基-l-酒石酸反应,得到所需的产物。新合成的糖共轭物通过 FT-IR、1H 和 13C-NMR 光谱分析方法进行了表征。对所有目标化合物(8a-e)进行了体外测试,以不同浓度对抗各种细菌和真菌菌株。结果表明,目标化合物具有令人鼓舞的抗菌和抗真菌潜力。此外,还研究了目标化合物对热带利什曼原虫的抗利什曼活性。该研究表明,目标化合物(8a-e)与所选细菌和真菌菌株之间的有利相互作用所产生的复合物的对接得分和结合能值最小。对接结果表明,目标化合物(8a-e)对所选细菌和真菌具有良好的抗菌和抗真菌活性。
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来源期刊
Open Chemistry
Open Chemistry CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
3.80
自引率
4.30%
发文量
90
审稿时长
6 weeks
期刊介绍: Open Chemistry is a peer-reviewed, open access journal that publishes original research, reviews and short communications in the fields of chemistry in an ongoing way. The central goal is to provide a hub for researchers working across all subjects to present their discoveries, and to be a forum for the discussion of the important issues in the field. The journal is the premier source for cutting edge research in fundamental chemistry and it provides high quality peer review services for its authors across the world. Moreover, it allows for libraries everywhere to avoid subscribing to multiple local publications, and to receive instead all the necessary chemistry research from a single source available to the entire scientific community.
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