Chemical reactivity of alliin and its molecular interactions with the M proteasepro of SARS-COV-2

IF 1 4区 化学 Q4 CHEMISTRY, MULTIDISCIPLINARY Journal of The Serbian Chemical Society Pub Date : 2023-01-01 DOI:10.2298/jsc230817078l
Wendolyne López-Orozco, Humberto Mendoza-Huizar, Giaan Álvarez-Romero, Jesús Torres-Valencia, Maricruz Sanchez-Zavala
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Abstract

In the present work a computational study of the chemical reactivity of alliin at the X/DGDZVP level of theory (where X=B3LYP, M06, M06L and wB97XD) was performed. The distribution of active sites on alliin was determined by evaluating the Fukui function. For electrophilic attacks, the more reactive sites are on the carbon atoms of the prop-2-ene moiety. The more active sites for nucleophilic attacks are located on the thioether group. In the case of free radical attacks, the more reactive sites are on the carbonyl, thioether and prop-2-ene moieties. Additionally, the molecular docking study revealed that, alliin is able to dock to the Mproteasepro of SARS-CoV-2 through interactions with the catalytic CYS145-HSD164 dyad via Van der Waals interactions, with MET49 with interactions alkyl-type ions and with PHE140 by hydrogen bonds. Also, the molecular dynamic study indicates that alliin remains in the pocket site. Last result suggests that this molecule is a potential candidate for further in vitro evaluation as a drug for the treatment of the major protease-based SARS-CoV-2 virus.
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蒜素的化学反应性及其与SARS-COV-2 M蛋白酶pro的分子相互作用
在本工作中,在理论的X/DGDZVP水平(其中X=B3LYP, M06, M06L和wB97XD)上进行了蒜素化学反应性的计算研究。通过评价福井函数确定了大蒜素上活性位点的分布。对于亲电攻击,反应性更强的位点在2-丙烯部分的碳原子上。亲核攻击的活性位点位于硫醚基团上。在自由基攻击的情况下,更活跃的位点在羰基、硫醚和2-丙烯基团上。此外,分子对接研究表明,蒜素可以通过范德华作用与催化体CYS145-HSD164二元体相互作用,通过烷基型离子与MET49相互作用,通过氢键与PHE140相互作用,与SARS-CoV-2的Mproteasepro进行对接。此外,分子动力学研究表明,蒜素仍然存在于口袋部位。最后的结果表明,该分子作为治疗主要蛋白酶型SARS-CoV-2病毒的药物,有可能进一步进行体外评估。
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来源期刊
CiteScore
1.80
自引率
0.00%
发文量
76
审稿时长
1 months
期刊介绍: The Journal of the Serbian Chemical Society -JSCS (formerly Glasnik Hemijskog društva Beograd) publishes articles original papers that have not been published previously, from the fields of fundamental and applied chemistry: Theoretical Chemistry, Organic Chemistry, Biochemistry and Biotechnology, Food Chemistry, Technology and Engineering, Inorganic Chemistry, Polymers, Analytical Chemistry, Physical Chemistry, Spectroscopy, Electrochemistry, Thermodynamics, Chemical Engineering, Textile Engineering, Materials, Ceramics, Metallurgy, Geochemistry, Environmental Chemistry, History of and Education in Chemistry.
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