Synthesis of Protected D-Glucopyranosides as Mucormycosis Inhibitors: DFT, Docking, ADMET, and SAR Studies | ||
Egyptian Journal of Chemistry | ||
Volume 66, Issue 7, July 2023, Pages 153-164 PDF (1.18 M) | ||
Document Type: Original Article | ||
DOI: 10.21608/ejchem.2022.133698.5895 | ||
Authors | ||
Priyanka Matin1; S. M. Abdul Nayeem1; Mohammed Mahbubul Matin* 2; Md. Rezaur Rahman3; Suman Das4; Dipankar Chakraborty4 | ||
1Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong, 4331, Bangladesh | ||
2Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong, Bangladesh | ||
3Department of Chemical Engineering and Energy Sustainability, Faculty of Engineering, Universiti Malaysia Sarawak, Kota Samarahan, 94300, Malaysia | ||
4Chemical Research Division, Bangladesh Council of Scientific & Industrial Research (BCSIR) Laboratories, Chittagong, 4220, Bangladesh | ||
Abstract | ||
Fungal infections especially mucormycosis cause devastating health problems worldwide and the recent invasion of mucormycosis (Mucorales) after SARS-CoV-2 infection worsens the severity of patient conditions leading to increased deaths. Non-ionic sugar esters (SEs) with amphiphilic properties show antimicrobial activities and have potential applications in medicines, foods, agriculture, and pharmaceutical industries. Several benzylidene-protected glucopyranoside esters were synthesized and their in vitro antifungal potentialities were assessed. With encouraging results against Alternaria alternata their potentialities were checked by molecular docking with three black fungus-related proteins (PDB ID: 4BFN, 4BFO, and 2WTP) which indicated that the presence of hexanoyl group at the C-2 position of glucopyranoside skeleton highly increased its binding affinities. Hence, it can be an alternative to azole drugs for the treatment of mucormycosis infections. Molecular orbital, global reactivity descriptors, drug-likeness, and structure-activity relationship are used to rationalize these binding results and to ensure that the compounds are safe for humans. | ||
Keywords | ||
Antifungal; Black fungus; Methyl α -D-glucopyranoside; Molecular docking; Glucose esters | ||
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