Synthesis of Protected D-Glucopyranosides as Mucormycosis Inhibitors: DFT, Docking, ADMET, and SAR Studies
Matin, P., Nayeem, S., Matin, M., Rahman, M., Das, S., Chakraborty, D. (2023). Synthesis of Protected D-Glucopyranosides as Mucormycosis Inhibitors: DFT, Docking, ADMET, and SAR Studies. EKB Journal Management System, 66(7), 153-164. doi: 10.21608/ejchem.2022.133698.5895
Priyanka Matin; S. M. Abdul Nayeem; Mohammed Mahbubul Matin; Md. Rezaur Rahman; Suman Das; Dipankar Chakraborty. "Synthesis of Protected D-Glucopyranosides as Mucormycosis Inhibitors: DFT, Docking, ADMET, and SAR Studies". EKB Journal Management System, 66, 7, 2023, 153-164. doi: 10.21608/ejchem.2022.133698.5895
Matin, P., Nayeem, S., Matin, M., Rahman, M., Das, S., Chakraborty, D. (2023). 'Synthesis of Protected D-Glucopyranosides as Mucormycosis Inhibitors: DFT, Docking, ADMET, and SAR Studies', EKB Journal Management System, 66(7), pp. 153-164. doi: 10.21608/ejchem.2022.133698.5895
Matin, P., Nayeem, S., Matin, M., Rahman, M., Das, S., Chakraborty, D. Synthesis of Protected D-Glucopyranosides as Mucormycosis Inhibitors: DFT, Docking, ADMET, and SAR Studies. EKB Journal Management System, 2023; 66(7): 153-164. doi: 10.21608/ejchem.2022.133698.5895

Synthesis of Protected D-Glucopyranosides as Mucormycosis Inhibitors: DFT, Docking, ADMET, and SAR Studies

Egyptian Journal of Chemistry
Volume 66, Issue 7, July 2023, Page 153-164  XML PDF (1.18 MB)
Document Type: Original Article
DOI: 10.21608/ejchem.2022.133698.5895
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Authors
Priyanka Matinorcid 1; S. M. Abdul Nayeemorcid 1; Mohammed Mahbubul Matin email orcid 2; Md. Rezaur Rahmanorcid 3; Suman Dasorcid 4; Dipankar Chakrabortyorcid 4
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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