Acyl glucopyranosides : synthesis, PASS predication, antifungal activities and molecular docking

: Sugar esters (SEs) with fatty acyl chains showed diverse applications including antimicrobial inhibition against multidrug-resistant (MDR) microorganisms. Thus, fatty acid esters, especially 6-O-stearoyl glucopyranoside ester was prepared by the treatment of glucopyranoside with unimolar stearoy...

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Main Authors: Sanaullah, Abul F.M, Mohammed Mahbubul, Matin, Md. Rezaur, Rahman, S. M. Abdul, Nayeem
Format: Article
Language:English
Published: ACG Publications 2022
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Online Access:http://ir.unimas.my/id/eprint/38561/1/Acyl%20glucopyranosides%20-%20Copy.pdf
http://ir.unimas.my/id/eprint/38561/
https://www.acgpubs.org/doc/20220316132101120-OC-2201-2307.pdf
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Institution: Universiti Malaysia Sarawak
Language: English
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spelling my.unimas.ir.385612022-06-10T02:39:20Z http://ir.unimas.my/id/eprint/38561/ Acyl glucopyranosides : synthesis, PASS predication, antifungal activities and molecular docking Sanaullah, Abul F.M Mohammed Mahbubul, Matin Md. Rezaur, Rahman S. M. Abdul, Nayeem TP Chemical technology : Sugar esters (SEs) with fatty acyl chains showed diverse applications including antimicrobial inhibition against multidrug-resistant (MDR) microorganisms. Thus, fatty acid esters, especially 6-O-stearoyl glucopyranoside ester was prepared by the treatment of glucopyranoside with unimolar stearoyl chloride at low temperature. The 6- O-stearoyl ester thus obtained was further modified to four newer 2,3,4-O-acyl esters to incorporate decanoyl, lauroyl, palmitoyl, and benzoyl chains in the glucopyranoside skeleton. Prediction of activity spectrum for substances (PASS) analyses suggested that these fatty acid esters are more prone to fungal pathogens compared to bacterial pathogens. Guided by PASS analyses in vitro antifungal activities were screened against four fungal pathogens, which supported the PASS observation. To validate the findings molecular docking was conducted with lanosterol 14α-demethylase (CYP51), a significant fungal enzyme, which is the principal target of antifungal drugs. Corroboration of in vitro results with binding affinity revealed the possibility of glucopyranoside-based fatty acyl esters with stearoyl, decanoyl and lauroyl chains as highly potential compared to antifungal azole drugs. ACG Publications 2022 Article PeerReviewed text en http://ir.unimas.my/id/eprint/38561/1/Acyl%20glucopyranosides%20-%20Copy.pdf Sanaullah, Abul F.M and Mohammed Mahbubul, Matin and Md. Rezaur, Rahman and S. M. Abdul, Nayeem (2022) Acyl glucopyranosides : synthesis, PASS predication, antifungal activities and molecular docking. Organic Communications, 15 (1). pp. 32-43. ISSN 1307-6175 https://www.acgpubs.org/doc/20220316132101120-OC-2201-2307.pdf DOI: http://doi.org/10.25135/acg.oc.120.2201.2307
institution Universiti Malaysia Sarawak
building Centre for Academic Information Services (CAIS)
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaysia Sarawak
content_source UNIMAS Institutional Repository
url_provider http://ir.unimas.my/
language English
topic TP Chemical technology
spellingShingle TP Chemical technology
Sanaullah, Abul F.M
Mohammed Mahbubul, Matin
Md. Rezaur, Rahman
S. M. Abdul, Nayeem
Acyl glucopyranosides : synthesis, PASS predication, antifungal activities and molecular docking
description : Sugar esters (SEs) with fatty acyl chains showed diverse applications including antimicrobial inhibition against multidrug-resistant (MDR) microorganisms. Thus, fatty acid esters, especially 6-O-stearoyl glucopyranoside ester was prepared by the treatment of glucopyranoside with unimolar stearoyl chloride at low temperature. The 6- O-stearoyl ester thus obtained was further modified to four newer 2,3,4-O-acyl esters to incorporate decanoyl, lauroyl, palmitoyl, and benzoyl chains in the glucopyranoside skeleton. Prediction of activity spectrum for substances (PASS) analyses suggested that these fatty acid esters are more prone to fungal pathogens compared to bacterial pathogens. Guided by PASS analyses in vitro antifungal activities were screened against four fungal pathogens, which supported the PASS observation. To validate the findings molecular docking was conducted with lanosterol 14α-demethylase (CYP51), a significant fungal enzyme, which is the principal target of antifungal drugs. Corroboration of in vitro results with binding affinity revealed the possibility of glucopyranoside-based fatty acyl esters with stearoyl, decanoyl and lauroyl chains as highly potential compared to antifungal azole drugs.
format Article
author Sanaullah, Abul F.M
Mohammed Mahbubul, Matin
Md. Rezaur, Rahman
S. M. Abdul, Nayeem
author_facet Sanaullah, Abul F.M
Mohammed Mahbubul, Matin
Md. Rezaur, Rahman
S. M. Abdul, Nayeem
author_sort Sanaullah, Abul F.M
title Acyl glucopyranosides : synthesis, PASS predication, antifungal activities and molecular docking
title_short Acyl glucopyranosides : synthesis, PASS predication, antifungal activities and molecular docking
title_full Acyl glucopyranosides : synthesis, PASS predication, antifungal activities and molecular docking
title_fullStr Acyl glucopyranosides : synthesis, PASS predication, antifungal activities and molecular docking
title_full_unstemmed Acyl glucopyranosides : synthesis, PASS predication, antifungal activities and molecular docking
title_sort acyl glucopyranosides : synthesis, pass predication, antifungal activities and molecular docking
publisher ACG Publications
publishDate 2022
url http://ir.unimas.my/id/eprint/38561/1/Acyl%20glucopyranosides%20-%20Copy.pdf
http://ir.unimas.my/id/eprint/38561/
https://www.acgpubs.org/doc/20220316132101120-OC-2201-2307.pdf
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