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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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 |
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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 |
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: 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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