Synthesis, spectroscopic characterization, molecular docking, and ADMET studies of mannopyranoside esters as antimicrobial agents

Matin, Mohammed Mahbubul; Hasan, Md. Saif; Uzzaman, Monir; Bhuiyan, M. M. H.; Kibria, Sayed M.; Hossain, Md. Emdad; Roshid, Mohammad Harun Or

doi:10.1016/j.molstruc.2020.128821

Cited by 42 publications

(39 citation statements)

References 35 publications

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“…Interestingly, the results as shown in Table 2, antifungal and anti-carcinogenic properties of uridine esters with saturated aliphatic chains (5, 7-12) were found more promising than the sulphonyl ester (6) or chloro-substituted benzoyl derivatives (13-15). These results are in agreement with our previous study for monosaccharide esters (Matin, Chakraborty, et al, 2020;Matin, Hasan, et al, 2020;.…”

Section: Computational-based Biological Activities: Passsupporting

confidence: 94%

“…All hetero atoms, inhibitors and water molecules were erased using PyMol (version 1.3) software packages. Energy minimization of the protein implemented by Swiss-Pdb viewer software (version 4.1.0) (Matin, Chakraborty, et al, 2020 ; Matin, Hasan, et al, 2020 ; Matin, Roshid, et al, 2020 ). The optimized structures were subjected for molecular docking study against 7BQY, CYP51A1 and 1R51 considering the protein as macromolecule and uridine esters as ligand.…”

Section: Methodsmentioning

confidence: 99%

“…Online computational approaches were made to predict absorption, distribution, metabolism, excretion and toxicity (ADMET) for 5′- O -(4- t -butylbenzoyl)uridine ( 4 ) and its 2′,3′-di- O -acyl derivatives 5 – 15 (Matin, Chakraborty, et al, 2020 ; Matin, Hasan, et al, 2020 ; Matin, Roshid, et al, 2020 ). The computational prediction of drug could avoid the tremendous cost and time associated with the in vivo experiments, and has attracted more and more attention.…”

Section: Methodsmentioning

confidence: 99%

“…However, investigations indicated that selective esterification (acylation) uridine ( 1 ) creates difficulties due to the presence of one 1° OH group, two 2° OH groups and a NH group. Hence, various methods like direct acylation (Matin, Bhattacharjee, et al, 2019 ; Matin, Bhuiyan, et al, 2019 ; Matin, Chakraborty, et al, 2020 ; Matin, Hasan, et al, 2020 ; Matin, Roshid, et al, 2020 ), dibutyltin oxide (DBTO) method (Kabir, Matin, & Kawsar, 1998 ; Kabir, Matin, Kawsar, & Anwar, 1998 ; Kabir, Matin, Mridha, et al, 1998 ; Kabir et al, 1997 , 1998a , 1998 b), coupling technique (Steglich esterification) (Clayden et al, 2012 ), protection–deprotection (Matin et al, 2017 ) and enzymatic method (Du et al, 2018 ) were reported. Among these methods, direct method generally furnished 5′- O -substituted esters (Kabir, Matin, & Kawsar, 1998 ; Kabir, Matin, Kawsar, & Anwar, 1998 ; Kabir, Matin, Mridha, et al, 1998 ; Kabir et al, 1997 , 1998a , 1998 b) whereas DBTOmethod gave 3′- O -substituted products (Kabir, Matin, & Kawsar, 1998 ; Kabir, Matin, Kawsar, & Anwar, 1998 ; Kabir, Matin, Mridha, et al, 1998 ; Kabir et al, 1997 , 1998a , 1998 b, 2002 ).…”

Section: Introductionmentioning

confidence: 99%

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In vitro antimicrobial, physicochemical, pharmacokinetics and molecular docking studies of benzoyl uridine esters against SARS-CoV-2 main protease

Matin

Uzzaman

Chowdhury

et al. 2020

Journal of Biomolecular Structure and Dynamics

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Different esters were found potential against microorganisms, and could be a better choice to solve the multidrug resistant (MDR) pathogenic global issue due to their improved biological and pharmacokinetic properties. In this view, several 4- t -butylbenzoyl uridine esters 4–15 with different aliphatic and aromatic groups were synthesized for antimicrobial, physicochemical and biological studies. In vitro antimicrobial tests against nine bacteria and three fungi along with prediction of activity spectra for substances (PASS) indicated promising antifungal functionality of these uridine esters compared to the antibacterial activities. In support of this observation their cytotoxicity and molecular docking studies have been performed against lanosterol 14α-demethylase (CYP51A1) and Aspergillus flavus (1R51). Significant binding affinities were observed against SARS-CoV-2 main protease (7BQY) considering hydroxychloroquine (HCQ) as standard. ADMET predictions were investigated to evaluate their absorption, metabolism and toxic properties. Most of the uridine esters showed better results than that of the HCQ. Overall, the present study might be useful for the development of uridine-based novel MDR antimicrobial and COVID-19 drugs.

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Section: Computational-based Biological Activities: Passsupporting

confidence: 94%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

In vitro antimicrobial, physicochemical, pharmacokinetics and molecular docking studies of benzoyl uridine esters against SARS-CoV-2 main protease

Matin

Uzzaman

Chowdhury

et al. 2020

Journal of Biomolecular Structure and Dynamics

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“…Most of the antifungal and antiprotozoal drugs are designed through targeting sterol 14α-demethylase (CYP51) inhibition [ 34 ] such as azoles (fluconazole; VNI; Fig. 2 ).…”

Section: Introductionmentioning

confidence: 99%

Novel mannopyranoside esters as sterol 14α-demethylase inhibitors: Synthesis, PASS predication, molecular docking, and pharmacokinetic studies

Matin

Chakraborty

Alam

et al. 2020

Carbohydrate Research

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Direct unimolar one-step valeroylation of methyl α- d -mannopyranoside (MDM) furnished mainly 6- O -valeroate. However, similar reaction catalyzed by DMAP resulted 3,6-di- O -valeroate (21%) and 6- O -valeroate (47%) indicating reactivity sequence as 6-OH>3-OH>2-OH,4-OH. To get potential antimicrobial agents, 6- O -valeroate was converted into four 2,3,4-di- O -acyl esters, and 3,6-di- O -valeroate was converted into 2,4-di- O -acetate. Direct tetra- O -valeroylation of MDM gave a mixture of 2,3,4,6-tetra- O -valeroate and 2,3,6-tri- O -valeroate indicating that the C2–OH is more reactive than the equatorial C4–OH. The activity spectra analysis along with in vitro antimicrobial evaluation clearly indicated that these novel MDM esters had better antifungal activities over antibacterial agents. In this connection, molecular docking indicated that these MDM esters acted as competitive inhibitors of sterol 14α-demethylase (CYP51), an essential enzyme for clinical target to cure several infectious diseases. Furthermore, pharmacokinetic studies revealed that these MDM esters may be worth considering as potent candidates for oral and topical administration. Structure activity relationship (SAR) affirmed that saturated valeric chain (C5) in combination with caprylic (C8) chains was more promising CYP51 inhibitor over conventional antifungal antibiotics.

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Esterification of sugars and polyphenols with fatty acids: techniques, bioactivities, and applications

Marathe

Dedhia

2022

Current Opinion in Food Science

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Synthesis, spectroscopic characterization, molecular docking, and ADMET studies of mannopyranoside esters as antimicrobial agents

Cited by 42 publications

References 35 publications

In vitro antimicrobial, physicochemical, pharmacokinetics and molecular docking studies of benzoyl uridine esters against SARS-CoV-2 main protease

In vitro antimicrobial, physicochemical, pharmacokinetics and molecular docking studies of benzoyl uridine esters against SARS-CoV-2 main protease

Novel mannopyranoside esters as sterol 14α-demethylase inhibitors: Synthesis, PASS predication, molecular docking, and pharmacokinetic studies

Esterification of sugars and polyphenols with fatty acids: techniques, bioactivities, and applications

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