Stearoyl Glucopyranosides: Selective Synthesis, PASS Analysis, In Vitro Antimicrobial, and SAR Study

Sanaullah, A.F.M.; Bhuiyan, M. M. H.; Matin, Mohammed Mahbubul

doi:10.21608/ejchem.2022.111831.5080

Cited by 4 publications

(4 citation statements)

References 20 publications

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“…Antibacterial activities. The disc diffusion method [40] was used for the antibacterial activity test against one Gram-positive (Staphylococcus aureus) and two Gram-negative (Escherichia coli and Pseudomonas aeruginosa) bacteria. The antibacterial results are reported as the diameter of the inhibition zone (in mm; Table 3; Figure 4a and Figures S53-S55).…”

Section: In Vitro Antimicrobial Activities Of Mdg Esters 4-12mentioning

confidence: 99%

“…Initially, a 2% solution of each compound was prepared in DMF (dimethylformamide). The diameter of the zone of inhibition against these bacterial organisms was determined following the disc diffusion method [40]. The results are compared with the standard drug tetracycline (Square Pharmaceuticals Ltd., Bangladesh).…”

Section: In Vitro Antimicrobial Potentiality Evaluationmentioning

confidence: 99%

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Novel Galactopyranoside Esters: Synthesis, Mechanism, In Vitro Antimicrobial Evaluation and Molecular Docking Studies

et al. 2022

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One-step direct unimolar valeroylation of methyl α-D-galactopyranoside (MDG) mainly furnished the corresponding 6-O-valeroate. However, DMAP catalyzed a similar reaction that produced 2,6-di-O-valeroate and 6-O-valeroate, with the reactivity sequence as 6-OH > 2-OH > 3-OH,4-OH. To obtain novel antimicrobial agents, 6-O- and 2,6-di-O-valeroate were converted into several 2,3,4-tri-O- and 3,4-di-O-acyl esters, respectively, with other acylating agents in good yields. The PASS activity spectra along with in vitro antimicrobial evaluation clearly indicated that these MDG esters had better antifungal activities than antibacterial agents. To rationalize higher antifungal potentiality, molecular docking was conducted with sterol 14α-demethylase (PDB ID: 4UYL, Aspergillus fumigatus), which clearly supported the in vitro antifungal results. In particular, MDG ester 7–12 showed higher binding energy than the antifungal drug, fluconazole. Additionally, these compounds were found to have more promising binding energy with the SARS-CoV-2 main protease (6LU7) than tetracycline, fluconazole, and native inhibitor N3. Detailed investigation of Ki values, absorption, distribution, metabolism, excretion, and toxicity (ADMET), and the drug-likeness profile indicated that most of these compounds satisfy the drug-likeness evaluation, bioavailability, and safety tests, and hence, these synthetic novel MDG esters could be new antifungal and antiviral drugs.

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Section: In Vitro Antimicrobial Activities Of Mdg Esters 4-12mentioning

confidence: 99%

Section: In Vitro Antimicrobial Potentiality Evaluationmentioning

confidence: 99%

Novel Galactopyranoside Esters: Synthesis, Mechanism, In Vitro Antimicrobial Evaluation and Molecular Docking Studies

et al. 2022

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“…The use of synthetic SFAE, especially those enzymatically prepared monoesters, has been extensively investigated as antimicrobials [16]. Sucrose monolaurate and sucrose monocaprate, in particular, have been shown to inhibit the growth of several Gram-positive bacteria [5].…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of Mannopyranoside-Based Fatty Acyl Esters: Effects of Acyl Groups on Antimicrobial Activities

Rahaman,

Rahman,

Hasnain

et al. 2023

Preprint

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The approval of sucrose fatty acid esters (SFAEs) as food additives/preservatives has triggered enormous interest in discovering new applications for these materials. Accordingly, many researchers reported that SFAEs consist of various sugar moieties, and hydrophobic side chains are highly active against certain fungal species. The combination of chain length and site of acylation is crucial in endowing the SFAE with high antimicrobial potency against Aspergillus species. Following several important studies, we herein present the synthesis and an assessment of the effects of acylation site and chain length (i.e., C-6 vs. C-2, C-3, C-4, and long-chain vs. short-chain) on the antimicrobial activity of mannopyranoside fatty acid esters. In vitro tests revealed that the fatty acid chain length in mannopyranoside esters significantly affects the antifungal activity where C12 chains are more potent against Aspergillus species. In terms of acylation site, mannopyranoside esters with a C8 chain substituted at the C-6 position are more active in antifungal inhibition. Molecular docking also revealed that these mannopyranoside esters had comparatively better stable binding energy, and hence better inhibition, with the fungal enzymes lanosterol 14-alpha-demethylase (3LD6), urate oxidase (1R51), and glucoamylase (1KUL) than the standard antifungal drug fluconazole. Additionally, the thermodynamic, orbital, drug-likeness, and safety profiles of these mannopyranoside esters were calculated and discussed, along with the structure-activity relationships (SAR). This study thus highlights the importance of the acylation site and lipid-like fatty acid chain length that govern the antimicrobial activity of mannopyranoside-based SFAE.

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“…Considering the improved yield and regioselectivity [30], direct acylation method was used for protected D-glucofuranose in the current study. Synthetic SEs-protected glucose esters have been discovered to be suited to boost therapeutic characteristics in hyperproliferative and inflammatory drugs and open the door to the synthesis of newer bioactive compounds by regulating hydrophobic alkyl chains [31][32][33][34]. For instance, it has been discovered that 3-O-acyl glucofuranoses (1a-c; Figure 1) significantly regulate unchecked cell development in erythroid tumor cells [35].…”

mentioning

confidence: 99%

1,2-O-Isopropylidene-3-O-butylglucofuranose-derived Ester, and Ether: Synthesis, Characterization, and Antimicrobial Study

Anisa

Islam

Matin

2023

Orbital: Electron. J. Chem.

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Sugar-fatty acid esters (SFAEs, especially sucrose- and glucose-based ones) have dominated the chemical industries for more than 50 years. In comparison to other carbohydrate products, SFAEs serve essential roles in a variety of industries, including the food, pharmaceutical, and cosmetic industries. In this context, the 6-O-hexanoyl ester of 3-O-butyl-1,2-O-isopropylidene-α-D-glucofuranose was synthesized from commercially available D-glucose in a few steps. For a comparative biological study, the 5,6-di-O-benzyl ether of 3-O-butyl-1,2-O-isopropylidene-α-D-glucofuranose was also prepared and characterized. An in vitro antimicrobial test of all the ester and ether compounds indicated that these compounds are more susceptible to fungi than bacteria. Also, they have more potential for A. niger than A. flavus. According to Prediction of Spectra for Substances (PASS), the chemicals found in the current investigation have a variety of potential biological functions.

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Stearoyl Glucopyranosides: Selective Synthesis, PASS Analysis, In Vitro Antimicrobial, and SAR Study

Cited by 4 publications

References 20 publications

Novel Galactopyranoside Esters: Synthesis, Mechanism, In Vitro Antimicrobial Evaluation and Molecular Docking Studies

Novel Galactopyranoside Esters: Synthesis, Mechanism, In Vitro Antimicrobial Evaluation and Molecular Docking Studies

Efficient Synthesis of Mannopyranoside-Based Fatty Acyl Esters: Effects of Acyl Groups on Antimicrobial Activities

1,2-O-Isopropylidene-3-O-butylglucofuranose-derived Ester, and Ether: Synthesis, Characterization, and Antimicrobial Study

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