Synthesis, Antimicrobial, Anticancer, PASS, Molecular Docking, Molecular Dynamic Simulations &amp; Pharmacokinetic Predictions of Some Methyl β-D-Galactopyranoside Analogs

Amin, Md Ruhul; Yasmin, Farhana; Hosen, Anowar; Dey, Sujan; Mahmud, Shafi; Saleh, Md. Abu; Emran, Talha Bin; Hasan, Imtiaj; Fujii, Yuki; Yamada, Masakazu; Ozeki, Yasuhiro; Kawsar, Sarkar M. A.

doi:10.3390/molecules26227016

Cited by 38 publications

(10 citation statements)

References 56 publications

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“…Methylgalactoside was recently reported to possess potential antimicrobial activities against Bacillus subtilis, Escherichia coli, and in-silico ability to inhibit SAR-CoV-2 by binding proteases 39 . Another study by Amin et al 40 revealed that acylation of beta-D-galactopyranoside with different acyl halides resulted in methyl esters with antifungal, antibacterial and anticancer activities. Modi ed beta-D-galactopyranoside containing tri-and tetravalent glycoclusters inhibited Pseudomonas aeruginosa d-galactose-speci c lectin PA-IL (LecA); a virulence factor that is cytotoxic and also aids adhesion to host's cells 41 .…”

Section: Discussionmentioning

confidence: 99%

Deciphering the effects of co-culturing on the metabolite profiles of Ligilactobacillus reuteri ZJ625 and Limosilactobacillus salivarius ZJ614 using untargeted metabolomics

Kwoji

Okpeku

Aiyegoro

et al. 2022

Preprint

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Ligilactobacillus reuteri ZJ625 (ZJ625) and Limosilactobacillus salivarius ZJ614 (ZJ614) are important lactic acid bacteria with the potential for use as probiotics. To better understand the mechanisms of cell-to-cell interactions between ZJ625 and ZJ614 and elucidate their probiotics potentials, we studied the effects of co-culturing in defined media on the metabolomes. The strains were cultured singly (L. reuteri ZJ625 or L. salivarius ZJ614) and in co-cultures (L. reuteri ZJ625 plus L. salivarius ZJ614) and harvested at the mid-exponential phase. Single-phase extraction method was used to extract the metabolites from pre-weighed cells for the two-dimensional gas-column time-of-flight-mass spectrometry (GCxGC- TOFMS) analysis. The data was obtained using a Leco corporation ChromaTOF software and exported for statistical, pathway enrichment, and impact analyses using MetaboAnalyst 5.0. Principal component analysis (PCA) indicated an overlap of the samples from the two batches, indicating no significant batch effect. The data was then analyzed using the group allocations. This study revealed 1388 metabolites from L. reuteri ZJ625 and L. salivarius ZJ614 single and co-cultures in defined media, of which 18.87% were significantly expressed (p < 0.05). Of the significantly expressed metabolites, 28% DEMs were identified (p < 0.05, VIP > 1), of which 51.3% were annotated while 48.6% are currently not annotated in the databases. The whole metabolome of the strains in single and co-cultures revealed the expression of several important metabolites, including arabinofuranose, methyl-galactoside, N-acetyl-glutamic acid, phosphoric acid, decanoic acid, metyrosine, and deoxypentafuranose which play roles in different metabolic and biosynthetic pathways, hence confirming the probiotic potential as single- or multi-strain cultures. The co-culturing of the strains influenced the metabolites profiles of the strains showing additive and regulatory differential metabolites expressions. Pathway enrichment and impact analyses revealed the association of the differentially expressed metabolites with functional effects such as antihypertensive, antimicrobial, and microbiome stimulation.

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Section: Discussionmentioning

confidence: 99%

Deciphering the effects of co-culturing on the metabolite profiles of Ligilactobacillus reuteri ZJ625 and Limosilactobacillus salivarius ZJ614 using untargeted metabolomics

Kwoji

Okpeku

Aiyegoro

et al. 2022

Preprint

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“…Based on a strong literature report, diverse biologically effective molecules have aromatic rings, heteroaromatic rings, and aliphatic chain substituents (Amin et al 2021;Alam et al 2021aAlam et al , 2022Bulbul et al 2021a;Farhana et al 2021a;Hosen et al 2022;Kawsar et al , 2021aKawsar et al , 2022aMaowa et al 2021). It was found that benzene ring, substituted benzene ring, nitro, sulfur, and halogen-based groups are very potent to enhance the biochemical and biological activity of the carbohydratebased compound (Rana et al 2020;Islam et al 2022;Nasrin et al 2022;Kawsar et al 2021bKawsar et al , 2022bHosen et al 2021;Tahmida et al 2021).…”

Section: Introductionmentioning

confidence: 99%

Investigation of Structural, Physicochemical, Pharmacokinetics, PASS Prediction, and Molecular Docking Analysis of Methyl 6-O-Myristoyl-α-D -Glucopyranoside Derivatives against SARS-CoV-2

Uddin¹,

Hosen²,

Ozeki³

et al. 2022

Philipp J Sci

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Monosaccharide derivatives are of importance in the field of carbohydrate chemistry because of their effectiveness in the synthesis of biologically active products. As a consequence, the chemistry and biochemistry of carbohydrate derivatives are an essential part of biochemical and medicinal research. In this work, we have explored the speciation of acylated methyl 6-O-myristoyl-α-D-glucopyranoside derivatives (2−9) to find the pharmacodynamics, toxicity profiles, and biological activities by using ADMET studies. PASS prediction also indicated that these acylated derivatives (2−9) are more potent as anticarcinogenic agents than as antioxidant agents. Quantum mechanical study employing density functional theory with B3LYP/6-31G(d,p) for investigating the enthalpies (ΔH), Gibbs free energies (ΔG), entropies (ΔS), and molecular orbital (HOMO−LUMO gap, hardness, softness, chemical potential, and electrophilicity index), dipole moment and natural bond orbital revealed that these derivatives are thermodynamically stable. The molecular docking study revealed that ivermectin has the highest binding affinity (−8.1 kcal mol−1) and, among the tested compounds, 2 and 3 (−5.7 kcal mol−1) showed the highest binding affinity, followed by 4 and 5 (−5.5 kcal mol−1). These results of acylated derivatives (2−9) could be useful for the development of drugs.

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“…They are the source of the metabolic energy supply and are also useful for the fine-tuning of cell-cell interactions and other crucial processes (Varki 1993;Seeberger and Werz 2007). It was found from the literature survey that a large number of biologically active compounds also possess aromatic, heteroaromatic, and acyl substituents (Amin et al 2021(Amin et al , 2022Lepenies et al 2010;Rana et al 2020;Bulbul et al 2021a, b;Arifuzzaman et al 2018;Maowa et al 2021a;Alam et al 2021a). The benzene, substituted benzene, and also nitrogen, sulfur, and halogen-containing substituents are known to enhance the biological activity of the parent compound (Rana et al 2021;Farhana et al 2021a;Devi et al 2019;Alam et al 2021b).…”

Section: Introductionmentioning

confidence: 99%

Physicochemical, ADMET, and Molecular Dynamics Simulations against Bacillus subtilis HmoB for Antibacterial Potentiality of Methyl 𝜶-D-glucopyranoside Derivatives

Kawsar¹,

Ouassaf²,

Hosen³

et al. 2022

Philipp J Sci

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Monosaccharide derivatives are important in the field of biological chemistry because of their effectiveness against bacterial pathogens, as well as to synthesize biologically active products. Designing novel antibacterial agents with new structural scaffolds that combat drug-resistant pathogens is an urgent task. Therefore, the present study targets to identify the binding affinity of a series of previously synthesized methyl α-D-glucopyranoside (MDGP) derivatives with molecular docking and molecular dynamics along with their physicochemical and pharmacokinetic properties. The density functional theory (DFT) calculations were executed for the MDGP derivatives using B3LYP/3–21G, which was also used for the illustration of partial atomic charge and molecular electrostatic potential (MEP). The designed derivatives were evaluated for their antimicrobial activities through a molecular docking study with Bacillus subtilis HmoB heme oxygenase by AutoDock. The binding affinity from molecular docking score for Derivatives 8–10 (–10.11, –10.41, and –12.20 kcal/mol) against the bacterial pathogen B. subtilis HmoB gives the evidence for being potential antimicrobial agents. Furthermore, a 100-ns molecular dynamics simulation study revealed the stable conformation and binding pattern of MDGP derivatives in a stimulating environment. In addition, in silico ADMET study, toxicity and bioactivity parameters were calculated for MDGP and its derivatives for evaluating their safe uses and predicting the pre-study of clinical phases as drug molecules by using software and an online database. Our designed new MDGP derivatives might be exhibited as first-rate and superior pharmacological profiles in medicinal chemistry, which may give the leading information for further studies about their biological activity.

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Synthesis, Antimicrobial, Anticancer, PASS, Molecular Docking, Molecular Dynamic Simulations & Pharmacokinetic Predictions of Some Methyl β-D-Galactopyranoside Analogs

Cited by 38 publications

References 56 publications

Deciphering the effects of co-culturing on the metabolite profiles of Ligilactobacillus reuteri ZJ625 and Limosilactobacillus salivarius ZJ614 using untargeted metabolomics

Deciphering the effects of co-culturing on the metabolite profiles of Ligilactobacillus reuteri ZJ625 and Limosilactobacillus salivarius ZJ614 using untargeted metabolomics

Investigation of Structural, Physicochemical, Pharmacokinetics, PASS Prediction, and Molecular Docking Analysis of Methyl 6-O-Myristoyl-α-D -Glucopyranoside Derivatives against SARS-CoV-2

Physicochemical, ADMET, and Molecular Dynamics Simulations against Bacillus subtilis HmoB for Antibacterial Potentiality of Methyl 𝜶-D-glucopyranoside Derivatives

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