Molecules (Basel, Switzerland), 2021-11, Vol.26 (22), p.7016
2021
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- Autor(en) / Beteiligte
- Titel
- Synthesis, Antimicrobial, Anticancer, PASS, Molecular Docking, Molecular Dynamic Simulations & Pharmacokinetic Predictions of Some Methyl β-D-Galactopyranoside Analogs
- Ist Teil von
- Molecules (Basel, Switzerland), 2021-11, Vol.26 (22), p.7016
- Ort / Verlag
- Switzerland: MDPI AG
- Erscheinungsjahr
- 2021
- Quelle
- MEDLINE
- Beschreibungen/Notizen
- A series of methyl β-D-galactopyranoside (MGP, ) analogs were selectively acylated with cinnamoyl chloride in anhydrous , -dimethylformamide/triethylamine to yield 6- -substitution products, which was subsequently converted into 2,3,4-tri- -acyl analogs with different acyl halides. Analysis of the physicochemical, elemental, and spectroscopic data of these analogs revealed their chemical structures. In vitro antimicrobial testing against five bacteria and two fungi and the prediction of activity spectra for substances (PASS) showed promising antifungal functionality comparing to their antibacterial activities. Minimum inhibition concentration (MIC) and minimum bactericidal concentration (MBC) tests were conducted for four compounds ( , , , and ) based on their activity. MTT assay showed low antiproliferative activity of compound against Ehrlich's ascites carcinoma (EAC) cells with an IC value of 2961.06 µg/mL. Density functional theory (DFT) was used to calculate the thermodynamic and physicochemical properties whereas molecular docking identified potential inhibitors of the SARS-CoV-2 main protease (6Y84). A 150-ns molecular dynamics simulation study revealed the stable conformation and binding patterns in a stimulating environment. In-silico ADMET study suggested all the designed molecules to be non-carcinogenic, with low aquatic and non-aquatic toxicity. In summary, all these antimicrobial, anticancer and in silico studies revealed that newly synthesized MGP analogs possess promising antiviral activity, to serve as a therapeutic target for COVID-19.
- Sprache
- Englisch
- Identifikatoren
- ISSN: 1420-3049eISSN: 1420-3049DOI: 10.3390/molecules26227016Titel-ID: cdi_doaj_primary_oai_doaj_org_article_b8c474d5693f443ea778beb6a7bcf6a7
- Format
- –
- Schlagworte
- Analogs, Animals, Anti-Infective Agents - chemical synthesis, Anti-Infective Agents - chemistry, Anti-Infective Agents - pharmacokinetics, Anti-Infective Agents - pharmacology, Antibacterial activity, Antifungal Agents - chemistry, Antifungal Agents - pharmacokinetics, Antifungal Agents - pharmacology, Antimicrobial agents, Antineoplastic Agents - chemical synthesis, Antineoplastic Agents - chemistry, Antineoplastic Agents - pharmacokinetics, Antineoplastic Agents - pharmacology, Antiviral activity, Antiviral Agents - chemical synthesis, Antiviral Agents - chemistry, Antiviral Agents - pharmacokinetics, Antiviral Agents - pharmacology, Ascites, Biological activity, Cancer, Carbohydrates, Carcinogens, Cell Line, Tumor, Chloride, Conformation, Coronavirus 3C Proteases - chemistry, Coronaviruses, COVID-19, COVID-19 Drug Treatment, Density functional theory, Fungicides, Galactose - analogs & derivatives, Galactose - chemistry, Galactose - pharmacokinetics, Galactose - pharmacology, Genomes, Gram-positive bacteria, Gram-Positive Bacteria - drug effects, Halides, Hydrocarbons, methyl β-D-galactopyranoside, Mice, Microbial Sensitivity Tests, Minimum inhibitory concentration, Molecular docking, Molecular Docking Simulation, Molecular dynamics, Molecular Dynamics Simulation, PASS, Pharmacokinetic, Pharmacokinetics, Physicochemical properties, Proteins, SARS-CoV-2 - enzymology, Severe acute respiratory syndrome coronavirus 2, Static Electricity, synthesis, Thermodynamics, Toxicity, Triethylamine