FTIR, 1H-/13C-NMR spectral characterization, antimicrobial, anticancer, antioxidant, anti-inflammatory, PASS, SAR, and in silico properties of methyl α-D-glucopyranoside derivatives
A novel series of biologically active derivatives based on methyl α-D-glucopyranoside (MGP) has been developed, comprising 6-O-monosubstituted MGP derivatives obtained from methyl α-D-glucopyranoside. These derivatives were transformed into 2,3,4-tri-O-acyl MGP derivatives, incorporating diverse fun...
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Elsevier
2024-12-01
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| Series: | Chemical Physics Impact |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2667022424002974 |
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| author | Jannatul Ferdous Faizan Abul Qais Ferdausi Ali Debashis Palit Imtiaj Hasan Sarkar M.A. Kawsar |
| author_facet | Jannatul Ferdous Faizan Abul Qais Ferdausi Ali Debashis Palit Imtiaj Hasan Sarkar M.A. Kawsar |
| author_sort | Jannatul Ferdous |
| collection | DOAJ |
| description | A novel series of biologically active derivatives based on methyl α-D-glucopyranoside (MGP) has been developed, comprising 6-O-monosubstituted MGP derivatives obtained from methyl α-D-glucopyranoside. These derivatives were transformed into 2,3,4-tri-O-acyl MGP derivatives, incorporating diverse functionalities within a single molecular framework, aimed at producing new products for antimicrobial studies. All synthesized compounds were identified through spectral analyses (FTIR, 1H-NMR, and 13C-NMR) and elemental analysis. Antimicrobial in vitro testing revealed that these MGP derivatives have notable efficacy against various pathogenic microorganisms, along with the prediction of activity spectra for substances (PASS). Compounds 2 and 7 exhibited the highest inhibitory activity against Bacillus subtilis and Escherichia coli, with minimum inhibitory concentration (MIC) values ranging from 0.25 to 64.0 µg/mL and minimum bactericidal concentration (MBC) values ranging from 8.0 to 128.0 µg/mL. Moreover, these compounds demonstrated significant antioxidant properties compared with those of standard antioxidants according to the results of the DPPH free radical scavenging assay. An evaluation of the growth and proliferation of Ehrlich ascites carcinoma (EAC) cells revealed moderate cell growth inhibition by compounds 5 and 6, with IC50 values of 5958.54 and 5437.17 µg/mL, respectively, as determined via an MTT colorimetric assay. An analysis of the structure-activity relationship (SAR) revealed that the combination of the (p-CH3.C6H4CO-) and halo-aromatic [3-Cl.C6H4CO-] chains with sugar had the highest efficiency in pathogens. Molecular docking studies using AutoDock Vina highlighted compound 7 as a promising inhibitor of the carbapenemase, OmpF, and HmoB proteins, with binding energies of -11.53 kcal/mol, -2.26 kcal/mol, and -30.75 kcal/mol, respectively. A 100-ns molecular dynamics simulation study demonstrated the validity of stable conformation and binding patterns in a stimulating environment. Pharmacokinetic characterization and ADMET predictions indicated favorable drug-like properties. These substantial in vitro and in silico studies demonstrate the importance of additional investigations to confirm the efficacy of MGP derivatives as antimicrobial agents. |
| format | Article |
| id | doaj-art-a57cf5571ef04d4f9a9aec7d781ba95b |
| institution | Kabale University |
| issn | 2667-0224 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Elsevier |
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| series | Chemical Physics Impact |
| spelling | doaj-art-a57cf5571ef04d4f9a9aec7d781ba95b2024-11-27T05:03:46ZengElsevierChemical Physics Impact2667-02242024-12-019100753FTIR, 1H-/13C-NMR spectral characterization, antimicrobial, anticancer, antioxidant, anti-inflammatory, PASS, SAR, and in silico properties of methyl α-D-glucopyranoside derivativesJannatul Ferdous0Faizan Abul Qais1Ferdausi Ali2Debashis Palit3Imtiaj Hasan4Sarkar M.A. Kawsar5Laboratory of Carbohydrate and Nucleoside Chemistry, Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong 4331, BangladeshDepartment of Agricultural Microbiology, Faculty of Agricultural Sciences, Aligarh Muslim University, Aligarh 202002, IndiaDepartment of Microbiology, Faculty of Biological Science, University of Chittagong, Chittagong 4331, BangladeshLaboratory of Carbohydrate and Nucleoside Chemistry, Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong 4331, BangladeshDepartment of Microbiology, University of Rajshahi, Rajshahi 6205, Bangladesh; Department of Biochemistry and Molecular Biology, University of Rajshahi, Rajshahi 6205, BangladeshLaboratory of Carbohydrate and Nucleoside Chemistry, Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong 4331, Bangladesh; Corresponding author.A novel series of biologically active derivatives based on methyl α-D-glucopyranoside (MGP) has been developed, comprising 6-O-monosubstituted MGP derivatives obtained from methyl α-D-glucopyranoside. These derivatives were transformed into 2,3,4-tri-O-acyl MGP derivatives, incorporating diverse functionalities within a single molecular framework, aimed at producing new products for antimicrobial studies. All synthesized compounds were identified through spectral analyses (FTIR, 1H-NMR, and 13C-NMR) and elemental analysis. Antimicrobial in vitro testing revealed that these MGP derivatives have notable efficacy against various pathogenic microorganisms, along with the prediction of activity spectra for substances (PASS). Compounds 2 and 7 exhibited the highest inhibitory activity against Bacillus subtilis and Escherichia coli, with minimum inhibitory concentration (MIC) values ranging from 0.25 to 64.0 µg/mL and minimum bactericidal concentration (MBC) values ranging from 8.0 to 128.0 µg/mL. Moreover, these compounds demonstrated significant antioxidant properties compared with those of standard antioxidants according to the results of the DPPH free radical scavenging assay. An evaluation of the growth and proliferation of Ehrlich ascites carcinoma (EAC) cells revealed moderate cell growth inhibition by compounds 5 and 6, with IC50 values of 5958.54 and 5437.17 µg/mL, respectively, as determined via an MTT colorimetric assay. An analysis of the structure-activity relationship (SAR) revealed that the combination of the (p-CH3.C6H4CO-) and halo-aromatic [3-Cl.C6H4CO-] chains with sugar had the highest efficiency in pathogens. Molecular docking studies using AutoDock Vina highlighted compound 7 as a promising inhibitor of the carbapenemase, OmpF, and HmoB proteins, with binding energies of -11.53 kcal/mol, -2.26 kcal/mol, and -30.75 kcal/mol, respectively. A 100-ns molecular dynamics simulation study demonstrated the validity of stable conformation and binding patterns in a stimulating environment. Pharmacokinetic characterization and ADMET predictions indicated favorable drug-like properties. These substantial in vitro and in silico studies demonstrate the importance of additional investigations to confirm the efficacy of MGP derivatives as antimicrobial agents.http://www.sciencedirect.com/science/article/pii/S2667022424002974FTIR-1H-/13C-NMR spectraMethyl α-D-glucopyranoside (MGP)AntioxidantAnticancerIn silico |
| spellingShingle | Jannatul Ferdous Faizan Abul Qais Ferdausi Ali Debashis Palit Imtiaj Hasan Sarkar M.A. Kawsar FTIR, 1H-/13C-NMR spectral characterization, antimicrobial, anticancer, antioxidant, anti-inflammatory, PASS, SAR, and in silico properties of methyl α-D-glucopyranoside derivatives Chemical Physics Impact FTIR-1H-/13C-NMR spectra Methyl α-D-glucopyranoside (MGP) Antioxidant Anticancer In silico |
| title | FTIR, 1H-/13C-NMR spectral characterization, antimicrobial, anticancer, antioxidant, anti-inflammatory, PASS, SAR, and in silico properties of methyl α-D-glucopyranoside derivatives |
| title_full | FTIR, 1H-/13C-NMR spectral characterization, antimicrobial, anticancer, antioxidant, anti-inflammatory, PASS, SAR, and in silico properties of methyl α-D-glucopyranoside derivatives |
| title_fullStr | FTIR, 1H-/13C-NMR spectral characterization, antimicrobial, anticancer, antioxidant, anti-inflammatory, PASS, SAR, and in silico properties of methyl α-D-glucopyranoside derivatives |
| title_full_unstemmed | FTIR, 1H-/13C-NMR spectral characterization, antimicrobial, anticancer, antioxidant, anti-inflammatory, PASS, SAR, and in silico properties of methyl α-D-glucopyranoside derivatives |
| title_short | FTIR, 1H-/13C-NMR spectral characterization, antimicrobial, anticancer, antioxidant, anti-inflammatory, PASS, SAR, and in silico properties of methyl α-D-glucopyranoside derivatives |
| title_sort | ftir 1h 13c nmr spectral characterization antimicrobial anticancer antioxidant anti inflammatory pass sar and in silico properties of methyl α d glucopyranoside derivatives |
| topic | FTIR-1H-/13C-NMR spectra Methyl α-D-glucopyranoside (MGP) Antioxidant Anticancer In silico |
| url | http://www.sciencedirect.com/science/article/pii/S2667022424002974 |
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