Synthesis, in vitro enzyme kinetics and molecular docking studies of the 2-formylphenyl sulfonates and their hydrazone derivatives as potential anti-diabetic and anti-inflammatory agents
The in vitro anti-diabetes and anti-inflammatory inhibitory activities of the synthesized 2-formylphenyl sulfonates and their hydrazone derivatives were evaluated through enzymatic assays as potential α-glucosidase and lipoxygenase (LOX-15) inhibitors. The preliminary inhibitory results obtained, re...
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| Format: | Article |
| Language: | English |
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Elsevier
2024-01-01
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| Series: | Results in Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715624001498 |
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| author | Emmanuel N. Agbo Redolf S. Segodi N.J. Gumede Kgomotso W. Poopedi Tlabo C. Leboho W. Nxumalo |
| author_facet | Emmanuel N. Agbo Redolf S. Segodi N.J. Gumede Kgomotso W. Poopedi Tlabo C. Leboho W. Nxumalo |
| author_sort | Emmanuel N. Agbo |
| collection | DOAJ |
| description | The in vitro anti-diabetes and anti-inflammatory inhibitory activities of the synthesized 2-formylphenyl sulfonates and their hydrazone derivatives were evaluated through enzymatic assays as potential α-glucosidase and lipoxygenase (LOX-15) inhibitors. The preliminary inhibitory results obtained, revealed that the prepared compounds are good inhibitors of α-glucosidase as compared to lipoxygenase (LOX-15). Compounds 2 g and 3 h were found to exhibit significant inhibitory activities against α-glucosidase with IC50 values of 3.1 µM and 2.6 µM, respectively. Moderate inhibitory activity was also observed for compound 3a (IC50 = 7.3 µM) against this enzyme. Enzyme kinetics studies of the most active compound (3 h) suggested a mixed mode of inhibition for this compound against α-glucosidase. The molecular docking and molecular dynamics simulation of compounds 2 g, 3a and 3 h into the active sites of α-glucosidase were used to predict the binding modes and structure activity relationship for these compounds. The molecular dynamics simulation demonstrated that compound 3 h significant inhibitory activity is due to its ability to bind to both the catalytic and secondary sites of the enzyme. |
| first_indexed | 2024-04-24T19:48:41Z |
| format | Article |
| id | doaj.art-a01763677f1b4cf39136a1ccaa017fd4 |
| institution | Directory Open Access Journal |
| issn | 2211-7156 |
| language | English |
| last_indexed | 2024-04-24T19:48:41Z |
| publishDate | 2024-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj.art-a01763677f1b4cf39136a1ccaa017fd42024-03-25T04:17:30ZengElsevierResults in Chemistry2211-71562024-01-017101453Synthesis, in vitro enzyme kinetics and molecular docking studies of the 2-formylphenyl sulfonates and their hydrazone derivatives as potential anti-diabetic and anti-inflammatory agentsEmmanuel N. Agbo0Redolf S. Segodi1N.J. Gumede2Kgomotso W. Poopedi3Tlabo C. Leboho4W. Nxumalo5Department of Chemistry, School of Mineral and Physical Sciences, University of Limpopo, Limpopo, Sovenga, 0727, South Africa; Corresponding authors.Department of Chemistry, School of Mineral and Physical Sciences, University of Limpopo, Limpopo, Sovenga, 0727, South AfricaDepartment of Chemical and Physical Sciences, Walter Sisulu University, Private Bag X01, Mthatha 5099, South AfricaDepartment of Biochemistry, Microbiology and Biotechnology, University of Limpopo, Private Bag X1106, Sovenga 0727, South AfricaDepartment of Chemistry, School of Mineral and Physical Sciences, University of Limpopo, Limpopo, Sovenga, 0727, South AfricaDepartment of Chemistry, School of Mineral and Physical Sciences, University of Limpopo, Limpopo, Sovenga, 0727, South Africa; Corresponding authors.The in vitro anti-diabetes and anti-inflammatory inhibitory activities of the synthesized 2-formylphenyl sulfonates and their hydrazone derivatives were evaluated through enzymatic assays as potential α-glucosidase and lipoxygenase (LOX-15) inhibitors. The preliminary inhibitory results obtained, revealed that the prepared compounds are good inhibitors of α-glucosidase as compared to lipoxygenase (LOX-15). Compounds 2 g and 3 h were found to exhibit significant inhibitory activities against α-glucosidase with IC50 values of 3.1 µM and 2.6 µM, respectively. Moderate inhibitory activity was also observed for compound 3a (IC50 = 7.3 µM) against this enzyme. Enzyme kinetics studies of the most active compound (3 h) suggested a mixed mode of inhibition for this compound against α-glucosidase. The molecular docking and molecular dynamics simulation of compounds 2 g, 3a and 3 h into the active sites of α-glucosidase were used to predict the binding modes and structure activity relationship for these compounds. The molecular dynamics simulation demonstrated that compound 3 h significant inhibitory activity is due to its ability to bind to both the catalytic and secondary sites of the enzyme.http://www.sciencedirect.com/science/article/pii/S22117156240014982-formylphenyl sulfonatesHydrazoneAnti-inflammatoryAnti-diabeteslipoxygenase (LOX-15)α-glucosidase, molecular docking |
| spellingShingle | Emmanuel N. Agbo Redolf S. Segodi N.J. Gumede Kgomotso W. Poopedi Tlabo C. Leboho W. Nxumalo Synthesis, in vitro enzyme kinetics and molecular docking studies of the 2-formylphenyl sulfonates and their hydrazone derivatives as potential anti-diabetic and anti-inflammatory agents Results in Chemistry 2-formylphenyl sulfonates Hydrazone Anti-inflammatory Anti-diabetes lipoxygenase (LOX-15) α-glucosidase, molecular docking |
| title | Synthesis, in vitro enzyme kinetics and molecular docking studies of the 2-formylphenyl sulfonates and their hydrazone derivatives as potential anti-diabetic and anti-inflammatory agents |
| title_full | Synthesis, in vitro enzyme kinetics and molecular docking studies of the 2-formylphenyl sulfonates and their hydrazone derivatives as potential anti-diabetic and anti-inflammatory agents |
| title_fullStr | Synthesis, in vitro enzyme kinetics and molecular docking studies of the 2-formylphenyl sulfonates and their hydrazone derivatives as potential anti-diabetic and anti-inflammatory agents |
| title_full_unstemmed | Synthesis, in vitro enzyme kinetics and molecular docking studies of the 2-formylphenyl sulfonates and their hydrazone derivatives as potential anti-diabetic and anti-inflammatory agents |
| title_short | Synthesis, in vitro enzyme kinetics and molecular docking studies of the 2-formylphenyl sulfonates and their hydrazone derivatives as potential anti-diabetic and anti-inflammatory agents |
| title_sort | synthesis in vitro enzyme kinetics and molecular docking studies of the 2 formylphenyl sulfonates and their hydrazone derivatives as potential anti diabetic and anti inflammatory agents |
| topic | 2-formylphenyl sulfonates Hydrazone Anti-inflammatory Anti-diabetes lipoxygenase (LOX-15) α-glucosidase, molecular docking |
| url | http://www.sciencedirect.com/science/article/pii/S2211715624001498 |
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