Anti-hypertensive properties of 2-[N-(4-methylbenzenesulfonyl)-1-phenylformamido]-n-(4-nitrophenyl)-3-phenylpropenamide: Experimental and theoretical studies
Experimental and theoretical investigation of the anti-hypertensive activity of novel 2-[N-(4-methylbenzenesulfonyl)-1-phenylformamido]-N-(4-nitrophenyl)-3-phenylpropenamide (MBPNPP) was carried out. The experimental approach followed the dietary induction of spontaneously hypertensive adult male Wi...
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| Format: | Article |
| Language: | English |
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Elsevier
2023-06-01
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| Series: | Chemical Physics Impact |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2667022422000962 |
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| author | David I. Ugwu Fredrick C. Asogwa Sunday G. Olisaeloka James A. Ezugwu Sunday C. Ogbuke Innocent Benjamin Hitler Louis Terkumbur E. Gber Mirabel C. Ugwu Florence U. Eze Amanda-Lee E. Manicum |
| author_facet | David I. Ugwu Fredrick C. Asogwa Sunday G. Olisaeloka James A. Ezugwu Sunday C. Ogbuke Innocent Benjamin Hitler Louis Terkumbur E. Gber Mirabel C. Ugwu Florence U. Eze Amanda-Lee E. Manicum |
| author_sort | David I. Ugwu |
| collection | DOAJ |
| description | Experimental and theoretical investigation of the anti-hypertensive activity of novel 2-[N-(4-methylbenzenesulfonyl)-1-phenylformamido]-N-(4-nitrophenyl)-3-phenylpropenamide (MBPNPP) was carried out. The experimental approach followed the dietary induction of spontaneously hypertensive adult male Wistar rats (SHRs) using 66% w/v d-fructose and the angiotensin I-converting enzyme (ACE) inhibitory activity assay while the theoretical study was achieved using DFT calculations and molecular docking against hypertension responsive proteins. The Becke-3-Paramater-Lee-Yang-Parr (B3LYP) functional/6–311G++(d,p) basis set was adopted. The molecular electronic properties such as the highest occupied molecular orbital (HOMO), the lowest unoccupied molecular orbital (LUMO) and other chemical reactivity parameters were evaluated to bring to light, the reactivity and stabilization mechanisms of MBPNPP. The highest daily oral dose of MBPNPP (10 mg/kg) significantly prevented increase in systolic blood pressure (SBP) comparable to positive and normal control groups receiving captopril (10 mg/kg/day) and distilled water (5 ml/kg) ad libitum respectively from 167.23 (negative control) to 124.50 and 120.17 (positive control). Molecular simulation was also carried out with target proteins; 2ydm, 2 × 8Y, and 3ZQZ, and the theoretical data expresses a much plausible therapeutic significance towards the control of hypertension. The frontier orbital energy gap of 3.066 eV was an indicator that the charge transfer interaction occurred within the molecule and indicates high chemical reactivity. Relative to the reference drug, Spironolactone, the compound under study showed a significant binding affinity of -9.0 kcal/mol, -8.3 kcal/mol, and -7.9 kcal/mol with the target proteins and better protein-ligand hydrogen bond interactions. The data gathered from the experimental and theoretical analysis including the docking scores showed excellent anti-hypertensive activity by MBPNPP. |
| first_indexed | 2024-03-13T04:43:36Z |
| format | Article |
| id | doaj.art-a7fbf936b34846a6bc950298bae9a8fa |
| institution | Directory Open Access Journal |
| issn | 2667-0224 |
| language | English |
| last_indexed | 2024-03-13T04:43:36Z |
| publishDate | 2023-06-01 |
| publisher | Elsevier |
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| series | Chemical Physics Impact |
| spelling | doaj.art-a7fbf936b34846a6bc950298bae9a8fa2023-06-19T04:30:07ZengElsevierChemical Physics Impact2667-02242023-06-016100158Anti-hypertensive properties of 2-[N-(4-methylbenzenesulfonyl)-1-phenylformamido]-n-(4-nitrophenyl)-3-phenylpropenamide: Experimental and theoretical studiesDavid I. Ugwu0Fredrick C. Asogwa1Sunday G. Olisaeloka2James A. Ezugwu3Sunday C. Ogbuke4Innocent Benjamin5Hitler Louis6Terkumbur E. Gber7Mirabel C. Ugwu8Florence U. Eze9Amanda-Lee E. Manicum10Department of Pure & Industrial Chemistry, University of Nigeria, Nsukka, Enugu State, Nigeria; Corresponding authors.Computational and Bio-Simulation Research Group, Department of Pure and Applied Chemistry, University of Calabar, Calabar, Cross River State, Nigeria; Corresponding authors.Computational and Bio-Simulation Research Group, Department of Pure and Applied Chemistry, University of Calabar, Calabar, Cross River State, NigeriaDepartment of Pure & Industrial Chemistry, University of Nigeria, Nsukka, Enugu State, NigeriaDepartment of Pure & Industrial Chemistry, University of Nigeria, Nsukka, Enugu State, NigeriaComputational and Bio-Simulation Research Group, Department of Pure and Applied Chemistry, University of Calabar, Calabar, Cross River State, Nigeria; Department of Microbiology, Faculty of Biological Sciences, University of Calabar, Calabar, Cross River State, NigeriaComputational and Bio-Simulation Research Group, Department of Pure and Applied Chemistry, University of Calabar, Calabar, Cross River State, NigeriaComputational and Bio-Simulation Research Group, Department of Pure and Applied Chemistry, University of Calabar, Calabar, Cross River State, NigeriaFederal College of Dental Technology and Therapy, Enugu, Enugu State, NigeriaDepartment of Pure & Industrial Chemistry, University of Nigeria, Nsukka, Enugu State, NigeriaDepartment of Chemical Science, Tshwane University of Technology, P. O. Box X680, Pretoria 0001, South AfricaExperimental and theoretical investigation of the anti-hypertensive activity of novel 2-[N-(4-methylbenzenesulfonyl)-1-phenylformamido]-N-(4-nitrophenyl)-3-phenylpropenamide (MBPNPP) was carried out. The experimental approach followed the dietary induction of spontaneously hypertensive adult male Wistar rats (SHRs) using 66% w/v d-fructose and the angiotensin I-converting enzyme (ACE) inhibitory activity assay while the theoretical study was achieved using DFT calculations and molecular docking against hypertension responsive proteins. The Becke-3-Paramater-Lee-Yang-Parr (B3LYP) functional/6–311G++(d,p) basis set was adopted. The molecular electronic properties such as the highest occupied molecular orbital (HOMO), the lowest unoccupied molecular orbital (LUMO) and other chemical reactivity parameters were evaluated to bring to light, the reactivity and stabilization mechanisms of MBPNPP. The highest daily oral dose of MBPNPP (10 mg/kg) significantly prevented increase in systolic blood pressure (SBP) comparable to positive and normal control groups receiving captopril (10 mg/kg/day) and distilled water (5 ml/kg) ad libitum respectively from 167.23 (negative control) to 124.50 and 120.17 (positive control). Molecular simulation was also carried out with target proteins; 2ydm, 2 × 8Y, and 3ZQZ, and the theoretical data expresses a much plausible therapeutic significance towards the control of hypertension. The frontier orbital energy gap of 3.066 eV was an indicator that the charge transfer interaction occurred within the molecule and indicates high chemical reactivity. Relative to the reference drug, Spironolactone, the compound under study showed a significant binding affinity of -9.0 kcal/mol, -8.3 kcal/mol, and -7.9 kcal/mol with the target proteins and better protein-ligand hydrogen bond interactions. The data gathered from the experimental and theoretical analysis including the docking scores showed excellent anti-hypertensive activity by MBPNPP.http://www.sciencedirect.com/science/article/pii/S2667022422000962Anti-hypertensiveAngiotensinCaptoprilDFTMolecular dockingSpironolactone |
| spellingShingle | David I. Ugwu Fredrick C. Asogwa Sunday G. Olisaeloka James A. Ezugwu Sunday C. Ogbuke Innocent Benjamin Hitler Louis Terkumbur E. Gber Mirabel C. Ugwu Florence U. Eze Amanda-Lee E. Manicum Anti-hypertensive properties of 2-[N-(4-methylbenzenesulfonyl)-1-phenylformamido]-n-(4-nitrophenyl)-3-phenylpropenamide: Experimental and theoretical studies Chemical Physics Impact Anti-hypertensive Angiotensin Captopril DFT Molecular docking Spironolactone |
| title | Anti-hypertensive properties of 2-[N-(4-methylbenzenesulfonyl)-1-phenylformamido]-n-(4-nitrophenyl)-3-phenylpropenamide: Experimental and theoretical studies |
| title_full | Anti-hypertensive properties of 2-[N-(4-methylbenzenesulfonyl)-1-phenylformamido]-n-(4-nitrophenyl)-3-phenylpropenamide: Experimental and theoretical studies |
| title_fullStr | Anti-hypertensive properties of 2-[N-(4-methylbenzenesulfonyl)-1-phenylformamido]-n-(4-nitrophenyl)-3-phenylpropenamide: Experimental and theoretical studies |
| title_full_unstemmed | Anti-hypertensive properties of 2-[N-(4-methylbenzenesulfonyl)-1-phenylformamido]-n-(4-nitrophenyl)-3-phenylpropenamide: Experimental and theoretical studies |
| title_short | Anti-hypertensive properties of 2-[N-(4-methylbenzenesulfonyl)-1-phenylformamido]-n-(4-nitrophenyl)-3-phenylpropenamide: Experimental and theoretical studies |
| title_sort | anti hypertensive properties of 2 n 4 methylbenzenesulfonyl 1 phenylformamido n 4 nitrophenyl 3 phenylpropenamide experimental and theoretical studies |
| topic | Anti-hypertensive Angiotensin Captopril DFT Molecular docking Spironolactone |
| url | http://www.sciencedirect.com/science/article/pii/S2667022422000962 |
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