Theoretical probing to the reactivity and biological effects of the phytochemical, coumestrol and its derivatives
Coumestrol, a pytochemical, has been shown to have anti-inflammatory, neuroprotective, anti-oxidant, and anti-cancer properties. Herein, the effect of substitution at various positions of the coumestrol molecule was systematically investigated using density functional theory (DFT) calculations. Full...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2022-06-01
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| Series: | Chemical Physics Impact |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2667022422000196 |
| _version_ | 1818252817028087808 |
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| author | Vinduja Puthanveedu Chandana Pulikkool Nithin Poonkottil K. Muraleedharan |
| author_facet | Vinduja Puthanveedu Chandana Pulikkool Nithin Poonkottil K. Muraleedharan |
| author_sort | Vinduja Puthanveedu |
| collection | DOAJ |
| description | Coumestrol, a pytochemical, has been shown to have anti-inflammatory, neuroprotective, anti-oxidant, and anti-cancer properties. Herein, the effect of substitution at various positions of the coumestrol molecule was systematically investigated using density functional theory (DFT) calculations. Full electron donor acceptor maps (FEDAM) and donor acceptor maps (DAM) identified the radical scavenging ability of these molecules. The derivative prepared by substituting the 15th position of coumestrol with -NH2 group even outperformed coumestrol in terms of its powerful anti-oxidant character. This effect of -NH2 substitution is attributed to the low O-H bond dissociation enthalpy. Moreover, most of the derivatives exhibited significantly higher interaction with cancer causing kinase proteins compared to the parent molecule, as evident by the in silico molecular docking and thereby revealing potential anti-cancer applications. Coumestrol and its derivatives obey Lipinski's rule of five, showing that they are safe for oral consumption, implying their application as future drugs. |
| first_indexed | 2024-12-12T16:30:12Z |
| format | Article |
| id | doaj.art-213a4ca7971f4a29b480b931e0c3c995 |
| institution | Directory Open Access Journal |
| issn | 2667-0224 |
| language | English |
| last_indexed | 2024-12-12T16:30:12Z |
| publishDate | 2022-06-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Chemical Physics Impact |
| spelling | doaj.art-213a4ca7971f4a29b480b931e0c3c9952022-12-22T00:18:47ZengElsevierChemical Physics Impact2667-02242022-06-014100080Theoretical probing to the reactivity and biological effects of the phytochemical, coumestrol and its derivativesVinduja Puthanveedu0Chandana Pulikkool1Nithin Poonkottil2K. Muraleedharan3Department of Chemistry, University of Calicut, Calicut 673635, IndiaDepartment of Chemistry, University of Calicut, Calicut 673635, IndiaDepartment of Solid State Sciences, Krigjslaan 281, Ghent University, BelgiumDepartment of Chemistry, University of Calicut, Calicut 673635, India; Corresponding author.Coumestrol, a pytochemical, has been shown to have anti-inflammatory, neuroprotective, anti-oxidant, and anti-cancer properties. Herein, the effect of substitution at various positions of the coumestrol molecule was systematically investigated using density functional theory (DFT) calculations. Full electron donor acceptor maps (FEDAM) and donor acceptor maps (DAM) identified the radical scavenging ability of these molecules. The derivative prepared by substituting the 15th position of coumestrol with -NH2 group even outperformed coumestrol in terms of its powerful anti-oxidant character. This effect of -NH2 substitution is attributed to the low O-H bond dissociation enthalpy. Moreover, most of the derivatives exhibited significantly higher interaction with cancer causing kinase proteins compared to the parent molecule, as evident by the in silico molecular docking and thereby revealing potential anti-cancer applications. Coumestrol and its derivatives obey Lipinski's rule of five, showing that they are safe for oral consumption, implying their application as future drugs.http://www.sciencedirect.com/science/article/pii/S2667022422000196PhytochemicalCoumestrolFEDAMDAMAnti-oxidantAnticancer |
| spellingShingle | Vinduja Puthanveedu Chandana Pulikkool Nithin Poonkottil K. Muraleedharan Theoretical probing to the reactivity and biological effects of the phytochemical, coumestrol and its derivatives Chemical Physics Impact Phytochemical Coumestrol FEDAM DAM Anti-oxidant Anticancer |
| title | Theoretical probing to the reactivity and biological effects of the phytochemical, coumestrol and its derivatives |
| title_full | Theoretical probing to the reactivity and biological effects of the phytochemical, coumestrol and its derivatives |
| title_fullStr | Theoretical probing to the reactivity and biological effects of the phytochemical, coumestrol and its derivatives |
| title_full_unstemmed | Theoretical probing to the reactivity and biological effects of the phytochemical, coumestrol and its derivatives |
| title_short | Theoretical probing to the reactivity and biological effects of the phytochemical, coumestrol and its derivatives |
| title_sort | theoretical probing to the reactivity and biological effects of the phytochemical coumestrol and its derivatives |
| topic | Phytochemical Coumestrol FEDAM DAM Anti-oxidant Anticancer |
| url | http://www.sciencedirect.com/science/article/pii/S2667022422000196 |
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