Curcumin mimics of potential chemoprevention with NQO1 induction properties
Abstract Chemoprevention is one of the accessible strategies for preventing, delaying or reversing cancer processing utilizing chemical intervention of carcinogenesis. NAD(P)H quinone oxidoreductase 1 (NQO1) is a xenobiotic metabolizing cytosolic enzyme/protein with important functional properties t...
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Nature Portfolio
2025-01-01
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| Series: | Scientific Reports |
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| Online Access: | https://doi.org/10.1038/s41598-025-85588-w |
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| author | Dalia R. Aboshouk Ahmed R. Hamed Siva S. Panda Mohamed S. Bekheit M. Adel Youssef Adel S. Girgis |
| author_facet | Dalia R. Aboshouk Ahmed R. Hamed Siva S. Panda Mohamed S. Bekheit M. Adel Youssef Adel S. Girgis |
| author_sort | Dalia R. Aboshouk |
| collection | DOAJ |
| description | Abstract Chemoprevention is one of the accessible strategies for preventing, delaying or reversing cancer processing utilizing chemical intervention of carcinogenesis. NAD(P)H quinone oxidoreductase 1 (NQO1) is a xenobiotic metabolizing cytosolic enzyme/protein with important functional properties towards oxidation stress, supporting its ability in detoxification/chemoprotective role. A set of 3,5-diylidene-4-piperidones (as curcumin mimics) bearing alkyl sulfonyl group were synthesized with potential NQO1 induction properties. Compounds 5ab (R = 2-MeOC6H4, R’ = Me) and 5ac (R = 2-MeOC6H4, R’ = Et) are the most promising agents synthesized (% induction of NQO1 = 51.562, 45.793) relative to that of 4’-bromoflavone (4’-BF, reference standard) at 10 µM. LPS-induced iNOS production in RAW264.7 macrophages of the most promising agents discovered (5ab and 5ac) displayed concentration-dependent with comparable activities to the reference anti-inflammatory drug indomethacin. Molecular modeling studies (including QSAR, molecular docking and molecular dynamics) were accessed supporting the observed biological profiles. |
| format | Article |
| id | doaj-art-bc061f2e3ec542919cf62acf81884d53 |
| institution | Kabale University |
| issn | 2045-2322 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Scientific Reports |
| spelling | doaj-art-bc061f2e3ec542919cf62acf81884d532025-01-19T12:18:35ZengNature PortfolioScientific Reports2045-23222025-01-0115111710.1038/s41598-025-85588-wCurcumin mimics of potential chemoprevention with NQO1 induction propertiesDalia R. Aboshouk0Ahmed R. Hamed1Siva S. Panda2Mohamed S. Bekheit3M. Adel Youssef4Adel S. Girgis5Department of Pesticide Chemistry, National Research CentreChemistry of Medicinal Plants Department, National Research CentreDepartment of Chemistry & Biochemistry and Department of Biochemistry and Molecular Biology, Augusta UniversityDepartment of Pesticide Chemistry, National Research CentreDepartment of Chemistry, Faculty of Science, Helwan UniversityDepartment of Pesticide Chemistry, National Research CentreAbstract Chemoprevention is one of the accessible strategies for preventing, delaying or reversing cancer processing utilizing chemical intervention of carcinogenesis. NAD(P)H quinone oxidoreductase 1 (NQO1) is a xenobiotic metabolizing cytosolic enzyme/protein with important functional properties towards oxidation stress, supporting its ability in detoxification/chemoprotective role. A set of 3,5-diylidene-4-piperidones (as curcumin mimics) bearing alkyl sulfonyl group were synthesized with potential NQO1 induction properties. Compounds 5ab (R = 2-MeOC6H4, R’ = Me) and 5ac (R = 2-MeOC6H4, R’ = Et) are the most promising agents synthesized (% induction of NQO1 = 51.562, 45.793) relative to that of 4’-bromoflavone (4’-BF, reference standard) at 10 µM. LPS-induced iNOS production in RAW264.7 macrophages of the most promising agents discovered (5ab and 5ac) displayed concentration-dependent with comparable activities to the reference anti-inflammatory drug indomethacin. Molecular modeling studies (including QSAR, molecular docking and molecular dynamics) were accessed supporting the observed biological profiles.https://doi.org/10.1038/s41598-025-85588-wCancerChemopreventionCurcumin mimicPiperidoneNQO1iNOS |
| spellingShingle | Dalia R. Aboshouk Ahmed R. Hamed Siva S. Panda Mohamed S. Bekheit M. Adel Youssef Adel S. Girgis Curcumin mimics of potential chemoprevention with NQO1 induction properties Scientific Reports Cancer Chemoprevention Curcumin mimic Piperidone NQO1 iNOS |
| title | Curcumin mimics of potential chemoprevention with NQO1 induction properties |
| title_full | Curcumin mimics of potential chemoprevention with NQO1 induction properties |
| title_fullStr | Curcumin mimics of potential chemoprevention with NQO1 induction properties |
| title_full_unstemmed | Curcumin mimics of potential chemoprevention with NQO1 induction properties |
| title_short | Curcumin mimics of potential chemoprevention with NQO1 induction properties |
| title_sort | curcumin mimics of potential chemoprevention with nqo1 induction properties |
| topic | Cancer Chemoprevention Curcumin mimic Piperidone NQO1 iNOS |
| url | https://doi.org/10.1038/s41598-025-85588-w |
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