{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,17]],"date-time":"2026-10-17T00:23:30Z","timestamp":1792196610184,"version":"4.4.0"},"reference-count":70,"publisher":"Public Library of Science (PLoS)","issue":"8","license":[{"start":{"date-parts":[[2024,8,14]],"date-time":"2024-08-14T00:00:00Z","timestamp":1723593600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Deanship of Scientific Research at Northern Border University, Arar, KSA","award":["NBU-FFR-2024-80-01"],"award-info":[{"award-number":["NBU-FFR-2024-80-01"]}]},{"name":"Slovenian Research and Innovation Agency (ARIS) program","award":["P2-0046, P2-0438, L2-3175, J1-4398, L2-4430, J3-4498, J7-4638, J1-4414, J3-4497, J4-4633, I0-E015, and J1-2471"],"award-info":[{"award-number":["P2-0046, P2-0438, L2-3175, J1-4398, L2-4430, J3-4498, J7-4638, J1-4414, J3-4497, J4-4633, I0-E015, and J1-2471"]}]},{"name":"Slovenian Ministry of Science and Education project","award":["NOO"],"award-info":[{"award-number":["NOO"]}]},{"name":"Slovenian Ministry of Science and Education project","award":["NOO"],"award-info":[{"award-number":["NOO"]}]}],"content-domain":{"domain":["www.plosone.org"],"crossmark-restriction":false},"short-container-title":["PLoS ONE"],"abstract":"<jats:p>Multidrug resistance (MDR) mechanisms in cancer cells are greatly influenced by glutathione transferase P1-1 (hGSTP1-1). The use of synthetic or natural compounds as hGSTP1-1 inhibitors is considered an effective approach to overcome MDR. Nine compounds consisting of coumarin-6-sulfonamide linked to chalcone derivatives were synthesized and evaluated for their ability to inhibit hGSTP1-1. Among the synthetic derivatives, compounds <jats:bold>5g<\/jats:bold>, <jats:bold>5f<\/jats:bold>, and <jats:bold>5a<\/jats:bold> displayed the most potent inhibitory effect, with IC<jats:sub>50<\/jats:sub> values of 12.2 \u00b1 0.5 \u03bc\u039c, 12.7 \u00b1 0.7 and 16.3 \u00b1 0.6, respectively. Kinetic inhibition analysis of the most potent molecule, <jats:bold>5g<\/jats:bold>, showed that it behaves as a mixed-type inhibitor of the target enzyme. An <jats:italic>in vitro<\/jats:italic> cytotoxicity assessment of <jats:bold>5a<\/jats:bold>, <jats:bold>5f,<\/jats:bold> and <jats:bold>5g<\/jats:bold> against the human prostate cancer cell lines DU-145 and PC3, as well as the breast cancer cell line MCF-7, demonstrated that compound <jats:bold>5g<\/jats:bold> exhibited the most pronounced cytotoxic effect on all tested cell lines. Molecular docking studies were performed to predict the structural and molecular determinants of <jats:bold>5g<\/jats:bold>, <jats:bold>5f<\/jats:bold>, and <jats:bold>5a<\/jats:bold> binding to hGSTP1-1. In agreement with the experimental data, the results revealed that <jats:bold>5g<\/jats:bold> exhibited the lowest docking score among the three studied inhibitors as a consequence of shape complementarity, governed by van der Waals, hydrogen bonds and a \u03c0-\u03c0 stacking interaction. These findings suggest that coumarin-chalcone hybrids offer new perspectives for the development of safe and efficient natural product-based sensitizers that can target hGSTP1-1 for anticancer purposes.<\/jats:p>","DOI":"10.1371\/journal.pone.0306124","type":"journal-article","created":{"date-parts":[[2024,8,14]],"date-time":"2024-08-14T17:30:22Z","timestamp":1723656622000},"page":"e0306124","update-policy":"https:\/\/doi.org\/10.1371\/journal.pone.corrections_policy","source":"Crossref","is-referenced-by-count":10,"title":["Novel coumarin-6-sulfonamide-chalcone hybrids as glutathione transferase P1-1 inhibitors"],"prefix":"10.1371","volume":"19","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6976-0196","authenticated-orcid":true,"given":"Ahmed","family":"Sabt","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stefanos","family":"Kitsos","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Manal S.","family":"Ebaid","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Veronika","family":"Furlan","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Panagiota D.","family":"Pantiora","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Magdalini","family":"Tsolka","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Eslam B.","family":"Elkaeed","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mohamed Farouk","family":"Hamissa","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nikolaos","family":"Angelis","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ourania E.","family":"Tsitsilonis","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anastassios C.","family":"Papageorgiou","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Urban","family":"Bren","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nikolaos E.","family":"Labrou","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"340","published-online":{"date-parts":[[2024,8,14]]},"reference":[{"key":"pone.0306124.ref001","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1146\/annurev.pharmtox.45.120403.095857","article-title":"Glutathione transferases.","volume":"45","author":"JD Hayes","year":"2005","journal-title":"Annu Rev Pharmacol Toxicol"},{"key":"pone.0306124.ref002","doi-asserted-by":"crossref","first-page":"688","DOI":"10.3390\/biom13040688","article-title":"The Multifaceted Role of Glutathione S-Transferases in Health and Disease.","volume":"13","author":"AM Mazari","year":"2023","journal-title":"Biomolecules."},{"key":"pone.0306124.ref003","doi-asserted-by":"crossref","first-page":"1741","DOI":"10.3390\/nu11081741","article-title":"Glutathione Transferase P1-1 an Enzyme Useful in Biomedicine and as Biomarker in Clinical Practice and in Environmental Pollution.","volume":"11","author":"A Bocedi","year":"2019","journal-title":"Nutrients"},{"key":"pone.0306124.ref004","doi-asserted-by":"crossref","first-page":"330","DOI":"10.1002\/bip.22844","article-title":"Glutathione analogues as substrates or inhibitors that discriminate between allozymes of the MDR-involved human glutathione transferase P1-1.","volume":"106","author":"A Zompra","year":"2016","journal-title":"Pept Sci"},{"key":"pone.0306124.ref005","doi-asserted-by":"crossref","first-page":"645","DOI":"10.1111\/j.1432-1033.1994.tb18666.x","article-title":"X-ray crystal structures of cytosolic glutathione S-transferases. 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