دورية أكاديمية
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Novel coumarin-6-sulfonamide-chalcone hybrids as glutathione transferase P1-1 inhibitors.

التفاصيل البيبلوغرافية
العنوان: Novel coumarin-6-sulfonamide-chalcone hybrids as glutathione transferase P1-1 inhibitors.
المؤلفون: Sabt A; Chemistry of Natural Compounds Department, Pharmaceutical and Drug Industries Research Institute, National Research Center, Dokki, Cairo, Egypt., Kitsos S; Laboratory of Enzyme Technology, Department of Biotechnology, School of Applied Biology and Biotechnology, Agricultural University of Athens, Athens, Greece., Ebaid MS; Department of Chemistry, College of Science, Northern Border University, Arar, Saudi Arabia., Furlan V; Faculty of Chemistry and Chemical Engineering, University of Maribor, Maribor, Slovenia., Pantiora PD; Laboratory of Enzyme Technology, Department of Biotechnology, School of Applied Biology and Biotechnology, Agricultural University of Athens, Athens, Greece., Tsolka M; Laboratory of Enzyme Technology, Department of Biotechnology, School of Applied Biology and Biotechnology, Agricultural University of Athens, Athens, Greece., Elkaeed EB; Department of Pharmaceutical Sciences, College of Pharmacy, AlMaarefa University, Diriyah, Saudi Arabia., Hamissa MF; Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic., Angelis N; Section of Animal and Human Physiology, Department of Biology, National and Kapodistrian University of Athens (NKUA), Athens, Greece., Tsitsilonis OE; Section of Animal and Human Physiology, Department of Biology, National and Kapodistrian University of Athens (NKUA), Athens, Greece., Papageorgiou AC; Turku Bioscience Centre, University of Turku and Åbo Akademi University, Turku, Finland., Bren U; Faculty of Chemistry and Chemical Engineering, University of Maribor, Maribor, Slovenia.; Faculty of Mathematics, Natural Sciences and Information Technologies, University of Primorska, Koper, Slovenia.; Institute of Environmental Protection and Sensors, Maribor, Slovenia., Labrou NE; Laboratory of Enzyme Technology, Department of Biotechnology, School of Applied Biology and Biotechnology, Agricultural University of Athens, Athens, Greece.
المصدر: PloS one [PLoS One] 2024 Aug 14; Vol. 19 (8), pp. e0306124. Date of Electronic Publication: 2024 Aug 14 (Print Publication: 2024).
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: Public Library of Science Country of Publication: United States NLM ID: 101285081 Publication Model: eCollection Cited Medium: Internet ISSN: 1932-6203 (Electronic) Linking ISSN: 19326203 NLM ISO Abbreviation: PLoS One Subsets: MEDLINE
أسماء مطبوعة: Original Publication: San Francisco, CA : Public Library of Science
مواضيع طبية MeSH: Coumarins*/chemistry , Coumarins*/pharmacology , Molecular Docking Simulation* , Glutathione S-Transferase pi*/antagonists & inhibitors , Glutathione S-Transferase pi*/metabolism , Sulfonamides*/chemistry , Sulfonamides*/pharmacology, Humans ; Cell Line, Tumor ; Chalcone/chemistry ; Chalcone/pharmacology ; Antineoplastic Agents/pharmacology ; Antineoplastic Agents/chemistry ; Chalcones/chemistry ; Chalcones/pharmacology ; Enzyme Inhibitors/pharmacology ; Enzyme Inhibitors/chemistry ; MCF-7 Cells
مستخلص: 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 5g, 5f, and 5a displayed the most potent inhibitory effect, with IC50 values of 12.2 ± 0.5 μΜ, 12.7 ± 0.7 and 16.3 ± 0.6, respectively. Kinetic inhibition analysis of the most potent molecule, 5g, showed that it behaves as a mixed-type inhibitor of the target enzyme. An in vitro cytotoxicity assessment of 5a, 5f, and 5g against the human prostate cancer cell lines DU-145 and PC3, as well as the breast cancer cell line MCF-7, demonstrated that compound 5g exhibited the most pronounced cytotoxic effect on all tested cell lines. Molecular docking studies were performed to predict the structural and molecular determinants of 5g, 5f, and 5a binding to hGSTP1-1. In agreement with the experimental data, the results revealed that 5g 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 π-π 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.
Competing Interests: The authors have declared that no competing interests exist.
(Copyright: © 2024 Sabt et al. This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.)
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المشرفين على المادة: 0 (Coumarins)
EC 2.5.1.18 (Glutathione S-Transferase pi)
0 (Sulfonamides)
5S5A2Q39HX (Chalcone)
0 (Antineoplastic Agents)
0 (Chalcones)
0 (Enzyme Inhibitors)
EC 2.5.1.18 (GSTP1 protein, human)
تواريخ الأحداث: Date Created: 20240814 Date Completed: 20240814 Latest Revision: 20240817
رمز التحديث: 20240817
مُعرف محوري في PubMed: PMC11324126
DOI: 10.1371/journal.pone.0306124
PMID: 39141629
قاعدة البيانات: MEDLINE
الوصف
تدمد:1932-6203
DOI:10.1371/journal.pone.0306124