New (S)-verbenone-isoxazoline-1,3,4-thiadiazole hybrids: synthesis, anticancer activity and apoptosis-inducing effect.

Autor: Fawzi M; Laboratory of Molecular Chemistry, Unit of Organic Synthesis & Molecular Physicochemistry, Department of Chemistry, Faculty of Sciences Semlalia, PO Box 2390, Marrakech, 40001, Morocco., Bimoussa A; Laboratory of Molecular Chemistry, Unit of Organic Synthesis & Molecular Physicochemistry, Department of Chemistry, Faculty of Sciences Semlalia, PO Box 2390, Marrakech, 40001, Morocco., Laamari Y; Laboratory of Molecular Chemistry, Unit of Organic Synthesis & Molecular Physicochemistry, Department of Chemistry, Faculty of Sciences Semlalia, PO Box 2390, Marrakech, 40001, Morocco., Oussidi AN; Laboratory of Molecular Chemistry, Unit of Organic Synthesis & Molecular Physicochemistry, Department of Chemistry, Faculty of Sciences Semlalia, PO Box 2390, Marrakech, 40001, Morocco., Oubella A; Laboratory of Organic & Physical Chemistry, Applied Bioorganic Chemistry Team, Faculty of Sciences, IBNOU ZOHR University, Agadir, 80000, Morocco., Ketatni EM; Laboratory of Molecular Chemistry, Materials & Catalysis, Faculty of Sciences, & Technics, Sultan Moulay Slimane University, Beni-Mellal, BP 523, 23000, Morocco., Saadi M; Laboratoire de Chimie Appliquée des Matériaux, Centre des Sciences des Matériaux, Faculty of Sciences, Mohammed V University in Rabat, Avenue Ibn Batouta, PO Box 1014, Rabat, Morocco., Ammari LE; Laboratoire de Chimie Appliquée des Matériaux, Centre des Sciences des Matériaux, Faculty of Sciences, Mohammed V University in Rabat, Avenue Ibn Batouta, PO Box 1014, Rabat, Morocco., Morjani H; Unité BioSpecT, EA7506, SFR CAP-Santé, UFR de Pharmacie, Université de Reims Champagne-Ardenne, 51100, France., Ait Itto MY; Laboratory of Molecular Chemistry, Unit of Organic Synthesis & Molecular Physicochemistry, Department of Chemistry, Faculty of Sciences Semlalia, PO Box 2390, Marrakech, 40001, Morocco., Auhmani A; Laboratory of Molecular Chemistry, Unit of Organic Synthesis & Molecular Physicochemistry, Department of Chemistry, Faculty of Sciences Semlalia, PO Box 2390, Marrakech, 40001, Morocco.
Jazyk: angličtina
Zdroj: Future medicinal chemistry [Future Med Chem] 2023 Sep; Vol. 15 (17), pp. 1603-1619. Date of Electronic Publication: 2023 Sep 29.
DOI: 10.4155/fmc-2023-0173
Abstrakt: Background: This study aimed to develop novel isoxazoline-1,3,4-thiadiazole hybrids from (S)-verbenone for potential anticancer treatment, particularly focusing on cytotoxic and apoptotic effects in hormone-sensitive MCF-7 and triple-negative MDA-MB-231 breast cancer cells. Methods & results: (S)-verbenone was used to synthesize hybrids through 1,3-dipolar cycloaddition, followed by thorough characterization. The compounds were screened across cancer cell lines, showing significant anticancer effects. Compound 8b notably induced apoptosis via the caspase-3/7 pathway and cell cycle arrest, displaying noteworthy cytotoxicity against MCF-7 and MDA-MB-231 cells. Conclusion: These findings underscore the potential of (S)-verbenone isoxazoline-1,3,4-thiadiazole derivatives for breast cancer therapy due to their remarkable apoptotic activity. This study highlights a promising avenue for advancing breast cancer treatment using these derivatives, founded on (S)-verbenone, showcasing their distinct potential for inducing apoptosis.
Databáze: MEDLINE
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