Cytotoxic and apoptotic effects of 1,2-diborolanes with strong donor substitutes on human cancer cells

• Published in: Bioorganic chemistry Vol. 117; p. 105443
• Main Authors: Şahin, Yüksel, Aslantürk, Özlem Sultan, Çelik, Tülay, Sevinçek, Resul, Aygün, Muhittin, Metin, Kubilay, Fırıncı, Erkan, Özgener, Hüseyin
• Format: Journal Article
• Language: English
• Published: United States Elsevier Inc 01-12-2021
• Subjects: Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Apoptosis - drug effects; Boron Compounds - chemical synthesis; Boron Compounds - chemistry; Boron Compounds - pharmacology; Cancer; Cell Proliferation - drug effects; Cell Survival - drug effects; Cytotoxic effects; Diborolane; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; Humans; Membrane Potential, Mitochondrial - drug effects; Mitochondrial membrane potential; Molecular Structure; Structure-Activity Relationship; Tumor Cells, Cultured; Diborolane; Cytotoxic effects; Cancer; Mitochondrial membrane potential
• ISSN: 0045-2068; 1090-2120
• DOI: 10.1016/j.bioorg.2021.105443

New 1,2-diborolane derivatives were synthesized and characterized. The compounds exhibited highly cytotoxic effects on HepG2, Hep3B and MCF-7 cells. Mitochondrial membrane potential assay results also supported cytotoxicity results.
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•New 1,2-diborolane derivatives were synthesized and characterized.•The compounds exhibited highly cytotoxic effects on HepG2, Hep3B and MCF-7 cells.•Mitochondrial membrane potential assay results also supported cytotoxicity results.
In recent years, boron compounds have become more common as chemotherapy agents against certain types of cancers. Along with the development of boron-based therapeutic agents have come investigations into the various cancers and biochemical and molecular mechanisms affected by boron compounds and the relationships between boron compounds and chemical protection against cancer. In this preliminary study, the effects of new 1,2-N-substituted-1,2-diborolane derivatives on types of breast and liver cancers were examined for the first time. Four were found to significantly affect the cell viabilities and mitochondrial membrane potential changes in MCF-7, HepG2 and Hep3B cancer cells. Each was prepared in n-hexane at various concentrations (5, 10, 25, 50, 75 and 100 µg/mL). Human peripheral blood lymphocytes were used as control cells. Compounds 1, 2, 3a, and 3b 1,2-diborolane derivatives selectively killed cancer cells, but compound 1 was cytotoxic in a concentration-dependent manner on HepG2 and Hep3B and only at concentrations of at least 75 µg/mL on MCF-7 cells. Compound 3a exhibited cytotoxic effect on lymphocytes at 75 and 100 µgmL−1 concentrations, but compounds 1, 2 and 3b, 3c and 3d have not possessed significant cytotoxic effect on lymphocytes. Compounds 3c and 3d have not possessed significant cytotoxic effects. Mitochondrial membrane potential assay results supported these findings. Our results reveal that 1,2-diborolane derivates have high cytotoxic and apoptotic activities on human hepatocarcinoma cells and are therefore potential candidates in the development of new drugs against liver cancer.