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Here, we describe the synthesis, characterization, and in vitro biological evaluation of a series of transition metal complexes containing benzothiazole aniline (BTA). We employed BTA, which is known for its selective anticancer activity, and a salen-type Schiff-based ligand to coordinate several transition metals to achieve selective and synergistic cytotoxicity. The compounds obtained were characterized by NMR spectroscopy, mass spectrometry, Fourier transform infrared spectroscopy, and elemental analysis. The compounds <b>L</b>, <b>MnL</b>, <b>FeL</b>, <b>CoL</b>, and <b>ZnL</b> showed promising in vitro cytotoxicity against cancer cells, and they had a lower IC₅₀ than that of the clinically used cisplatin. In particular, <b>MnL</b> had synergistic cytotoxicity against liver, breast, and colon cancer cells. Moreover, <b>MnL</b>, <b>CoL</b>, and <b>CuL</b> promoted the production of reactive oxygen species in HepG2 tumor cell lines. The lead compound of this series, <b>MnL</b>, remained stable in physiological settings, and docking results showed that it interacted rationally with the minor groove of DNA. Therefore, <b>MnL</b> may serve as a viable alternative to platinum-based chemotherapy.