Influence of anchoring moieties on new benzimidazole-based Schiff base copper(ii) complexes towards estrogen dependent breast cancer cells. Issue 10 (26th February 2021)

• Record Type: Journal Article
• Authors: Paul, Anup; Singh, Priya; Kuznetsov, Maxim L.; Karmakar, Anirban; Guedes da Silva, M. Fátima C.; Koch, Biplob; Pombeiro, Armando J. L.
• Is Part Of: Dalton transactions. Volume 50:Issue 10(2021)
• Page Start: 3701
• Page End: 3716
• Publication Date: 2021-02-26
• Subjects: Chemistry, Inorganic -- Periodicals; Chemistry, Physical and theoretical -- Periodicals; Chemistry, Inorganic -- Periodicals; 546.05
• DOI: 10.1039/d0dt03873c
• Languages: English
• ISSNs: 1477-9226

Abstract

Abstract : Effects of triphenylphosphonium and triethylammonium linkers on new benzimidazole based Schiff base copper(ii ) complexes are described. A triphenylphosphonium anchored compound exhibits a better cytotoxic effect than cisplatin on the MCF-7 cell line. Abstract : Two new benzimidazole Schiff base copper(ii ) compounds [Cu(5-CH2 PPh3 -2-salmethylben)(NO3 )(H2 O)][BF4 ]·2/3(H2 O)·1/3(MeOH) (1 ) and [Cu(5-CH2 NEt3 -2-salmethylben)(Cl)][BF4 ] (2 ) were synthesised by mixing 2-(1-methyl-1 H -benzo[ d ]imidazol-2-yl)aniline, (3-formyl-4-hydroxybenzyl)triphenylphosphonium chloride or N, N -diethyl- N -(3-formyl-4-hydroxybenzyl)ethanaminium chloride and Cu(NO3 )2 ·3H2 O or CuCl2 ·2H2 O in the presence of tetrafluoroborate in a binary mixture of MeOH : H2 O under refluxing conditions. The structures of the compounds were established by elemental analysis, FT-IR, ESI-MS analytical techniques and, for 1, by single-crystal X-ray diffraction analysis. Absorption and fluorescence spectroscopic methods were performed to evaluate the calf thymus DNA interactions with the compounds. The calculated binding constants ( K b ) of 3.14 × 10 5 M −1 for 1 and 3.20 × 10 5 M −1 for 2 were established. The intercalative DNA binding mode was also verified by molecular docking studies. Both compounds demonstrated a notable in vitro cytotoxic effect against human A-549 (lung carcinoma), MCF-7 (breast cancer) and HeLa (cervical cancer) cancer cell lines. A substantial repressive effect on the proliferation of MCF-7 cells (breast cancer cells) was observed for compound 1 . The mechanism of action for the effective antiproliferative activity of 1 has additionally been confirmed by means of various biological studies such as morphological assessment through AO/EB, detection of apoptotic induction via Hoechst/PI dual staining, flow cytometry for detection of cell cycle arrest, quantitative analysis of apoptotic cells, DNA degradation, generation of reactive oxygen species (ROS) and by apoptotic induction through mitochondrial staining.