Details

Autor(en) / Beteiligte

• Paul, Anup
• Singh, Priya
• Kuznetsov, Maxim L
• Karmakar, Anirban
• Guedes da Silva, M. Fátima C
• Koch, Biplob
• Pombeiro, Armando J. L

Titel

Influence of anchoring moieties on new benzimidazole-based Schiff base copper() complexes towards estrogen dependent breast cancer cells

Ist Teil von

• Dalton transactions : an international journal of inorganic chemistry, 2021-03, Vol.5 (1), p.371-3716

Ort / Verlag

England: Royal Society of Chemistry

Erscheinungsjahr

2021

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Two new benzimidazole Schiff base copper( ii ) compounds [Cu(5-CH 2 PPh 3 -2-salmethylben)(NO 3 )(H 2 O)][BF 4 ]·2/3(H 2 O)·1/3(MeOH) ( 1 ) and [Cu(5-CH 2 NEt 3 -2-salmethylben)(Cl)][BF 4 ] ( 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(NO 3 ) 2 ·3H 2 O or CuCl 2 ·2H 2 O in the presence of tetrafluoroborate in a binary mixture of MeOH : H 2 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. 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.