Crystal structures and in vitro anticancer studies on new unsymmetrical copper(II) Schiff base complexes derived from meso-1,2-diphenyl-1,2-ethylenediamine: a comparison with related symmetrical ones |
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Authors: | Mahdi Behzad Leila Seifikar Ghomi Maryam Damercheli Bita Mehravi Hamideh Samari Jahromi |
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Institution: | 1. Department of Chemistry, Semnan University, Semnan, Iranmbehzad@semnan.ac.ir shafieeardestani@sina.tums.ac.ir;3. Department of Chemistry, Semnan University, Semnan, Iran;4. Faculty of Advanced Technology in Medicine, Department of Medical Nanotechnology, Iran University of Medical Science, Tehran, Iran;5. Environment and Biotechnology Division, Research Institute of Petroleum Industry (RIPI), Tehran, Iran |
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Abstract: | Two new unsymmetrical copper(II) Schiff base complexes, CuLn(py)]ClO4 (n = 1, 2) in which Ln represents a tridentate N2O type Schiff base ligand, were synthesized. Lns were derived from monocondensation of meso-1,2-diphenyl-1,2-ethylenediamine with salicylaldehyde or 3-methoxysalicylaldehyde. The reaction between CuLn(py)]ClO4 and other salicylaldehyde derivatives resulted in new N2O2 unsymmetrical tetradentate CuII complexes, CuL3–6. Crystal structures of CuL1(py)]ClO4, CuL4, and CuL5 were obtained. These new complexes as well as a series of related symmetrical ones (i.e. CuL7–12) were tested for their in vitro anticancer activity against human liver cancer cell line (Hep-G2) by MTT and apoptosis assay. All of the complexes showed considerable cytotoxic activity against tumor cell lines (IC50 = 5.13–16.24 μg mL?1). The symmetrical CuL7 was the most potent anticancer derivative (IC50 = 5.13 μg mL?1) compared to the control drug 5-FU (IC50 = 5.4 μg mL-1, p < 0.05). Flow cytometry experiments showed that the copper derivatives especially CuL2(py)]ClO4 and CuL7 induced more apoptosis on Hep-G2 tumor cell lines compared to 5-FU. |
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Keywords: | Unsymmetrical symmetrical Schiff base anticancer copper(II) |
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