Synthesis, characterization, anticancer activity and DNA interaction studies of new 2-aminobenzothiazole complexes; crystal structure and DFT calculations of [Ag(Habt)(2)]ClO4

摘要

The synthesis and characterization of new complexes of 2-aminobenzothiazole (Habt), [M(Habt) Cl-3] Cl, [M(L)(abt)]Cl (M(II) = Pd, Pt; L = bpy, phen), [Ir(Habt)(3)(H2O)Cl-2]Cl, [Ru(Habt)(3)(H2O)Cl-2], [Rh(Habt)(3)Cl-3], [OsO2(Habt)(2)(OH)(2)], [Zn(bpy)(Habt)Cl] Cl, [Zn(PPh3)(Habt)(2)Cl]Cl, [Ag(Habt)(2)]ClO4, [Ag(L)(Habt)]ClO4 (L = bpy, phen, PPh3) and [Au(Habt)(3)Cl]Cl-2 are reported. The structures are discussed on the bases of IR, Raman, UV-Vis, NMR (H-1, C-13 and P-31) and mass spectroscopy, elemental analysis, molar conductivity and thermal degradation measurements. In the X-ray crystal structure of the linear [Ag(Habt)(2)]ClO4 complex, Habt coordinates Ag(I) in a monodentate manner through the benzothiazol nitrogen atom. A theoretical study on [Ag(Habt)(2)]ClO4 was undertaken through DFT conformational analysis. The in vitro anticancer activity was evaluated against human breast cancer (MDA-MB231) and human ovarian cancer (OVCAR-8) cell lines. The complexes, [Ag(Habt)(PPh3)] ClO4, [Ag(phen)(Habt)]ClO4, [Pt(Habt)(3)Cl] Cl and [Pd(abt)(phen)] Cl, are more cytotoxic than is cisplatin to these cell lines, with mean IC50 values of 1.38, 1.78, 4.15 and 5.06 (MDA-MB231), and 1.26, 1.45, 4.04 and 5.20 (OVCAR-8) mu M, respectively. The DNA-binding properties of some of these complexes were studied using circular dichroism (CD) spectroscopy. The results indicate that the complexes may have intercalative CT-DNA binding capabilities. (C) 2014 Elsevier B.V. All rights reserved.