Synthesis, characterization and anticancer studies of bis-(N-methyl-1-phenyldithiocarbamato) Cu(II), Zn(II), and Pt(II) complexes: single crystal X-ray structure of the copper complex

Abstract

Cu(II), Pt(II), and Zn(II) complexes of N-methyl-1-phenyldithiocarbamate were synthesized and characterized by FTIR, NMR, UV-visible spectroscopy and elemental analysis. The complexes were formulated as [Cu(L)2], [Zn(L)2] and [Pt(L)2] (where L = N-methyl-1-phenyldithio­carbamate) in which two molecules of the ligands coordinate to the metal ions in a bidentate chelating fashion. This is confirmed by elemental analysis and the presence of strong single bands at 952, 951, and 955 cm−1 for Cu(II), Pt(II), and Zn(II) complexes, respectively, in the FTIR spectra. The electronic spectra of Pt(II) and Cu(II) complexes are consistent with four-coordinate square planar geometry. Single crystal X-ray of [Cu(N-mpDTC)2] confirmed square planar structural arrangement (CuS4) in which the ligands are asymmetrically bonded to the Cu(II) ion building a centrosymmetric monomer entity. The S-Cu-S bite angle is 77.95° (3) whereas the intramolecular N–C bond length is 1.318 Å and trans S11-Cu-S1 = S21-Cu-S2 is 180°, which are consistent with reported copper thiolates in square planar environment. In vitro antiproliferative activity of the complexes against three human cancer cell lines showed that the zinc complex has better activity compared to Cu and Pt complexes, with IC50 values of 14.28, 22.74 and 20.10 μM against TK10, UACC62, and MC7 cell lines, respectively.