Synthesis, Crystal Structures and Anticancer Studies of Morpholinyldithiocarbamato Cu(II) and Zn(II) Complexes

Molecules. 2020 Aug 6;25(16):3584. doi: 10.3390/molecules25163584.

Abstract

Cu(II) and Zn(II) morpholinyldithiocarbamato complexes, formulated as [Cu(MphDTC)2] and [Zn(μ-MphDTC)2(MphDTC)2], where MphDTC is morpholinyldithiocarbamate were synthesized and characterized by elemental analysis, spectroscopic techniques and single-crystal X-ray crystallography. The molecular structure of the Cu(II) complex revealed a mononuclear compound in which the Cu(II) ion was bonded to two morpholinyl dithiocarbamate ligands to form a four-coordinate distorted square planar geometry. The molecular structure of the Zn(II) complex was revealed to be dinuclear, and each metal ion was bonded to two morpholinyl dithiocarbamate bidentate anions, one acting as chelating ligand, the other as a bridge between the two Zn(II) ions. The anticancer activity of the morpholinyldithiocarbamate ligand, Cu(II) and Zn(II) complexes were evaluated against renal (TK10), melanoma (UACC62) and breast (MCF7) cancer cells by a Sulforhodamine B (SRB) assay. Morpholinyldithiocarbamate was more active than the standard drug parthenolide against renal and breast cancer cell lines, and [Zn(μ-MphDTC)2(MphDTC)2] was the most active complex against breast cancer. The copper(II) complex had a comparable activity with the standard against renal and breast cancer cell lines but showed an enhanced potency against melanoma when compared to parthenolide.

Keywords: Cu(II); Zn(II); anticancer studies; crystal structures; morpholinyldithiocarbamate.

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Chemistry Techniques, Synthetic
  • Coordination Complexes / chemical synthesis*
  • Coordination Complexes / chemistry
  • Coordination Complexes / pharmacology*
  • Copper / chemistry*
  • Crystallography, X-Ray
  • Humans
  • Models, Molecular
  • Molecular Conformation
  • Thiocarbamates / chemistry*
  • Zinc / chemistry*

Substances

  • Antineoplastic Agents
  • Coordination Complexes
  • Thiocarbamates
  • Copper
  • Zinc