Synthesis, characterization, and cytotoxic activity studies of new N4O complexes derived from 2-({3-[2-morpholinoethylamino]-N3-([pyridine-2-yl]methyl) propylimino} methyl)phenol

Rezaeivala M., Ahmadi M., Captain B., Sahin-Bolukbasi S. , Dehghani-Firouzabadi A. A. , Gable R. W.

APPLIED ORGANOMETALLIC CHEMISTRY, vol.34, no.2, 2020 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 34 Issue: 2
  • Publication Date: 2020
  • Doi Number: 10.1002/aoc.5325


A new unsymmetrical five-coordinate Schiff base ligand (HL) with an N4O donor set (2) has been prepared by condensation of N1-(2-morpholinoethyl)-N1-([pyridine-2-yl]methyl)propane-1,3-diamine with 2-hydroxy-benzaldehyde. Metal complexes [ML](n+) (M = Zn2+, Cd2+, Mn2+, Cu2+, Ni2+, Ag+, Fe3+, and Co2+ (3-10) were synthesized by the reaction of the ligand and metal salts in ethanol. The resulting products were characterized by elemental analyses, infrared, H-1 and C-13 nuclear magnetic resonance spectra (in the case of Cd and Zn complexes), UV-Vis, electrospray ionization-mass spectrometric, and conductivity measurements. The structure of the complexes [ZnL](ClO4) (3), [CdL](ClO4) (4), and [CuL](ClO4) (7) has been determined by single-crystal X-ray diffraction analysis. The metal complexes were determined to have a distorted trigonal bipyramidal (Zn and Cd) or a distorted square pyramidal (Cu) geometry. The cytotoxic potential of each compound (1-10) against MCF-7 and MDA-MB-231 (breast cancer cells), PC-3 (prostate cancer cells), and WI-38 human normal lung fibroblast cells was evaluated using the MTT (3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyl tetrazolium bromide) assay. Compounds 1, 2, and 10 did not display any activity toward any cell line tested. None of the compounds except compound 8 was cytotoxic toward PC-3. Compounds 4 and 8 showed the highest cytotoxic activity against the MCF-7 and MDA-MB-231 cell lines. Because compounds 3, 6, and 9 have similar half-maximal inhibitory concentration values against cancer cells and normal cells, these compounds displayed poor selectivity between cancer and normal cells. More importantly, it was observed that compound 5 acts differently toward different types of cell lines. For example, it displays lower cytotoxicity against the WI-38 normal cell line than it does against the MDA-MB-231 cell line.