2,6-diacetylpyridine bis(thiosemicarbazones) zinc complexes: synthesis, structure, and biological activity

J Inorg Biochem. 1995 May 15;58(3):157-75. doi: 10.1016/0162-0134(94)00043-a.

Abstract

The reaction of zinc chloride, acetate, or perchlorate with two bis(thiosemicarbazones) of 2,6-diacetylpyridine [H2daptsc = 2,6-diacetylpyridine bis(thiosemicarbazone) and H2dapipt = 2,6-diacetylpyridine bis(hydrazinopyruvoylthiosemicarbazone)] leads to the formation of four novel complexes that have been characterized by spectroscopic studies (NMR, IR) and biological properties. The crystal structures of the two compounds--[Zn(daptsc)]2.2DMF (1) and [Zn(H2dapipt)(OH2)2](CIO4)2.3H2O (2)--also have been determined by x-ray methods from diffractometer data. Compound (1) is dimeric and the two zinc atoms have a distorted octahedral coordination. The ligand is deprotonated. In compound (2), the coordination geometry about zinc is pentagonal--bipyramidal and the ligand is in the neutral form. The molecular structure of (2) consists of cations [Zn(H2dapipt)(OH2)]2+, CIO4- disordered anions, and three water molecules of solvation. Biological studies have shown that the ligands and the complexes Zn(daptsc).1/2EtOH and Zn(H2daptsc)Cl2 have an effect in vitro on cell proliferation and differentiation (inhibition); both are concentration dependent. [Zn(daptsc)]2.2DMF (1) shows the effects at lower concentration values with respect to other compounds.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Division / drug effects
  • Crystallography, X-Ray
  • Erythrocytes / drug effects
  • Erythropoiesis / drug effects
  • Friend murine leukemia virus
  • Magnetic Resonance Spectroscopy
  • Pyridines / chemistry
  • Pyridines / pharmacology
  • Spectrophotometry, Infrared
  • Thiosemicarbazones / chemistry*
  • Thiosemicarbazones / pharmacology
  • Tumor Cells, Cultured
  • Zinc Compounds / chemistry*
  • Zinc Compounds / pharmacology

Substances

  • Pyridines
  • Thiosemicarbazones
  • Zinc Compounds