Synthesis, structural characterization and influence on the phagocytic activity of human neutrophils of thiazoline and thiazine derivative ligands and their zinc(II) complexes

J Inorg Biochem. 2006 Nov;100(11):1861-70. doi: 10.1016/j.jinorgbio.2006.07.007. Epub 2006 Jul 26.

Abstract

The zinc(II) complexes dichloro[2-(3,4-dichlorophenyl)imino-kappaN-(2-thiazolin-kappaN-2-yl)thiazolidine]zinc(II) (1) and dichloro[2-(3,4-dichlorophenyl)imino-kappaN-(4H-5,6-dihydro-1,3-thiazin-kappaN-2-yl)tetrahydrothiazine]zinc(II) (2) have been isolated and characterized in the solid state by X-ray diffraction, elemental analysis and IR spectra. In both complexes, the environment around the zinc(II) ion may be described as a distorted tetrahedral geometry, with the metallic atom coordinated to two chlorine atoms [Zn-Cl(1)=2.218(1)A; Zn-Cl(2)=2.221(1)A], one imino nitrogen [Zn-N(3)=2.042(2)A] and one thiazoline nitrogen [Zn-N(1)=2.022(2)A] in complex 1 and to two chlorine atoms [Zn-Cl(1)=2.216(1)A; Zn-Cl(2)=2.192(1)A], one imino nitrogen [Zn-N(3)=2.045(2)A] and one thiazine nitrogen [Zn-N(1)=2.039(2)A] in complex 2. In addition, we also report in this study the crystal structure of the 2-(3,4-dichlorophenyl)imino-N-(2-thiazolin-2-yl)thiazolidine (TdTn) ligand as well as the synthesis and characterization by X-ray diffraction, (1)H and (13)C NMR spectra, elemental analysis, IR and electronic spectra of the 2-(3,4-dichlorophenyl)imino-N-(4H-5,6-dihydro-1,3-thiazin-2-yl)tetrahydrothiazine (TzTz) ligand. Besides, we study the phagocytic function in humans neutrophils treated with each complex and ligand aforementioned.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Humans
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Neutrophils / cytology
  • Neutrophils / drug effects*
  • Neutrophils / immunology
  • Phagocytosis / drug effects*
  • Thiazines / chemistry*
  • Thiazoles / chemistry*
  • Zinc Compounds / chemical synthesis
  • Zinc Compounds / chemistry
  • Zinc Compounds / pharmacology*

Substances

  • Ligands
  • Thiazines
  • Thiazoles
  • Zinc Compounds