[15]aneN4S: synthesis, thermodynamic studies and potential applications in chelation therapy

Molecules. 2014 Jan 3;19(1):550-67. doi: 10.3390/molecules19010550.

Abstract

The purpose of this work was to synthesize and characterize the thiatetraaza macrocycle 1-thia-4,7,10,13-tetraazacyclopentadecane ([15]aneN4S). Its acid-base behaviour was studied by potentiometry at 25 °C and ionic strength 0.10 M in KNO3. The protonation sequence of this ligand was investigated by 1H-NMR titration that also allowed the determination of protonation constants in D2O. Binding studies of [15]aneN4S with Mn2+, Fe2+, Co2+, Ni2+, Cu2+, Zn2+, Cd2+, Hg2+ and Pb2+ metal ions were further performed under the same experimental conditions. The results demonstrated that this compound has a higher selectivity and thermodynamic stability for Hg2+ and Cu2+, followed by Ni2+. The UV-visible-near IR spectroscopies and magnetic moment data for the Co(II) and Ni(II) complexes indicated a tetragonal distorted coordination geometry for both metal centres. The value of magnetic moment and the X-band EPR spectra of the Cu(II) complex are consistent with a distorted square pyramidal geometry.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aza Compounds / chemical synthesis
  • Aza Compounds / chemistry*
  • Aza Compounds / pharmacology
  • Chelating Agents / chemistry
  • Chelating Agents / pharmacology
  • Drug Stability
  • Macrocyclic Compounds / chemical synthesis
  • Macrocyclic Compounds / chemistry*
  • Macrocyclic Compounds / pharmacology
  • Metals / chemistry
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Thermodynamics

Substances

  • Aza Compounds
  • Chelating Agents
  • Macrocyclic Compounds
  • Metals