Syntheses, structures and antimicrobial activities of water-soluble silver(I)-oxygen bonding complexes with chiral and racemic camphanic acid (Hca) ligands

Dalton Trans. 2004 Nov 7:(21):3732-40. doi: 10.1039/B411859F. Epub 2004 Oct 1.

Abstract

Water-soluble, relatively light-stable, chiral and achiral silver(I) complexes [[Ag(2)(ca)(2)]](n) and [[Ag(2)(ca)(2)(Hca)(2)]](n)(R- and S-Hca =(1R,4S)- and (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid, respectively) prepared from the reaction of Ag(2)O with chiral and racemic Hca in 1:2 and 1:4 molar ratios were characterized by elemental analysis, TG/DTA, FTIR, and solution ((1)H, (13)C and (109)Ag) and solid-state ((13)C) NMR spectroscopy. Crystallography revealed that unique 2(1) helical polymer and zigzag structures were formed on self-assembly of the dimeric units in the crystals of [[Ag(2)(S-ca)(2)]](n) and three [[Ag(2)(ca)(2)(Hca)(2)]](n). In the crystal of [[Ag(2)(S-ca)(2)]](n) two 2(1) helices and a loop were observed in the stair-like polymer structure, whereas zigzag and a loop were seen in the crystals of three [[Ag(2)(ca)(2)(Hca)(2)]](n). Carbon NMR spectra in the solid state and in D(2)O indicated that these polymeric structures were loosely bound and fast ligand-exchange reactions took place in aqueous solution. The complexes, [[Ag(2)(ca)(2)]](n) and [[Ag(2)(ca)(2)(Hca)(2)]](n), showed a wide spectrum of effective antimicrobial activity as anticipated for weak silver(i)-O bonding complexes. Similar antimicrobial activity of [[Ag(2)(ca)(2)]](n) and [[Ag(2)(ca)(2)(Hca)(2)]](n) against selected microorganisms suggested that ligand exchangeability played an important role as well as the coordination geometry of the silver(i) ion.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents* / chemical synthesis
  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / pharmacology
  • Bridged-Ring Compounds / chemistry*
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Lactones / chemistry*
  • Ligands
  • Microbial Sensitivity Tests
  • Organometallic Compounds* / chemical synthesis
  • Organometallic Compounds* / chemistry
  • Organometallic Compounds* / pharmacology
  • Oxygen / chemistry*
  • Silver / chemistry*
  • Solubility
  • Stereoisomerism
  • Water / chemistry

Substances

  • Anti-Bacterial Agents
  • Bridged-Ring Compounds
  • Lactones
  • Ligands
  • Organometallic Compounds
  • camphanic acid
  • Water
  • Silver
  • Oxygen