Silver(I) complexes of 9-anthracenecarboxylic acid and imidazoles: synthesis, structure and antimicrobial activity

Dalton Trans. 2012 Jun 7;41(21):6516-27. doi: 10.1039/c2dt12166b. Epub 2012 Apr 5.

Abstract

[Ag(2)(9-aca)(2)] (1) (9-acaH = 9-anthracenecarboxylic acid) reacts with a series of imidazoles to give [Ag(imidH)(2.3)(CH(3)CN)(0.7)](9-aca) (3), [Ag(6)(imidH)(4)(9-aca)(6)(MeOH)(2)] (4), {[Ag(1-Me-imid)(2)](2)[Ag(4)(9-aca)(6)]} (5), {[Ag(1-Bu-imid)(2)](2)[Ag(4)(9-aca)(6)]} (6) and [Ag(apim)](9-aca)·H(2)O (7) (imidH = imidazole; 1-Me-imid = 1-methylimidazole; 1-Bu-imid = 1-butylimidazole; apim = 1-(3-aminopropyl)imidazole). The mononuclear complex 3, hexanuclear 4-6, and polymeric 7, were all characterised using X-ray crystallography. While many of the complexes possess excellent in vitro antifungal and antibacterial activities they are, unanimously, more effective against fungal cells. The insect, Galleria mellonella, can survive high doses of the Ag(i) complexes administered in vivo, and a number of the complexes offer significant protection to larvae infected with a lethal dose of pathogenic Candida albicans cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthracenes / chemistry*
  • Anti-Infective Agents / chemical synthesis
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology
  • Anti-Infective Agents / toxicity
  • Candida albicans / drug effects
  • Chemistry Techniques, Synthetic*
  • Escherichia coli / drug effects
  • Imidazoles / chemistry*
  • Lepidoptera / drug effects
  • Methicillin-Resistant Staphylococcus aureus / drug effects
  • Microbial Sensitivity Tests
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry*
  • Organometallic Compounds / pharmacology*
  • Organometallic Compounds / toxicity
  • Silver / chemistry*

Substances

  • Anthracenes
  • Anti-Infective Agents
  • Imidazoles
  • Organometallic Compounds
  • Silver
  • 9-anthroic acid