Synthesis, antifungal and haemolytic activity of a series of bis(pyridinium)alkanes

Bioorg Med Chem. 2007 May 15;15(10):3422-9. doi: 10.1016/j.bmc.2007.03.018. Epub 2007 Mar 13.

Abstract

A series of bis(pyridinium)alkanes have been prepared and their antifungal activity, haemolytic activity and ability to inhibit fungal phospholipase B1 have been investigated, together with those of the commercially available antiseptics octenidine and dequalinium. Removal of the amino substituents from the pyridinium rings resulted in a significant decrease in antifungal activity. However, shortening or removing the alkyl chains attached to the amino groups had little effect on antifungal activity and significantly reduced haemolytic activity. Only octenidine was a strong inhibitor of fungal phospholipase B1.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkanes / chemical synthesis*
  • Alkanes / pharmacology*
  • Amphotericin B / pharmacology
  • Anti-Infective Agents, Local / pharmacology
  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / pharmacology*
  • Candida albicans / drug effects
  • Cryptococcus neoformans / drug effects
  • Dequalinium / pharmacology
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / pharmacology
  • Fungi / drug effects
  • Fungi / enzymology
  • Hemolytic Agents / chemical synthesis*
  • Hemolytic Agents / pharmacology*
  • Humans
  • Imines
  • In Vitro Techniques
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Mycoses / microbiology
  • Phospholipases / antagonists & inhibitors
  • Pyridines / pharmacology
  • Pyridinium Compounds / chemical synthesis*
  • Pyridinium Compounds / pharmacology*
  • Structure-Activity Relationship

Substances

  • Alkanes
  • Anti-Infective Agents, Local
  • Antifungal Agents
  • Enzyme Inhibitors
  • Hemolytic Agents
  • Imines
  • Indicators and Reagents
  • Pyridines
  • Pyridinium Compounds
  • Amphotericin B
  • Dequalinium
  • Phospholipases
  • octenidine