Dialkylamino and nitrogen heterocyclic analogues of hexadecylphosphocholine and cetyltrimetylammonium bromide: effect of phosphate group and environment of the ammonium cation on their biological activity

Eur J Med Chem. 2009 Dec;44(12):4970-7. doi: 10.1016/j.ejmech.2009.08.011. Epub 2009 Sep 2.

Abstract

A series of dialkylamino and nitrogen heterocyclic analogues of hexadecylphosphocholine and cetyltrimethylammonium bromide have been synthesized. The prepared compounds exhibit significant cytotoxic, antifungal and antiprotozoal activities. Alkylphosphocholines possess higher antifungal activity against Candida albicans in comparison with quaternary ammonium compounds. However, quaternary ammonium compounds exhibit significant higher activity against human tumor cells and Acanthamoeba lugdunensis compared to alkylphosphocholines. In addition, their haemolytic toxicity has been investigated. The relationship between structure and biological activity of the tested compounds is discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents* / chemical synthesis
  • Antifungal Agents* / chemistry
  • Antifungal Agents* / pharmacology
  • Antineoplastic Agents* / chemical synthesis
  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / pharmacology
  • Candida albicans / drug effects
  • Cations
  • Cell Line, Tumor
  • Cetrimonium
  • Cetrimonium Compounds / chemistry*
  • Cetrimonium Compounds / pharmacology
  • Heterocyclic Compounds / chemistry*
  • Humans
  • Molecular Structure
  • Nitrogen* / chemistry
  • Phosphates / chemistry
  • Phosphorylcholine / analogs & derivatives*
  • Phosphorylcholine / chemistry
  • Phosphorylcholine / pharmacology
  • Quaternary Ammonium Compounds / chemistry

Substances

  • Antifungal Agents
  • Antineoplastic Agents
  • Cations
  • Cetrimonium Compounds
  • Heterocyclic Compounds
  • Phosphates
  • Quaternary Ammonium Compounds
  • Phosphorylcholine
  • miltefosine
  • Nitrogen
  • Cetrimonium