One-pot synthesis of polyunsaturated fatty acid amides with anti-proliferative properties

Bioorg Med Chem Lett. 2014 Dec 15;24(24):5635-5638. doi: 10.1016/j.bmcl.2014.10.084. Epub 2014 Nov 1.

Abstract

A one-pot environmentally friendly transamidation of ω-3 fatty acid ethyl esters to amides and mono- or diacylglycerols was investigated via the use of a polymer-supported lipase. The method was used to synthesize a library of fatty acid monoglyceryl esters and amides. These new derivatives were found to have potent growth inhibition effects against A549 lung cancer cells.

Keywords: Environmentally friendly synthesis; Growth inhibition; Polyunsaturated fatty acid amides; Transamidation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis
  • Amides / chemistry*
  • Amides / toxicity
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Enzymes, Immobilized / chemistry
  • Enzymes, Immobilized / metabolism
  • Esters
  • Fatty Acids, Unsaturated / chemical synthesis
  • Fatty Acids, Unsaturated / chemistry*
  • Fatty Acids, Unsaturated / toxicity
  • Humans
  • Lipase / chemistry
  • Lipase / metabolism
  • Structure-Activity Relationship

Substances

  • Amides
  • Enzymes, Immobilized
  • Esters
  • Fatty Acids, Unsaturated
  • Lipase