Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Synthesis of Phosphatidylcholine with Conjugated Linoleic Acid and Studies on Its Cytotoxic Activity

Natalia Niezgoda A , Paweł Mituła A , Katarzyna Kempińska B , Joanna Wietrzyk B and Czesław Wawrzeńczyk A C

A Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, PL-50-375 Wrocław, Poland.

B Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Department of Experimental Oncology, Weigla 12, PL-53-114 Wrocław, Poland.

C Corresponding author. Email: czeslaw.wawrzenczyk@up.wroc.pl

Australian Journal of Chemistry 66(3) 354-361 http://dx.doi.org/10.1071/CH12404
Submitted: 31 August 2012  Accepted: 19 November 2012   Published: 11 February 2013

Abstract

Phospholipids with conjugated linoleic acid (CLA), which are potential lipid prodrugs, were synthesised. CLA was obtained by the alkali-isomerisation of linoleic acid and was subsequently used in the synthesis of 1,2-di(conjugated)linoleoyl-sn-glycero-3-phosphocholine in good (82 %) yield. 1-Palmitoyl-2-(conjugated)linoleoyl-sn-glycero-3-phosphocholine was obtained by a two-step synthesis in 87 % yield. All the compounds were tested in an in vitro cytotoxicity assay against two human cancer cell lines, HL-60 and MCF-7, and a mouse fibroblast cell line, Balb/3T3. The free form of CLA exhibited the highest activity against all cancer cell lines. Results obtained for the Balb/3T3 line proved that phosphatidylcholine derivatives decreased the cytotoxic effect of CLA against healthy cell lines.

Graphical Abstract Image


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