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Article << Previous     |     Next >>   Contents Vol 66(3)

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


 
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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.





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