Phosphatidylcholine with cis-9,trans-11 and trans-10,cis-12 Conjugated Linoleic Acid Isomers: Synthesis and Cytotoxic Studies
Natalia Niezgoda A , Anna Gliszczyńska A , Witold Gładkowski A , Katarzyna Kempińska B , Joanna Wietrzyk B and Czesław Wawrzeńczyk A C
+ Author Affiliations
- Author Affiliations
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 68(7) 1065-1075 https://doi.org/10.1071/CH14606
Submitted: 4 July 2014 Accepted: 8 November 2014 Published: 29 January 2015
Abstract
Novel phosphatidylcholines and lysophosphatidylcholines with cis-9,trans-11 and trans-10,cis-12 conjugated linoleic acid (CLA) were synthesized in high yields (75–99 %). The in vitro cytotoxic activities of these compounds against three human cancer cell lines (HL-60, MCF-7, and HT-29) were evaluated. The results revealed that there are differences in the activity between phosphatidylcholine with cis-9,trans-11 and trans-10,cis-12 CLA acyl groups. 1,2-Di(9Z,11E)-octadecadienoyl-sn-glycero-3-phosphocholine was the most potent cytotoxic agent among all tested CLA derivatives and its IC50 (concentration of a compound that inhibits the proliferation of 50 % of the cancer cell population) was 29.4 µM against HL-60. Moreover, phosphatidylcholines with CLA acyls exhibited much lower cytotoxicity against non-cancer cells (Balb/3T3) than free CLA isomers.
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