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

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.

Rapid tin-mediated access to a lysophosphatidylethanolamine (LPE) library: Application to positional LC/MS analysis for hepatic LPEs in non-alcoholic steatohepatitis model mice

“…Moreover, this approach has already been successfully applied to the synthesis of LPCs by Servi et al (Fasoli, et al, 2006). When we applied this 9 approach to diol 6, we obtained trityl-protected LPEs 7'-17' in yields that were merely moderate (18-44%) compared to previously reported LPCs (Scheme 2) (Fasoli, et al, 2006;Niezgoda, et al, 2013). The results of these experiments are summarized in Table 1.…”

“…After deprotection, we observed regioselectivity ratios (2-LPE:1-LPE) of 3:1 to 7:3, with the exception of 3:2 for 15 (entry 9, Table 1). Even though these ratios are not as high as for the previously reported LPCs (Fasoli, et al, 2006;Niezgoda, et al, 2013), they are nevertheless acceptable, considering the aforementioned problematic acyl migration. Even if the acylation was highly regioselective, the acidic work-up should promote a 1,2-O-acyl migration and thus lower the selectivity.…”

Phosphatidylcholine with cis-9,trans-11 and trans-10,cis-12 Conjugated Linoleic Acid Isomers: Synthesis and Cytotoxic Studies

“…It is formed together with cis-9, trans-11 as the second major product of the alkaline isomerization of linoleic acid. [11] It has been observed that a difference in molecular structure of particular isomers can cause variation in their activity. For instance, the cis-9,cis-11 isomer showed the ability to inhibit more than 60 % of the breast cancer MCF-7 cell population, whereas cis-9,trans-11 CLA inhibited only 20 %.…”

Synthesis of a series of new racemic [2,3-bis(acyloxy)propyl]phosphonocholines

“…1 H NMR and 13 C NMR spectra of (4g) were analyzed according to earlier studies. 25 Esterification of (2,3-epoxypropyl)phosphonate (2) with palmitic acid anhydride was also tested. The reaction was carried out according to the procedure of Ali and Bittman.…”