Oxidatively modified fatty acyl chain determines physicochemical properties of aggregates of oxidized phospholipids |
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Authors: | Abhay H. Pande Subhabrata Kar Rajan K. Tripathy |
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Affiliation: | Department of Biotechnology, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S.A.S. Nagar (Mohali)-160062, Punjab, India |
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Abstract: | In vivo oxidation of glycerophospholipid generates a variety of products including truncated oxidized phospholipids (tOx-PLs). The fatty acyl chains at the sn-2 position of tOx-PLs are shorter in length than the parent non-oxidized phospholipids and contain a polar functional group(s) at the end. The effect of oxidatively modified sn-2 fatty acyl chain on the physicochemical properties of tOx-PLs aggregates has not been addressed in detail, although there are few reports that modified fatty acyl chain primarily determines the biological activities of tOx-PLs. In this study we have compared the properties of four closely related tOx-PLs which differ only in the type of modified fatty acyl chain present at the sn-2 position: 1-palmitoyl-2-azelaoyl-sn-glycero-3-phosphocholine (PazePC), 1-palmitoyl-2-(9′-oxo-nonanoyl)-sn-glycero-3-phosphocholine (PoxnoPC), 1-palmitoyl-2-glutaroyl-sn-glycero-3-phosphocholine (PGPC), and 1-palmitoyl-2-(5′-oxo-valeroyl)-sn-glycero-3-phosphocholine (POVPC). Aggregates of individual tOx-PL in aqueous solution were characterized by fluorescence spectroscopy, size exclusion chromatography, native polyacrylamide and agarose gel electrophoresis. The data suggest that aggregates of four closely related tOx-PLs form micelle-like particles of considerably different properties. Our result provides first direct evidence that because of the specific chemical composition of the sn-2 fatty acyl chain aggregates of particular tOx-PL possess a distinctive set of physicochemical properties. |
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Keywords: | ANS, 8-anilinonaphthalene-1-sulfonate CMC, critical micellar concentration DPH, 1,6-diphenyl-1,3,5-hexatriene Laurdan, 2-dimethylamino-(6-lauroyl)-naphthalene NBD-DMPG, 7-nitrobenz-2-oxa-1,3-diazol-4-yl labeled DMPG PazePC, 1-palmitoyl-2-azelaoyl-sn-glycero-3-phosphocholine PoxnoPC, 1-palmitoyl-2-(9&prime -oxo-nonanoyl)-sn-glycero-3-phosphocholine PGPC, 1-palmitoyl-2-glutaroyl-sn-glycero-3-phosphocholine POVPC, 1-palmitoyl-2-(5&prime -oxo-valeroyl)-sn-glycero-3-phosphocholine tOx-PLs, oxidized phospholipids |
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