Oxidatively modified fatty acyl chain determines physicochemical properties of aggregates of oxidized phospholipids

• Published in: Biochimica et biophysica acta 2010-03, Vol.1798 (3), p.442-452
• Main Authors: Pande, Abhay H., Kar, Subhabrata, Tripathy, Rajan K.
• Format: Article
• Language: English
• Subjects: 2-Naphthylamine - analogs & derivatives; 2-Naphthylamine - chemistry; Anilino Naphthalenesulfonates - chemistry; Anisotropy; Chemical Phenomena; Chromatography, Gel; Critical micelle concentration; Diphenylhexatriene - chemistry; Electrophoresis, Agar Gel; Electrophoresis, Polyacrylamide Gel; Fatty Acids - chemistry; Generalized polarization; Laurates - chemistry; Micelles; Microfluidity; Micropolarity; Molecular Probes - chemistry; Oxazines - chemistry; Oxidation-Reduction; Phospholipids - chemistry; Spectrometry, Fluorescence; Stokes diameter; Surface potential
• ISSN: 0005-2736; 0006-3002; 1879-2642
• DOI: 10.1016/j.bbamem.2009.12.028

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.