Oxidatively modified fatty acyl chain determines physicochemical properties of aggregates of oxidized phospholipids.
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.
Pande
Abhay H
AH
Department of Biotechnology, National Institute of Pharmaceutical Education and Research, Sector 67, S.A.S. Nagar (Mohali)-160062, Punjab, India. apande@niper.ac.in
Kar
Subhabrata
S
Tripathy
Rajan K
RK
D015081:2-Naphthylamine / Q000031:analogs & derivatives / Q000737:chemistry; D000817:Anilino Naphthalenesulfonates / Q000737:chemistry; D016880:Anisotropy; D055598:Chemical Phenomena; D002850:Chromatography, Gel; D004161:Diphenylhexatriene / Q000737:chemistry; D004587:Electrophoresis, Agar Gel; D004591:Electrophoresis, Polyacrylamide Gel; D005227:Fatty Acids / Q000737:chemistry*; D007848:Laurates / Q000737:chemistry; D008823:Micelles; D015335:Molecular Probes / Q000737:chemistry; D010078:Oxazines / Q000737:chemistry; D010084:Oxidation-Reduction; D010743:Phospholipids / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
C515594:8-anilino-1-naphthalenesulfonic acid; D000817:Anilino Naphthalenesulfonates; D005227:Fatty Acids; D007848:Laurates; D008823:Micelles; D015335:Molecular Probes; D010078:Oxazines; D010743:Phospholipids; D004161:Diphenylhexatriene; D015081:2-Naphthylamine; C044808:nile red; C065580:laurdan