title: Photoreactive cardiolipin analogues.
abstract: New photoreactive analogues of cardiolipin have been chemically synthesized. Photoreactive aryl azido acyl groups were placed at two different locations within the cardiolipin molecule: at the 2-sn position of the 2-sn glycerol of cardiolipin; at the 2-sn position of the 3-sn-phosphatidyl group; or at both locations to provide a dual labeled analogue. Thus three different cardiolipin analogues distinguished by the positions of the aryl azido acyl groups were prepared. Two different aryl azido acyl groups were employed in the above syntheses and the site of acylation was stereospecifically identified using several phospholipids of known specificity for cardiolipin. Acylation of cardiolipin with the symmetrical anhydride of either acyl aryl azido fatty acid analogue, 2-(N-4-azido-2-nitrophenyl)beta-alanine or 12-(N-4-azido-2-nitrophenyl)aminododecanoic acid provided 1-(3-sn-phosphatidyl)-2-(acyl aryl azido)-3-(3-sn-phosphatidyl)-sn-glycerol. Acylation of monolysocardiolipin (1-(3-sn-phosphatidyl)-3-(1-acyl-2-lyso-glycero(3)phospho)-sn-glyce++ + rol provided two products. 1-(3-sn-phosphatidyl)-3-(1-acyl-2-(acyl aryl azido)-glycero(3)phospho)-sn-glycerol and the doubly labeled 1-(3-sn-phosphatidyl)-2-(acyl aryl azido)-3-(1-acyl-2-(acyl aryl azido)glycero(3)phospho)-sn-glycerol. These are the first reported photoreactive analogues for cardiolipin. The analogues were positive effectors for cytochrome P-450sec, and as shown by SDS-PAGE, they labeled the single subunit of cytochrome P-450sec and the smallest subunits of cytochrome c oxidase from beef heart.
authors.affiliation: Department of Biochemistry, Emory School of Medicine, Atlanta, GA 30322.
authors.forename: W T
authors.initials: WT
authors.lastname: Fowler
authors.forename: J D
authors.initials: JD
authors.lastname: Lambeth
authors.forename: G L
authors.initials: GL
authors.lastname: Powell
mesh_terms: D001386:Azides / Q000032:analysis / Q000138:chemical synthesis; D002308:Cardiolipins / Q000032:analysis / Q000138:chemical synthesis*; D003577:Cytochrome P-450 Enzyme System / Q000528:radiation effects; D003576:Electron Transport Complex IV / Q000528:radiation effects; D010710:Phosphates / Q000032:analysis; D010777:Photochemistry
chemical_list: D001386:Azides; D002308:Cardiolipins; D010710:Phosphates; D003577:Cytochrome P-450 Enzyme System; D003576:Electron Transport Complex IV