Effect of N-alkyl-N,N,N-trimethylamonium bromides on the auto-peroxidation of egg yolk phosphatidylcholine in liposomes.
N-alkyl-N,N,N-trimethylamonium bromides (cnTMA, n = number of carbons in alkyl) stimulate and inhibit the autoperoxidation of egg yolk phosphatidylcholine (EYPC) in liposomes at n less than 12 and n greater than 12, respectively, with maximum stimulation for n = 8. CnTMA intercalate between EYPC molecules (decreasing the yield of ROO. + RH----ROOH+R. reaction, where RH is an unsaturated EYPC acyl chain, R. - EYPC acyl radical, and ROO. - peroxy radical of the EYPC acyl chain) and disorder the hydrophobic region of the bilayer (increasing the oxygen solubility there and thus yield of R. + O2----ROO. reaction). The final level of oxidation is affected by a summation of the EYPC lateral separation and disordering effects.
Filípek
J
J
Research Institute of Gerontology, Zámocká ul., Malacky, Czechoslovakia.
Kovács
P
P
Balgavý
P
P
D002855:Chromatography, Thin Layer; D004530:Egg Yolk / Q000737:chemistry; D007700:Kinetics; D015227:Lipid Peroxidation / Q000187:drug effects* / Q000502:physiology; D008081:Liposomes / Q000378:metabolism*; D010713:Phosphatidylcholines / Q000378:metabolism*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry / Q000494:pharmacology*
D008081:Liposomes; D010713:Phosphatidylcholines; D000644:Quaternary Ammonium Compounds