Interaction of trichloromethyl radicals with phenylalanine.
Chemically or enzymatically generated trichloromethyl free radicals interact with liposoluble derivatives of phenylalanine. In vitro, in a chemical system to produce .CCl3 (benzoyl peroxide catalysis), this radical attacked N-acetyl-d,l-phenylalanine methyl ester (PheMeAc) to give a monochlorinated derivative (I) and an unsaturated imine type derivative of PheMeAc (II). Using a liver microsomal system to produce .CCl3 (microsomes + NADPH + CCl4 under nitrogen), the attack of PheMeAc did not result in I or II formation, but in production of benzene. The phenylalanine content in liver microsomal proteins from rats treated with CCl4 6 h before, was not significantly decreased. The results suggest that phenylalanine is a potential target of .CCl3.
Castro
G D
GD
Centro de Investigaciones Toxicológicas (CEITOX), CITEFA/CONICET, Pcia. de Buenos Aires, Argentina.
Díaz Gómez
M I
MI
Castro
J A
JA
D000818:Animals; D002251:Carbon Tetrachloride / Q000031:analogs & derivatives* / Q000378:metabolism / Q000633:toxicity; D005609:Free Radicals; D008401:Gas Chromatography-Mass Spectrometry; D008297:Male; D008862:Microsomes, Liver / Q000737:chemistry / Q000378:metabolism; D010649:Phenylalanine / Q000378:metabolism*; D011506:Proteins / Q000378:metabolism; D051381:Rats; D011919:Rats, Inbred Strains
D005609:Free Radicals; D011506:Proteins; C025280:trichloromethyl free radical; D010649:Phenylalanine; D002251:Carbon Tetrachloride