Reactive intermediates from 3-hydroxybenzo[a]pyrene and its glucuronide.

Autor: Ribeiro, Odartey, Kirkby, Charles A., Hirom, Paul C., Millburn, Peter
Zdroj: Carcinogenesis; 1986, Vol. 7 Issue 3, p481-484, 4p
Abstrakt: 3-Hydroxybenzo[a]pyrene (3-OH-BaP) is oxidized by the horseradish peroxidase/HO system to benzo[a]pyrene-3, 6-quinone. In the presence of N-acetylcysteine one other product is also formed. This was identified by its chemical, and u.v., mass and n.m.r. spectral properties as 6-(-acetylcystein-S-yl)-3-hydroxybenzo[a]pyrene (6-NAc-cys-3-OH-BaP). Replacement of the -acetylcysteine by glutathione leads to the formation of a 3-OH-BaP -glutathione adduct. Enzymic hydrolysis of benzo[a]pyrene-3-glucuronide in the presence of -acetykysteine yields, in addition to 3-OH-BaP, a product which co-chromatographs with 6-NAc-cys-3-OH-BaP and has identical chemical and spectral characteristics. [ABSTRACT FROM PUBLISHER]
Databáze: Complementary Index