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The presumed ultimate carcinogenic metabolite of the rat hepatocarcinogen N-methyl-4-aminoazobenzene (MAB), N-sulphonyloxy-MAB, was synthesized and reacted with glutathione (GSH) to yield the stable ring-substituted conjugates, 3-, 2'- and 4'-glutathion-S-yl-MAB (3-, 2'- and 4'-GSMAB) and the unstable methylene-substituted conjugate, N-(glutathion-S-methylene)-4-aminoazobenzene. Reaction of the model ultimate carcinogen, N-benzoyloxy-MAB, or the proximate carcinogen, N-hydroxy-MAB, with GSH also gave the same four conjugates. The ratio of ring-substitution relative to methylene conjugate formation increased with stronger leaving groups; i.e., ring-substitution increased in the order: N-hydroxy: N-benzoyloxy: N-sulphonyloxy. The ratio of 3-GSMAB to 2'- plus 4'-GSMAB was constant for all three MAB derivatives.
B Coles, and
B Ketterer, and
F A Beland, and
F F Kadlubar
September 1979,
Cancer research,
B Coles, and
B Ketterer, and
F A Beland, and
F F Kadlubar
April 1979,
Chemico-biological interactions,
B Coles, and
B Ketterer, and
F A Beland, and
F F Kadlubar
February 1982,
Chemico-biological interactions,
B Coles, and
B Ketterer, and
F A Beland, and
F F Kadlubar
March 1976,
Cancer research,
B Coles, and
B Ketterer, and
F A Beland, and
F F Kadlubar
September 1980,
Chemico-biological interactions,
B Coles, and
B Ketterer, and
F A Beland, and
F F Kadlubar
September 1987,
Nucleic acids research,
B Coles, and
B Ketterer, and
F A Beland, and
F F Kadlubar
October 1983,
Cancer research,
B Coles, and
B Ketterer, and
F A Beland, and
F F Kadlubar
August 1975,
Taiwan yi xue hui za zhi. Journal of the Formosan Medical Association,
B Coles, and
B Ketterer, and
F A Beland, and
F F Kadlubar
December 1981,
National Cancer Institute monograph,
B Coles, and
B Ketterer, and
F A Beland, and
F F Kadlubar
December 1981,
National Cancer Institute monograph,
