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Deacylation of carcinogenic 5-nitrofuran derivatives by mammalian tissues
Authors:C Y Wang  G T Bryan
Affiliation:Division of Clinical Oncology, University of Wisconsin Medical School, Madison, Wis. 53706 U.S.A.
Abstract:The deacylations of N-[4-(5-nitro-2-furyl)-2-thiazolyl] fonnamide (FANFT), N-[4-(5-nitro-2-furyl)-2-thiazolyl] acetarnide (NFTA) and formic acid 2-[4-(5-nitro-2-furyl)-2-thiazolyl] hydrazide (FNT) by liver, kidney, small intestines and stomach of mouse, rat, hamster and guinea pig were investigated. FANFT was deformylated to 2-amino-4-(5-nitro-2-furyl)thiazole (ANFT). FANFT formamidase activity was higher in the liver and small intestines of mouse, hamster and guinea pig, and small intestines and stomach of rat. There was no detectable FANFT formamidase activity in the stomach of the mouse and hamster. Neither NFTA nor FNT was deacylated by the rodent tissue homogenates studied. It is suggested that (1)4 ANFT is a metabolite of FANFT but not NFTA; (2) 2-hydrazino-4-(5-nitro-2-furyl)thiazole (HNFT) may not be a metabolite of FNT; and (3) the induction of tumors by FANFT, NFTA and FNT may not be due to a common carcinogenic metabolite, although these chemicals demonstrate similar organ specificities in some of these rodents.
Keywords:ANFT  2-amino-4-(5-nitro-2-furyl)-thiazole  DMF  dimethylformamide  FANFT  N-[4-(5-nitro-2-iuryl)-2-thiazolyl]formamide  FNT  formic acid 2-[4-(5-nitro-2-furyl)-2-thiazolyl] hydrazide  HNFT  2-hydrazino-4-(5-nitro-2-furyl)thiazole  NFTA  N-[4-(5-nitro-2-furyl)-2-thiazolyl]acet amide
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