Disease relevance of CCRIS 5166

• With E. coli beta-glucuronidase at pH 7.0, selectivity was demonstrated by the complete hydrolysis of N-hydroxy-N-acetyl-4-aminobiphenyl O-glucuronide in the presence of N-acetylbenzidine N-glucuronide, which was not hydrolyzed [1].

High impact information on CCRIS 5166

• Thus, a combination of human recombinant NAT and liver slice experiments has demonstrated that benzidine and N-acetylbenzidine are both preferred substrates for NAT1 [2].
• This report examines the mechanism by which PHS from ram seminal vesicle microsomes catalyzes the oxidation of the reducing cofactor N-acetylbenzidine (ABZ) [3].
• The K(m) values for N-acetylbenzidine metabolism by UGT1A1 and UGT1A4 were 0.37 +/- 0.14 and 1.8 +/- 0.4 mM, respectively [4].
• UGT1A4 N-glucuronidated N'-hydroxy- N-acetylbenzidine at the highest relative rate compared with the other transferases [4].
• Individuals with rapid NAT2 genotypes formed 1.4-fold more N-acetylbenzidine than slow acetylators [5].

Biological context of CCRIS 5166

• N-Acetylbenzidine was converted to mutagens by PHS but not HRP, with enhanced mutagenicity observed in bacteria with high acetylation activity [6].

Anatomical context of CCRIS 5166

• Results are consistent with cytochrome P4501A1/1A2 playing the major role in N-acetylbenzidine and N,N'-diacetylbenzidine metabolism by liver microsomes from control and beta-naphthoflavone-treated rats [7].
• Isolated monkey hepatocytes, in contrast to human hepatocytes, appeared to activate benzidine (BZ), N-acetylbenzidine (MABZ), N,N'-diacetylbenzidine (DABZ), 2-aminofluorene (2-AF) and 2-acetylaminofluorene (2-AAF) poorly [8].
• The investigations generally support a key role of N-acetylbenzidine at the target site of the urothelium [9].

Associations of CCRIS 5166 with other chemical compounds

• Covalent binding of benzidine and N-acetylbenzidine to DNA at the C-8 atom of deoxyguanosine in vivo and in vitro [10].
• N-Oxidation of N-acetylbenzidine (ABZ) and N,N'-diacetylbenzidine (DABZ) was found to occur with NADPH-, NADH-fortified microsomes, although total oxidation at both nitrogens of ABZ was substantially faster than the N-oxidation of DABZ (four times for the mouse and 48 times for the rat) [11].
• A glucuronide of N-acetylbenzidine was synthesized and identified by mass spectrometry as N-acetylbenzidine-N'-glucuronide [12].
• This report considers peroxidation as an alternative pathway for aromatic amine metabolism and examines horseradish peroxidase metabolism of N-acetylbenzidine (ABZ) in the presence of glutathione [13].

Analytical, diagnostic and therapeutic context of CCRIS 5166

• We used reverse- phase HPLC to characterize the metabolites of N-acetylbenzidine formed by PHS and HRP.(ABSTRACT TRUNCATED AT 250 WORDS)[6]
• Urine samples were collected from 29 workers in three textile dyehouses, two tanneries, and two dyestuff quality control laboratories in West Yorkshire and Lancashire. In 200 samples, obtained over a period of 15 months and analysed by gas chromatography/mass spectrometry, no free benzidine or monoacetylbenzidine was detected [14].

References