Disease relevance of p-Aminoazobenzene

• Nine spontaneous hepatocellular carcinomas (HCCs) and 34 chemically induced HCCs (induced by single intraperitoneal injections of N-nitrosodiethylamine [DEN] [8 HCCs], 7,12-dimethylbenz[a]anthracene [DMBA] [8 HCCs], 4-aminoazobenzene [8 HCCs], and N-OH-2-acetylaminofluorene [10 HCCs]) were examined for mutations in exons 5-8 of the p53 gene [1].
• 15 aminoazobenzene dyes and 7 of their reductive-cleavage products were examined in the Salmonella/microsome assay with strains TA98, TA100, TA1535, TA1537 and TA1538 [2].
• Partial degradation of p-aminoazobenzene by a defined mixed culture of Bacillus subtilis and Stenotrophomonas maltophilia [3].
• Differences in DNA damage induced by mutagenic and nonmutagenic 4-aminoazobenzene derivatives in Escherichia coli [4].
• Allergic reactions to p-aminoazobenzene were frequently observed (6.0%), but the relevance of these reactions is still obscure [5].

High impact information on p-Aminoazobenzene

• Adult Syrian golden hamster hepatocytes were shown to have a high capacity to metabolize carcinogens, such as diethylnitrosamine, 2-nitrofluorene, and 4-aminoazobenzene, to a form that transforms mammalian cells [6].
• 4-Aminoazobenzene and N-hydroxy-2-acetylaminofluorene also caused the Ki-ras codon 13 mutation [7].
• Active clones were selected by a simple visual test for their ability to decolorize 4-aminoazobenzene in bacterial medium by acetylation [8].
• Although under the same conditions the N-acetylation rates for the two NAT1s declined by > 50%, below 5 microM 2-AF or AAB, the NAT rate data fit Michaelis-Menten kinetics, and the apparent K(m) values were 0.2-0.9 microM [8].
• Resonance Raman spectra of 4-sulfonamido -4'-dimethylaminoazobenzene, 4-sulfonamido-4'-hydroxyazobenzene, and 4-sulfonamideo-4' aminoazobenzene bound to various isoenzymes of carbonic anhydrase were obtained by exciting into the sulfonamide absorption bands in the 400-500-nm region [9].

Chemical compound and disease context of p-Aminoazobenzene

• The mutagenicity of 8 azo dyes and 6 p-phenylenediamine derivatives, which comprised the metabolites of carcinogenic 4-aminoazobenzene derivatives, was studied on Salmonella typhimurium TA98 and TA100 [10].
• The commercial disperse dye product CI Disperse Blue 291 containing the aminoazobenzene 2-[(2-bromo-4,6-dinitrophenyl)azo]-5-(diethylamino)-4-methoxyacetanilide (CAS registry no. 56548-64-2) was tested for mutagenic activity in the Salmonella assay [11].

Biological context of p-Aminoazobenzene

• After the application of AB phosphorylation of the proteins of rat liver nuclear ribonucleoprotein particles decreased to 70% and in regenerating liver to 61% of the phosphorylation of particle proteins in control liver [12].

Anatomical context of p-Aminoazobenzene

• The carcinogens we studied were p-aminoazobenzene, auramine, 2,4-diaminotoluene, p-dichlorobenzene, ethylene thiourea (ETU), styrene-7,8-oxide, phenobarbital sodium, and benzene-1,2,3,4,5,6-hexachloride (BHC); except for p-aminoazobenzene, they do not induce micronuclei in mouse bone marrow cells [13].
• 4-DAB was found to be metabolized to give two major products, 4-aminoazobenzene and N-hydroxy-4-aminoazobenzene, only when incubated with liver microsomes [14].

Associations of p-Aminoazobenzene with other chemical compounds

• NAT I primarily catalyzed the AcCoA-dependent acetylation of PABA; NAT II catalyzed, N,N-acetyltransfer (N-OH-AAF/AAB), AcCoA/PA N-acetyltransfer and N-OH-AAF N,O-acyltransfer (AHAT) activities [15].
• The commonest allergens were paraphenylenediamine (PPD) in 6 patients (0.72% of 826 PPD tests), elecampane (Inula helenium) and black-eyed Susan (Rudbeckia sp. hybr.) extracts in 3 patients, and 4-aminoazobenzene and Disperse Orange 3 in 2 patients [16].
• Effects of 3'-methyl-4-dimethylaminoazobenzene and 4-aminoazobenzene on plating efficiency, mitotic index, and macromolecular synthesis of cultured liver cells [17].

Gene context of p-Aminoazobenzene

• Induction of a high spin form of microsomal cytochrome P-448 in rat liver by 4-aminoazobenzene derivatives [18].
• It is found that the concentration of both AgNO3 and p-aminoazobenzene (PA) molecules has a significant effect on the formation and growth of these novel nanostructures [19].
• Allergy to dyes was found in 54 patients, most patients being allergic to PPD, p-aminoazobenzene and disperse orange 3 [20].

Analytical, diagnostic and therapeutic context of p-Aminoazobenzene

• Determination of total and free sulfur dioxide in wine by flow injection analysis and gas-diffusion using p-aminoazobenzene as the colorimetric reagent [21].
• 32P-postlabeling analysis of DNA adducts in rat livers after treatment with genotoxic and non-genotoxic 4-aminoazobenzene derivatives [22].

References