Disease relevance of 2AF

• 2-Aminophenol 1,6-dioxygenase was purified from the cell extracts of Pseudomonas sp. AP-3 grown on 2-aminophenol [1].
• The close biochemical relationships among the classical catechol meta-cleavage pathway in Comamonas sp. JS765, 2-aminophenol meta-cleavage pathways in P. pseudoalcaligenes JS45, and an alternative 2-aminophenol meta-cleavage pathway in Pseudomonas sp. AP-3 suggest a common evolutionary origin [2].
• A novel 2-aminophenol 1,6-dioxygenase involved in the degradation of p-chloronitrobenzene by Comamonas strain CNB-1: purification, properties, genetic cloning and expression in Escherichia coli [3].
• A novel meta-cleavage dioxygenase that cleaves a carboxyl-group-substituted 2-aminophenol. Purification and characterization of 4-amino-3-hydroxybenzoate 2,3-dioxygenase from Bordetella sp. strain 10d [4].

High impact information on 2AF

• The GT activity (o-aminophenol as acceptor) is located entirely in the membranes of the endoplasmic reticulum (ER) and the question arises whether ER increases along with GT [5].
• However, three aniline metabolites--phenylhydroxylamine, 2-aminophenol, and 4-aminophenol--catalyze methemoglobin formation in erythrocyte suspensions and, hence, could contribute to methemoglobin formation in vivo after aniline [6].
• Detection limits of 10 nM for determination of o-aminophenol and o- and p-phenylenediamine achieved with a tobacco peroxidase-modified electrode give a promise for further improvements in sensitivities and detection limits of biosensors [7].
• Synthesis and topical antiinflammatory and antiallergic activities of antioxidant o-aminophenol derivatives [8].
• UDP-glucuronyltransferase activity of neonatal-chick liver or phenobarbital-treated chick-embryo liver catalysed the glucuronidation of 1-naphthol, 4-nitrophenol and 2-aminophenol [9].

Chemical compound and disease context of 2AF

• Pseudomonas pseudoalcaligenes JS45 grows on nitrobenzene by a partially reductive pathway in which the intermediate hydroxylaminobenzene is enzymatically rearranged to 2-aminophenol by hydroxylaminobenzene mutase (HAB mutase) [10].
• Comparison of the downstream pathways for degradation of nitrobenzene by Pseudomonas pseudoalcaligenes JS45 (2-aminophenol pathway) and by Comamonas sp. JS765 (catechol pathway) [2].
• Nitrobenzene is degraded by Pseudomonas pseudoalcaligenes JS45 via 2-aminophenol to 2-aminomuconic semialdehyde, which is further degraded to pyruvate and acetaldehyde [2].
• Sequence similarity studies suggest that the beta-subunits of both 2-aminophenol 1,6-dioxygenases are distantly related to homoprotocatechuate 2,3-dioxygenase from Escherichia coli strains W and C and then to catechol 2, 3-dioxygenase from Alcaligenes eutrophus [11].

Biological context of 2AF

• These data are consistent with the existence of more than one binding site for o-aminophenol on UDP-glucuronyltransferase [12].
• 7. From this and from evidence previously presented we suggest that glucocorticoids, which are known to increase in rat foetuses between days 17 and 20 of gestation, trigger the normal development in utero of hepatic transferase activity towards o-aminophenol which occurs at that time [13].
• The predicted amino acid sequences of these proteins are highly homologous to those of the corresponding proteins involved in the metabolism of 2-aminophenol (e.g., AmnCDEFGH in Pseudomonas sp. strain AP-3) [14].
• Rapid release of ammonia from 2-aminophenol transformation indicated that hydrolysis of the imine intermediate was the dominant reaction [15].
• On the other hand, the genes nbzC, nbzD, and nbzE, involved in the ring cleavage pathway of 2-aminophenol, are localized on the 6.6-kb SnaBI-SmaI fragment of pNB1 and clustered in the order nbzC-nbzD-nbzE as an operon [16].

Anatomical context of 2AF

• In liver sections, GlcuTase activity with o-aminophenol as acceptor was located primarily on the endothelial cells [17].
• 3. Aniline was mainly metabolized to acetanilide and to a lesser extent to 2-aminophenol by isolated hepatocytes, but neither hydroxylated acetanilide nor conjugates were found in vitro whereas they were present in bile and urine of trout treated with this chemical [18].
• Because 2 metabolites of aniline, o-aminophenol and phenylhydroxylamine, can induce sister chromatid exchanges (SCEs), we examined the ability of RBCs and hemoglobin to activate aniline to genotoxic intermediates as evidenced by SCE induction in human lymphocytes [19].

Associations of 2AF with other chemical compounds

• Possible multiple binding sites for o-aminophenol on uridine diphosphate glucuronyltransferase [12].
• 1. A precocious development of UDP-glucuronosyltransferase activity (EC 2.4.1.17) towards o-aminophenol is demonstrated in 15-17 day foetal rat liver in utero after dexamethasone administration to the mother [13].
• To examine the relationship between this enzyme and other dioxygenases, 2-aminophenol 1,6-dioxygenase has been purified by ethanol precipitation, gel filtration, and ion exchange chromatography [20].
• The order of biliary excretion of radioactivity, as well as the o-aminophenol UDP-glucuronyltransferase activity, in the treated animals was: omeprazole > lansoprazole > pantoprazole [21].
• A method utilizing reverse-phase liquid chromatography/electrochemistry (LC/EC) was developed for the simultaneous determination of aniline and its hydroxylated derivatives, p-aminophenol, o-aminophenol, m-aminophenol, and N-phenylhydroxylamine [22].

Gene context of 2AF

• The soxS promoter was strongly induced by 4-aminophenol and 2-aminophenol [23].
• Regulation of onset of development of UDP-glucuronosyltransferase activity towards o-aminophenol by glucocorticoids in late-foetal rat liver in utero [13].
• 4-Aminophenol and 2-aminophenol were also significantly more toxic than aniline in a superoxide dismutase deficient yeast strain [23].
• Since the method is applicable in aqueous media, a successful quantitation of p- and o-aminophenol formed by cytochrome P-450 model systems was carried out [24].

Analytical, diagnostic and therapeutic context of 2AF

• The final product of o-aminophenol was identified as 2-aminophenoxazine-3-one, by using spectrophotometry and HPLC [25].

References