Disease relevance of p-Nitrotoluene

• In vivo construction of a hybrid pathway for metabolism of 4-nitrotoluene in Pseudomonas fluorescens [1].
• Reactions involved in the lower pathway for degradation of 4-nitrotoluene by Mycobacterium strain HL 4-NT-1 [2].
• A two-generation reproductive toxicity study of 4-nitrotoluene in rats [3].

High impact information on p-Nitrotoluene

• 2-Nitrotoluene (2NT), 3-nitrotoluene, or 4-nitrotoluene was administered by gavage to male F344 rats [4].
• The nitroarene p-nitrotoluene is converted with a selectivity higher than 85% to the corresponding carbamate at room temperature and atmospheric pressure, using photoexcited particles of TiO2 as catalyst and EtOH as carbonylating species [5].
• During growth of Pseudomonas putida strain TW3 on 4-nitrotoluene (4NT) or its metabolite 4-nitrobenzoate (4NB), the culture medium gradually becomes yellow-orange with a lambda(max) of 446 nm [6].
• It is postulated that APOC is formed by the oxidative dimerization of 4A3HB, although 4A3HB has not been reported to be a metabolite of 4NT or a product of 4NB catabolism by strain TW3 [6].
• Here we report the elucidation of the pathway of 2-amino-4-methylphenol (6-amino-m-cresol) metabolism during the degradation of 4-nitrotoluene by Mycobacterium strain HL 4-NT-1 and the comparison of the substrate specificities of the relevant enzymes in strains JS45 and HL 4-NT-1 [2].

Chemical compound and disease context of p-Nitrotoluene

• Pseudomonas fluorescens 410PR grows on 4-nitrobenzoate but does not metabolize 4-nitrotoluene [1].
• Pseudomonas sp. strain TW3 is able to oxidatively metabolize 4-nitrotoluene and toluene via a route analogous to the upper pathway of the TOL plasmids [7].
• A bacterial strain, Mycobacterium sp. strain HL 4-NT-1, enriched with 4-nitrotoluene as its sole source of nitrogen, was able to metabolize 2,4,6-trinitrotoluene under aerobic conditions [8].

Biological context of p-Nitrotoluene

• The substrate specificity of the enzyme expressed from the cloned and overexpressed gene was similar to the activity expressed from strain TW3 grown on 4-nitrotoluene, providing evidence that ntnD is the previously unidentified gene in the pathway of 4-nitrotoluene catabolism [9].
• Methylation of reduced avian lyase with 1 mM 4-methylnitrobenzene sulfonate results in rapid inactivation of the enzyme with a k(inact) of 0.178 min-1 [10].
• To address this, we examined the effects of p-nitrotoluene, an endocrine disruptor, on rat behavior and gene expression [11].
• Inhibition of enterohepatic circulation by bile duct cannulation resulted in a decrease in hepatic macromolecular covalent binding by 98, 75, and 78% in male rats, and by 85, 44, and 45% in female rats after 2NT, 3NT, or 4NT, respectively.(ABSTRACT TRUNCATED AT 250 WORDS)[12]
• 4-Nitrotoluene (4-NT) was administered orally at doses of 0, 40, 80, or 160 mg/kg/day by gavage to 24 Crj:CD (SD)IGS rats of each sex per group over two successive generations, and the effects on reproductive capacity in the parental animals and growth and development of the offspring were investigated [3].

Anatomical context of p-Nitrotoluene

• Hepatocytes were incubated with [U-14C]2NT, 3NT, or 4NT at concentrations from 25 to 1000 microM for up to 60 min [13].
• Kidney toxicity was observed in male rats receiving o-, m-, or p-nitrotoluene and included hyaline droplet nephropathy and an associated increase in the renal concentration of alpha 2U-globulin [14].

Associations of p-Nitrotoluene with other chemical compounds

• This conforms with the observation that the benzyl alcohol dehydrogenase expressed during growth on 4-nitrotoluene and toluene differs significantly from the XylB protein, requiring assay via dye-linked electron transfer rather than through a nicotinamide cofactor [7].
• The photoluminescence from functionalized single-walled carbon nanotubes was found to be highly sensitive to the presence of nitroaromatic compounds such as nitrobenzene, 4-nitrotoluene, and 2,4-dinitrotoluene [15].

References