Evaluation of secondary nitroalkanes, their nitronates, primary nitroalkanes, nitrocarbinols, and other aliphatic nitro compounds in the Ames Salmonella assay.

@article{Conaway1991EvaluationOS,
  title={Evaluation of secondary nitroalkanes, their nitronates, primary nitroalkanes, nitrocarbinols, and other aliphatic nitro compounds in the Ames Salmonella assay.},
  author={C. Clifford Conaway and N S Hussain and B M Way and Emerich S. Fiala},
  journal={Mutation research},
  year={1991},
  volume={261 3},
  pages={
          197-207
        }
}
The secondary nitroalkanes 2-nitropropane, 2-nitrobutane, 3-nitropentane and nitrocyclopentane, as well as their anionic forms (nitronates); the primary nitroalkanes 1-nitropropane, 1-nitrobutane, and 1-nitropentane and their respective nitronates; the nitrocarbinols 2-nitro-1-propanol, 2-nitro-1-butanol, 3-nitro-2-butanol, and 3-nitro-2-pentanol and their respective nitronates; 2-methyl-2-nitropropane, and 2-nitroso-2-nitropropane were tested in the Ames Salmonella assay using strains TA98… 
Secondary nitroalkanes: induction of DNA repair in rat hepatocytes, activation by aryl sulfotransferase and hepatocarcinogenicity of 2-nitrobutane and 3-nitropentane in male F344 rats.
TLDR
In a carcinogenicity assay using male F344 rats, the secondary nitroalkanes, 2-nitrobutane and 3-nitropentane, produced a highly significant incidence of hepatocarcinoma with metastases to the lungs, whereas the primary nitroalksane, 1-nitRObutane, was not carcinogenic.
Comparison of oxidative damage to rat liver DNA and RNA by primary nitroalkanes, secondary nitroalkanes, cyclopentanone oxime, and related compounds.
TLDR
The results suggest the possibility, still to be rigorously tested, that hepatocarcinogenicity may be associated not only with 2-nitropropane but also with other secondary nitroalkanes as well as with those ketoximes that are capable of being converted to secondary nit roalkanes in vivo.
Propane 2-nitronate is more rapidly denitrified and is more genotoxic than 2-nitropropane in cultured rat hepatoma cells.
TLDR
The results indicate that the nitro/nitronate equilibration in intact liver cells is slow, suggesting that nitronate formation represents the rate-limiting step in the metabolic activation of 2-NP.
Effects of short-chain nitrocompounds against Campylobacter jejuni and Campylobacter coli in vitro.
TLDR
Viable cell counts measured during incubation revealed main effects (P < 0.05) of all nitrocompounds on the survivability of C. jejuni, and the superior inhibitory effect of 2-nitro-l-propanol was reiterated.
Slow oxidation of acetoxime and methylethyl ketoxime to the corresponding nitronates and hydroxy nitronates by liver microsomes from rats, mice, and humans.
TLDR
The observed results show that formation of sec-nitronates from ketoximes occurs slowly, but is not the only pathway involved in the oxidative biotransformation of these compounds.
Toxicity and metabolism of nitroalkanes and substituted nitroalkanes.
TLDR
The toxicological profiles, especially as related to events occurring during metabolism and biotransformation, which contribute to toxicological end points of established nitroaliphatic compounds are reviewed.
Catalysis of nitro-aci tautomerism of the genotoxicant 2-nitropropane by cytosol from rodent and human liver.
TLDR
The results suggest that the nitro-aci tautomerism of secondary nitroalkanes is catalysed by a hepatic enzyme which resides predominantly in the cytosol and may thus contribute to the generation of the toxic species via which 2-NP exerts its toxicity.
Denitrification of the genotoxicant 2-nitropropane: relationship to its mechanism of toxicity.
  • C. Kohl, A. Gescher
  • Chemistry, Medicine
    Xenobiotica; the fate of foreign compounds in biological systems
  • 1997
TLDR
The dye also enhanced NO2- formation from P2N and 2-NP in the presence of hepatocytes or serum proteins, with a concomitant enhancement of both 2- NP and P2n toxicity.
Sulfotransferase-mediated genotoxicity of propane 2-nitronate in cultured ovine seminal vesicle cells.
TLDR
Investigation of the genotoxicity of 2-NP and its anionic form, propane 2-nitronate (P2N), in cultured ovine seminal vesicle (OSV) cells shows that cytochrome P450-dependent monooxygenases are not required for the metabolic conversion of secondary nitroalkanes or their nitronates into DNA-damaging products, nor is PHS involved in the metabolic activation.
Aliphatic Nitro, Nitrate, And Nitrite Compounds
Although aliphatic nitro compounds, aliphatic nitrates, and aliphatic nitrites have several features in common (nitrogen-oxygen grouping, explosiveness, methemoglobin formation), there are
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TLDR
It is suggested that the genotoxicity of 2- NP nitronate may be due to the generation of DNA-damaging reactive forms of oxygen or 2-NP free radicals.
Mutagenic evaluation of nitroparaffins in the Salmonella typhimurium/mammalian-microsome test and the micronucleus test.
TLDR
2-nitropropane has the potential for causing point mutations in a microbial test system, however, this compound probably will not cause a chromosome mutation of the clastogenic type.
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TLDR
The results suggest that the primary nitroalkanes are much less hepatotoxic and mutagenic than 2-nitropropane.
Comparison of oxidative damage to rat liver DNA and RNA by primary nitroalkanes, secondary nitroalkanes, cyclopentanone oxime, and related compounds.
TLDR
The results suggest the possibility, still to be rigorously tested, that hepatocarcinogenicity may be associated not only with 2-nitropropane but also with other secondary nitroalkanes as well as with those ketoximes that are capable of being converted to secondary nit roalkanes in vivo.
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Abstract The photodecomposition of 2-nitro-2-nitrosopropane (2-propylpseudonitrole) with light of λ > 540 nm was studied. The product distribution changes drastically with the nature of the solvent
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TLDR
It is demonstrated that 1- AP, and probably 2-AP, like other aliphatic azoxy compounds thus far examined, are carcinogenic in rats.
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A 10- and 12-fold increase of revertant numbers could be demonstrated for 2-nitropropane (2-NP of greater than 99% purity) tested in the preincubation assay with Salmonella typhimurium strains TA 100
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TLDR
The in vitro DNA-modifying activity of 2-nitropropane is demonstrated, and evidence is presented to suggest that genetic activity of this nitroalkane may not be dependent on the enzymic reduction of the nitro function to the corresponding hydroxylamine.
Subchronic inhalation toxicity of nitromethane and 2-nitropropane.
: Nitromethane (NM) and 2-nitropropane (2-NP) and versatile compounds employed in a wide variety of industrial applications, thus providing ample opportunity for occupational exposure. The purpose of
Genotoxicity of 1- and 2-nitropropane in the rat.
TLDR
The liver micronucleus test revealed a clastogenic effect of 2- NP in the liver, which indicates that 2-NP induces chromosome aberrations as well as DNA repair in vivo, but it seems to act organospecifically.
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