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Chemical Compound Review:

AGN-PC-00H1KB 2-methyl-3,5-dinitro-aniline

Synonyms: CCRIS 5187, AG-A-44115, AG-F-23215, CPD-10450, AC-10511, ...

Conder, J.M. et al., Liu, Y.Y. et al., Zeng, K. et al., Saka, M., Alvarez, M.A. et al., et al.

Conder, Point, Bowen, Saka, Banerjee, Hawkins, Dutta, Smoot,

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Disease relevance of CCRIS 5187

This isolate, Pseudomonas aeruginosa MA01, metabolized TNT by first reducing one nitro group to form either 2-amino-4,6-dinitrotoluene (2ADNT) or 4-amino-2,6-dinitrotoluene (4ADNT) [1].

High impact information on CCRIS 5187

In this study of riboflavin-sensitized photolysis of 2,4,6-trinitrotoluene (TNT), the final photoproducts were found to include 2-amino-4,6-dinitrotoluene, 4-amino-2,6-dinitrotoluene, and 3,5-dinitroaniline [2].
Although 4ADNT (96-h EC50 = 85.8 microM) induced various tadpole malformations, it was a weak teratogen compared with TNT (96-h EC50 = 9.78 microM) and 2ADNT (96-h EC50 = 16.9 microM) [3].
We examined the toxicokinetics and metabolism of 2,4,6-trinitirotoluene (TNT) and four of its major reduced metabolites (2-amino-4,6-dinitrotoluene (2ADNT), 4-amino-2,6-dinitrotoluene (4ADNT), and 2,4-diamino-6-nitrotoluene (2,4DANT)) in the freshwater, aquatic oligochaete Tubifex tubifex exposed to spiked, reconstituted water [4].
Effects of 2-amino-4,6-dinitrotoluene on p53 tumor suppressor gene expression [5].
Glutathione-mediated mineralization of 14C-labeled 2-amino-4,6-dinitrotoluene by manganese-dependent peroxidase H5 from the white-rot fungus Phanerochaete chrysosporium [6].

Biological context of CCRIS 5187

Radioactivity covalently bound to globin and the hepatic proteins was susceptible to dilute acid hydrolysis from which 2-amino-4,6-dinitrotoluene (2A) and 4-amino 2,6-dinitrotoluene (4A) were the major products recovered by solvent extraction [7].

References

Pseudomonas aeruginosa strain MA01 aerobically metabolizes the aminodinitrotoluenes produced by 2,4,6-trinitrotoluene nitro group reduction. Alvarez, M.A., Kitts, C.L., Botsford, J.L., Unkefer, P.J. Can. J. Microbiol. (1995) [Pubmed]
Assessing cytotoxicity of photosensitized transformation products of 2,4,6-trinitrotoluene (TNT) and atrazine with freshwater microbial assemblages. Zeng, K., Hwang, H.M., Zhang, Y., Cook, S. Environ. Toxicol. (2004) [Pubmed]
Developmental toxicity of p,p'-dichlorodiphenyltrichloroethane, 2,4,6-trinitrotoluene, their metabolites, and benzo[a]pyrene in Xenopus laevis embryos. Saka, M. Environ. Toxicol. Chem. (2004) [Pubmed]
Preliminary kinetics and metabolism of 2,4,6-trinitrotoluene and its reduced metabolites in an aquatic oligochaete. Conder, J.M., Point, T.W., Bowen, A.T. Aquat. Toxicol. (2004) [Pubmed]
Effects of 2-amino-4,6-dinitrotoluene on p53 tumor suppressor gene expression. Banerjee, H., Hawkins, Z., Dutta, S., Smoot, D. Mol. Cell. Biochem. (2003) [Pubmed]
Glutathione-mediated mineralization of 14C-labeled 2-amino-4,6-dinitrotoluene by manganese-dependent peroxidase H5 from the white-rot fungus Phanerochaete chrysosporium. Van Aken, B., Cameron, M.D., Stahl, J.D., Plumat, A., Naveau, H., Aust, S.D., Agathos, S.N. Appl. Microbiol. Biotechnol. (2000) [Pubmed]
In vivo covalent binding of [14C]trinitrotoluene to proteins in the rat. Liu, Y.Y., Lu, A.Y., Stearns, R.A., Chiu, S.H. Chem. Biol. Interact. (1992) [Pubmed]

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