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Chemical Compound Review

Dintrobenzenes     1,4-dinitrobenzene

Synonyms: Dithane A-4, CHEMBL349400, NSC-3809, ACMC-1BQ9D, CCRIS 3092, ...
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Disease relevance of HSDB 4485

  • However, 1,4-dinitrobenzene, but not 1,2-dinitrobenzene, was of a potency similar to that of 1,3-DNB in producing cyanosis and splenic enlargement in these animals, indicating that different mechanisms are probably responsible for these two toxic effects [1].

High impact information on HSDB 4485

  • Monoclonal antibodies have been elicited and selected after injection of crystals of 1,4-dinitrobenzene (1,4-DNB) and cholesterol monohydrate in mice [2].
  • Tetryl and p-dinitrobenzene were the most efficient nitroaromatic substrates with a k(cat) of 1.8 and 2.8 s(-1), respectively, at pH 7.0 and 25 degrees C using 50 muM NADPH [3].
  • Definitive X-ray structures of "separated" versus "contact" ion pairs, together with their spectral (UV-NIR, ESR) characterizations, provide the quantitative basis for evaluating the complex equilibria and intrinsic (self-exchange) electron-transfer rates for the potassium salts of p-dinitrobenzene radical anion (DNB(-)) [4].
  • In contrast, the modeled binding site of the antibody which recognizes the flat (101) face of 1,4-dinitrobenzene crystals is remarkably flat [5].
  • Our comparable estimates for 1,3- and 1,4-dinitrobenzene interaction enthalpies are near -90 kJ/mol [6].

Anatomical context of HSDB 4485


Associations of HSDB 4485 with other chemical compounds


  1. A comparison of the effects of the three isomers of dinitrobenzene on the testis in the rat. Blackburn, D.M., Gray, A.J., Lloyd, S.C., Sheard, C.M., Foster, P.M. Toxicol. Appl. Pharmacol. (1988) [Pubmed]
  2. Monoclonal antibodies that specifically recognize crystals of dinitrobenzene. Kessler, N., Perl-Treves, D., Addadi, L. FASEB J. (1996) [Pubmed]
  3. Interactions of nitroaromatic compounds with the mammalian selenoprotein thioredoxin reductase and the relation to induction of apoptosis in human cancer cells. Cenas, N., Prast, S., Nivinskas, H., Sarlauskas, J., Arnér, E.S. J. Biol. Chem. (2006) [Pubmed]
  4. Intermolecular electron-transfer mechanisms via quantitative structures and ion-pair equilibria for self-exchange of anionic (dinitrobenzenide) donors. Rosokha, S.V., Lü, J.M., Newton, M.D., Kochi, J.K. J. Am. Chem. Soc. (2005) [Pubmed]
  5. Structural and chemical complementarity between antibodies and the crystal surfaces they recognize. Kessler, N., Perl-Treves, D., Addadi, L., Eisenstein, M. Proteins (1999) [Pubmed]
  6. Thermodynamics of nitroaromatic compound adsorption from water by smectite clay. Li, H., Teppen, B.J., Johnston, C.T., Boyd, S.A. Environ. Sci. Technol. (2004) [Pubmed]
  7. Identification of a mitochondrial p-dinitrobenzene reductase activity in rat liver. Abou-Khalil, S., Abou-Khalil, W.H., Yunis, A.A. Pharmacology (1985) [Pubmed]
  8. Relationship between red blood cell uptake and methemoglobin production by nitrobenzene and dinitrobenzene in vitro. Goldstein, R.S., Rickert, D.E. Life Sci. (1985) [Pubmed]
  9. Spectroscopic study of nitroaromatic-smectite sorption mechanisms. Johnston, C.T., de Oliveira, M.F., Teppen, B.J., Sheng, G., Boyd, S.A. Environ. Sci. Technol. (2001) [Pubmed]
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