Summary: Benzene derivatives which are substituted with two nitro groups in the ortho, meta or para positions.

Top Publications

  1. Paredez A, Persson S, Ehrhardt D, Somerville C. Genetic evidence that cellulose synthase activity influences microtubule cortical array organization. Plant Physiol. 2008;147:1723-34 pubmed publisher
  2. Bisgrove S, Kropf D. Cytokinesis in brown algae: studies of asymmetric division in fucoid zygotes. Protoplasma. 2004;223:163-73 pubmed
    ..Pharmacological agents were used to investigate the roles of microtubules, actin, and secretion in cytokinesis. The findings indicate a mechanism of cytokinesis that may be unique to the brown algae. ..
  3. Wintz H, Yoo L, Loguinov A, Wu Y, Steevens J, Holland R, et al. Gene expression profiles in fathead minnow exposed to 2,4-DNT: correlation with toxicity in mammals. Toxicol Sci. 2006;94:71-82 pubmed
    ..We present possible modes of action of 2,4-DNT toxicity and suggest that fathead minnow cDNA microarrays can be useful to identify mechanisms of toxicity in fish and as a predictive tool for toxicity in mammals. ..
  4. Grandjean O, Vernoux T, Laufs P, Belcram K, Mizukami Y, Traas J. In vivo analysis of cell division, cell growth, and differentiation at the shoot apical meristem in Arabidopsis. Plant Cell. 2004;16:74-87 pubmed
    ..In this case, cell growth and, later, cell differentiation were inhibited, suggesting an important role for DNA synthesis in growth and patterning. ..
  5. de las Heras A, Chavarría M, De Lorenzo V. Association of dnt genes of Burkholderia sp. DNT with the substrate-blind regulator DntR draws the evolutionary itinerary of 2,4-dinitrotoluene biodegradation. Mol Microbiol. 2011;82:287-99 pubmed publisher
  6. Fortner J, Zhang C, Spain J, Hughes J. Soil column evaluation of factors controlling biodegradation of DNT in the vadose zone. Environ Sci Technol. 2003;37:3382-91 pubmed
    ..Under conditions evaluated in laboratory-scale studies, 2,4-DNT biodegradation enhanced the rate of contaminant loss from the vadose zone by a factor of 10 when compared to the washout due to leaching. ..
  7. Nagatomo K, Kawaguchi T, Miura N, Toko K, Matsumoto K. Development of a sensitive surface plasmon resonance immunosensor for detection of 2,4-dinitrotoluene with a novel oligo (ethylene glycol)-based sensor surface. Talanta. 2009;79:1142-8 pubmed publisher
    ..Additionally, the fabricated OEG-based surface effectively prevented non-specific adsorption of proteins, and the specific response to anti-DNPh-KLH-400 antibody was maintained for more than 30 measurement cycles. ..
  8. Chen T, Sheng Z, Wang K, Wang F, Xia X. Determination of explosives using electrochemically reduced graphene. Chem Asian J. 2011;6:1210-6 pubmed publisher
    ..Experimental results showed that electrochemical reduction of GO on the GC electrode was a fast, simple, and controllable method for the construction of a graphene-modified electrode for sensing NACs and other sensing applications. ..
  9. Johnson G, Spain J. Evolution of catabolic pathways for synthetic compounds: bacterial pathways for degradation of 2,4-dinitrotoluene and nitrobenzene. Appl Microbiol Biotechnol. 2003;62:110-23 pubmed
    ..Molecular genetic analysis with comparative biochemistry reveals how the pathways were assembled in response to the recent appearance of the two synthetic chemicals in the biosphere. ..

More Information


  1. Nipper M, Carr R, Biedenbach J, Hooten R, Miller K. Toxicological and chemical assessment of ordinance compounds in marine sediments and porewaters. Mar Pollut Bull. 2002;44:789-806 pubmed
    ..Degradation products may have played a role in observed toxicity. ..
  2. Manne J, Mastrangelo M, Sato T, Berd D. TCR rearrangement in lymphocytes infiltrating melanoma metastases after administration of autologous dinitrophenyl-modified vaccine. J Immunol. 2002;169:3407-12 pubmed
    ..Our study indicates that DNP vaccine induces the expansion of particular T cell clones that may be agents of its antitumor effects. ..
  3. Corson F, Hamant O, Bohn S, Traas J, Boudaoud A, Couder Y. Turning a plant tissue into a living cell froth through isotropic growth. Proc Natl Acad Sci U S A. 2009;106:8453-8 pubmed publisher
    ..If not, a "cell froth" very similar to that observed experimentally is obtained. Our results suggest strong physical constraints on the mechanisms of growth regulation. ..
  4. Kivisaar M. Evolution of catabolic pathways and their regulatory systems in synthetic nitroaromatic compounds degrading bacteria. Mol Microbiol. 2011;82:265-8 pubmed publisher
    ..This research addresses some fundamental questions about bottlenecks to be solved during evolution of new catabolic operons. ..
  5. Gust K, Pirooznia M, Quinn M, Johnson M, Escalon L, Indest K, et al. Neurotoxicogenomic investigations to assess mechanisms of action of the munitions constituents RDX and 2,6-DNT in Northern bobwhite (Colinus virginianus). Toxicol Sci. 2009;110:168-80 pubmed publisher
  6. Rawat A, Gust K, Deng Y, Garcia Reyero N, Quinn M, Johnson M, et al. From raw materials to validated system: the construction of a genomic library and microarray to interpret systemic perturbations in Northern bobwhite. Physiol Genomics. 2010;42:219-35 pubmed publisher
    ..Furthermore, the systemic impact of dinitrotoluenes on liver function appears conserved across species as PPAR signaling is similarly affected in fathead minnow liver tissue after exposure to 2,4-DNT...
  7. Wiesler B, Wang Q, Nick P. The stability of cortical microtubules depends on their orientation. Plant J. 2002;32:1023-32 pubmed
    ..The results are discussed in terms of direction-dependent differences in the lifetime of microtubules...
  8. Galvão T, Mencía M, De Lorenzo V. Emergence of novel functions in transcriptional regulators by regression to stem protein types. Mol Microbiol. 2007;65:907-19 pubmed
    ..It thus seems that transcriptional factors are likely to regress into functionally multipotent forms (i.e. stem protein types) as a first step towards the divergence of a new specificity. ..
  9. Smirnova I, Dian C, Leonard G, McSweeney S, Birse D, Brzezinski P. Development of a bacterial biosensor for nitrotoluenes: the crystal structure of the transcriptional regulator DntR. J Mol Biol. 2004;340:405-18 pubmed
    ..The implications of this model for the mechanism of transcription regulation by LysR proteins are discussed. ..
  10. Hamant O, Heisler M, Jonsson H, Krupinski P, Uyttewaal M, Bokov P, et al. Developmental patterning by mechanical signals in Arabidopsis. Science. 2008;322:1650-5 pubmed publisher
  11. Johnson G, Jain R, Spain J. Origins of the 2,4-dinitrotoluene pathway. J Bacteriol. 2002;184:4219-32 pubmed
    ..The presence of the transposon remnants and vestigial genes suggests that the pathway for 2,4-DNT degradation evolved relatively recently because the extraneous elements have not been eliminated from the region. ..
  12. Tchounwou P, Wilson B, Ishaque A, Schneider J. Transcriptional activation of stress genes and cytotoxicity in human liver carcinoma cells (HepG2) exposed to 2,4,6-trinitrotoluene, 2,4-dinitrotoluene, and 2,6-dinitrotoluene. Environ Toxicol. 2001;16:209-16 pubmed
    ..Within the range of concentrations tested (0-300 mg TNT or DNT/mL in 1% DMSO), no significant inductions (p > 0.05) of NFKBRE, p53RE, CRE, and RARE were found. ..
  13. Hilmi A, Luong J, Nguyen A. Determination of explosives in soil and ground water by liquid chromatography-amperometric detection. J Chromatogr A. 1999;844:97-110 pubmed
  14. Parales R, Emig M, Lynch N, Gibson D. Substrate specificities of hybrid naphthalene and 2,4-dinitrotoluene dioxygenase enzyme systems. J Bacteriol. 1998;180:2337-44 pubmed
    ..These studies indicate that the small subunit of the oxygenase is essential for activity but does not play a major role in determining the specificity of these enzymes. ..
  15. Suen W, Spain J. Cloning and characterization of Pseudomonas sp. strain DNT genes for 2,4-dinitrotoluene degradation. J Bacteriol. 1993;175:1831-7 pubmed
    ..Subcloning analysis suggests that the DNT dioxygenase is a multicomponent enzyme system and that the genes for the DNT pathway are organized in at least three different operons. ..
  16. Schwartz J, Aldridge B, Lasley B, Snyder P, Stott J, Mohr F. Chronic fuel oil toxicity in American mink (Mustela vison): systemic and hematological effects of ingestion of a low-concentration of bunker C fuel oil. Toxicol Appl Pharmacol. 2004;200:146-58 pubmed
  17. Stringer R, Gangopadhyay S, Grant S. Comparison of molecular imprinted particles prepared using precipitation polymerization in water and chloroform for fluorescent detection of nitroaromatics. Anal Chim Acta. 2011;703:239-44 pubmed publisher
  18. Mavroudis G, Prior M, Lister T, Nolan C, Ray D. Neurochemical and oedematous changes in 1,3-dinitrobenzene-induced astroglial injury in rat brain from a 1H-nuclear magnetic resonance perspective. J Neural Transm (Vienna). 2006;113:1263-78 pubmed
  19. Mwandumba H, Russell D, Nyirenda M, Anderson J, White S, Molyneux M, et al. Mycobacterium tuberculosis resides in nonacidified vacuoles in endocytically competent alveolar macrophages from patients with tuberculosis and HIV infection. J Immunol. 2004;172:4592-8 pubmed
    ..This confirms, for the first time in humans with tuberculosis and HIV, the conclusions from previous animal and in vitro studies. ..
  20. Lothrop A, Ruggles E, Hondal R. No selenium required: reactions catalyzed by mammalian thioredoxin reductase that are independent of a selenocysteine residue. Biochemistry. 2009;48:6213-23 pubmed publisher
    ..7 in the full-length mammalian enzyme (83-142 nM), but surprisingly the truncated enzyme showed much stronger inhibition (25 nM). This contrasts with auranofin, where the absence of Sec more strongly perturbed inhibition...
  21. Del Bubba M, Cincinelli A, Checchini L, Lepri L. Chiral separations and quantitative analysis of optical isomers on cellulose tribenzoate plates. J Chromatogr A. 2011;1218:2737-44 pubmed publisher
  22. Bhaumik J, Weissleder R, McCarthy J. Synthesis and photophysical properties of sulfonamidophenyl porphyrins as models for activatable photosensitizers. J Org Chem. 2009;74:5894-901 pubmed publisher
    ..These systems may prove useful in the treatment of a number of disease states, such as cancer and bacterial infection. ..
  23. Julínek O, Urbanová M, Lindner W. Enantioselective complexation of carbamoylated quinine and quinidine with N-blocked amino acids: vibrational and electronic circular dichroism study. Anal Bioanal Chem. 2009;393:303-12 pubmed publisher
    ..The VCD technique revealed similarities between the strongly bound diastereomeric complex of chiral DNB-Leu and SO and the complex of achiral DNB-Gly and SO, highlighting the leading role of SO in the formation of SA-SO complex. ..
  24. Bauer M, Hilpert F, Arnold N, Pfisterer J, Jonat W, Kruse H. Simultaneous congener-specific determination of selected organochlorine compounds and nitro musks in human whole blood samples by solid-phase extraction and capillary gas chromatography with electron capture detection. J Anal Toxicol. 2005;29:110-7 pubmed
    ..The time and technical effort is small, so the method is feasible for epidemiological studies with regard to the impact of organochlorines and nitro musks on certain diseases. ..
  25. Iyer A, August A. The Tec family kinase, IL-2-inducible T cell kinase, differentially controls mast cell responses. J Immunol. 2008;180:7869-77 pubmed
    ..Our results also suggest that Itk differentially modulates mast cell degranulation and cytokine production in part by regulating expression and activation of NFAT proteins in these cells. ..
  26. Qu X, Xiao L, Zhu D. Site-specific adsorption of 1,3-dinitrobenzene to bacterial surfaces: a mechanism of n-pi electron-donor-acceptor interactions. J Environ Qual. 2008;37:824-9 pubmed publisher
  27. Leungsakul T, Keenan B, Yin H, Smets B, Wood T. Saturation mutagenesis of 2,4-DNT dioxygenase of Burkholderia sp. strain DNT for enhanced dinitrotoluene degradation. Biotechnol Bioeng. 2005;92:416-26 pubmed
    ..strain DNT and B. cepacia R34 are more closely related than originally reported. This is the first report of engineering an enzyme for enhanced degradation of nitroaromatic compounds and the first report of degrading 2,5-DNT. ..
  28. Park J, Lee J, Kwon S, Cha J, Carr P, McNeff C. Separation of racemic 2,4-dinitrophenyl amino acids on 9-O-(phenyloxycarbonyl)quinine-bonded carbon-clad zirconia in reversed-phase liquid chromatography. J Chromatogr A. 2004;1050:151-7 pubmed
    ..The QNCZ CSP showed in general the better enantioselectivity for most of the amino acids studied. ..
  29. Suski J, Salice C, Houpt J, Bazar M, Talent L. Dose-related effects following oral exposure of 2,4-dinitrotoluene on the Western fence lizard, Sceloporus occidentalis. Environ Toxicol Chem. 2008;27:352-9 pubmed publisher
    ..The present study indicates Sceloporus occidentalis is suitable for evaluating toxicity of compounds to reptilian species. ..
  30. Franco C, Casarin N, Domingues F, Omoto C. [Resistance of Brevipalpus phoenicis (Geijskes) (Acari: Tenuipalpidae) to acaricides that inhibit cellular respiration in citrus: cross-resistance and fitness cost]. Neotrop Entomol. 2007;36:565-75 pubmed
    ..phoenicis resistance to propargite, based on biological parameters evaluated. Therefore, the use of these acaricides should also be done very carefully in resistance management of B. phoenicis to acaricides...
  31. Wang R, Hosaka M, Han L, Yokota Hashimoto H, Suda M, Mitsushima D, et al. Molecular probes for sensing the cholesterol composition of subcellular organelle membranes. Biochim Biophys Acta. 2006;1761:1169-81 pubmed
    ..We suggest that cholesterol-sensing probes, AO and DAMP, are useful tools for investigating cholesterol compositions in acidic organelle membranes. ..
  32. Rocheleau S, Kuperman R, Simini M, Hawari J, Checkai R, Thiboutot S, et al. Toxicity of 2,4-dinitrotoluene to terrestrial plants in natural soils. Sci Total Environ. 2010;408:3193-9 pubmed publisher
  33. Pengo P, Polizzi S, Pasquato L, Scrimin P. Carboxylate-imidazole cooperativity in dipeptide-functionalized gold nanoparticles with esterase-like activity. J Am Chem Soc. 2005;127:1616-7 pubmed
    ..Such a mechanism is absent with an analogous monomeric dipeptide, and this results in a more than 300-fold rate acceleration of the hydrolytic process at low pH in the presence of the functional nanoparticles. ..
  34. Menzel E, Bouldin K, Murdock R. Trace explosives detection by photoluminescence. ScientificWorldJournal. 2004;4:55-66 pubmed
  35. Pramanik S, Joarder S, Das S, Roy S, Bhattacharyya A. Photodegradation of Oryzalin in aqueous isopropanol and acetonitrile. J Environ Sci Health B. 2016;51:287-97 pubmed publisher
    ..The plausible mechanism of phototransformation involved was hydrolysis, breaking of sulfonic bond, and loss of amino and sulfonic acid group. ..
  36. Lönneborg R, Varga E, Brzezinski P. Directed evolution of the transcriptional regulator DntR: isolation of mutants with improved DNT-response. PLoS ONE. 2012;7:e29994 pubmed publisher
    ..The functional role of some substitutions found in this clone is discussed in the framework of the structural changes observed when comparing the recently determined structures of DntR with and without bound inducer ligand. ..
  37. Madeira P, Bessa A, Alvares Ribeiro L, Aires Barros M, Reis C, Rodrigues A, et al. Salt effects on solvent features of coexisting phases in aqueous polymer/polymer two-phase systems. J Chromatogr A. 2012;1229:38-47 pubmed publisher
  38. Walsh M, Walsh M, Hewitt A. Energetic residues from field disposal of gun propellants. J Hazard Mater. 2010;173:115-22 pubmed publisher
    ..These tests demonstrate that environmental factors, especially in winter, can play a significant role in the effectiveness of field-expedient disposal of propellants. ..
  39. Yang Y, Aisa H, Ito Y. Mathematical model of computer-programmed intermittent dual countercurrent chromatography applied to hydrostatic and hydrodynamic equilibrium systems. J Chromatogr A. 2009;1216:6310-8 pubmed publisher
    ..1M hydrochloric acid (1:1:1:1 and 4:5:4:5, v/v). ..
  40. Gardonio D, Siemann S. Chelator-facilitated chemical modification of IMP-1 metallo-beta-lactamase and its consequences on metal binding. Biochem Biophys Res Commun. 2009;381:107-11 pubmed publisher
    ..The consequences arising from chemical modification of Cys221 are thus distinct from those reported for Cys-->Ala/Ser mutants of IMP-1 and other metallo-beta-lactamases, which are mononuclear. ..
  41. Sedbrook J, Ehrhardt D, Fisher S, Scheible W, Somerville C. The Arabidopsis sku6/spiral1 gene encodes a plus end-localized microtubule-interacting protein involved in directional cell expansion. Plant Cell. 2004;16:1506-20 pubmed
    ..These observations suggest that SPR1 is involved in microtubule polymerization dynamics and/or guidance, which in turn influences touch-induced directional cell expansion and axial twisting. ..
  42. Yoshida K, Inoue N, Sonobe S, Shimmen T. Involvement of microtubules in rhizoid differentiation of Spirogyra species. Protoplasma. 2003;221:227-35 pubmed
    ..MT-destabilizing drugs (oryzalin and propyzamide) induced swelling of rhizoids, and neither rosette-shaped nor rod-shaped rhizoids were formed. The role of MTs in rhizoid differentiation was discussed. ..
  43. Ketelaar T, de Ruijter N, Emons A. Unstable F-actin specifies the area and microtubule direction of cell expansion in Arabidopsis root hairs. Plant Cell. 2003;15:285-92 pubmed
    ..Oryzalin alone, at the same concentration, had no influence on root hair elongation. These results represent an important step toward understanding the spatial and directional regulation of root hair growth. ..
  44. Apostolakos P, Livanos P, Galatis B. Microtubule involvement in the deposition of radial fibrillar callose arrays in stomata of the fern Asplenium nidus L. Cell Motil Cytoskeleton. 2009;66:342-9 pubmed publisher
    ..The MTs seem to orient callose synthases in the plasmalemma, thus determining the fibrillar nature of callose deposits and their radial mode of arrangement. The cellulose microfibrils are not involved in the callose fibril alignment. ..
  45. Elkin N, Piner J, Sharpe R. Toxicant-induced leakage of germ cell-specific proteins from seminiferous tubules in the rat: relationship to blood-testis barrier integrity and prospects for biomonitoring. Toxicol Sci. 2010;117:439-48 pubmed publisher
  46. Mathias C, Freyschmidt E, Oettgen H. Immunoglobulin E antibodies enhance pulmonary inflammation induced by inhalation of a chemical hapten. Clin Exp Allergy. 2009;39:417-25 pubmed publisher
    ..Our data indicate that IgE antibodies non-specifically enhance the development of airway inflammation induced by exposure to chemical antigens. ..
  47. Thomas J, Hernandez R, Kuo C. Single-step treatment of 2,4-dinitrotoluene via zero-valent metal reduction and chemical oxidation. J Hazard Mater. 2008;155:193-8 pubmed publisher
    ..The data shows that iron reduced the 2,4-DNT and ozone oxidized these products resulting in a 73% removal of TOC and a 96% decrease in 2,4-DNT concentration. ..
  48. Oh S, Son J, Lim O, Chiu P. The role of black carbon as a catalyst for environmental redox transformation. Environ Geochem Health. 2012;34 Suppl 1:105-13 pubmed publisher
    ..The results suggest that BC may influence the fate of organic pollutants in reducing subsurface environments through redox transformation in addition to sorption. ..
  49. Cenas N, Prast S, Nivinskas H, Sarlauskas J, Arner E. Interactions of nitroaromatic compounds with the mammalian selenoprotein thioredoxin reductase and the relation to induction of apoptosis in human cancer cells. J Biol Chem. 2006;281:5593-603 pubmed
    ..Based on these findings, we suggested that targeting of intracellular TrxR by alkylating nitroaromatic or quinone compounds may contribute to the induction of apoptosis in exposed human cancer cells. ..
  50. Shimamura M, Brown R, Lemmon B, Akashi T, Mizuno K, Nishihara N, et al. Gamma-tubulin in basal land plants: characterization, localization, and implication in the evolution of acentriolar microtubule organizing centers. Plant Cell. 2004;16:45-59 pubmed
    ..We conclude that gamma-tubulin is a highly conserved protein associated with microtubule nucleation in basal land plants and that it has a cell cycle-dependent distribution essential for the orderly succession of microtubule arrays...
  51. Mehilal -, Sikder A, Sinha R, Gandhe B. Cost-effective synthesis of 5,7-diamino-4,6-dinitrobenzofuroxan (CL-14) and its evaluation in plastic bonded explosives. J Hazard Mater. 2003;102:137-45 pubmed
    ..The thermal, mechanical and explosive properties of PBX composition from preliminary tests are also reported. Good thermal stability as well as good insensitiveness are indicated. ..
  52. Kamimura A, Toyoshima S. Preparation of SRN1-type coupling adducts from aliphatic gem-dinitro compounds in ionic liquids. Molecules. 2012;17:4782-90 pubmed publisher
    ..The reaction rate is slower than the corresponding S(RN)1 reaction in DMSO, but no acceleration on irradiation or no inhibition in the presence of m-DNB are observed. ..
  53. Era A, Kutsuna N, Higaki T, Hasezawa S, Nakano A, Ueda T. Microtubule stability affects the unique motility of F-actin in Marchantia polymorpha. J Plant Res. 2013;126:113-9 pubmed publisher
    ..polymorpha thallus cells. These results suggest that microtubules play regulatory roles in the unique F-actin dynamics in M. polymorpha...