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Chemical Compound Review

2,4-Dnp     2,4-dinitrophenol

Synonyms: Aldifen, Dinofan, Fenoxyl, DINITROPHENOL, Dinitrofenolo, ...
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Disease relevance of 2,4-dinitrophenol

  • Antigen receptors on murine T lymphocytes in contact sensitivity. I. Functional inhibition of effector T cells by monovalent 2,4-dinitrophenol: implication for a two-receptor model [1].
  • Inhibiting oxidative metabolism with hypoxia, dinitrophenol (10(-5)M), or Na-azide (10(-3)M) caused marked suppression of tension (by 73 +/- 5, 65 +/- 8, and 50 +/- 14%, respectively) and a small increase in [K+]0 (0.8 +/- 0.4, 0.5 +/- 0.25, and 0.4 +/- 0.2 mM, respectively) after 10 min [2].
  • Treatment of developing colonies of Podocoryne carnea, a hydractiniid hydroid, with dilute solutions of 2,4-dinitrophenol (DNP), an uncoupler of oxidative phosphorylation, accelerates the usual ontogenetic trajectory of polyp and stolon production [3].
  • Although Jeggo's Chinese hamster ovary cells were more responsive to mAMSA, novo still abrogated mAMSA toxicity in the mutant cells as well as in the parental Chinese hamster ovary cells 2,4-Dinitrophenol acted similarly to novo with respect to mAMSA killing, but neither compound reduced the ATP content of V79 cells [4].
  • Effects of 2,4-dinitrophenol and other metabolic inhibitors on the thermograms of Ehrlich ascites carcinoma cells registered with a microcalorimeter [5].

Psychiatry related information on 2,4-dinitrophenol

  • 0. It also showed a fast response time (t95% < 1.5 min) when the sensor was applied to 2,4-dinitrophenol solution at concentration levels of 5.26 x 10(-6) and 2.10 x 10(-5) mol L(-1) alternatively [6].

High impact information on 2,4-dinitrophenol


Chemical compound and disease context of 2,4-dinitrophenol


Biological context of 2,4-dinitrophenol


Anatomical context of 2,4-dinitrophenol

  • Because fetal DNP precursors from spleens and livers that had been incubated in organ culture resulted in a greater proportion of clones secreting IgG compared with age-matched uncultured controls, it was concluded that the maturation with regard to the ability to secrete IgG can occur in vitro [16].
  • This alteration in the cell membrane responsiveness was reversible upon further incubation in the absence of DNP [20].
  • The separated junctional membranes, expected to be highly impermeable, contain particles regularly and tightly packed as in hypoxic or DNP-treated junctions [21].
  • Electron microscope examination of dividing guard mother cells fixed during azide and dinitrophenol treatment reveals that spindle microtubules are still present [19].
  • Intact erythrocytes become immediately crenated upon addition of 2,4-dinitrophenol (DNP) or pyrenebutyric acid (PBA) [20].

Associations of 2,4-dinitrophenol with other chemical compounds

  • Dinitrophenol- (DNP) or trinitrophenol-modified mouse spleen cells (SC) induced suppressors in donors able to transfer suppression to normal recipients [22].
  • Secretion of IL-1 beta is blocked by methylamine, low temperature or serum free medium, and is increased by raising the culture temperature to 42 degrees C or by the presence of calcium ionophores, brefeldin A, monensin, dinitrophenol or carbonyl cyanide chlorophenylhydrazone [23].
  • The uncoupling is produced by in vitro treatment of crayfish abdominal cords either with a Ca++, Mg++-free solution containing EDTA, followed by return to normal saline (Van Harreveld's solution), or with VAn Harreveld's solution containing dinitrophenol (DNP) [24].
  • In contrast, uptake of unilamellar dipalmitoyl lecithin vesicles and multilamellar dipalmitoyl lecithin liposomes is only partially inhibited at 4 degrees C, by dinitrophenol and by prior fixation of the amoebae with glutaraldehyde, each of which inhibits pinocytosis [25].
  • It is reduced to zero by the mitochondrial uncoupler 2,4-dinitrophenol but is relatively unaffected by ouabain, which inhibits the Na+/K+-pump located on the apical membrane of this epithelium [26].

Gene context of 2,4-dinitrophenol

  • The results obtained with the control bcy strain, the RAS2(Val-19) strain under conditions in which RAS1 is expressed, and with dinitrophenol show that the inability of the oncogene product to mediate the cAMP signal is not due to feedback inhibition by the high protein kinase activity in strains containing the RAS2(Val-19) oncogene [27].
  • In strains carrying the cif1 mutation the intracellular concentration of ATP decreased immediately after addition of glucose while the intracellular concentration of cAMP did not increase. cAMP concentration increased in response to galactose or 2,4-dinitrophenol [28].
  • Subcellular fractionation studies revealed that the amount of mature caspase-8 but not pro-caspase at the membrane was increased following CD95-stimulation in the presence of DNP [29].
  • Other antioxidants such as catalase, Cu/Zn-SOD and GSHPx were not activated by DNP treatment [30].
  • Although DNP slightly elevated Mn-SOD activity, the rate of increase in Mn-SOD (1.3-fold) was smaller than that in MT (3.7-fold) [30].

Analytical, diagnostic and therapeutic context of 2,4-dinitrophenol

  • Recently we demonstrated that low-pH compartments can be visualized with the electron microscope using a basic congener of dinitrophenol, 3-(2,4-dinitroanilino)-3'-amino-N-methyldipropylamine (DAMP), which concentrates in acidic compartments and can be detected by immunocytochemistry with a monoclonal anti-dinitrophenol antibody [31].
  • However, if tolerogen were present for 3--5 d during organ culture there was near total elimination of potential DNP clones [16].
  • Perfusion with partially calcium-loaded nitrophen often caused a loading transient--slow secretion for up to 1 min due to displacement of Ca2+ by cytoplasmic Mg2+ [32].
  • Treatment of Fao cells with 2,4-dinitrophenol for 45 min depleted cellular ATP by 80% and equally inhibited insulin-stimulated receptor autophosphorylation, as determined by immunoprecipitation of surface-iodinated or [32P]phosphate-labeled cells with anti-phosphotyrosine antibody [33].
  • Normal saline, when administered in a similar manner, did not increase either ventilation or cardiac output, and simple denervation without previous infusions of DNP also had no effect [34].


  1. Antigen receptors on murine T lymphocytes in contact sensitivity. I. Functional inhibition of effector T cells by monovalent 2,4-dinitrophenol: implication for a two-receptor model. Moorhead, J.W. J. Exp. Med. (1981) [Pubmed]
  2. Functional compartmentation of glycolytic versus oxidative metabolism in isolated rabbit heart. Weiss, J., Hiltbrand, B. J. Clin. Invest. (1985) [Pubmed]
  3. Treatment with 2,4-dinitrophenol mimics ontogenetic and phylogenetic changes in a hydractiniid hydroid. Blackstone, N.W., Buss, L.W. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  4. Abrogation by novobiocin of cytotoxicity due to the topoisomerase II inhibitor amsacrine in Chinese hamster cells. Utsumi, H., Shibuya, M.L., Kosaka, T., Buddenbaum, W.E., Elkind, M.M. Cancer Res. (1990) [Pubmed]
  5. Effects of 2,4-dinitrophenol and other metabolic inhibitors on the thermograms of Ehrlich ascites carcinoma cells registered with a microcalorimeter. Ito, E., Sakihama, H., Toyama, K., Matsui, K. Cancer Res. (1984) [Pubmed]
  6. A selective PVC membrane for di- or trinitrophenol based on N,N-dibenzyl-3,3',5,5'-tetramethylbenzidine. Yang, R.H., Wang, K.M., Long, L.P., Chan, W.H., Yang, X.H. The Analyst. (2002) [Pubmed]
  7. Uncoupling protein-2 prevents neuronal death and diminishes brain dysfunction after stroke and brain trauma. Mattiasson, G., Shamloo, M., Gido, G., Mathi, K., Tomasevic, G., Yi, S., Warden, C.H., Castilho, R.F., Melcher, T., Gonzalez-Zulueta, M., Nikolich, K., Wieloch, T. Nat. Med. (2003) [Pubmed]
  8. Cloning of complementary DNA encoding T-cell replacing factor and identity with B-cell growth factor II. Kinashi, T., Harada, N., Severinson, E., Tanabe, T., Sideras, P., Konishi, M., Azuma, C., Tominaga, A., Bergstedt-Lindqvist, S., Takahashi, M. Nature (1986) [Pubmed]
  9. Engraftment and development of human T and B cells in mice after bone marrow transplantation. Lubin, I., Faktorowich, Y., Lapidot, T., Gan, Y., Eshhar, Z., Gazit, E., Levite, M., Reisner, Y. Science (1991) [Pubmed]
  10. Uncoupling agents distinguish between the effects of metabolic inhibitors and transport inhibitors. Weiner, M.W. Science (1979) [Pubmed]
  11. Studies of acid and alkaline secretion by rabbit gastric fundus in vitro: effect of low concentrations of sodium taurocholate. Rees, W.D., Garner, A., Turnberg, L.A. Gastroenterology (1982) [Pubmed]
  12. Parallel temperature dependence of contracture-associated enzyme release due to anoxia, 2,4-dinitrophenol (DNP), or caffeine and the calcium paradox. Ganote, C.E., Sims, M.A. Am. J. Pathol. (1984) [Pubmed]
  13. Adenosine 5'-monophosphate-activated protein kinase and p38 mitogen-activated protein kinase participate in the stimulation of glucose uptake by dinitrophenol in adult cardiomyocytes. Pelletier, A., Joly, E., Prentki, M., Coderre, L. Endocrinology (2005) [Pubmed]
  14. Hypoxia-induced upregulation of eNOS gene expression is redox-sensitive: a comparison between hypoxia and inhibitors of cell metabolism. Hoffmann, A., Gloe, T., Pohl, U. J. Cell. Physiol. (2001) [Pubmed]
  15. Bactericidal activity of M14659 enhanced in low-iron environments. Mochizuki, H., Yamada, H., Oikawa, Y., Murakami, K., Ishiguro, J., Kosuzume, H., Aizawa, N., Mochida, E. Antimicrob. Agents Chemother. (1988) [Pubmed]
  16. Ontogenic development of B-lymphocyte function and tolerance susceptibility in vivo and in an in vitro organ culture system. Teale, J.M., Mandel, T.E. J. Exp. Med. (1980) [Pubmed]
  17. Role of sarcolemmal K(ATP) channels in cardioprotection against ischemia/reperfusion injury in mice. Suzuki, M., Sasaki, N., Miki, T., Sakamoto, N., Ohmoto-Sekine, Y., Tamagawa, M., Seino, S., Marbán, E., Nakaya, H. J. Clin. Invest. (2002) [Pubmed]
  18. Energy-dependent intracellular translocation of proparathormone. Chu, L.L., MacGregor, R.R., Cohn, D.V. J. Cell Biol. (1977) [Pubmed]
  19. Metabolic inhibitors block anaphase A in vivo. Hepler, P.K., Palevitz, B.A. J. Cell Biol. (1986) [Pubmed]
  20. Control of the erythrocyte membrane shape: recovery from the effect of crenating agents. Alhanaty, E., Sheetz, M.P. J. Cell Biol. (1981) [Pubmed]
  21. Gap junctions. Structural changes after uncoupling procedures. Peracchia, C. J. Cell Biol. (1977) [Pubmed]
  22. Suppressor cells in tolerance to contact sensitivity active against hapten-syngeneic and hapten-allogeneic determinants. Claman, H.N., Miller, S.D., Sy, M.S. J. Exp. Med. (1977) [Pubmed]
  23. A novel secretory pathway for interleukin-1 beta, a protein lacking a signal sequence. Rubartelli, A., Cozzolino, F., Talio, M., Sitia, R. EMBO J. (1990) [Pubmed]
  24. Low resistance junctions in crayfish. Structural changes with functional uncoupling. Peracchia, C., Dulhunty, A.F. J. Cell Biol. (1976) [Pubmed]
  25. Interaction of phospholipid vesicles with cells. Endocytosis and fusion as alternate mechanisms for the uptake of lipid-soluble and water-soluble molecules. Batzri, S., Korn, E.D. J. Cell Biol. (1975) [Pubmed]
  26. Fluid transport across retinal pigment epithelium is inhibited by cyclic AMP. Miller, S.S., Hughes, B.A., Machen, T.E. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  27. Requirement of one functional RAS gene and inability of an oncogenic ras variant to mediate the glucose-induced cyclic AMP signal in the yeast Saccharomyces cerevisiae. Mbonyi, K., Beullens, M., Detremerie, K., Geerts, L., Thevelein, J.M. Mol. Cell. Biol. (1988) [Pubmed]
  28. Molecular cloning of CIF1, a yeast gene necessary for growth on glucose. González, M.I., Stucka, R., Blázquez, M.A., Feldmann, H., Gancedo, C. Yeast (1992) [Pubmed]
  29. Enhancement of death-receptor induced caspase-8-activation in the death-inducing signalling complex by uncoupling of oxidative phosphorylation. Vier, J., Gerhard, M., Wagner, H., Häcker, G. Mol. Immunol. (2004) [Pubmed]
  30. Specific induction of metallothionein synthesis by mitochondrial oxidative stress. Kondoh, M., Inoue, Y., Atagi, S., Futakawa, N., Higashimoto, M., Sato, M. Life Sci. (2001) [Pubmed]
  31. Vesicles and cisternae in the trans Golgi apparatus of human fibroblasts are acidic compartments. Anderson, R.G., Pathak, R.K. Cell (1985) [Pubmed]
  32. Multiple calcium-dependent processes related to secretion in bovine chromaffin cells. Neher, E., Zucker, R.S. Neuron (1993) [Pubmed]
  33. Tyrosine phosphorylation of the insulin receptor is not required for receptor internalization: studies in 2,4-dinitrophenol-treated cells. Backer, J.M., Kahn, C.R., White, M.F. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  34. Afferent neural pathway in the regulation of cardiopulmonary responses to tissue hypermetabolism. Liang, C.S., Hood, W.B. Circ. Res. (1976) [Pubmed]
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