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Chemical Compound Review

Trinitrobenzenes     1,3,5-trinitrobenzene

Synonyms: Benzite, Trinitrobenzol, CCRIS 3093, CHEBI:48113, HSDB 6005, ...
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Disease relevance of symmetric Trinitrobenzene

  • Mice treated with anti-mouse CEACAM1-specific monoclonal antibody (mAb) CC1 during the effector phase exhibited a reduced severity of trinitrobenzene sulfonic acid colitis in association with decreased interferon (IFN)-gamma production [1].
  • Therapeutic effects of vasoactive intestinal peptide in the trinitrobenzene sulfonic acid mice model of Crohn's disease [2].
  • RESULTS: Ghrelin ameliorated significantly the clinical and histopathologic severity of the trinitrobenzene sulfonic acid-induced colitis; abrogating body weight loss, diarrhea, and inflammation; and increasing survival [3].
  • Methods: We examined the therapeutic action of DC(VIP) in the colitis induced by intracolonic administration of trinitrobenzene sulfonic acid, evaluating diverse clinical signs of the disease including weight loss, diarrhea, colitis, and histopathology [4].
  • After 24 h, mucosal ulceration and hemorrhage were observed in TNB/ethanol-, 50% ethanol-, and to a lesser extent, in TNB/saline-treated rats [5].

Psychiatry related information on symmetric Trinitrobenzene


High impact information on symmetric Trinitrobenzene


Chemical compound and disease context of symmetric Trinitrobenzene


Biological context of symmetric Trinitrobenzene

  • Effects of LPA on intestinal wound healing in vivo were studied by using the trinitrobenzene model of colitis in rats [16].
  • With large molar excesses of the reagent, the reactions obey pseudo-first order kinetics and the rates of inactivations are directly proportional to the concentrations of trinitrobenzene sulfonate; thus, there is no indication of reversible complexation of reagent with enzyme [17].
  • Body temperature was monitored by telemetry from conscious, unrestrained male rats treated with trinitrobenzene sulphonic acid or saline [18].
  • Formation of the Meisenheimer complex or sigma-complex [1-(S-glutathionyl)-2,4,6-trinitrocyclohexadienate] between glutathione (GSH) and 1,3,5-trinitrobenzene (TNB) can be observed at the active sites of isoenzymes 3-3 and 4-4 of rat liver GSH transferase [19].
  • Conversely, CCR6 deficiency alters leukocyte homeostasis and the cytokine environment in the intestinal mucosa; these changes are sufficient to confer susceptibility to trinitrobenzene sulfonic acid-induced intestinal inflammation in the otherwise resistant C57BL/6J mouse strain [20].

Anatomical context of symmetric Trinitrobenzene

  • RESULTS: Normal mature IEC expressed low TRAIL levels, whereas, in inflammatory lesions, TRAIL messenger RNA and protein were markedly up-regulated in IEC and lamina propria lymphocytes at levels comparable with trinitrobenzene sulfonic acid-induced colitis [21].
  • On the contrary, single intracolonic administration of trinitrobenzene sulfonic acid/ethanol induced a biphasic response consisting of an early pool of radiolabeled feces (T25 = 4.03 +/- 0.55 hours) with a delayed total one (T50 = 11.74 +/- 0.83 hours; T75 = 13.70 +/- 0.49 hours) [22].
  • The interval between the release of newly synthesized proteins from ribosomes and their appearance at the cell surface, where they became accessible to trinitrobenzene sulfonic acid, was studied in pulse-chase experiments [23].
  • Modification of spleen cells from the strain or origin (129) of this teratoma line with trinitrobenzene sulfonic acid allows the generation of syngeneic killer cells that display a cytotoxic effect against trinitrophenyl-modified splenic targets, but not against trinitrophenyl-modified F9 targets [24].
  • Plasma membrane PE was distinguished from intracellular PE by its derivatization with an amino-reactive reagent, trinitrobenzene sulfonic acid, under nonpermeating conditions [25].

Associations of symmetric Trinitrobenzene with other chemical compounds


Gene context of symmetric Trinitrobenzene

  • Recent studies suggest that the induction of HO-1 expression plays a critical protective role in intestinal damage models induced by trinitrobenzene sulphonic acid or dextran sulphate sodium, indicating that activation of HO-1 may act as an endogenous defensive mechanism to reduce inflammation and tissue injury in the intestinal tract [30].
  • MATERIALS AND METHODS: Body weight, histological scores, and myeloperoxidase activity were evaluated in trinitrobenzene sulfonic acid colitis [31].
  • Gliotoxin reduces the severity of trinitrobenzene sulfonic acid-induced colitis in mice: evidence of the connection between heme oxygenase-1 and the nuclear factor-kappaB pathway in vitro and in vivo [31].
  • We studied the effects of HGF in mice with trinitrobenzene sulfonic acid-induced colitis, which shows clinical and molecular resemblance to Crohn's disease [32].
  • This pretreatment protected IFN-gamma(-/-) mice from trinitrobenzene sulfonic acid-induced colitis; however, in normal mice this weekly treatment was less protective [33].

Analytical, diagnostic and therapeutic context of symmetric Trinitrobenzene


  1. Specific regulation of T helper cell 1-mediated murine colitis by CEACAM1. Iijima, H., Neurath, M.F., Nagaishi, T., Glickman, J.N., Nieuwenhuis, E.E., Nakajima, A., Chen, D., Fuss, I.J., Utku, N., Lewicki, D.N., Becker, C., Gallagher, T.M., Holmes, K.V., Blumberg, R.S. J. Exp. Med. (2004) [Pubmed]
  2. Therapeutic effects of vasoactive intestinal peptide in the trinitrobenzene sulfonic acid mice model of Crohn's disease. Abad, C., Martinez, C., Juarranz, M.G., Arranz, A., Leceta, J., Delgado, M., Gomariz, R.P. Gastroenterology (2003) [Pubmed]
  3. Therapeutic action of ghrelin in a mouse model of colitis. Gonzalez-Rey, E., Chorny, A., Delgado, M. Gastroenterology (2006) [Pubmed]
  4. Therapeutic treatment of experimental colitis with regulatory dendritic cells generated with vasoactive intestinal Peptide. Gonzalez-Rey, E., Delgado, M. Gastroenterology (2006) [Pubmed]
  5. Inflammatory mediators of experimental colitis in rats. Rachmilewitz, D., Simon, P.L., Schwartz, L.W., Griswold, D.E., Fondacaro, J.D., Wasserman, M.A. Gastroenterology (1989) [Pubmed]
  6. On-line monitoring of cell growth and cytotoxicity using electric cell-substrate impedance sensing (ECIS). Xiao, C., Luong, J.H. Biotechnol. Prog. (2003) [Pubmed]
  7. Treatment of experimental (Trinitrobenzene sulfonic acid) colitis by intranasal administration of transforming growth factor (TGF)-beta1 plasmid: TGF-beta1-mediated suppression of T helper cell type 1 response occurs by interleukin (IL)-10 induction and IL-12 receptor beta2 chain downregulation. Kitani, A., Fuss, I.J., Nakamura, K., Schwartz, O.M., Usui, T., Strober, W. J. Exp. Med. (2000) [Pubmed]
  8. Specific suppression of allograft rejection by trinitrophenyl (TNP)-induced suppressor cells in recipients treated with TNP-haptenated donor alloantigens. Hutchinson, I.V., Barber, W.H., Morris, P.J. J. Exp. Med. (1985) [Pubmed]
  9. Treatment of murine Th1- and Th2-mediated inflammatory bowel disease with NF-kappa B decoy oligonucleotides. Fichtner-Feigl, S., Fuss, I.J., Preiss, J.C., Strober, W., Kitani, A. J. Clin. Invest. (2005) [Pubmed]
  10. Inhibition of indoleamine 2,3-dioxygenase augments trinitrobenzene sulfonic acid colitis in mice. Gurtner, G.J., Newberry, R.D., Schloemann, S.R., McDonald, K.G., Stenson, W.F. Gastroenterology (2003) [Pubmed]
  11. Therapeutic effects of interleukin-4 gene transfer in experimental inflammatory bowel disease. Hogaboam, C.M., Vallance, B.A., Kumar, A., Addison, C.L., Graham, F.L., Gauldie, J., Collins, S.M. J. Clin. Invest. (1997) [Pubmed]
  12. Curcumin prevents and ameliorates trinitrobenzene sulfonic acid-induced colitis in mice. Sugimoto, K., Hanai, H., Tozawa, K., Aoshi, T., Uchijima, M., Nagata, T., Koide, Y. Gastroenterology (2002) [Pubmed]
  13. Exacerbation of experimental colitis by nonsteroidal anti-inflammatory drugs is not related to elevated leukotriene B4 synthesis. Wallace, J.L., Keenan, C.M., Gale, D., Shoupe, T.S. Gastroenterology (1992) [Pubmed]
  14. A stable nitroxide radical effectively decreases mucosal damage in experimental colitis. Karmeli, F., Eliakim, R., Okon, E., Samuni, A., Rachmilewitz, D. Gut (1995) [Pubmed]
  15. Non-viral delivery of nuclear factor-{kappa}B decoy ameliorates murine inflammatory bowel disease and restores tissue homeostasis. De Vry, C.G., Prasad, S., Komuves, L., Lorenzana, C., Parham, C., Le, T., Adda, S., Hoffman, J., Kahoud, N., Garlapati, R., Shyamsundar, R., Mai, K., Zhang, J., Muchamuel, T., Dajee, M., Schryver, B., McEvoy, L.M., Ehrhardt, R.O. Gut (2007) [Pubmed]
  16. Modulation of intestinal epithelial wound healing in vitro and in vivo by lysophosphatidic acid. Sturm, A., Sudermann, T., Schulte, K.M., Goebell, H., Dignass, A.U. Gastroenterology (1999) [Pubmed]
  17. Ionization constants of two active-site lysyl epsilon-amino groups of ribulosebisphosphate carboxylase/oxygenase. Hartman, F.C., Milanez, S., Lee, E.H. J. Biol. Chem. (1985) [Pubmed]
  18. Compromised neuroimmune status in rats with experimental colitis. Boissé, L., Van Sickle, M.D., Sharkey, K.A., Pittman, Q.J. J. Physiol. (Lond.) (2003) [Pubmed]
  19. Formation of the 1-(S-glutathionyl)-2,4,6-trinitrocyclohexadienate anion at the active site of glutathione S-transferase: evidence for enzymic stabilization of sigma-complex intermediates in nucleophilic aromatic substitution reactions. Graminski, G.F., Zhang, P.H., Sesay, M.A., Ammon, H.L., Armstrong, R.N. Biochemistry (1989) [Pubmed]
  20. CCR6 has a non-redundant role in the development of inflammatory bowel disease. Varona, R., Cadenas, V., Flores, J., Martínez-A, C., Márquez, G. Eur. J. Immunol. (2003) [Pubmed]
  21. Implication of TNF-related apoptosis-inducing ligand in inflammatory intestinal epithelial lesions. Begue, B., Wajant, H., Bambou, J.C., Dubuquoy, L., Siegmund, D., Beaulieu, J.F., Canioni, D., Berrebi, D., Brousse, N., Desreumaux, P., Schmitz, J., Lentze, M.J., Goulet, O., Cerf-Bensussan, N., Ruemmele, F.M. Gastroenterology (2006) [Pubmed]
  22. Leukotriene D4 participates in colonic transit disturbances induced by intracolonic administration of trinitrobenzene sulfonic acid in rats. Pons, L., Droy-Lefaix, M.T., Bueno, L. Gastroenterology (1992) [Pubmed]
  23. Insertion and turnover of macrophage plasma membrane proteins. Kaplan, G., Unkeless, J.C., Cohn, Z.A. Proc. Natl. Acad. Sci. U.S.A. (1979) [Pubmed]
  24. Absence of H-2 antigens capable of reacting with cytotoxic T cells on a teratoma line expressing a T/t locus antigen. Forman, J., Vitetta, E.S. Proc. Natl. Acad. Sci. U.S.A. (1975) [Pubmed]
  25. Rapid appearance of newly synthesized phosphatidylethanolamine at the plasma membrane. Sleight, R.G., Pagano, R.E. J. Biol. Chem. (1983) [Pubmed]
  26. Adenosine 5'-phosphosulfate kinase from Penicillium chrysogenum. Determining ligand dissociation constants of binary and ternary complexes from the kinetics of enzyme inactivation. Renosto, F., Seubert, P.A., Knudson, P., Segel, I.H. J. Biol. Chem. (1985) [Pubmed]
  27. The role of arginyl residues in porphyrin binding to ferrochelatase. Dailey, H.A., Fleming, J.E. J. Biol. Chem. (1986) [Pubmed]
  28. Binding of thyroglobulin to bovine thyroid membranes. Role of specific amino acids in receptor recognition. Shifrin, S., Kohn, L.D. J. Biol. Chem. (1981) [Pubmed]
  29. Inhibition of fibronectin-mediated adhesion of hamster fibroblasts to substratum: effects of tunicamycin and some cell surface modifying reagents. Butters, T.D., Devalia, V., Aplin, J.D., Hughes, R.C. J. Cell. Sci. (1980) [Pubmed]
  30. Heme oxygenase-1: a new therapeutic target for inflammatory bowel disease. Naito, Y., Takagi, T., Yoshikawa, T. Aliment. Pharmacol. Ther. (2004) [Pubmed]
  31. Gliotoxin reduces the severity of trinitrobenzene sulfonic acid-induced colitis in mice: evidence of the connection between heme oxygenase-1 and the nuclear factor-kappaB pathway in vitro and in vivo. Jun, C.D., Kim, Y., Choi, E.Y., Kim, M., Park, B., Youn, B., Yu, K., Choi, K.S., Yoon, K.H., Choi, S.C., Lee, M.S., Park, K.I., Choi, M., Chung, Y., Oh, J. Inflamm. Bowel Dis. (2006) [Pubmed]
  32. Ameliorating effect of hepatocyte growth factor on inflammatory bowel disease in a murine model. Oh, K., Iimuro, Y., Takeuchi, M., Kaneda, Y., Iwasaki, T., Terada, N., Matsumoto, T., Nakanishi, K., Fujimoto, J. Am. J. Physiol. Gastrointest. Liver Physiol. (2005) [Pubmed]
  33. Elimination of colonic patches with lymphotoxin beta receptor-Ig prevents Th2 cell-type colitis. Dohi, T., Rennert, P.D., Fujihashi, K., Kiyono, H., Shirai, Y., Kawamura, Y.I., Browning, J.L., McGhee, J.R. J. Immunol. (2001) [Pubmed]
  34. Cholestasis with altered structure and function of hepatocyte tight junction and decreased expression of canalicular multispecific organic anion transporter in a rat model of colitis. Kawaguchi, T., Sakisaka, S., Mitsuyama, K., Harada, M., Koga, H., Taniguchi, E., Sasatomi, K., Kimura, R., Ueno, T., Sawada, N., Mori, M., Sata, M. Hepatology (2000) [Pubmed]
  35. Biosynthesis of gp160, the major trypsin-sensitive surface glycoprotein of macrophages. Remold-O'Donnell, E. J. Biol. Chem. (1982) [Pubmed]
  36. Oral administration of recombinant cholera toxin subunit B inhibits IL-12-mediated murine experimental (trinitrobenzene sulfonic acid) colitis. Boirivant, M., Fuss, I.J., Ferroni, L., De Pascale, M., Strober, W. J. Immunol. (2001) [Pubmed]
  37. A quantitative assessment of heterogeneity for surface-immobilized proteins. Vijayendran, R.A., Leckband, D.E. Anal. Chem. (2001) [Pubmed]
  38. The effect of berberine chloride on experimental colitis in rats in vivo and in vitro. Zhou, H., Mineshita, S. J. Pharmacol. Exp. Ther. (2000) [Pubmed]
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