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Chemical Compound Review

Oxazolone     (4Z)-4-(ethoxymethylidene)-2- phenyl-1,3...

Synonyms: AC1LVUKP, SureCN248341, SBB038827, STL133422, ZINC12403085, ...
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Disease relevance of Oxazolone


Psychiatry related information on Oxazolone

  • Our data establish that the H chain gene complex consists of a single VH germ-line gene that is identical to VH Oxazolone-1, encoding the H chain of another highly conserved and dominant cross-reactive Id family associated with the primary response to Oxazolone [6].

High impact information on Oxazolone

  • In the present study, patterns of ocular dominance and orientation selectivity were obtained repeatedly from the same patch of cortex using the dye merocyanine oxazolone, together with current image-processing techniques [7].
  • We conclude that somatic mutation of germ-line encoded genes plays a major role in the generation of antibodies with increased affinity for oxazolone with time after immunization [8].
  • Both interleukin-4 and IFN-gamma gene-deficient mice exhibited less severe colitis induction by oxazolone [9].
  • Oxazolone colitis: A murine model of T helper cell type 2 colitis treatable with antibodies to interleukin 4 [3].
  • To examine the role of the MSH2 mismatch repair protein in hypermutation, Msh2-/- mice were immunized with oxazolone, and B cells were analyzed for mutation in their VkappaOx1 light chain genes [10].

Chemical compound and disease context of Oxazolone


Biological context of Oxazolone


Anatomical context of Oxazolone

  • At concentrations as low as 4 microM, reserpine profoundly suppressed baseline or antigen-augmented levels of [3H]thymidine incorporation by immune lymph node cells obtained from mice sensitized to the contactant oxazolone [I-LNC(Ox)] [21].
  • The induction of the CD4+ and CD8+ T cells producing the polarized patterns of cytokines was not restricted to BALB/c mice, as cells from Ox sensitized C57B1/6 and B10.D2 mice produced the same patterns [22].
  • The localization of nonblastic (small) 51Cr-labeled lymphocytes on the other hand is substantial only in lymphoid tissue and during the induction of an immune reaction after oxazolone application, the increase in localization of these cells in the draining lymph node is positively correlated with increased blood flow to the node [23].
  • Oxazolone colitis is a T helper cell type 2 (Th2)-mediated process since stimulated T cells from lesional tissue produce markedly increased amounts of interleukin (IL)-4 and IL-5; in addition, anti-IL-4 administration leads to a striking amelioration of disease, whereas anti-IL-12 administration either has no effect or exacerbates disease [3].
  • The basis for this proposal comes from the kinetic analysis of a set of murine hybridomas derived from defined stages of the immune response to 2-phenyl-5-oxazolone (Ox) [24].

Associations of Oxazolone with other chemical compounds


Gene context of Oxazolone


Analytical, diagnostic and therapeutic context of Oxazolone


  1. Oxazolone colitis, a Th2 colitis model resembling ulcerative colitis, is mediated by IL-13-producing NK-T cells. Heller, F., Fuss, I.J., Nieuwenhuis, E.E., Blumberg, R.S., Strober, W. Immunity (2002) [Pubmed]
  2. L-selectin-deficient mice have impaired leukocyte recruitment into inflammatory sites. Tedder, T.F., Steeber, D.A., Pizcueta, P. J. Exp. Med. (1995) [Pubmed]
  3. Oxazolone colitis: A murine model of T helper cell type 2 colitis treatable with antibodies to interleukin 4. Boirivant, M., Fuss, I.J., Chu, A., Strober, W. J. Exp. Med. (1998) [Pubmed]
  4. Heparin's anti-inflammatory effects require glucosamine 6-O-sulfation and are mediated by blockade of L- and P-selectins. Wang, L., Brown, J.R., Varki, A., Esko, J.D. J. Clin. Invest. (2002) [Pubmed]
  5. N-(fluorenyl-9-methoxycarbonyl) amino acids, a class of antiinflammatory agents with a different mechanism of action. Burch, R.M., Weitzberg, M., Blok, N., Muhlhauser, R., Martin, D., Farmer, S.G., Bator, J.M., Connor, J.R., Green, M., Ko, C. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  6. Nucleotide sequence of messenger RNA encoding VHDJH and VKJK of a highly conserved idiotype-defined primary response anti-hapten antibody. Lou, S.C., Winter, D., Mayers, G.L., Bankert, R.B. J. Immunol. (1992) [Pubmed]
  7. Voltage-sensitive dyes reveal a modular organization in monkey striate cortex. Blasdel, G.G., Salama, G. Nature (1986) [Pubmed]
  8. Somatic mutation and the maturation of immune response to 2-phenyl oxazolone. Griffiths, G.M., Berek, C., Kaartinen, M., Milstein, C. Nature (1984) [Pubmed]
  9. 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]
  10. Increased hypermutation at G and C nucleotides in immunoglobulin variable genes from mice deficient in the MSH2 mismatch repair protein. Phung, Q.H., Winter, D.B., Cranston, A., Tarone, R.E., Bohr, V.A., Fishel, R., Gearhart, P.J. J. Exp. Med. (1998) [Pubmed]
  11. Gamma delta T cells from tolerized alpha beta T cell receptor (TCR)-deficient mice inhibit contact sensitivity-effector T cells in vivo, and their interferon-gamma production in vitro. Szczepanik, M., Anderson, L.R., Ushio, H., Ptak, W., Owen, M.J., Hayday, A.C., Askenase, P.W. J. Exp. Med. (1996) [Pubmed]
  12. Mycophenolate mofetil impairs the maturation and function of murine dendritic cells. Mehling, A., Grabbe, S., Voskort, M., Schwarz, T., Luger, T.A., Beissert, S. J. Immunol. (2000) [Pubmed]
  13. Immunopotentiating effects of amphotericin B. I. Enhanced contact sensitivity in mice. Shirley, S.F., Little, J.R. J. Immunol. (1979) [Pubmed]
  14. Contact hypersensitivity reactions to dinitrofluorobenzene mediated by monoclonal IgE anti-DNP antibodies. Ray, M.C., Tharp, M.D., Sullivan, T.J., Tigelaar, R.E. J. Immunol. (1983) [Pubmed]
  15. Involvement of the Cannabinoid CB2 Receptor and Its Endogenous Ligand 2-Arachidonoylglycerol in Oxazolone-Induced Contact Dermatitis in Mice. Oka, S., Wakui, J., Ikeda, S., Yanagimoto, S., Kishimoto, S., Gokoh, M., Nasui, M., Sugiura, T. J. Immunol. (2006) [Pubmed]
  16. Suppression of antibody responses by cells from mice treated with picryl sulfonic acid: T cells that suppress IgG antibody without inhibiting concomitant IgE responses. Thomas, W.R., Watkins, M.C., Cox, K.O., Asherson, G.L. J. Immunol. (1981) [Pubmed]
  17. Gamma delta T cells assist alpha beta T cells in adoptive transfer of contact sensitivity. Ptak, W., Askenase, P.W. J. Immunol. (1992) [Pubmed]
  18. Tolerance and contact sensitivity to DNFB in mice. VI. Inhibition of afferent sensitivity by suppressor T cells in adoptive tolerance. Moorhead, J.W. J. Immunol. (1976) [Pubmed]
  19. Topical FK506 suppresses cytokine and costimulatory molecule expression in epidermal and local draining lymph node cells during primary skin immune responses. Homey, B., Assmann, T., Vohr, H.W., Ulrich, P., Lauerma, A.I., Ruzicka, T., Lehmann, P., Schuppe, H.C. J. Immunol. (1998) [Pubmed]
  20. Fine-specificity of the immune response to oxazolones. II. Cytolytic T cells. Kaartinen, M., Ferreira, A.M., Hurme, M., Mäkelä, O. J. Immunol. (1981) [Pubmed]
  21. Reevaluation of reserpine-induced suppression of contact sensitivity. Evidence that reserpine interferes with T lymphocyte function independently of an effect on mast cells. Mekori, Y.A., Weitzman, G.L., Galli, S.J. J. Exp. Med. (1985) [Pubmed]
  22. T cell populations primed by hapten sensitization in contact sensitivity are distinguished by polarized patterns of cytokine production: interferon gamma-producing (Tc1) effector CD8+ T cells and interleukin (Il) 4/Il-10-producing (Th2) negative regulatory CD4+ T cells. Xu, H., DiIulio, N.A., Fairchild, R.L. J. Exp. Med. (1996) [Pubmed]
  23. Regional blood flow and its relationship to lymphocyte and lymphoblast traffic during a primary immune reaction. Ottaway, C.A., Parrott, D.M. J. Exp. Med. (1979) [Pubmed]
  24. Conformational isomerism and the diversity of antibodies. Foote, J., Milstein, C. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  25. Hapten-specific T cell lines mediating delayed hypersensitivity to contact-sensitizing agents. Thomas, W.R., Mottram, P.L., Miller, J.F. J. Exp. Med. (1982) [Pubmed]
  26. Alpha 6 integrins are required for Langerhans cell migration from the epidermis. Price, A.A., Cumberbatch, M., Kimber, I., Ager, A. J. Exp. Med. (1997) [Pubmed]
  27. IgE antibody-mediated cutaneous basophil hypersensitivity reactions in guinea pigs. Graziano, F.M., Gunderson, L., Larson, L., Askenase, P.W. J. Immunol. (1983) [Pubmed]
  28. Synchrony of high endothelial venules and lymphatic vessels revealed by immunization. Liao, S., Ruddle, N.H. J. Immunol. (2006) [Pubmed]
  29. Action potentials of isolated single muscle fibers recorded by potential-sensitive dyes. Nakajima, S., Gilai, A. J. Gen. Physiol. (1980) [Pubmed]
  30. Contribution of the CD28 molecule to allergic and irritant-induced skin reactions in CD28 -/- mice. Kondo, S., Kooshesh, F., Wang, B., Fujisawa, H., Sauder, D.N. J. Immunol. (1996) [Pubmed]
  31. Synthesis, structure-activity relationships, and in vivo evaluations of substituted di-tert-butylphenols as a novel class of potent, selective, and orally active cyclooxygenase-2 inhibitors. 1. Thiazolone and oxazolone series. Song, Y., Connor, D.T., Doubleday, R., Sorenson, R.J., Sercel, A.D., Unangst, P.C., Roth, B.D., Gilbertsen, R.B., Chan, K., Schrier, D.J., Guglietta, A., Bornemeier, D.A., Dyer, R.D. J. Med. Chem. (1999) [Pubmed]
  32. Tachykinins and calcitonin gene-related peptide in oxazolone-induced allergic contact dermatitis in mice. Ek, L., Theodorsson, E. J. Invest. Dermatol. (1990) [Pubmed]
  33. Distinct roles for B7 costimulation in contact hypersensitivity and humoral immune responses to epicutaneous antigen. Rauschmayr-Kopp, T., Williams, I.R., Borriello, F., Sharpe, A.H., Kupper, T.S. Eur. J. Immunol. (1998) [Pubmed]
  34. Isolation and partial characterization of an antigen-specific T-cell factor associated with the suppression of delayed type hypersensitivity. Rosenstein, R.W., Murray, J.H., Cone, R.E., Ptak, W., Iverson, G.M., Gershon, R.K. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  35. Generation and function of reactive oxygen species in dendritic cells during antigen presentation. Matsue, H., Edelbaum, D., Shalhevet, D., Mizumoto, N., Yang, C., Mummert, M.E., Oeda, J., Masayasu, H., Takashima, A. J. Immunol. (2003) [Pubmed]
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