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Chemical Compound Review

pyrazolium     pyrazole

Synonyms: AC1N04IC, 1H-pyrazol-1-ium, 157131-EP2286915A2
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Disease relevance of 53153-43-8

 

Psychiatry related information on 53153-43-8

 

High impact information on 53153-43-8

  • Pyrazole-induced thyroid necrosis: a distinct organ lesion [7].
  • One oral dose of pyrazole caused necrosis of rat thyroid follicular epithelial cells but spared the parafollicular (C) cells and the parathyroid glands [7].
  • Further, although both inhibitors delayed the incorporation of radioactivity from [14C]DMN into hepatic subcellular organelles, pyrazole was significantly more effective than was 3-AT [1].
  • Through detailed structural analysis of the interaction of the initially discovered pyrazole carboxylic ester scaffold with PDE4D using X-ray crystallography, we identified three sites of chemical substitution and designed small selective libraries of scaffold derivatives with modifications at these sites [8].
  • A 4,000-fold increase in the potency of this PDE4 inhibitor was achieved after only two rounds of chemical synthesis and the structural analysis of seven pyrazole derivatives bound to PDE4B or PDE4D, revealing the robustness of this approach for identifying new inhibitors that can be further developed into drug candidates [8].
 

Chemical compound and disease context of 53153-43-8

 

Biological context of 53153-43-8

 

Anatomical context of 53153-43-8

  • Similar results were found in hepatocytes from pyrazole-treated rats with high levels of CYP2E1 [17].
  • One of the seven MAbs tested, 1-91-3, inhibited enzyme activity of acetone-, pyrazole-, or methylpyrazole-induced microsomes by 54, 47, and 48%, respectively [18].
  • Potent inhibition of Ca2+ release-activated Ca2+ channels and T-lymphocyte activation by the pyrazole derivative BTP2 [19].
  • Kupffer cells were the only macrophages showing significant MCP-1 release, which was markedly reduced by E2 or propyl pyrazole triol in wild-type and in ER-beta-/- mice [20].
  • A pyrazole derivative potently inhibits lymphocyte Ca2+ influx and cytokine production by facilitating transient receptor potential melastatin 4 channel activity [21].
 

Associations of 53153-43-8 with other chemical compounds

 

Gene context of 53153-43-8

  • HO-1 induction was observed in the livers of chronic alcohol-fed mice or pyrazole-treated rats, conditions known to elevate CYP2E1 levels [25].
  • To test these hypotheses, female B57BL/J6 mice received E2 (50 microg/25 g) or vehicle after trauma-hemorrhage and female 129 Sve ER-beta-/- transgenic mice and ovariectomized wild-type mice received E2 or ER-alpha agonist propyl pyrazole triol (50 microg/25 g) after trauma-hemorrhage [20].
  • We also show that a specific hepatotoxic inducer of the Cyp2a5 gene, pyrazole, increases the cytoplasmic levels of hnRNP A1 in vivo [26].
  • Kinetic characterization of novel pyrazole TGF-beta receptor I kinase inhibitors and their blockade of the epithelial-mesenchymal transition [27].
  • PCR amplification of a 1 kb region in Cyp2a-4/5-mRNA-derived cDNA, followed by cutting at the diagnostic PstI site, showed that most of the steady-state mRNA consisted of Cyp2a-5, which is also the form most affected by pyrazole [28].
 

Analytical, diagnostic and therapeutic context of 53153-43-8

  • CYP2E1-knockout mice exhibited only minor liver injury after treatment with pyrazole/LPS, but wild-type mice exhibited severe liver injury [13].
  • LPS-induced liver injury was enhanced by pyrazole, as indicated by pathological changes and increases in ALT and AST, and positive TUNEL staining [13].
  • Human liver alcohol dehydrogenase (ADH, EC 1.1.1.1) was purified by double ternary complex affinity chromatography on Sepharose-4-(3-[N-6 aminocaproyl]aminopropyl) pyrazole [29].
  • Similar studies in obese fasted subjects pretreated with an intravenous infusion of insulin (1.0 U/hr. for eight hours) before receiving Pyrazole resulted in a 65 plus or minus 5 per cent decrease in plasma Beta-OHB [30].
  • Similar results were observed in co-culture with primary hepatocytes from saline- or pyrazole-treated (with high levels of CYP2E1) rats [31].

References

  1. Effects of pyrazole and 3-amino-1,2,4-triazole on the metabolism and toxicity of dimethylnitrosamine in the rat. Phillips, J.C., Lake, B.G., Gangolli, S.D., Grasso, P., Lloyd, A.G. J. Natl. Cancer Inst. (1977) [Pubmed]
  2. Cyclooxygenase-2 inhibition prevents delayed death of CA1 hippocampal neurons following global ischemia. Nakayama, M., Uchimura, K., Zhu, R.L., Nagayama, T., Rose, M.E., Stetler, R.A., Isakson, P.C., Chen, J., Graham, S.H. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  3. Pyrazole effects on mutagenicity and toxicity of dimethylnitrosamine in Wistar rats. Evarts, R.P., Raab, M.M., Haliday, E., Brown, C. Cancer Res. (1983) [Pubmed]
  4. Helicobacter pylori-selective antibacterials based on inhibition of pyrimidine biosynthesis. Copeland, R.A., Marcinkeviciene, J., Haque, T.S., Kopcho, L.M., Jiang, W., Wang, K., Ecret, L.D., Sizemore, C., Amsler, K.A., Foster, L., Tadesse, S., Combs, A.P., Stern, A.M., Trainor, G.L., Slee, A., Rogers, M.J., Hobbs, F. J. Biol. Chem. (2000) [Pubmed]
  5. A pyrazole derivative, YM-58483, potently inhibits store-operated sustained Ca2+ influx and IL-2 production in T lymphocytes. Ishikawa, J., Ohga, K., Yoshino, T., Takezawa, R., Ichikawa, A., Kubota, H., Yamada, T. J. Immunol. (2003) [Pubmed]
  6. Effects of pyrazole treatment of physical status and brain biogenic amines in rats. MacDonald, E. Med. Biol. (1977) [Pubmed]
  7. Pyrazole-induced thyroid necrosis: a distinct organ lesion. Szabo, S., Horbath, E., Kovacs, K., Larsen, P.R. Science (1978) [Pubmed]
  8. A family of phosphodiesterase inhibitors discovered by cocrystallography and scaffold-based drug design. Card, G.L., Blasdel, L., England, B.P., Zhang, C., Suzuki, Y., Gillette, S., Fong, D., Ibrahim, P.N., Artis, D.R., Bollag, G., Milburn, M.V., Kim, S.H., Schlessinger, J., Zhang, K.Y. Nat. Biotechnol. (2005) [Pubmed]
  9. Role of p38 MAPK in CYP2E1-dependent arachidonic acid toxicity. Wu, D., Cederbaum, A.I. J. Biol. Chem. (2003) [Pubmed]
  10. Synergistic toxicity of iron and arachidonic acid in HepG2 cells overexpressing CYP2E1. Caro, A.A., Cederbaum, A.I. Mol. Pharmacol. (2001) [Pubmed]
  11. Antiviral activity of Win 41258-3, a pyrazole compound, against herpes simplex virus in mouse genital infection and in guinea pig skin infection. Pancic, F., Steinberg, B.A., Diana, G.D., Carabateas, P.M., Gorman, W.G., Came, P.E. Antimicrob. Agents Chemother. (1981) [Pubmed]
  12. Production of a novel tryptophan analog, beta-1-indazole-L-alanine with tryptophan synthase of Escherichia coli. Tanaka, H., Tanizawa, K., Arai, T., Saito, K., Arai, T., Soda, K. FEBS Lett. (1986) [Pubmed]
  13. Enhancement by pyrazole of lipopolysaccharide-induced liver injury in mice: role of cytochrome P450 2E1 and 2A5. Lu, Y., Cederbaum, A.I. Hepatology (2006) [Pubmed]
  14. Non-alcohol dehydrogenase-mediated metabolism of methylazoxymethanol in the deer mouse, Peromyscus maniculatus. Fiala, E.S., Caswell, N., Sohn, O.S., Felder, M.R., McCoy, G.D., Weisburger, J.H. Cancer Res. (1984) [Pubmed]
  15. Induction of cytochrome P450 2E1 increases hepatotoxicity caused by Fas agonistic Jo2 antibody in mice. Wang, X., Lu, Y., Cederbaum, A.I. Hepatology (2005) [Pubmed]
  16. Complementary DNA and protein sequences of ethanol-inducible rat and human cytochrome P-450s. Transcriptional and post-transcriptional regulation of the rat enzyme. Song, B.J., Gelboin, H.V., Park, S.S., Yang, C.S., Gonzalez, F.J. J. Biol. Chem. (1986) [Pubmed]
  17. Proteasome inhibition potentiates CYP2E1-mediated toxicity in HepG2 cells. Pérez, M.J., Cederbaum, A.I. Hepatology (2003) [Pubmed]
  18. Monoclonal antibodies to ethanol-induced rat liver cytochrome P-450 that metabolizes aniline and nitrosamines. Ko, I.Y., Park, S.S., Song, B.J., Patten, C., Tan, Y.Z., Hah, Y.C., Yang, C.S., Gelboin, H.V. Cancer Res. (1987) [Pubmed]
  19. Potent inhibition of Ca2+ release-activated Ca2+ channels and T-lymphocyte activation by the pyrazole derivative BTP2. Zitt, C., Strauss, B., Schwarz, E.C., Spaeth, N., Rast, G., Hatzelmann, A., Hoth, M. J. Biol. Chem. (2004) [Pubmed]
  20. Kupffer cells and their mediators: the culprits in producing distant organ damage after trauma-hemorrhage. Hildebrand, F., Hubbard, W.J., Choudhry, M.A., Frink, M., Pape, H.C., Kunkel, S.L., Chaudry, I.H. Am. J. Pathol. (2006) [Pubmed]
  21. A pyrazole derivative potently inhibits lymphocyte Ca2+ influx and cytokine production by facilitating transient receptor potential melastatin 4 channel activity. Takezawa, R., Cheng, H., Beck, A., Ishikawa, J., Launay, P., Kubota, H., Kinet, J.P., Fleig, A., Yamada, T., Penner, R. Mol. Pharmacol. (2006) [Pubmed]
  22. Design of a potent and selective inhibitor of the intermediate-conductance Ca2+-activated K+ channel, IKCa1: a potential immunosuppressant. Wulff, H., Miller, M.J., Hansel, W., Grissmer, S., Cahalan, M.D., Chandy, K.G. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  23. Alcohol:NAD+ oxidoreductase is present in rat liver peroxisomes. Sakuraba, H., Noguchi, T. J. Biol. Chem. (1995) [Pubmed]
  24. Altered proline uptake by mouse liver cells after chronic exposure to ethanol and its metabolites. Mendenhall, C.L., Chedid, A., Kromme, C. Gut (1984) [Pubmed]
  25. Increased expression of cytochrome P450 2E1 induces heme oxygenase-1 through ERK MAPK pathway. Gong, P., Cederbaum, A.I., Nieto, N. J. Biol. Chem. (2003) [Pubmed]
  26. Heterogeneous nuclear ribonucleoprotein A1 and regulation of the xenobiotic-inducible gene Cyp2a5. Raffalli-Mathieu, F., Glisovic, T., Ben-David, Y., Lang, M.A. Mol. Pharmacol. (2002) [Pubmed]
  27. Kinetic characterization of novel pyrazole TGF-beta receptor I kinase inhibitors and their blockade of the epithelial-mesenchymal transition. Peng, S.B., Yan, L., Xia, X., Watkins, S.A., Brooks, H.B., Beight, D., Herron, D.K., Jones, M.L., Lampe, J.W., McMillen, W.T., Mort, N., Sawyer, J.S., Yingling, J.M. Biochemistry (2005) [Pubmed]
  28. Effect of pyrazole, cobalt and phenobarbital on mouse liver cytochrome P-450 2a-4/5 (Cyp2a-4/5) expression. Hahnemann, B., Salonpää, P., Pasanen, M., Mäenpää, J., Honkakoski, P., Juvonen, R., Lang, M.A., Pelkonen, O., Raunio, H. Biochem. J. (1992) [Pubmed]
  29. Immunohistochemical localization of human liver alcohol dehydrogenase in liver tissue, cultured fibroblasts, and HeLa cells. Buehler, R., Hess, M., Von Wartburg, J.P. Am. J. Pathol. (1982) [Pubmed]
  30. Physiologic mechanisms in the development of starvation ketosis in man. Grey, N.J., Karl, I., Kipnis, D.M. Diabetes (1975) [Pubmed]
  31. Increased Sp1-dependent transactivation of the LAMgamma 1 promoter in hepatic stellate cells co-cultured with HepG2 cells overexpressing cytochrome P450 2E1. Nieto, N., Cederbaum, A.I. J. Biol. Chem. (2003) [Pubmed]
 
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