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Chemical Compound Review

Aquathol     7-oxabicyclo[2.2.1]heptane- 5,6...

Synonyms: Aquothol, Endothal, Hydrothol, endothall, Hydout, ...
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Disease relevance of Hydout


High impact information on Hydout

  • In an in vitro assay, purified PP2A(c) dephosphorylated a GST-NHE1 fusion protein containing aa 625-747 of the NHE1 regulatory domain, which had been pre-phosphorylated by recombinant RSK; such dephosphorylation was inhibited by the PP2A-selective phosphatase inhibitor endothall [3].
  • In intact ARVM, the ability of CPA to attenuate the phenylephrine-induced increase in NHE1 phosphorylation and activity was lost in the presence of endothall [3].
  • Either RRAT or RGET was sufficient for PKA activation of hClC-2 at pH(o) 7.4, as long as phosphatase inhibitors (cyclosporin A or endothal) were present [4].
  • This down-regulation of the cyt path likely requires events outside the mitochondrion and is effectively blocked by cantharidin or endothall, indicating that protein dephosphorylation is one critical process involved [5].
  • We used endothall (ET) as a cell-permeable inhibitor of serine/threonine-specific protein phosphatases to alter cytological and biochemical characteristics of cell division in cultured alfalfa cells [6].

Biological context of Hydout

  • The toxicity of the herbicide endothal (exo,exo-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid) to mice (ip LD50 = 14 mg/kg) is attributed to the inhibition of protein phosphatase 2A (PP2A) at the cantharidin binding site [7].
  • The [3H]ETA binding site of liver cytosol is inhibited 75-80% by LD50 doses of 2,3-dimethylendothall anhydride and thioanhydride but only 24% by an LD50 dose of endothall thioanhydride, with assays 30 min after ip treatment.(ABSTRACT TRUNCATED AT 250 WORDS)[8]
  • Endothal (1diacid) and [3H]cantharidic acid ([3H]CA) bind with high affinity to the catalytic subunit of protein phosphatase 2A (PP2A) [9].

Anatomical context of Hydout


Associations of Hydout with other chemical compounds


Gene context of Hydout

  • CA and three analogues (cantharidic acid, palasonin and endothall) inhibited PP2A and protein phosphatase 1 (PP1) but not PP2B or PP2C [11].
  • The potency sequence of ETA > CA > endothall was established for the inhibition of PP1 and PP2A in vivo and shows close correlation with the sequence of relative toxicity [10].
  • All compounds inhibited PP activity in homogenates of rat aorta with a rank order of potency of Cant = cantharidic acid > endothall [14].
  • Interestingly the protein phosphatase (PP) inhibitors, cantharidin, endothall, and okadaic acid, rapidly and potently up-regulated the JIOsPR10 expression, suggesting involvement of the phosphorylation/dephosphorylation events [15].
  • On the cardiac contractile, electrophysiological and biochemical effects of endothall, a protein phosphatase inhibitor [16].


  1. Cantharidin-binding protein: identification as protein phosphatase 2A. Li, Y.M., Casida, J.E. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  2. Hepatocellular carcinoma cell lines from diethylnitrosamine phenobarbital-treated rats. Characterization and sensitivity to endothall, a protein serine/threonine phosphatase-2A inhibitor. Thièry, J.P., Blazsek, I., Legras, S., Marion, S., Reynes, M., Anjo, A., Adam, R., Misset, J.L. Hepatology (1999) [Pubmed]
  3. A novel role for protein phosphatase 2A in receptor-mediated regulation of the cardiac sarcolemmal Na+/H+ exchanger NHE1. Snabaitis, A.K., D'Mello, R., Dashnyam, S., Avkiran, M. J. Biol. Chem. (2006) [Pubmed]
  4. Sites of protein kinase A activation of the human ClC-2 Cl(-) channel. Cuppoletti, J., Tewari, K.P., Sherry, A.M., Ferrante, C.J., Malinowska, D.H. J. Biol. Chem. (2004) [Pubmed]
  5. Induction of mitochondrial alternative oxidase in response to a cell signal pathway down-regulating the cytochrome pathway prevents programmed cell death. Vanlerberghe, G.C., Robson, C.A., Yip, J.Y. Plant Physiol. (2002) [Pubmed]
  6. Inhibition of serine/threonine-specific protein phosphatases causes premature activation of cdc2MsF kinase at G2/M transition and early mitotic microtubule organisation in alfalfa. Ayaydin, F., Vissi, E., Mészáros, T., Miskolczi, P., Kovács, I., Fehér, A., Dombrádi, V., Erdödi, F., Gergely, P., Dudits, D. Plant J. (2000) [Pubmed]
  7. Retro-Diels-Alder reaction: possible involvement in the metabolic activation of 7-oxabicyclo[2.2.1]hepta-2(3),5(6)-diene-2,3-dicarboxylates and a phosphonate analog. Mahajna, M., Quistad, G.B., Casida, J.E. Chem. Res. Toxicol. (1996) [Pubmed]
  8. Endothall thioanhydride: structural aspects of unusually high mouse toxicity and specific binding site in liver. Kawamura, N., Li, Y.M., Engel, J.L., Dauben, W.G., Casida, J.E. Chem. Res. Toxicol. (1990) [Pubmed]
  9. 2-Carboxymethylendothal analogues as affinity probes for stabilized protein phosphatase 2A. Laidley, C.W., Dauben, W.G., Guo, Z.R., Lam, J.Y., Casida, J.E. Bioorg. Med. Chem. (1999) [Pubmed]
  10. Endothall thioanhydride inhibits protein phosphatases-1 and -2A in vivo. Erdödi, F., Tóth, B., Hirano, K., Hirano, M., Hartshorne, D.J., Gergely, P. Am. J. Physiol. (1995) [Pubmed]
  11. Protein phosphatase 2A and its [3H]cantharidin/[3H]endothall thioanhydride binding site. Inhibitor specificity of cantharidin and ATP analogues. Li, Y.M., Mackintosh, C., Casida, J.E. Biochem. Pharmacol. (1993) [Pubmed]
  12. A novel rice (Oryza sativa L.) acidic PR1 gene highly responsive to cut, phytohormones, and protein phosphatase inhibitors. Agrawal, G.K., Jwa, N.S., Rakwal, R. Biochem. Biophys. Res. Commun. (2000) [Pubmed]
  13. Isolation and characterization of the catalytic subunit of protein phosphatase 2A from Neurospora crassa. Szöör, B., Fehér, Z., Bakó, E., Erdödi, F., Szabó, G., Gergely, P., Dombrádi, V. Comp. Biochem. Physiol. B, Biochem. Mol. Biol. (1995) [Pubmed]
  14. Cantharidin enhances norepinephrine-induced vasoconstriction in an endothelium-dependent fashion. Knapp, J., Bokník, P., Linck, B., Lüss, H., Müller, F.U., Petertönjes, L., Schmitz, W., Neumann, J. J. Pharmacol. Exp. Ther. (2000) [Pubmed]
  15. Molecular cloning and characterization of a novel Jasmonate inducible pathogenesis-related class 10 protein gene, JIOsPR10, from rice (Oryza sativa L.) seedling leaves. Jwa, N.S., Kumar Agrawal, G., Rakwal, R., Park, C.H., Prasad Agrawal, V. Biochem. Biophys. Res. Commun. (2001) [Pubmed]
  16. On the cardiac contractile, electrophysiological and biochemical effects of endothall, a protein phosphatase inhibitor. Bokník, P., Vahlensieck, U., Huke, S., Knapp, J., Linck, B., Lüss, H., Müller, F.U., Neumann, J., Schmitz, W. Pharmacology (2000) [Pubmed]
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