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Chemical Compound Review

ISETHIONIC ACID     2-hydroxyethanesulfonic acid

Synonyms: Isethionate, AC-538, CHEBI:1157, AG-D-22854, HMDB03903, ...
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Disease relevance of ISETHIONIC ACID


Psychiatry related information on ISETHIONIC ACID

  • Ten minutes following an (i.p.) simultaneous administration of ethanol (0.0, 1.5, 2.0, 2.5, 3.0, 3.5 g/kg) and isethionic acid (0.0, 22.5, 45.0, 90.0, 180.0 mg/kg), mice were placed in the open-field chambers and locomotor activity was measured during a ten-minute testing period [6].

High impact information on ISETHIONIC ACID

  • Since Li+ and NO3- are more permeable, and choline and isethionate are less permeable than Na+ and Cl-, respectively, these results suggest that the BADF is dependent on the permeability of the substituting cations and anions and thus support the hypothesis that solvent drag and diffusion play an important role in BADF [7].
  • These studies demonstrate that exchange of medium chloride with isethionate inhibits the synthesis of prolactin at the level of transcription [8].
  • Exchange of medium chloride with benzoate or isethionate significantly inhibited the stimulated release of prolactin (IC50 at approximately 60 mM exchange) regardless of the secretagogue utilized (phorbol ester, forskolin, depolarization plus BAY K8644, or TRH) [9].
  • These results suggest that exchange of chloride with isethionate is inhibiting the synthesis of prolactin [8].
  • Both basal and hormone-stimulated synthesis of chloramphenicol acetyltransferase driven by the prolactin promoter was inhibited by isethionate exchange [8].

Chemical compound and disease context of ISETHIONIC ACID


Biological context of ISETHIONIC ACID

  • When ATP was added to chromaffin ghosts suspended in a medium in which chloride was substituted by isethionate, a transmembrane potential, inside positive, of 45 mV and no transmembrane proton gradient, was measured [12].
  • Increasing the internal Cl- concentration reduces isethionate block without affecting its voltage dependence, suggesting that Cl- and isethionate compete for a binding site in the pore [13].
  • Isethionate blocks the channel from the cytoplasmic side with fast kinetics, but has no measurable effect when applied extracellularly [13].
  • Replacement of Cl- with Br- had no significant effect on salivary secretion rate, but replacement with the other anions tested caused secretory rate to fall, by 38% (I-), 50% (NO3-), 61% (isethionate, ise -), and 66% ( CH3SO4 -), respectively [14].
  • GES, beta-alanine, and isethionic acid had a significant effect on cell count, protein content, and incorporation of [3H]thymidine into DNA [15].

Anatomical context of ISETHIONIC ACID


Associations of ISETHIONIC ACID with other chemical compounds


Gene context of ISETHIONIC ACID


Analytical, diagnostic and therapeutic context of ISETHIONIC ACID


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  4. Antitumor drug cross-resistance in vivo in a murine P388 leukemia resistant to ethyl 5-amino-1,2-dihydro-2-methyl-3-phenylpyrido[3,4-b]pyrazin-7 - ylcarbamate 2-hydroxyethanesulfonate hydrate (NSC 370,147) 370147. Waud, W.R., Harrison, S.D., Temple, C.G., Griswold, D.P. Cancer Chemother. Pharmacol. (1992) [Pubmed]
  5. Enzymes and genes of taurine and isethionate dissimilation in Paracoccus denitrificans. Brüggemann, C., Denger, K., Cook, A.M., Ruff, J. Microbiology (Reading, Engl.) (2004) [Pubmed]
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  7. Importance of solvent drag and diffusion in bile acid-dependent bile formation: ion substitution studies in isolated perfused rat liver. Anwer, M.S., Hegner, D. Hepatology (1982) [Pubmed]
  8. Prolactin synthesis in cultured pituitary cells is chloride-dependent. Day, R.N., Hinkle, P.M. J. Biol. Chem. (1988) [Pubmed]
  9. Osmotic regulation of prolactin secretion. Possible role of chloride. Day, R.N., Hinkle, P.M. J. Biol. Chem. (1988) [Pubmed]
  10. Bilateral microsporidial keratoconjunctivitis in an immunocompetent non-contact lens wearer. Lewis, N.L., Francis, I.C., Hawkins, G.S., Coroneo, M.T. Cornea (2003) [Pubmed]
  11. Physical and biochemical characterization of the qacA gene encoding antiseptic and disinfectant resistance in Staphylococcus aureus. Tennent, J.M., Lyon, B.R., Midgley, M., Jones, I.G., Purewal, A.S., Skurray, R.A. J. Gen. Microbiol. (1989) [Pubmed]
  12. Biological amine transport in chromaffin ghosts. Coupling to the transmembrane proton and potential gradients. Johnson, R.G., Pfister, D., Carty, S.E., Scarpa, A. J. Biol. Chem. (1979) [Pubmed]
  13. Probing an open CFTR pore with organic anion blockers. Zhou, Z., Hu, S., Hwang, T.C. J. Gen. Physiol. (2002) [Pubmed]
  14. The anionic basis of fluid secretion by the rabbit mandibular salivary gland. Case, R.M., Hunter, M., Novak, I., Young, J.A. J. Physiol. (Lond.) (1984) [Pubmed]
  15. Inhibition of rat vascular smooth muscle cell proliferation by taurine and taurine analogues. Zhang, X., Tenner, T.E., Lombardini, J.B. Biochem. Pharmacol. (1999) [Pubmed]
  16. Ascorbic acid and catecholamine secretion from cultured chromaffin cells. Levine, M., Asher, A., Pollard, H., Zinder, O. J. Biol. Chem. (1983) [Pubmed]
  17. Cerebroprotective effect of lamotrigine after focal ischemia in rats. Smith, S.E., Meldrum, B.S. Stroke (1995) [Pubmed]
  18. Electrogenic sulfate/chloride exchange in Xenopus oocytes mediated by murine AE1 E699Q. Chernova, M.N., Jiang, L., Crest, M., Hand, M., Vandorpe, D.H., Strange, K., Alper, S.L. J. Gen. Physiol. (1997) [Pubmed]
  19. Neither a purine nor VIP is the mediator of inhibitory nerves of opossum oesophageal smooth muscle. Daniel, E.E., Helmy-Elkholy, A., Jager, L.P., Kannan, M.S. J. Physiol. (Lond.) (1983) [Pubmed]
  20. Actions of extracellular chloride ion substitution on contractility of isolated ventricular myocardium. Fry, C.H., Griffiths, H., Hall, S.K. Cardiovasc. Res. (1993) [Pubmed]
  21. GABA and glycine channels in isolated ganglion cells from the goldfish retina. Cohen, B.N., Fain, G.L., Fain, M.J. J. Physiol. (Lond.) (1989) [Pubmed]
  22. Calcium-dependent chloride currents in isolated cells from rat lacrimal glands. Evans, M.G., Marty, A. J. Physiol. (Lond.) (1986) [Pubmed]
  23. Immunosuppression by hydroxystilbamidine isethionate, a lysosome-stabilizing, anti-proteolytic, antifungal drug. Folds, J.D., Orlando, G., Spitznagel, J.K. Infect. Immun. (1975) [Pubmed]
  24. Regulation of acetylcholine release by intracellular acidification of developing motoneurons in Xenopus cell cultures. Chen, Y.H., Wu, M.L., Fu, W.M. J. Physiol. (Lond.) (1998) [Pubmed]
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  26. Chloride-dependency of amyloid beta protein-induced enhancement of glutamate neurotoxicity in cultured rat hippocampal neurons. Zhang, N.Y., Kitagawa, K., Wu, B., Xiong, Z.M., Otani, H., Inagaki, C. Neurosci. Lett. (2006) [Pubmed]
  27. Activation of an apical Cl- conductance by extracellular ATP in Necturus gallbladder is mediated by cAMP and not by [Ca2+]i. Vank, C., Frömter, E., Kottra, G. Pflugers Arch. (1999) [Pubmed]
  28. Antibacterial resistance and their genetic location in MRSA isolated in Kuwait hospitals, 1994-2004. Udo, E.E., Al-Sweih, N., Mokaddas, E., Johny, M., Dhar, R., Gomaa, H.H., Al-Obaid, I., Rotimi, V.O. BMC Infect. Dis. (2006) [Pubmed]
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