Phenylacetic acids and the structurally related non-steroidal anti-inflammatory drug diclofenac bind to specific γ-hydroxybutyric acid sites in rat brain

Fundamental and Clinical Pharmacology

Volumn 23, Issue 2, 2009, Pages 207-213

  Wellendorph, Petrine ^a   Høg, Signe ^a   Skonberg, Christian ^a   Bräuner Osborne, Hans ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

hydroxybutyric acid; Binding; Diclofenac; Non steroidal anti inflammatory drug; Phenylacetic acid

Indexed keywords

4 (BIPHEN 4 YL) 4 HYDROXYBUTIRIC ACID; 4 AMINOBUTYRIC ACID; 4 HYDROXYBUTYRIC ACID; ACETIC ACID; ACETYLSALICYLIC ACID; BUTYRIC ACID; CLOFIBRIC ACID; DICLOFENAC; DICLON; FELBINAC; FENBUFEN; FLURBIPROFEN; IBUPROFEN; INDOMETACIN; KETOPROFEN; LUMIRACOXIB; MEFENAMIC ACID; METHOXYPHENYL ACETIC ACID; NONSTEROID ANTIINFLAMMATORY AGENT; PHENYLACETIC ACID; PHENYLOXYACETIC ACID; PHENYLTHIOACETIC ACID; SUCCINIC ACID; SUCCINIC SEMIALDEHYDE; TOLMETIN; UNCLASSIFIED DRUG; ZOMEPIRAC;

ANIMAL EXPERIMENT; ARTICLE; BINDING SITE; CONTROLLED STUDY; DRUG BINDING; DRUG INHIBITION; DRUG SCREENING; DRUG STRUCTURE; MALE; NONHUMAN; PRIORITY JOURNAL; RAT;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; BINDING SITES; BRAIN; DICLOFENAC; HYDROXYBUTYRATES; LIGANDS; MALE; PHENYLACETATES; PROTEIN BINDING; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, CELL SURFACE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 63049124925     PISSN: 07673981     EISSN: 14728206     Source Type: Journal    
DOI: 10.1111/j.1472-8206.2008.00664.x     Document Type: Article

References (33)

1. Robinson D.M., Keating G.M. Sodium oxybate: a review of its use in the management of narcolepsy. CNS Drugs (2007) 21 337 354.
2. Gallimberti L., Spella M.R., Soncini C.A., Gessa G.L. Gamma-hydroxybutyric acid in the treatment of alcohol and heroin dependence. Alcohol (2000) 20 257 262.
3. Drasbek K.R., Christensen J., Jensen K. Gamma-hydroxybutyrate - a drug of abuse. Acta Neurol. Scand. (2006) 114 145 156.
4. Benavides J., Rumigny J.F., Bourguignon J.J. et al. High affinity binding sites for γ-hydroxybutyric acid in rat brain. Life Sci. (1982) 30 953 961.
5. B)-receptor mediation of different in vivo effects of γ-butyrolactone. J. Pharmacol. Sci. (2008) 106 199 207.
6. BR) binding sites are distinctive from one another: molecular evidence. Neuropharmacology (2004) 47 1146 1156.
7. B(1)-deficient mice. Eur. J. Neurosci. (2003) 18 2722 2730.
8. Castelli M.P., Ferraro L., Mocci I. et al. Selective γ- hydroxybutyric acid receptor ligands increase extracellular glutamate in the hippocampus, but fail to activate G protein and to produce the sedative/hypnotic effect of γ-hydroxybutyric acid. J. Neurochem. (2003) 87 722 732.
9. Brancucci A., Berretta N., Mercuri N.B., Francesconi W. Presynaptic modulation of spontaneous inhibitory postsynaptic currents by gamma-hydroxybutyrate in the substantia nigra pars compacta. Neuropsychopharmacology (2004) 29 537 543.
10. Kemmel V., Taleb O., Andriamampandry C., Aunis D., Maitre M. γ-Hydroxybutyrate receptor function determined by stimulation of rubidium and calcium movements from NCB-20 neurons. Neuroscience (2003) 116 1021 1031.
11. 3H](2E)-(5-hydroxy-5,7,8,9-tetrahydro-6H-benzo[a][7] annulen-6-ylidene) ethanoic acid in the rat brain. J. Pharmacol. Exp. Ther. (2001) 299 1148 1153.
12. Castelli M.P., Mocci I., Pistis M. et al. Stereoselectivity of NCS-382 binding to γ-hydroxybutyrate receptor in the rat brain. Eur. J. Pharmacol. (2002) 446 1 5.
13. Wu H., Zink N., Carter L.P. et al. A tertiary alcohol analog of γ-hydroxybutyric acid as a specific γ-hydroxybutyric acid receptor ligand. J. Pharmacol. Exp. Ther. (2003) 305 675 679.
14. Macias A.T., Hernandez R.J., Mehta A.K., MacKerell A.D. Jr., Ticku M.K., Coop A. 3-chloropropanoic acid (UMB66): a ligand for the gamma-hydroxybutyric acid receptor lacking a 4-hydroxyl group. Bioorg. Med. Chem. (2004) 12 1643 1647.
15. Chen W., Wu H., Hernandez R.J. et al. Ethers of 3-hydroxyphenylacetic acid as selective gamma-hydroxybutyric acid receptor ligands. Bioorg. Med. Chem. Lett. (2005) 15 3201 3202.
16. B receptor agonists. J. Pharmacol. Exp. Ther. (2005) 313 1314 1323.
17. Bourguignon J.J., Schmitt M., Didier B. Design and structure-activity relationship analysis of ligands of γ-hydroxybutyric acid receptors. Alcohol (2000) 20 227 236.
18. Wellendorph P., Høg S., Greenwood J.R. et al. Novel cyclic γ-hydroxybutyrate (GHB) analogs with high affinity and stereoselectivity of binding to GHB sites in rat brain. J. Pharmacol. Exp. Ther. (2005) 315 346 351.
19. Speirs C.J. Comparison of the safety of several nonsteroidal anti-inflammatory drugs currently or formerly marketed in the United Kingdom. J. Clin. Pharmacol. (1988) 28 S8 S12.
20. Kerwar S.S. Pharmacologic properties of fenbufen. Am. J. Med. (1983) 75 62 69.
21. 3H]MK-801 binding to the N-methyl-D-aspartate receptor-ion channel complex by L-glutamate, glycine, and polyamines. J. Neurochem. (1988) 51 830 836.
22. 50) of an enzymatic reaction. Biochem. Pharmacol. (1973) 22 3099 3108.
23. Chiccarelli F.S., Eisner H.J., Van Lear G.E. Disposition and metabolism of fenbufen in several laboratory animals. Arzneimittelforschung (1980) 30 707 715.
24. Mattia C., Coluzzi F. COX-2 inhibitors: pharmacological data and adverse effects. Minerva Anestesiol. (2005) 71 461 470.
25. Blobaum A.L., Marnett L.J. Molecular determinants for the selective inhibition of cyclooxygenase-2 by lumiracoxib. J. Biol. Chem. (2007) 282 16379 16390.
26. Molnár T., Fekete E.K., Kardos J., Simon-Trompler E., Palkovits M., Emri Z. Metabolic GHB precursor succinate binds to γ-hydroxybutyrate receptors: characterization of human basal ganglia areas nucleus accumbens and globus pallidus. J. Neurosci. Res. (2006) 84 27 36.
27. Maitre M., Hechler V., Vayer P. et al. A specific γ-hydroxybutyrate receptor ligand possesses both antagonistic and anticonvulsant properties. J. Pharmacol. Exp. Ther. (1990) 255 657 663.
28. Høg S., Wellendorph P., Nielsen B. et al. Novel high-affinity and selective biaromatic 4-substituted γ-hydroxybutyric acid (GHB) analogues as GHB ligands: design, synthesis and binding studies. J. Med. Chem 2009) in press.
29. Burian M., Tegeder I., Seegel M., Geisslinger G. Peripheral and central antihyperalgesic effects of diclofenac in a model of human inflammatory pain. Clin. Pharmacol. Ther. (2003) 74 113 120.
30. Chandrasekharan N.V., Dai H., Roos K.L.T. et al. COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: cloning, structure, and expression. Proc. Natl. Acad. Sci. U.S.A. (2002) 99 13926 13931.
31. Bjorkman R., Hedner J., Hedner T., Henning M. Central, naloxone-reversible antinociception by diclofenac in the rat. Naunyn Schmiedebergs Arch. Pharmacol. (1990) 342 171 176.
32. Kudo C., Kori M., Matsuzaki K. et al. Diclofenac inhibits proliferation and differentiation of neural stem cells. Biochem. Pharmacol. (2003) 66 289 295.
33. Zecca L., Ferrario P., Costi P. Determination of diclofenac and its metabolites in plasma and cerebrospinal fluid by high-performance liquid chromatography with electrochemical detection. J. Chromatogr.: Biomed. Appl. (1991) 567 425 432.