Positive allosteric modulatory effects of ajulemic acid at strychnine-sensitive glycine α1- and α1β- receptors

Naunyn-Schmiedeberg's Archives of Pharmacology

Volumn 379, Issue 4, 2009, Pages 371-378

  Ahrens, Jörg ^a   Leuwer, Martin ^b   Demir, Reyhan ^a   Krampfl, Klaus ^a   De La Roche, Jeanne ^a   Foadi, Nilufar ^a   Karst, Matthias ^a   Haeseler, Gertrud ^a  

^a HANNOVER MEDICAL SCHOOL   (Germany)

^b UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

Ajulemic acid (CT 3); Cannabinoids; Glycine receptor; Neuropathic pain

Indexed keywords

AJULEMIC ACID; GLYCINE RECEPTOR; GLYCINE RECEPTOR ALPHA1; GLYCINE RECEPTOR ALPHA1BETA; STRYCHNINE; UNCLASSIFIED DRUG;

ALLOSTERISM; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG EFFECT; DRUG MECHANISM; DRUG RECEPTOR BINDING; HUMAN; HUMAN CELL; NEUROPATHIC PAIN; SPINAL CORD DORSAL HORN;

CELL LINE; ELECTROPHYSIOLOGICAL PHENOMENA; GLYCINE; HUMANS; PATCH-CLAMP TECHNIQUES; PROTEIN CONFORMATION; RECEPTORS, GLYCINE; RECEPTORS, NEUROTRANSMITTER; TETRAHYDROCANNABINOL; TRANSFECTION;

EID: 60849085164     PISSN: 00281298     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00210-008-0366-8     Document Type: Article

References (45)

1. N Agarwal P Pacher I Tegeder F Amaya CE Constantin GJ Brenner T Rubino CW Michalski G Marsicano K Monory K Mackie C Marian S Batkai D Parolaro MJ Fischer P Reeh G Kunos M Kress B Lutz CJ Woolf R Kuner 2007 Cannabinoids mediate analgesia largely via peripheral type 1 cannabinoid receptors in nociceptors Nat Neurosci 10 7 870 879
2. S Ahmadi S Lippross WL Neuhuber HU Zeilhofer 2002 PGE(2) selectively blocks inhibitory glycinergic neurotransmission onto rat superficial dorsal horn neurons Nat Neurosci 5 1 34 40
3. J Ahrens G Haeseler M Leuwer B Mohammadi K Krampfl R Dengler J Bufler 2004 2,6 Di-tert-butylphenol, a nonanesthetic propofol analog, modulates alpha1beta glycine receptor function in a manner distinct from propofol Anesth Analg 99 1 91 96
4. 1β receptor. Anesth Analg 107, (in press)
5. JC Ashton 2007 Cannabinoids for the treatment of inflammation Curr Opin Investig Drugs 8 5 373 384
6. C Batista M Berisha M Karst K Salim U Schneider R Brenneisen 2005 Determination of ajulemic acid and its glucuronide in human plasma by gas chromatography-mass spectrometry J Chromatogr B Analyt Technol Biomed Life Sci 820 1 77 82
7. H Betz B Laube 2006 Glycine receptors: recent insights into their structural organization and functional diversity J Neurochem 97 6 1600 1610
8. H Bolay MA Moskowitz 2002 Mechanisms of pain modulation in chronic syndromes Neurology 59 5 Suppl 2 S2 S7
9. TA Brooks BT Hawkins JD Huber RD Egleton TP Davis 2005 Chronic inflammatory pain leads to increased blood-brain barrier permeability and tight junction protein alterations Am J Physiol Heart Circ Physiol 289 2 H738 H743
10. S Burstein 2005 Ajulemic acid (IP-751): synthesis, proof of principle, toxicity studies, and clinical trials AAPS J 7 1 E143 E148
11. SH Burstein M Karst U Schneider RB Zurier 2004 Ajulemic acid: a novel cannabinoid produces analgesia without a "high" Life Sci 75 12 1513 1522
12. Y Chen TJ Dai YM Zeng 2007 Strychnine-sensitive glycine receptors mediate the analgesic but not hypnotic effects of emulsified volatile anesthetics Pharmacology 80 2-3 151 157
13. B Costa 2007 On the pharmacological properties of Delta9- tetrahydrocannabinol (THC) Chem Biodivers 4 8 1664 1677
14. JA Coull D Boudreau K Bachand SA Prescott F Nault A Sik P De Koninck Y De Koninck 2003 Trans-synaptic shift in anion gradient in spinal lamina I neurons as a mechanism of neuropathic pain Nature 424 6951 938 942
15. A Dyson M Peacock A Chen JP Courade M Yaqoob A Groarke C Brain Y Loong A Fox 2005 Antihyperalgesic properties of the cannabinoid CT-3 in chronic neuropathic and inflammatory pain states in the rat Pain 116 1-2 129 137
16. A Fox S Bevan 2005 Therapeutic potential of cannabinoid receptor agonists as analgesic agents Expert Opin Investig Drugs 14 6 695 703
17. C Franke H Hatt J Dudel 1987 Liquid filament switch for ultra-fast exchanges of solutions at excised patches of synaptic membrane of crayfish muscle Neurosci Lett 77 2 199 204
18. M Froh RG Thurman MD Wheeler 2002 Molecular evidence for a glycine-gated chloride channel in macrophages and leukocytes Am J Physiol Gastrointest Liver Physiol 283 4 856 863
19. EJ Geiman W Zheng JM Fritschy FJ Alvarez 2002 Glycine and GABA(A) receptor subunits on Renshaw cells: relationship with presynaptic neurotransmitters and postsynaptic gephyrin clusters J Comp Neurol 444 3 275 289
20. T Gordh H Chu HS Sharma 2006 Spinal nerve lesion alters blood-spinal cord barrier function and activates astrocytes in the rat Pain 124 1-2 211 221
21. J Grudzinska R Schemm S Haeger A Nicke G Schmalzing H Betz B Laube 2005 The beta subunit determines the ligand binding properties of synaptic glycine receptors Neuron 45 5 727 739
22. J Guindon AG Hohmann 2008 Cannabinoid CB2 receptors: a therapeutic target for the treatment of inflammatory and neuropathic pain Br J Pharmacol 153 2 319 334
23. G Haeseler J Ahrens K Krampfl J Bufler R Dengler H Hecker JK Aronson M Leuwer 2005 Structural features of phenol derivatives determining potency for activation of chloride currents via alpha(1) homomeric and alpha(1)beta heteromeric glycine receptors Br J Pharmacol 145 7 916 925
24. OP Hamill A Marty E Neher B Sakmann FJ Sigworth 1981 Improved patch-clamp techniques for high-resolution current recording from cells and cell-free membrane patches Pflugers Arch 391 2 85 100
25. N Hejazi C Zhou M Oz H Sun JH Ye L Zhang 2006 Delta9-tetrahydrocannabinol and endogenous cannabinoid anandamide directly potentiate the function of glycine receptors Mol Pharmacol 69 3 991 997
26. NM Iatsenko T Tsintsadze NO Lozova 2007 The synthetic cannabinoid analog WIN 55,212-2 potentiates the amplitudes of glycine-activated currents Fiziol Zh 53 3 31 37
27. TJ Jentsch V Stein F Weinreich AA Zdebik 2002 Molecular structure and physiological function of chloride channels Physiol Rev 82 2 503 568
28. M Karst K Salim S Burstein I Conrad L Hoy U Schneider 2003 Analgesic effect of the synthetic cannabinoid CT-3 on chronic neuropathic pain: a randomized controlled trial JAMA 290 13 1757 1762
29. J Knabl R Witschi K Hosl H Reinold UB Zeilhofer S Ahmadi J Brockhaus M Sergejeva A Hess K Brune JM Fritschy U Rudolph H Mohler HU Zeilhofer 2008 Reversal of pathological pain through specific spinal GABAA receptor subtypes Nature 451 7176 330 334
30. D Langosch L Thomas H Betz 1988 Conserved quaternary structure of ligand-gated ion channels: the postsynaptic glycine receptor is a pentamer Proc Natl Acad Sci U S A 85 19 7394 7398
31. B Laube G Maksay R Schemm H Betz 2002 Modulation of glycine receptor function: a novel approach for therapeutic intervention at inhibitory synapses? Trends Pharmacol Sci 23 11 519 527
32. JW Lynch RJ Callister 2006 Glycine receptors: a new therapeutic target in pain pathways Curr Opin Investig Drugs 7 1 48 53
33. BH McCarberg RL Barkin 2007 The future of cannabinoids as analgesic agents: a pharmacologic, pharmacokinetic, and pharmacodynamic overview Am J Ther 14 5 475 483
34. SJ Mihic Q Ye MJ Wick VV Koltchine MD Krasowski SE Finn MP Mascia CF Valenzuela KK Hanson EP Greenblatt RA Harris NL Harrison 1997 Sites of alcohol and volatile anaesthetic action on GABA(A) and glycine receptors Nature 389 6649 385 389
35. S Mitrirattanakul N Ramakul AV Guerrero Y Matsuka T Ono H Iwase K Mackie KF Faull I Spigelman 2006 Site-specific increases in peripheral cannabinoid receptors and their endogenous ligands in a model of neuropathic pain Pain 126 1-3 102 114
36. KA Moore T Kohno LA Karchewski J Scholz H Baba CJ Woolf 2002 Partial peripheral nerve injury promotes a selective loss of GABAergic inhibition in the superficial dorsal horn of the spinal cord J Neurosci 22 15 6724 6731
37. I Pribilla T Takagi D Langosch J Bormann H Betz 1992 The atypical M2 segment of the beta subunit confers picrotoxinin resistance to inhibitory glycine receptor channels EMBO J 11 12 4305 4311
38. MH Rhee Z Vogel J Barg M Bayewitch R Levy L Hanus A Breuer R Mechoulam 1997 Cannabinol derivatives: binding to cannabinoid receptors and inhibition of adenylylcyclase J Med Chem 40 20 3228 3233
39. K Salim U Schneider S Burstein L Hoy M Karst 2005 Pain measurements and side effect profile of the novel cannabinoid ajulemic acid Neuropharmacology 48 8 1164 1171
40. Q Shan ST Nevin JL Haddrill JW Lynch 2003 Asymmetric contribution of alpha and beta subunits to the activation of alphabeta heteromeric glycine receptors J Neurochem 86 2 498 507
41. Q Tao SD McAllister J Andreassi KW Nowell GA Cabral DP Hurst K Bachtel MC Ekman PH Reggio ME Abood 1999 Role of a conserved lysine residue in the peripheral cannabinoid receptor (CB2): evidence for subtype specificity Mol Pharmacol 55 3 605 613
42. AJ Todd C Watt RC Spike W Sieghart 1996 Colocalization of GABA, glycine, and their receptors at synapses in the rat spinal cord J Neurosci 16 3 974 982
43. CJ Weir AT Ling D Belelli JA Wildsmith JA Peters JJ Lambert 2004 The interaction of anaesthetic steroids with recombinant glycine and GABAA receptors Br J Anaesth 92 5 704 711
44. I Yamamoto T Kimura A Kamei H Yoshida K Watanabe IK Ho H Yoshimura 1998 Competitive inhibition of delta8-tetrahydrocannabinol and its active metabolites for cannabinoid receptor binding Biol Pharm Bull 21 4 408 410
45. HU Zeilhofer 2005 The glycinergic control of spinal pain processing Cell Mol Life Sci 62 18 2027 2035