Identification of short-acting κ-opioid receptor antagonists with anxiolytic-like activity

European Journal of Pharmacology

Volumn 661, Issue 1-3, 2011, Pages 27-34

  Peters, Matthew F ^a   Zacco, Anna ^a   Gordon, John ^a   MacIag, Carla M ^a   Litwin, Linda C ^a   Thompson, Carolann ^a   Schroeder, Patricia ^a   Sygowski, Linda A ^a   Piser, Timothy M ^a   Brugel, Todd A ^a  

^a ASTRAZENECA   (United Kingdom)

Author keywords

Opioid receptor; Anxiety; Depression; Diuresis; Long lasting antagonism

Indexed keywords

3 [8 [(5 METHYLTHIOPHEN 2 YL)METHYL] 8 AZABICYCLO[3.2.1]OCTAN 3 YLOXY]BENZAMIDE; 4 [4 [[2 (3,5 DIMETHYLPHENYL)PYRROLIDIN 1 YL]METHYL]PHENOXY] 3 FLUOROBENZAMIDE; ETHYL 4 (3 CARBAMOYLBENZYL) 1 (CYCLOHEXYLMETHYL)PIPERIDINE 4 CARBOXYLATE; KAPPA OPIATE RECEPTOR ANTAGONIST; SHORT ACTING DRUG; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANXIETY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DIURESIS; DRUG MECHANISM; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; FEMALE; LIGAND BINDING; MALE; MAZE TEST; MOOD DISORDER; NONHUMAN; PRENATAL STRESS; PRIORITY JOURNAL; RAT; TRANQUILIZING ACTIVITY;

ANIMALS; ANTI-ANXIETY AGENTS; BEHAVIOR, ANIMAL; DIURESIS; DRUG EVALUATION, PRECLINICAL; INHIBITION (PSYCHOLOGY); MALE; MAZE LEARNING; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, OPIOID, KAPPA; STRESS, PSYCHOLOGICAL; TIME FACTORS;

EID: 79956202458     PISSN: 00142999     EISSN: 18790712     Source Type: Journal    
DOI: 10.1016/j.ejphar.2011.04.017     Document Type: Article

References (28)

1. M.J. Banker, T.H. Clark, and J.A. Williams Development and validation of a 96-well equilibrium dialysis apparatus for measuring plasma protein binding J. Pharm. Sci. 92 2003 967 974 doi:10.1002/jps.10332 (Pubitemid 36523442)
2. J. Barre, J.M. Chamouard, G. Houin, and J.P. Tillement Equilibrium dialysis, ultrafiltration, and ultracentrifugation compared for determining the plasma-protein-binding characteristics of valproic acid Clin. Chem. 31 1985 60 64 (Pubitemid 15079346)
3. D.P. Brooks, G. Giardina, M. Gellai, G. Dondio, R.M. Edwards, G. Petrone, P.D. DePalma, M. Sbacchi, M. Jugus, and P. Misiano Opiate receptors within the blood-brain barrier mediate kappa agonist-induced water diuresis J. Pharmacol. Exp. Ther. 266 1993 164 171 (Pubitemid 23315643)
4. M.R. Bruchas, and C. Chavkin Kinase cascades and ligand-directed signaling at the κ-opioid receptor Psychopharmacology (Berl) 210 2010 137 147
5. M.R. Bruchas, T. Yang, S. Schreiber, M. Defino, S.C. Kwan, S. Li, and C. Chavkin Long-acting κ-opioid antagonists disrupt receptor signaling and produce noncompetitive effects by activating c-Jun N-terminal kinase J. Biol. Chem. 282 2007 29803 29811 (Pubitemid 350035286)
6. T.A. Brugel, R.W. Smith, M. Balestra, C. Becker, T. Daniels, T.N. Hoerter, G.M. Koether, S.R. Throner, L.M. Panko, J.J. Folmer, J. Cacciola, A.M. Hunter, R. Liu, P.D. Edwards, D.G. Brown, J. Gordon, N.C. Ledonne, M. Pietras, P. Schroeder, L.A. Sygowski, L.T. Hirata, A. Zacco, and M.F. Peters Discovery of 8-azabicyclo[3.2.1]octan-3-yloxy-benzamides as selective antagonists of the κ-opioid receptor. Part 1 Bioorg. Med. Chem. Lett. 20 2010 5847 5852
7. T.A. Brugel, R.W. Smith, M. Balestra, C. Becker, T. Daniels, G.M. Koether, S.R. Throner, L.M. Panko, D.G. Brown, R. Liu, J. Gordon, and M.F. Peters SAR development of a series of 8-azabicyclo[3.2.1]octan-3-yloxy- benzamides as κ-opioid receptor antagonists. Part 2 Bioorg. Med. Chem. Lett. 20 2010 5405 5410
8. N.D. Buezo, C. Pedregal-Tercero, D.L. McKinzie, and C.H. Mitch Kappa selective opioid receptor antagonist 2009 12/352,869
9. I. Carroll, J.B. Thomas, L.A. Dykstra, A.L. Granger, R.M. Allen, J.L. Howard, G.T. Pollard, M.D. Aceto, and L.S. Harris Pharmacological properties of JDTic: a novel κ-opioid receptor antagonist Eur. J. Pharmacol. 501 2004 111 119 (Pubitemid 39298943)
10. R.M. Craft, and D.M. McNiel Agonist/antagonist properties of nalbuphine, butorphanol and (-)-pentazocine in male vs. female rats Pharmacol. Biochem. Behav. 75 2003 235 245 (Pubitemid 36577599)
11. R.M. Craft, C.M. Ulibarri, and D.J. Raub Kappa opioid-induced diuresis in female vs. male rats Pharmacol. Biochem. Behav. 65 2000 53 59 (Pubitemid 30017995)
12. T.I. Cremers, M.G. de Vries, K.D. Huinink, J.P. van Loon, M. v d Hart, B. Ebert, B.H. Westerink, and E.C. De Lange Quantitative microdialysis using modified ultraslow microdialysis: direct rapid and reliable determination of free brain concentrations with the MetaQuant technique J. Neurosci. Methods 178 2009 249 254
13. H.B. Gottlieb, K.J. Varner, V.A. Kenigs, A.M. Cabral, and D.R. Kapusta Differential cardiovascular and renal responses produced by microinjection of the {kappa}-opioid U-50488H [(trans-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl) cyclohexyl]-benzene-acetamide) methane sulfonate] into subregions of the paraventricular nucleus J. Pharmacol. Exp. Ther. 312 2005 678 685 (Pubitemid 40189566)
14. P. Horan, J. Taylor, H.I. Yamamura, and F. Porreca Extremely long-lasting antagonistic actions of nor-binaltorphimine (nor-BNI) in the mouse tail-flick test J. Pharmacol. Exp. Ther. 260 1992 1237 1243
15. J.P. Huidobro-Toro, and S. Parada Kappa-opiates and urination: pharmacological evidence for an endogenous role of the kappa-opiate receptor in fluid and electrolyte balance Eur. J. Pharmacol. 107 1984 1 10 (Pubitemid 15193383)
16. R.C. Kessler, P. Berglund, O. Demler, R. Jin, D. Koretz, K.R. Merikangas, A.J. Rush, E.E. Walters, P.S. Wang, and National Comorbidity Survey Replication The epidemiology of major depressive disorder: results from the National Comorbidity Survey Replication (NCS-R) JAMA 289 2003 3095 3105 (Pubitemid 37432885)
17. A.T. Knoll, and W.A. Carlezon Jr. Dynorphin, stress, and depression Brain Res. 1314 2010 56 73
18. M.C. Ko, K.J. Willmont, H. Lee, G.S. Flory, and J.H. Woods Ultra-long antagonism of kappa opioid agonist-induced diuresis by intracisternal nor-binaltorphimine in monkeys Brain Res. 982 2003 38 44 (Pubitemid 37288796)
19. J.I. Koenig, G.I. Elmer, P.D. Shepard, P.R. Lee, C. Mayo, B. Joy, E. Hercher, and D.L. Brady Prenatal exposure to a repeated variable stress paradigm elicits behavioral and neuroendocrinological changes in the adult offspring: potential relevance to schizophrenia Behav. Brain Res. 156 2005 251 261 (Pubitemid 39576065)
20. E.J. Melief, M. Miyatake, M.R. Bruchas, and C. Chavkin Ligand-directed c-Jun N-terminal kinase activation disrupts opioid receptor signaling Proc. Natl. Acad. Sci. USA 107 2010 11608 11613
21. P. Pechtel, and D.A. Pizzagalli Effects of early life stress on cognitive and affective function: an integrated review of human literature Psychopharmacology (Berl) 214 2011 55 70
22. A. Pfeiffer, V. Brantl, A. Herz, and H.M. Emrich Psychotomimesis mediated by kappa opiate receptors Science 233 1986 774 776 (Pubitemid 16016229)
23. S.R. Secoli, and N.A. Teixeira Chronic prenatal stress affects development and behavioral depression in rats Stress 2 1998 273 280 (Pubitemid 29074585)
24. Y. Shirayama, H. Ishida, M. Iwata, G.I. Hazama, R. Kawahara, and R.S. Duman Stress increases dynorphin immunoreactivity in limbic brain regions and dynorphin antagonism produces antidepressant-like effects J. Neurochem. 90 2004 1258 1268 (Pubitemid 39167359)
25. M.H. Trivedi, A.J. Rush, S.R. Wisniewski, A.A. Nierenberg, D. Warden, L. Ritz, G. Norquist, R.H. Howland, B. Lebowitz, P.J. McGrath, K. Shores-Wilson, M.M. Biggs, G.K. Balasubramani, M. Fava STAR*D Study Team Evaluation of outcomes with citalopram for depression using measurement-based care in STAR*D: implications for clinical practice Am. J. Psychiatry 163 2006 28 40 (Pubitemid 43050100)
26. E. Ur, D.M. Wright, P.M. Bouloux, and A. Grossman The effects of spiradoline (U-62066E), a κ-opioid receptor agonist, on neuroendocrine function in man Br. J. Pharmacol. 120 1997 781 784 (Pubitemid 27122716)
27. H.M. van Praag Can stress cause depression? Prog. Neuropsychopharmacol. Biol. Psychiatry 28 2004 891 907 (Pubitemid 39206298)
28. P. Willner Chronic mild stress (CMS) revisited: consistency and behavioural-neurobiological concordance in the effects of CMS Neuropsychobiology 52 2005 90 110 (Pubitemid 41160326)