BU08073 a buprenorphine analogue with partial agonist activity at μ-receptors in vitro but long-lasting opioid antagonist activity in vivo in mice

British Journal of Pharmacology

Volumn 172, Issue 2, 2015, Pages 668-680

  Khroyan, T V ^a   Wu, J ^b   Polgar, W E ^a   Cami Kobeci, G ^c   Fotaki, N ^c   Husbands, Stephen M ^c   Toll, Lawrence ^b  

^a SRI INTERNATIONAL   (United States)

^b TORREY PINES INSTITUTE FOR MOLECULAR STUDIES   (United States)

^c University of Bath   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

3,4 DICHLORO N METHYL N [2 (1 PYRROLIDINYL)CYCLOHEXYL]BENZENEACETAMIDE; BU 08073; BUPRENORPHINE; DELTA OPIATE RECEPTOR; GUANOSINE 5' O (3 THIOTRIPHOSPHATE) S 35; KAPPA OPIATE RECEPTOR; MORPHINE; MU OPIATE RECEPTOR; MU OPIATE RECEPTOR AGONIST; NARCOTIC ANALGESIC AGENT; OPIATE ANTAGONIST; PLASMA PROTEIN; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG; BU08073; ENKEPHALIN[2 DEXTRO ALANINE 4 METHYLPHENYLALANINE 5 GLYCINE]; NARCOTIC ANTAGONIST;

ANALGESIC ACTIVITY; ANIMAL CELL; ANIMAL EXPERIMENT; ANXIETY; ARTICLE; BINDING AFFINITY; BLOOD BRAIN BARRIER; CELL MEMBRANE POTENTIAL; CONTROLLED STUDY; DRUG PENETRATION; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG SOLUBILITY; DRUG STRUCTURE; ELEVATED ZERO MAZE TEST; FEMALE; FLUORESCENCE ANALYSIS; IN VITRO STUDY; IN VIVO STUDY; MALE; MOUSE; NONHUMAN; PROTEIN EXPRESSION; STRUCTURE ACTIVITY RELATION; TAIL FLICK TEST; TRANQUILIZING ACTIVITY; WHOLE CELL; AGONISTS; ANALOGS AND DERIVATIVES; ANIMAL; ANIMAL BEHAVIOR; ANTAGONISTS AND INHIBITORS; CHO CELL LINE; CRICETULUS; DRUG EFFECTS; HEAT; HUMAN; INSTITUTE FOR CANCER RESEARCH MOUSE; MEMBRANE POTENTIAL; PAIN; PATHOPHYSIOLOGY; PHYSIOLOGY;

ANALGESICS, OPIOID; ANIMALS; ANXIETY; BEHAVIOR, ANIMAL; BUPRENORPHINE; CHO CELLS; CRICETULUS; ENKEPHALIN, ALA(2)-MEPHE(4)-GLY(5)-; HOT TEMPERATURE; HUMANS; MALE; MEMBRANE POTENTIALS; MICE, INBRED ICR; NARCOTIC ANTAGONISTS; PAIN; RECEPTORS, OPIOID, MU;

EID: 84920139196     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1111/bph.12796     Document Type: Article

References (63)

1. Alexander SPH, Benson HE, Faccenda E, Pawson AJ, Sharman JL, Spedding M, et al. (2013). The Concise Guide to PHARMACOLOGY 2013/14: G Protein-Coupled Receptors. Br J Pharmacol 170: 1459-1581.
2. Anseloni VC, Coimbra NC, Morato S, Brandao ML, (1999). A comparative study of the effects of morphine in the dorsal periaqueductal gray and nucleus accumbens of rats submitted to the elevated plus-maze test. Exp Brain Res 129: 260-268.
3. Bloms-Funke P, Gillen C, Schuettler AJ, Wnendt S, (2000). Agonistic effects of the opioid buprenorphine on the nociceptin/OFQ receptor. Peptides 21: 1141-1146.
4. Braun AA, Skelton MR, Vorhees CV, Williams MT, (2011). Comparison of the elevated plus and elevated zero mazes in treated and untreated male Sprague-Dawley rats: effects of anxiolytic and anxiogenic agents. Pharmacol Biochem Behav 97: 406-415.
5. Bruchas MR, Yang T, Schreiber S, Defino M, Kwan SC, Li S, et al. (2007). Long-acting kappa opioid antagonists disrupt receptor signaling and produce noncompetitive effects by activating c-Jun N-terminal kinase. J Biol Chem 282: 29803-29811.
6. Calo G, Rizzi A, Marzola G, Guerrini R, Salvadori S, Beani L, et al. (1998). Pharmacological characterization of the nociceptin receptor mediating hyperalgesia in the mouse tail withdrawal assay. Br J Pharmacol 125: 373-378.
7. Cami-Kobeci G, Polgar WE, Khroyan TV, Toll L, Husbands SM, (2011). Structural determinants of opioid and NOP receptor activity in derivatives of buprenorphine. J Med Chem 54: 6531-6537.
8. Carroll I, Thomas JB, Dykstra LA, Granger AL, Allen RM, Howard JL, et al. (2004). Pharmacological properties of JDTic: a novel kappa-opioid receptor antagonist. Eur J Pharmacol 501: 111-119.
9. Cheng Y, Prusoff WH, (1973). Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem Pharmacol 22: 3099-3108.
10. Ciccocioppo R, Economidou D, Fedeli A, Angeletti S, Weiss F, Heilig M, et al. (2004). Attenuation of ethanol self-administration and of conditioned reinstatement of alcohol-seeking behaviour by the antiopioid peptide nociceptin/orphanin FQ in alcohol-preferring rats. Psychopharmacology (Berl) 172: 170-178.
11. Ciccocioppo R, Economidou D, Rimondini R, Sommer W, Massi M, Heilig M, (2007). Buprenorphine reduces alcohol drinking through activation of the nociceptin/orphanin FQ-NOP receptor system. Biol Psychiatry 61: 4-12.
12. Cowan A, Lewis JW, Macfarlane IR, (1977). Agonist and antagonist properties of buprenorphine, a new antinociceptive agent. Br J Pharmacol 60: 537-545.
13. Cox BM, Christie MJ, Devi L, Toll L, Traynor JR, (2015). Challenges for opioid receptor nomenclature: IUPHAR Review 9. Br J Pharmacol 172: 317-323.
14. Dahan A, Yassen A, Bijl H, Romberg R, Sarton E, Teppema L, et al. (2005). Comparison of the respiratory effects of intravenous buprenorphine and fentanyl in humans and rats. Br J Anaesth 94: 825-834.
15. Dooley CT, Spaeth CG, Berzetei-Gurske IP, Craymer K, Adapa ID, Brandt SR, et al. (1997). Binding and in vitro activities of peptides with high affinity for the nociceptin/orphanin FQ receptor, ORL1. J Pharmacol Exp Ther 283: 735-741.
16. Greedy BM, Bradbury F, Thomas MP, Grivas K, Cami-Kobeci G, Archambeau A, et al. (2013). Orvinols with mixed kappa/mu opioid receptor agonist activity. J Med Chem 56: 3207-3216.
17. Guerrini R, Calo G, Rizzi A, Bigoni R, Bianchi C, Salvadori S, et al. (1998). A new selective antagonist of the nociceptin receptor. Br J Pharmacol 123: 163-165.
18. Horan P, Taylor J, Yamamura HI, Porreca F, (1992). Extremely long-lasting antagonistic actions of nor-binaltorphimine (nor-BNI) in the mouse tail-flick test. J Pharmacol Exp Ther 260: 1237-1243.
19. Huang P, Kehner GB, Cowan A, Liu-Chen LY, (2001). Comparison of pharmacological activities of buprenorphine and norbuprenorphine: norbuprenorphine is a potent opioid agonist. J Pharmacol Exp Ther 297: 688-695.
20. Husbands SM, (2013). Buprenorphine and related orvinols. In:, Ko MCH, Husbands SM, (eds). Research and Development of Opioid-Related Analgesics, Vol. 1131. American Chemical Society Symposium Series: Washington, DC, pp. 127-144.
21. Jones DN, Holtzman SG, (1992). Long term kappa-opioid receptor blockade following nor-binaltorphimine. Eur J Pharmacol 215: 345-348.
22. Khroyan TV, Polgar WE, Jiang F, Zaveri NT, Toll L, (2009). Nociceptin/orphanin FQ receptor activation attenuates antinociception induced by mixed nociceptin/orphanin FQ/mu-opioid receptor agonists. J Pharmacol Exp Ther 331: 946-953.
23. Khroyan TV, Polgar WE, Cami-Kobeci G, Husbands SM, Zaveri NT, Toll L, (2011). The first universal opioid ligand, (2S)-2-[(5R,6R,7R,14S)-N-cyclopropylmethyl-4,5-epoxy-6,14-ethano-3-hydroxy -6-methoxymorphinan-7-yl]-3,3-dimethylpentan-2-ol (BU08028): characterization of the in vitro profile and in vivo behavioral effects in mouse models of acute pain and cocaine-induced reward. J Pharmacol Exp Ther 336: 952-961.
24. Khroyan TV, Zhang J, Yang L, Zou B, Xie J, Pascual C, et al. (2012). Rodent motor and neuropsychological behavior measured in home cages using the integrated modular platform-SmartCage(TM). Clin Exp Pharmacol Physiol 39: 614-622.
25. Kilkenny C, Browne W, Cuthill IC, Emerson M, Altman DG, (2010). Animal research: Reporting in vivo experiments: the ARRIVE guidelines. Br J Pharmacol 160: 1577-1579.
26. Knapman A, Abogadie F, McIntrye P, Connor M, (2014). A real-time, fluorescence-based assay for measuring mu-opioid receptor modulation of adenylyl cyclase activity in Chinese hamster ovary cells. J Biomol Screen 19: 223-231.
27. Kotlinska J, Rafalski P, Biala G, Dylag T, Rolka K, Silberring J, (2003). Nociceptin inhibits acquisition of amphetamine-induced place preference and sensitization to stereotypy in rats. Eur J Pharmacol 474: 233-239.
28. Law PY, Reggio PH, Loh HH, (2013). Opioid receptors: toward separation of analgesic from undesirable effects. Trends Biochem Sci 38: 275-282.
29. Lelong-Boulouard V, Quentin T, Moreaux F, Debruyne D, Boulouard M, Coquerel A, (2006). Interactions of buprenorphine and dipotassium clorazepate on anxiety and memory functions in the mouse. Drug Alcohol Depend 85: 103-113.
30. Lewis JW, Husbands SM, (2004). The orvinols and related opioids-high affinity ligands with diverse efficacy profiles. Curr Pharm Des 10: 717-732.
31. Liu-Chen LY, Li SX, Wheeler-Aceto H, Cowan A, (1991). Effects of intracerebroventricular beta-funaltrexamine on mu and delta opioid receptors in the rat: dichotomy between binding and antinociception. Eur J Pharmacol 203: 195-202.
32. Lutfy K, Cowan A, (2004). Buprenorphine: a unique drug with complex pharmacology. Cur Neuropharmacol 2: 395-402.
33. Lutfy K, Eitan S, Bryant CD, Yang YC, Saliminejad N, Walwyn W, et al. (2003). Buprenorphine-induced antinociception is mediated by mu-opioid receptors and compromised by concomitant activation of opioid receptor-like receptors. J Neurosci 23: 10331-10337.
34. Manglik A, Kruse AC, Kobilka TS, Thian FS, Mathiesen JM, Sunahara RK, et al. (2012). Crystal structure of the micro-opioid receptor bound to a morphinan antagonist. Nature 485: 321-326.
35. Martin WR, (1983). Pharmacology of opioids. Pharmacol Rev 35: 283-323.
36. Martin WR, Eades CG, Thompson JA, Huppler RE, Gilbert PE, (1976). The effects of morphine- and nalorphine- like drugs in the nondependent and morphine-dependent chronic spinal dog. J Pharmacol Exp Ther 197: 517-532.
37. McGrath J, Drummond G, McLachlan E, Kilkenny C, Wainwright C, (2010). Guidelines for reporting experiments involving animals: the ARRIVE guidelines. Br J Pharmacol 160: 1573-1576.
38. Melief EJ, Miyatake M, Bruchas MR, Chavkin C, (2010). Ligand-directed c-Jun N-terminal kinase activation disrupts opioid receptor signaling. Proc Natl Acad Sci U S A 107: 11608-11613.
39. Melief EJ, Miyatake M, Carroll FI, Beguin C, Carlezon WA Jr, Cohen BM, et al. (2011). Duration of action of a broad range of selective kappa-opioid receptor antagonists is positively correlated with c-Jun N-terminal kinase-1 activation. Mol Pharmacol 80: 920-929.
40. Mello NK, Mendelson JH, Bree MP, Lukas SE, (1989). Buprenorphine suppresses cocaine self-administration in rhesus monkeys. NIDA Res Monogr 95: 333-334.
41. Mello NK, Mendelson JH, Lukas SE, Gastfriend DR, Teoh SK, Holman BL, (1993). Buprenorphine treatment of opiate and cocaine abuse: clinical and preclinical studies. Harv Rev Psychiatry 1: 168-183.
42. Metcalf MD, Coop A, (2005). Kappa opioid antagonists: past successes and future prospects. AAPS J 7: E704-E722.
43. Montoya ID, Gorelick DA, Preston KL, Schroeder JR, Umbricht A, Cheskin LJ, et al. (2004). Randomized trial of buprenorphine for treatment of concurrent opiate and cocaine dependence. Clin Pharmacol Ther 75: 34-48.
44. National Research Council (US) Committee on Guidelines for the Use of Animals in Neuroscience and Behavioral Research (2003). Guidelines for the Care and Use of Mammals in Neuroscience and Behavioral Research. National Academies Press: Washington, DC.
45. Okawa H, Nicol B, Bigoni R, Hirst RA, Calo G, Guerrini R, et al. (1999). Comparison of the effects of [Phe1psi(CH2-NH)Gly2]nociceptin(1-13)NH2 in rat brain, rat vas deferens and CHO cells expressing recombinant human nociceptin receptors. Br J Pharmacol 127: 123-130.
46. Patkar KA, Wu J, Ganno ML, Singh HD, Ross NC, Rasakham K, et al. (2013). Physical presence of nor-binaltorphimine in mouse brain over 21 days after a single administration corresponds to its long-lasting antagonistic effect on kappa-opioid receptors. J Pharmacol Exp Ther 346: 545-554.
47. Pawson AJ, Sharman JL, Benson HE, Faccenda E, Alexander SP, Buneman OP, et al. (2014). The IUPHAR/BPS Guide to PHARMACOLOGY: an expert-driven knowledge base of drug targets and their ligands. Nucleic Acids Research 42 (Database Issue): D1098-D1106.
48. Perrine SA, Hoshaw BA, Unterwald EM, (2006). Delta opioid receptor ligands modulate anxiety-like behaviors in the rat. Br J Pharmacol 147: 864-872.
49. Picard N, Cresteil T, Djebli N, Marquet P, (2005). In vitro metabolism study of buprenorphine: evidence for new metabolic pathways. Drug Metab Dispos 33: 689-695.
50. Portoghese PS, Larson DL, Sayre LM, Fries DS, Takemori AE, (1980). A novel opioid receptor site directed alkylating agent with irreversible narcotic antagonistic and reversible agonistic activities. J Med Chem 23: 233-234.
51. Saitoh A, Kimura Y, Suzuki T, Kawai K, Nagase H, Kamei J, (2004). Potential anxiolytic and antidepressant-like activities of SNC80, a selective delta-opioid agonist, in behavioral models in rodents. J Pharmacol Sci 95: 374-380.
52. Sakoori K, Murphy NP, (2004). Central administration of nociceptin/orphanin FQ blocks the acquisition of conditioned place preference to morphine and cocaine, but not conditioned place aversion to naloxone in mice. Psychopharmacology (Berl) 172: 129-136.
53. Shepherd JK, Grewal SS, Fletcher A, Bill DJ, Dourish CT, (1994). Behavioural and pharmacological characterisation of the elevated 'zero-maze' as an animal model of anxiety. Psychopharmacology (Berl) 116: 56-64.
54. Shoblock JR, Wichmann J, Maidment NT, (2005). The effect of a systemically active ORL-1 agonist, Ro 64-6198, on the acquisition, expression, extinction, and reinstatement of morphine conditioned place preference. Neuropharmacology 49: 439-446.
55. Spagnolo B, Carra G, Fantin M, Fischetti C, Hebbes C, McDonald J, et al. (2007). Pharmacological characterization of the nociceptin/orphanin FQ receptor antagonist SB-612111 [(-)-cis-1-methyl-7-[[4-(2,6-dichlorophenyl)piperidin-1-yl]methyl]-6,7,8,9 -tetrahydro-5H-benzocyclohepten-5-ol]: in vitro studies. J Pharmacol Exp Ther 321: 961-967.
56. Spagnolo B, Calo G, Polgar WE, Jiang F, Olsen CM, Berzetei-Gurske I, et al. (2008). Activities of mixed NOP and mu-opioid receptor ligands. Br J Pharmacol 153: 609-619.
57. Takemori AE, Larson DL, Portoghese PS, (1981). The irreversible narcotic antagonistic and reversible agonistic properties of the fumaramate methyl ester derivative of naltrexone. Eur J Pharmacol 70: 445-451.
58. Toll L, Berzetei-Gurske IP, Polgar WE, Brandt SR, Adapa ID, Rodriguez L, et al. (1998). Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications. NIDA Res Monogr 178: 440-466.
59. Traynor JR, Nahorski SR, (1995). Modulation by mu-opioid agonists of guanosine-5′-O-(3-[35S]thio)triphosphate binding to membranes from human neuroblastoma SH-SY5Y cells. Mol Pharmacol 47: 848-854.
60. Vergura R, Balboni G, Spagnolo B, Gavioli E, Lambert DG, McDonald J, et al. (2008). Anxiolytic- and antidepressant-like activities of H-Dmt-Tic-NH-CH(CH2-COOH)-Bid (UFP-512), a novel selective delta opioid receptor agonist. Peptides 29: 93-103.
61. Wnendt S, Kruger T, Janocha E, Hildebrandt D, Englberger W, (1999). Agonistic effect of buprenorphine in a nociceptin/OFQ receptor-triggered reporter gene assay. Mol Pharmacol 56: 334-338.
62. Yu G, Yan LD, Li YL, Wen Q, Dong HJ, Gong ZH, (2011). TH-030418: a potent long-acting opioid analgesic with low dependence liability. Naunyn Schmiedebergs Arch Pharmacol 384: 125-131.
63. Zhang Z, Schulteis G, (2008). Withdrawal from acute morphine dependence is accompanied by increased anxiety-like behavior in the elevated plus maze. Pharmacol Biochem Behav 89: 392-403.