Characterization of a novel bivalent morphinan possessing κ agonist and μ agonist/antagonist properties

Journal of Pharmacology and Experimental Therapeutics

Volumn 315, Issue 2, 2005, Pages 821-827

  Mathews, Jennifer L ^a   Peng, Xuemei ^b   Xiong, Wennan ^b   Zhang, Ao ^b   Stevens Negus, S ^b   Neumeyer, John L ^b   Bidlack, Jean M ^a  

^a UNIVERSITY OF ROCHESTER SCHOOL OF MEDICINE AND DENTISTRY   (United States)

^b MCLEAN HOSPITAL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXY N CYCLOBUTYLMETHYLMORPHINAN MANDELATE; BETA FUNALTREXAMINE; BIS(N CYCLOBUTYLMETHYLMORPHINAN)FUMARATE; CYCLORPHAN; GUANOSINE 5' O (3 THIOTRIPHOSPHATE); KAPPA OPIATE RECEPTOR; KAPPA OPIATE RECEPTOR AGONIST; MCL 101; MCL 145; MORPHINAN DERIVATIVE; MORPHINE; MU OPIATE RECEPTOR; MU OPIATE RECEPTOR AGONIST; MU OPIATE RECEPTOR ANTAGONIST; NORBINALTORPHIMINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANTINOCICEPTION; ARTICLE; BINDING ASSAY; CONTROLLED STUDY; DOSE RESPONSE; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; RADIOASSAY; TAIL FLICK TEST;

ANALGESICS, OPIOID; ANIMALS; BINDING, COMPETITIVE; DOSE-RESPONSE RELATIONSHIP, DRUG; FUMARATES; GTP-BINDING PROTEINS; GUANOSINE 5'-O-(3-THIOTRIPHOSPHATE); INJECTIONS, INTRAVENTRICULAR; MALE; MICE; MICE, INBRED ICR; MORPHINANS; MORPHINE; PAIN MEASUREMENT; PROTEIN BINDING; RADIOLIGAND ASSAY; REACTION TIME; RECEPTORS, OPIOID, DELTA; RECEPTORS, OPIOID, KAPPA; RECEPTORS, OPIOID, MU;

EID: 27144519663     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.105.084343     Document Type: Article

References (28)

1. Archer S, Glick SD, and Bidlack JM (1996) Cyclazocine revisited. J Neurochem Res 21:1367-1371.
2. Bilsky EJ, Calderon SN, Wang T, Bernstein RN, Davis P, Hruby VJ, McNutt RW, Rothman RB, Rice KC, and Porreca F (1995) SNC 80, a selective, nonpeptidic and systemically active opioid δ agonist. J Pharmacol Exp Ther 273:359-366.
3. Bowen CA, Negus SS, Zong R, Neumeyer JL, Bidlack JM, and Mello NK (2003) Effects of mixed-action kappa/mu opioids on cocaine self-administration and cocaine-discrimination by rhesus monkeys. Neuropsychopharmacology 28:1125-1139.
4. Chavkin C, James IF, and Goldstein A (1982) Dynorphin is a specific endogenous ligand of the opioid receptor. Science (Wash DC) 215:413-415.
5. Crawford CA, McDougall SA, Bolanos CA, Hall S, and Berger SP (1995) The effects of the κ agonist U50,488 on cocaine-induced conditioned and unconditioned behaviors and fos immunoreactivity. Psychopharmacology 120:392-399.
6. Devine DP, Leone P, Pocock D, and Wise RA (1993) Differential involvement of ventral tegmental area μ, δ and κ opioid receptors in modulation of basal mesolimbic dopamine release: in vivo microdialysis studies. J Pharmacol Exp Ther 266:1236-1246.
7. DiChiara G and Imperato A (1988) Drugs abused by humans preferentially increase synaptic dopamine concentrations in the mesolimbic system of freely moving rats. Proc Natl Acad Sci USA 85:5274-5278.
8. Glick SD, Maissoneuve IM, Raucci J, and Archer S (1995)κ Opioid inhibition of morphine and cocaine self-administration in rats. Brain Res 681:147-152.
9. He L, Fong J, Von Zastrow M, and Whistler JL (2002) Regulation of opioid receptor trafficking and morphine tolerance by receptor oligomerization. Cell 108:271-282.
10. Hokfelt T, Vincent SR, Dalsgaard CJ, Herrera-Marschitz M, Understedt U, Schultzberg M, Christensson I, and Terenius L (1984) Some aspects on distribution and role of opioid peptides in the central and peripheral nervous system, in Central and Peripheral Endorphins: Basic and Clinical Aspects (Muller EE and Genazzani AT eds) pp 1-16, Raven Press, New York.
11. Jannsen PAJ, Niemegeers CJE, and Dorg JGH (1963) The inhibitory effects of fentanyl and other morphine-like analgesics on the warm water-induced tailwithdrawal reflex in rats. Arzneim-Forsch 13:502-505.
12. Maissoneuve IM, Archer S, and Glick SD (1994) U50,488, a κ opioid receptor agonist, attenuates cocaine-induced increases in extracellular dopamine in the nucleus accumbens. Neurosci Lett 181:57-60.
13. Mansour A, Fox CA, Burke S, Meng F, Thompson RC, Akil H, and Watson SJ (1994)μ, δ and κ opioid receptor mRNA expression in rat CNS: an in situ hybridization study. J Comp Neurol 350:412-438.
14. Mansour A, Khachaturian H, Lewis ME, Akil H, and Watson SJ (1987) Autoradiographic differentiation of μ, δ and κ opioid receptors in rat forebrain and midbrain. J Neurosci 7:2445-2464.
15. Mansour A, Khachaturian H, Lewis ME, Akil H, and Watson SJ (1988) Anatomy of CNS opioid receptors. Trends Neurosci 11:308-314.
16. Mello NK and Negus SS (1998) Effects of κ opioid agonists on cocaine- and foodmaintained responding by rhesus monkeys. J Pharmacol Exp Ther 286:812-824.
17. Mogil JS, Wilson SG, Bon K, Lee SE, Chung K, Raber P, Pieper JO, Hain HS, Belknap JK, Hubert L, et al. (1999) Heritability of nociception I: responses of 11 inbred mouse strains on 12 measures of nociception. Pain 80:67-82.
18. Negus SS, Mello NK, Portoghese PS, and Lin CE (1997) Effects of κ opioids on cocaine self-administration by rhesus monkeys. J Pharmacol Exp Ther 282:44-55.
19. Neumeyer JL, Bidlack JM, Zong R, Bakthavachalam V, Gao P, Cohen DJ, Negus SS, and Mello NK (2000) Synthesis and opioid receptor affinity of morphinan and benzomorphan derivatives. Mixed κ agonists and μ agonists/antagonists as potential pharmacotherapeutics for cocaine dependence. J Med Chem 43:114-122.
20. Neumeyer JL, Zhang A, Xiong W, Gu X-H, Hilbert JE, Knapp BI, Negus SS, Mello NK, and Bidlack JM (2003) Design and synthesis of novel dimeric morphinan ligands for κ and μ opioid receptors. J Med Chem 46:5162-5170.
21. Porreca F, Mosberg HI, Hurst R, Hruby VJ, and Burks TF (1984) Roles of μ, δ and κ opioid receptors in spinal and supraspinal mediation of gastrointestinal transit effects and hot-plate analgesia in the mouse. J Pharmacol Exp Ther 230:341-348.
22. Schenk S, Partridge B, and Shippenberg TS (1999) U69593, a κ-opioid agonist, decreases cocaine self-administration and decreases cocaine-produced drugseeking. Psychopharmacology 144:339-346.
23. Schenk S, Partridge B, and Shippenberg TS (2000) Reinstatement of extinguished drug-taking behavior in rats: effect of the κ-opioid receptor agonist, U69593. Psychopharmacology 51:85-90.
24. Shippenberg TS, LeFevour A, and Heidbreder CH (1996) κ-Opioid receptor agonists prevent sensitization to the conditioned rewarding effects of cocaine. J Pharmacol Exp Ther 276:545-554.
25. Spanagel R, Herz A, and Shippenberg TS (1992) Opposing tonically active endoge-nous opioid systems modulate the mesolimbic dopaminergic pathway. Proc Natl Acad Sci USA 89:2046-2050.
26. Suzuki T, Shiozaki Y, Masukawa Y, Misawa M, and Nagase H (1992) The role of μ-and κ-opioid receptors in cocaine-induced conditioned place preference. Jpn J Pharmacol 58:435-442.
27. Tallarida RJ and Murray RB (1986) Manual of Pharmacologic Calculations with Computer Programs, 2nd ed, Springer, New York.
28. Ukai M, Mizutani M, and Kameyama T (1994) Opioid peptides selective for receptor types modulate cocaine-induced behavioral responses in mice. Yakubutsu Seishin Kodo 14:153-159.