Study on the activation of the opioid receptors by a set of morphine derivatives in a well-defined assay system

Neurochemical Research

Volumn 37, Issue 2, 2012, Pages 410-416

  Zhang, Yan ^a   Wang, Zhiwei ^a   Cox, D Phillip ^b   Civelli, Olivier ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Noramco Inc   (United States)

Author keywords

Opiate; Opioid receptor; Structure activity relationship

Indexed keywords

CHIMERIC PROTEIN; CODEINE; DELTA OPIATE RECEPTOR; DELTA OPIATE RECEPTOR AGONIST; GUANINE NUCLEOTIDE BINDING PROTEIN; HYDROCODONE; HYDROMORPHONE; HYDROXYL GROUP; KAPPA OPIATE RECEPTOR; KAPPA OPIATE RECEPTOR AGONIST; KETONE; METHYL GROUP; MORPHINE DERIVATIVE; MU OPIATE RECEPTOR; MU OPIATE RECEPTOR AGONIST; ORIPAVINE; OXYCODONE; OXYMORPHONE; THEBAINE;

ARTICLE; CALCIUM CELL LEVEL; CELL ASSAY; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DRUG MECHANISM; DRUG STRUCTURE; EMBRYO; GENETIC TRANSFECTION; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MOLECULAR INTERACTION; PRIORITY JOURNAL; PROTEIN PROTEIN INTERACTION; STRUCTURE ACTIVITY RELATION;

CELL LINE; FLUOROMETRY; HUMANS; MORPHINE; RECEPTORS, OPIOID;

EID: 84856396885     PISSN: 03643190     EISSN: 15736903     Source Type: Journal    
DOI: 10.1007/s11064-011-0627-7     Document Type: Article

References (35)

1. Ling GS, Spiegel K, Nishimura SL, Pasternak GW (1983) Dissociation of morphine's analgesic and respiratory depressant actions. Eur J Pharmacol 86:487-488. doi: (Pubitemid 13171535)
2. Jones KL, Barr GA (1995) Ontogeny of morphine withdrawal in the rat. Behav Neurosci 109:1189-1198. doi: (Pubitemid 26001482)
3. Conklin BR, Farfel Z, Lustig KD, Julius D, Bourne HR (1993) Substitution of 3 amino-acids switches receptor specificity of G(q)alpha to that of G(i)alpha. Nature 363:274-276. doi: (Pubitemid 23158533)
4. Saito Y, Nothacker HP, Wang Z, Lin SH, Leslie F, Civelli O (1999) Molecular characterization of the melanin-concentrating-hormone receptor. Nature 400:265-269. doi: (Pubitemid 29334141)
5. HWD Matthes R Maldonado F Simonin O Valverde S Slowe I Kitchen K Befort A Dierich M LeMeur P Dolle E Tzavara J Hanoune BP Roques BL Kieffer 1996 Loss of morphine-induced analgesia, reward effect and withdrawal symptoms in mice lacking the mu-opioid-receptor gene Nature 383 819 823 10.1038/383819a0 8893006 10.1038/383819a0 1:CAS:528:DyaK28Xms1Sjtbw%3D Matthes HWD, Maldonado R, Simonin F, Valverde O, Slowe S, Kitchen I, Befort K, Dierich A, LeMeur M, Dolle P, Tzavara E, Hanoune J, Roques BP, Kieffer BL (1996) Loss of morphine-induced analgesia, reward effect and withdrawal symptoms in mice lacking the mu-opioid-receptor gene. Nature 383:819-823. doi: 10.1038/383819a0
6. Sora I, Takahashi N, Funada M, Ujike H, Revay RS, Donovan DM, Miner LL, Uhl GR (1997) Opiate receptor knockout mice define mu receptor roles in endogenous nociceptive responses and morphine-induced analgesia. Proc Natl Acad Sci USA 94:1544-1549. doi: (Pubitemid 27087888)
7. Roy S, Barke RA, Loh HH (1998) MU-opioid receptor-knockout mice: role of mu-opioid receptor in morphine mediated immune functions. Mol Brain Res 61:190-194. doi: (Pubitemid 28511362)
8. Kieffer BL, Gaveriaux-Ruff C (2002) Exploring the opioid system by gene knockout. Prog Neurobiol 66:285-306. doi: (Pubitemid 34518287)
9. New DC, Wong YH (2002) The ORL1 receptor: molecular pharmacology and signalling mechanisms. Neurosignals 11:197-212. doi: (Pubitemid 37494399)
10. JC Meunier L Mouledous CM Topham 2000 The nociceptin (ORL1) receptor: molecular cloning and functional architecture Peptides 21 893 900 10.1016/S0196-9781(00)00225-4 10998522 10.1016/S0196-9781(00)00225-4 1:CAS:528:DC%2BD3cXms1WrsLo%3D Meunier JC, Mouledous L, Topham CM (2000) The nociceptin (ORL1) receptor: molecular cloning and functional architecture. Peptides 21:893-900. doi: 10.1016/S0196-9781(00)00225-4
11. CB Pert SH Snyder 1973 Opiate receptor: demonstration in nervous tissue Science 179 1011 1014 10.1126/science.179.4077.1011 4687585 10.1126/science.179. 4077.1011 1:CAS:528:DyaE3sXktVShs7k%3D Pert CB, Snyder SH (1973) Opiate receptor: demonstration in nervous tissue. Science 179:1011-1014. doi: 10.1126/science.179.4077.1011
12. Armstrong SC, Cozza KL (2003) Pharmacokinetic drug interactions of morphine, codeine, and their derivatives: theory and clinical reality, part II. Psychosomatics 44:515-520 (Pubitemid 37352231)
13. Braenden OJ, Eddy NB, Halbach H (1955) Synthetic substances with morphine-like effect; relationship between chemical structure and analgesic action. Bull World Health Organ 13:937-998
14. Eddy NB, Halbach H, Braenden OJ (1956) Synthetic substances with morphine-like effect; relationship between analgesic action and addiction liability, with a discussion of the chemical structure of addiction-producing substances. Bull World Health Organ 14:353-402
15. Dunbar PJ, Chapman CR, Buckley FP, Gavrin JR (1996) Clinical analgesic equivalence for morphine and hydromorphone with prolonged PCA. Pain 68:265-270. doi: (Pubitemid 27025883)
16. ZR Chen RJ Irvine AA Somogyi F Bochner 1991 Mu receptor binding of some commonly used opioids and their metabolites Life Sci 48 2165 2171 10.1016/0024-3205(91)90150-A 1851921 10.1016/0024-3205(91)90150-A 1:CAS:528:DyaK3MXksVWhu7g%3D Chen ZR, Irvine RJ, Somogyi AA, Bochner F (1991) Mu receptor binding of some commonly used opioids and their metabolites. Life Sci 48:2165-2171. doi: 10.1016/0024-3205(91)90150-A
17. Mayyas F, Fayers P, Kaasa S, Dale O (2010) A systematic review of oxymorphone in the management of chronic pain. J Pain Symptom Manage 39:296-308
18. NB Eddy LE Lee Jr 1959 The analgesic equivalence to morphine and relative side action liability of oxymorphone (14-hydroxydihydro morphinone) J Pharmacol Exp Ther 125 116 121 10.1016/j.jpainsymman.2009.07.010 13631610 1:CAS:528:DyaG1MXlt1CjtA%3D%3D Eddy NB, Lee LE Jr (1959) The analgesic equivalence to morphine and relative side action liability of oxymorphone (14-hydroxydihydro morphinone). J Pharmacol Exp Ther 125:116-121. doi: 10.1016/j.jpainsymman.2009.07.010
19. Narita M, Nakamura A, Ozaki M, Imai S, Miyoshi K, Suzuki M, Suzuki T (2008) Comparative pharmacological profiles of morphine and oxycodone under a neuropathic pain-like state in mice: evidence for less sensitivity to morphine. Neuropsychopharmacology 33:1097-1112. doi: (Pubitemid 351367533)
20. Lemberg KK, Kontinen VK, Siiskonen AO, Viljakka KM, Yli-Kauhaluoma JT, Korpi ER, Kalso EA (2006) Antinociception by spinal and systemic oxycodone: why does the route make a difference? In vitro and in vivo studies in rats. Anesthesiology 105:801-812. doi: (Pubitemid 44477327)
21. Bostrom E, Simonsson US, Hammarlund-Udenaes M (2006) In vivo blood-brain barrier transport of oxycodone in the rat: indications for active influx and implications for pharmacokinetics/pharmacodynamics. Drug Metab Dispos 34:1624-1631. doi: (Pubitemid 44285405)
22. Tunblad K, Jonsson EN, Hammarlund-Udenaes M (2003) Morphine blood-brain barrier transport is influenced by probenecid co-administration. Pharm Res 20:618-623. doi: (Pubitemid 36438906)
23. Aceto MD, Harris LS, Abood ME, Rice KC (1999) Stereoselective mu- and delta-opioid receptor-related antinociception and binding with (+)-thebaine. Eur J Pharmacol 365:143-147. doi: (Pubitemid 29070758)
24. Tortella FC, Cowan A, Adler MW (1984) Studies on the excitatory and inhibitory influence of intracerebroventricularly injected opioids on seizure thresholds in rats. Neuropharmacology 23:749-754. doi: (Pubitemid 14089156)
25. Vardanyan RS, Hruby VJ (eds) (2006) Synthesis of essential drugs. Elsevier, USA
26. NB Eddy 1948 Pharmacology of metopon and other new analgesic opium derivatives Ann NY Acad Sci 51 51 58 10.1111/j.1749-6632.1948.tb27250.x 18890117 10.1111/j.1749-6632.1948.tb27250.x 1:CAS:528:DyaH1MXovVKi Eddy NB (1948) Pharmacology of metopon and other new analgesic opium derivatives. Ann NY Acad Sci 51:51-58. doi: 10.1111/j.1749-6632.1948.tb27250.x
27. Blane GF, Boura ALA, Fitzgera AE, Lister RE (1967) Actions of etorphine hydrochloride (m99) - A potent morphine like agent. Br J Pharmacol Chemother 30:11-22
28. Yeh SY (1981) Analgesic activity and toxicity of oripavine and phi-dihydrothebaine in the mouse and rat. Arch Int Pharmacodyn Ther 254:223-240
29. Nikolaev VO, Boettcher C, Dees C, Bunemann M, Lohse MJ, Zenk MH (2007) Live cell monitoring of mu-opioid receptor-mediated G-protein activation reveals strong biological activity of close morphine biosynthetic precursors. J Biol Chem 282:27126-27132. doi: (Pubitemid 47501971)
30. Carl F, Schmidt AEL (1932) A note concerning the actions of pseudomorphine. J Pharmacol Exp Ther 47:473-485
31. Travell J (1931) A contribution to the pharmacology of pseudomorphine. J Pharmacol Exp Ther 42:123-150
32. Gong J, Strong JA, Zhang S, Yue X, DeHaven RN, Daubert JD, Cassel JA, Yu G, Mansson E, Yu L (1998) Endomorphins fully activate a cloned human mu opioid receptor. FEBS Lett 439:152-156. doi: (Pubitemid 28537883)
33. Chavkin C, Sud S, Jin W, Stewart J, Zjawiony JK, Siebert DJ, Toth BA, Hufeisen SJ, Roth BL (2004) Salvinorin A, an active component of the hallucinogenic sage salvia divinorum is a highly efficacious kappa-opioid receptor agonist: structural and functional considerations. J Pharmacol Exp Ther 308:1197-1203. doi: (Pubitemid 38263998)
34. S Charpentier S Sagan A Delfour P Nicolas 1991 Dermenkephalin and deltorphin I reveal similarities within ligand-binding domains of mu- and delta-opioid receptors and an additional address subsite on the delta-receptor Biochem Biophys Res Commun 179 1161 1168 10.1016/0006-291X(91)91693-7 1656944 10.1016/0006-291X(91)91693-7 1:CAS:528:DyaK3MXmslSrsbY%3D Charpentier S, Sagan S, Delfour A, Nicolas P (1991) Dermenkephalin and deltorphin I reveal similarities within ligand-binding domains of mu- and delta-opioid receptors and an additional address subsite on the delta-receptor. Biochem Biophys Res Commun 179:1161-1168. doi: 10.1016/0006-291X(91)91693-7
35. RK Reinscheid HP Nothacker A Bourson A Ardati RA Henningsen JR Bunzow DK Grandy H Langen FJ Monsma O Civelli 1995 Orphanin-FQ-a neuropeptide that activates an opioid-like g-protein-coupled receptor Science 270 792 794 10.1126/science.270.5237.792 7481766 10.1126/science.270.5237.792 1:CAS:528:DyaK2MXptV2isr4%3D Reinscheid RK, Nothacker HP, Bourson A, Ardati A, Henningsen RA, Bunzow JR, Grandy DK, Langen H, Monsma FJ, Civelli O (1995) Orphanin-FQ-a neuropeptide that activates an opioid-like g-protein-coupled receptor. Science 270:792-794. doi: 10.1126/science.270.5237.792