Development of muscarinic analgesics derived from epibatidine: Role of the M4 receptor subtype

Journal of Pharmacology and Experimental Therapeutics

Volumn 288, Issue 3, 1999, Pages 1143-1150

  Ellis, James L ^a   Harman, Dean ^b   Gonzalez, Javier ^b   Spera, Michael L ^b   Liu, Ronggang ^b   Shen, T Y ^b   Wypij, Donna M ^a   Zuo, Fangming ^a  

^a Atmospheric and Environmental   (United States)

^b UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 [5 (3 AMINO 1,2,4 OXODIAZOLYL)] [2.2.1.] AZABICYCLOHEPTANE; 2 [5 (3 METHYL 1,2,4 OXADIAZOLYL)] [2.2.1.] 7 AZABICYLOHEPTANE; ATROPINE; CMI 1145; CMI 936; EPIBATIDINE; EPIBATIDINE DERIVATIVE; GUANINE NUCLEOTIDE BINDING PROTEIN; HIMBACINE; MECAMYLAMINE; MUSCARINIC AGENT; MUSCARINIC M4 RECEPTOR; MUSCARINIC RECEPTOR BLOCKING AGENT; PERTUSSIS TOXIN; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANTINOCICEPTION; ARTICLE; BODY TEMPERATURE; CONTROLLED STUDY; DRUG INHIBITION; FEMALE; INTRATHECAL DRUG ADMINISTRATION; MOUSE; NOCICEPTION; NONHUMAN; PRIORITY JOURNAL; SALIVATION; TAIL FLICK TEST;

ALKALOIDS; ANALGESICS, NON-NARCOTIC; ANIMALS; BICYCLO COMPOUNDS, HETEROCYCLIC; BODY TEMPERATURE; FEMALE; FURANS; MICE; MUSCARINIC AGONISTS; NAPHTHALENES; OXADIAZOLES; PIPERIDINES; PYRIDINES; RECEPTOR, MUSCARINIC M4; RECEPTORS, MUSCARINIC; SALIVATION;

EID: 0033056473     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (36)

1. Badio B and Daly JW (1994) Epibatidine, a potent analgetic and nicotinic agonist. Mol Pharmacol 45:563-569.
2. Bartolini A, Ghelardini C, Fantetti L, Malcangio M, Malmberg-Aiello P and Giotti A (1992) Role of muscarinic receptor subtypes in central antinociception. Br J Pharmacol 105:77-82.
3. Bonhaus DW, Bley KR, Broka CA, Fontana DJ, Leung E, Lewis R, Shieh A and Wong EHF (1995) Characterization of the electrophysiological, biochemical and behavioral action of epibatidine. J Pharmacol Exp Ther 272:1199-1203.
4. Borenstein MT, Santiago M, Valentine HH and Potter LT (1996) Autoradiographic evidence that m4 muscarinic receptors modulate nociception in the human spinal cord. Neurosci Abstr 22:871.
5. Carroll FI, Gray JL, Abraham P, Kuzemko MA, Lewin AH and Kuhar MJ (1993) 3-Aryl-2-(3′-substituted-1′,2′,4′-oxadiazol-5′-yl) tropane analogues of cocaine: Affinities at the cocaine binding site at the dopamine, serotonin, and norepinephrine transporter. J Med Chem 36:2886-2890.
6. Caulfield MP (1993) Muscarinic receptors-characterization, coupling and function. Pharmacol Ther 58:319-379.
7. Chen G (1958) The anti-tremorine effect of some drugs as determined by Hoffner's method of testing analgesia in mice. J Pharmacol Exp Ther 124:73-76.
8. Chung KM, Song DK, Suh HW, Lee MH and Kim YK (1994) Effects of intrathecal or intracerebroventricular pretreatment with pertussis toxin on antinociception induced by b-endorphin or morphine administered intracerebroventricularly in mice. Naunyn-Schmiedeberg's Arch Pharmacol 349:388-593.
9. Dawson GR, Johnstone S, Boyley P and Iverson SD (1991) The effects of a novel muscarinic agonist, L-689,666 in the mouse tail-flick test of antinociception. Br J Pharmacol 104:458P.
10. Dorje F, Wess J, Lambrecht G, Tacke R, Mutschler E and Brann MR (1991) Antagonist binding profiles of five cloned human muscarinic receptor subtypes. J Pharmacol Exp Ther 256:727-733.
11. Eglen RM and Watson N (1996) Selective muscarinic receptor agonists and antagonists. Pharmacol Toxicol 78:59-68.
12. Galeotti N, Ghelardini C and Bartolini A (1996) Effect of pertussis toxin on morphine, diphenhydramine, baclofen, clomipramine and physostigmine antinociception. Eur J Pharmacol 308:125-133.
13. Gonzalez J, Koontz JI, Myers WH, Hodges LM, Sabat M, Nilsson KR, Neely LK and Harman WD (1995) Osmium-promoted dipolar cycloadditions with pyrroles: An efficient, stereoselective synthesis of 7-azanorbornanes. J Am Chem Soc 117:3405-3421.
14. Herz A (1962) Actions of arecoline on the central nervous system. Naunyn-Schmiedeberg's Arch Exp Pathol Pharmakol 242:414-429.
15. Hildebrandt JD, Sekura RD, Codina J, Iyengar R, Manclark CR and Birnbaumer J (1983) Stimulation and inhibition of adenyl cyclases mediated by distinct regulatory proteins. Nature (London) 302:706-708.
16. Hoehn K, Reid A and Sawynok J (1988) Pertussis toxin inhibits antinociception produced by intrathecal injection of morphine, noradrenaline and baclofen. Eur J Pharmacol 146:65-72.
17. Höglund AU and Baghdoyan HA (1997) M2, M3 and M4, but not M1, muscarinic receptor subtypes are present in rat spinal cord. J Pharmacol Exp Ther 281:470-477.
18. Huang DF and Shen TY (1993) A versatile total synthesis of epibatidine and analogs Tetrahedron Lett 34:4477-4480.
19. Hulme EC, Birdsall NJM and Buckley NJ (1990) Muscarinic receptor subtypes. Anna Rev Pharmacol Toxicol 30:633-673.
20. Hylden JLK and Wilcox GL (1980) Intrathecal morphine in mice: A new technique. Eur J Pharmacol 67:313-316.
21. Iwamoto ET and Marion L (1993) Characterization of the antinociception produced by intrathecally administered muscarinic agonists in rats. J Pharmacol Exp Ther 266:329-338.
22. Jolkkonen M, van Giersbergen PLM, Hellman U, Wernstedt C and Karlsson E (1994) A toxin from the green mamba Dendroaspis angusticeps: Amino acid sequence and selectivity for muscarinic m4 receptors. FEBS Lett 352:91-94.
23. Liang JS, Carsi-Gabrenas JM, Krajewski JL, McCafferty JM, Purkerson SL, Santiago MP, Straus WL, Valentine HH and Potter LT (1996) Anti-muscarinic toxins from Dendroaspis angusticeps. Toxicon 34:1257-1267.
24. Max SI, Liang J-S, Purkerson SL and Potter LT (1993) M4-Toxin, a selective, reversible allosteric antagonist of m4 muscarinic receptors. Neurosci Abstr 19:464.
25. Miller JH, Aagaard PJ, Gibson VA and McKinney M (1992) Binding and functional selectivity of himbacine for cloned and neuronal muscarinic receptors. JPharmacol Exp Ther 263:663-667.
26. Naguib M and Yaksh TL (1997) Characterization of muscarinic receptor subtypes that mediate antinociception in the rat spinal cord. Anesth Analg 85:847-85.
27. Pedigo NW, Dewey WL and Harris LS (1975) Determination and characterization of the antinociceptive activity of intraventricularly administered acetylcholine in mice. J Pharmacol Exp Ther 193:845-852.
28. Qian C, Li T, Shen T, Libertine-Garahan L, Eckman J, Biftu T and Ip S (1993) Epibatidine is a nicotinic analgesic. Eur J Pharmacol 250:13-14.
29. Sauerberg P, Olesen PH, Sheardown MJ, Suzdak PD, Shannon HE, Bymaster FP, Calligaro DO, Mitch CH, Ward JS and Swedberg MDB (1995) Muscarinic agonists as analgesics. Antinociceptive activity versus M1 activity: SAR of alkylthio-TZTP's and related 1,2,5-thiadiazole analogs. Life Sci 56:807-814.
30. Shannon HE, Sheardown MJ, Bymaster FP, Calligaro DO, Delapp NW, Gidda J, Mitch CH, Sawyer BD, Stengel PW, Ward JS, Wong DT, Olesen PH, Suzdak PD, Sauerberg P and Swedberg MDB (1997) Pharmacology of butylthio[2.2.2] (LY297802/NNC11-1053): A novel analgesic with mixed muscarinic receptor agonist and antagonist activity. J Pharmacol Exp Ther 281:884-894.
31. Sheardown MJ, Shannon SE, Swedberg DB, Suzdak PD, Bymaster FP, Olesen PH, Mitch CH, Ward JS and Sauerberg P (1997) M1 receptor agonist activity is not a requirement for muscarinic antinociception. J Pharmacol Exp Ther 281:868-875.
32. Spande TF, Garrafo HM, Edwards MW, Yeh HJC, Pannel L and Daly JW (1992) A novel (chloropyridyl)azabicycloheptane with potent analgesic activity from an Ecuadorian poison frog. J Am Chem Soc 114:3475-3480.
33. Sternweis PC and Robishaw JD (1984) Isolation of two proteins with high affinity for guanine nucleotides from membranes of bovine brain. J Biol Chem 259:13806-13811.
34. Sullivan JP, Decker MW, Brioni JD, Donnelly-Roberts D, Anderson DJ, Bannon AW, Kang CH, Adams P, Piattoni-Kaplan M, Buckley MJ, Gopalakrishnan M, Williams M and Arneric SP (1994) (±)-Epibatidine elicits a diversity of in vitro and in vivo effects mediated by nicotinic acetylcholine receptors. J Pharmacol Exp Ther 271: 624-631.
35. Waelbroeck M, Gillard M, Robberecht P and Christophe J (1990) Binding of selective antagonists to four muscarinic receptors (M1 to M4) in rat forebrain. Mol Pharmacol 38:267-273.
36. Widman M, Tucker S, Brase DA and Dewey WL (1985) Cholinergic agents: Antinociception without morphine-type dependence in rats. Life Sci 36:2007-2015.