The opioid receptor independent actions of kappa receptor agonists in the cardiovascular system

Current Pharmaceutical Design

Volumn 10, Issue 20, 2004, Pages 2429-2444

  Pugsley, Michael K ^a  

^a FOREST RESEARCH INSTITUTE   (United States)

Author keywords

Arylacetamide; Cardiac arrhythmia; Ischaemia; Opioid; Ventricular fibrillation

Indexed keywords

3,4 DICHLORO N METHYL N [2 (1 PYRROLIDINYL)CYCLOHEXYL]BENZENEACETAMIDE METHANESULFONATE; 5,9 DIETHYL 2 (3 FURYLMETHYL) 2' HYDROXY 6,7 BENZOMORPHAN; ACETAMIDE DERIVATIVE; ANALGESIC AGENT; ANTIARRHYTHMIC AGENT; ANTIDEPRESSANT AGENT; BETA ENDORPHIN; CALCIUM ION; DELTA OPIATE RECEPTOR; ENADOLINE; ENDORPHIN; GUANINE NUCLEOTIDE BINDING PROTEIN; KAPPA OPIATE RECEPTOR; KAPPA OPIATE RECEPTOR AGONIST; LOCAL ANESTHETIC AGENT; MORPHINE; N ALLYLNORMETAZOCINE; N METHYL N [2 (1 PYRROLIDINYL)CYCLOHEXYL]BENZO[B]THIOPHENE 4 ACETAMIDE; N METHYL N [7 (1 PYRROLIDINYL) 1 OXASPIRO[4.5]DEC 8 YL]BENZENEACETAMIDE; NALOXONE; NALTREXONE DERIVATIVE; NORBINALTORPHIMINE; OPIATE ANTAGONIST; OPIATE RECEPTOR; PD 129290; POTASSIUM ION; QUADAZOCINE; SODIUM ION; SPIRADOLINE MESILATE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANALGESIC ACTIVITY; ARRHYTHMOGENESIS; BINDING AFFINITY; CARDIOTOXICITY; CARDIOVASCULAR SYSTEM; CENTRAL NERVOUS SYSTEM; DISEASE MODEL; DRUG RECEPTOR BINDING; DRUG STRUCTURE; HEART ARRHYTHMIA; IN VITRO STUDY; IN VIVO STUDY; MOLECULAR MECHANICS; NONHUMAN; PRIORITY JOURNAL; PROTEIN FUNCTION; REGULATORY MECHANISM; RESPIRATION DEPRESSION; REVIEW; STRUCTURE ANALYSIS;

ANALGESICS, OPIOID; ANIMALS; CARDIOVASCULAR PHYSIOLOGY; DISEASE MODELS, ANIMAL; HUMANS; MOLECULAR STRUCTURE; RECEPTORS, OPIOID, KAPPA;

EID: 3242886584     PISSN: 13816128     EISSN: None     Source Type: Journal    
DOI: 10.2174/1381612043383917     Document Type: Review

References (102)

1. Martin WR. Opioid antagonists. Pharmacol Rev 1967; 19: 464-521.
2. Beckett AH, Casy AF. Synthetic analgesics: stereochemical considerations. J Pharm Pharmacol 1954; 6: 986-99.
3. Pert CB, Snyder SH. Opiate receptor: Demonstration in nervous tissue. Science 1973; 179: 1011-4.
4. Hughes J, Smith TW, Kosterlitz HW, Fothergill LA, Morgan BA, Morris HR. Identification of two related pentapeptides from the brain with potent opiate agonist activity. Nature 1975; 25: 577-9.
5. Fowler CJ, Fraser GL. μ-, δ-, and κ-opioid receptors and their subtypes. A critical review with emphasis on radioligand binding experiments. Neurochem Int 1994; 24: 401-26.
6. Martin WR, Eades CG, Thompson JA, Huppler RE, Gilbert PE. The effects of morphine and nalorphine-like drugs on the non-dependent and morphine-dependent chronic spinal dog. J Pharmacol Exp Therap 1976; 197: 517-32.
7. Martin WR. Pharmacology of opioids. Pharmacol Rev 1984; 35: 285-323.
8. Pugsley MK. The diverse molecular mechanisms responsible for the actions of opioids on the cardiovascular system. Pharm Therap 2002 93: 51-75.
9. Evans CJ, Keith DE, Morrison H, Magendzo K, Edwards RH. Cloning of a delta opioid receptor by functional expression. Science 1992; 258: 1952-5.
10. Reisine T, Bell GI. Molecular biology of opioid receptors. TINS 1993; 16: 506-10.
11. Knapp RJ, Malatynska E, Collins N, Fang L, Wang JY, Hruby VJ, Roeske WR, Yamamura HI. Molecular biology and pharmacology of cloned opioid receptors. FASEB J 1995; 9: 516-25.
12. Meng F, Hoversten MT, Thompson RC, Taylor L, Watson SJ, Akil H. A chimeric study of the molecular basis of affinity and selectivity of the κ and the δ opioid receptors: potential role of extracellular domains. J Biol Chem 1995; 270: 12730-6.
13. Wang JB, Imai Y, Eppler CM, Gregor P, Spivak CE, Uhl GR. Mu opiate receptor: cDNA cloning and expression. Proc Natl Acad Sci 1993; 90: 10230-4.
14. Krumins SA, Faden AE, Feuerstein G. Opiate binding in rat hearts. modulation of binding after hemorrhagic shock. Biochem Biophys Res Comm 1985; 127: 120-8.
15. Xie G, Meng F, Mansour A, Thompson RC, Hoversten MT, Golkstein A, et al. Primary structure and functional expression of a guinea pig κ opioid (dynorphin) receptor. Proc Nat Acad Sci 1994: 91: 3779-83.
16. Yasuda K, Raynor K, Kong H, Breder CD, Takeda J, Reisine T, Bell GI. Cloning and functional comparison of kappa and delta opioid receptors from mouse brain. Proc Natl Acad Sci USA 1993; 90: 6736-40.
17. Minami M, Toya T, Katai Y, Maekawa K, Nakamura S, Onogi T, Kaneko S, Satoh M. Cloning and expression of a cDNA for the rat κ -opioid receptor. FEBS Lett 1993; 329: 291-5.
18. Mansson E, Bare L, Yang D. Isolation of a human κ opioid receptor cDNA from placenta. Biochem Biophys Res Comm 1994; 202: 1431-7.
19. z coupling to the rat κ-opioid receptor. FEBS Lett 1995; 360: 97-9.
20. Zhu Y, Hsu MS, Pintar JE. Developmental expression of the mu, kappa, and delta opioid receptor mRNAs in mouse. J Neurosci 1998; 18: 2538-49.
21. Mansour A, Khachaturian H, Lewis ME. Anatomy of CNS opioid receptors. TINS 1988; 11: 309-14.
22. Barron BA, Jones CE, Caffrey JL. Pericardial repair depresses canine cardiac catecholamines and met-enkephalin. Regul Pept 1995; 59: 313-20.
23. Barron BA. Opioid peptides and the heart. Cardiovasc Res 1999; 43: 13-6.
24. Millington WR, Rosenthal DW, Unal CB, Nyquist-Battie C. Localization of pro-opiomelanocortin mRNA transcripts and peptide immunoreactivity in rat heart. Cardiovasc Res 1999; 43: 107-16.
25. Vargish T, Beamer KC. Delta and run receptor agonists correlate with greater depression of cardiac function than morphine sulfate in perfused rat hearts. Circ Shock 1989; 27: 245-51.
26. Grudt TJ, Williams JT. κ-opioid receptors also increase potassium conductance. Proc Nat Acad Sci USA 1993; 90: 11429-32.
27. Moore SD, Madma SG, Schweitzer P, Siggins R. Voltage-dependent effects of opioid peptides on hippocampal CA3 pyramidal neurons in vitro. J Neurosci 1994; 14: 809-20.
28. Frazier DT, Ohta M, Narahashi T. Nature of the morphine receptor present in the squid axon. Proc Soc Exp Biol Med 1973; 143: 1209-14.
29. Carratu MR, Mitolo-Chieppa D. Inhibition of ionic currents in frog node of ranvier treated with naloxone. Br J Pharmacol 1982; 77: 115-9.
30. Alzheimer C, ten Bruggencate GT. Nonopioid actions of the κ-opioid receptor agonists, U-50,488H and U-69,593, on electrophysiologic properties of hippocampal CA3 neurons in vitro. J Pharmacol Exp Therap 1990; 255: 900-5.
31. Pugsley MK, Penz WP, Walker MJA. Cardiovascular actions of U-50,488H and related kappa agonists. Cardiovasc Drug Rev 1993; 11: 151-164,
32. Pugsley MK, Saint DA, Walker MJA. An electrophysiological basis for the antiarrhythmic actions of the κ-opioid receptor agonist U-50,488H. Eur J Pharmacol 1994; 261: 303-9.
33. Szmuszkovicz J, Von Voigtlander P. Benzeneacetamide amines: structurally novel non-μ opioids. J Med Chem 1982; 25: 1125-6.
34. Von Voigtlander PF, Collins RJ, Lewis RA, Neff GL. U-50,488H (trans-3,4-dichloro-N -methyl-N-[2-(1- pyrrolidinyl)cyclohexyl]-benzeneacetamide): Prototype for a new class of opioid analgesics. Pharmacologist 1981; 23: 134.
35. Von Voigtlander PF, Lewis RA. A comparison of putative kappa receptor agonists: analgesic mechanisms and narcotic antagonist activity in mice. Fed Proc 1982; 41: 1314.
36. Von Voigtlander PF, Lewis RA. U-50,488H, a selective kappa opioid agonist: comparison to other reputed kappa agonists. Prog-Neuropsychopharmacol Biol-Psych 1982; 6: 467-70.
37. Clarke CR, Halfpenny PR, Hill RG, Horwell DC, Hughes J, Jarvis TC, Rees DC, Schofield D. Highly selective kappa opioid analgesics. Synthesis and structure-activity relationships of novel N-[(2-aminocyclohexyl)aryl]acetamide and N-[(2-aminocyclohexyl)aryloxy]acetamide derivatives. J Med Chem 1988; 31: 831-6.
38. Hunter JC, Leighton GE, Meecham KG, Boyle SJ, Horwell DC, Rees DC, Hughes J. CI-977, a novel and selective agonist for the kappa-opioid receptor. Br J Pharmacol. 1990; 101: 183-9.
39. Lahti RA, Von Voigtlander PF, Barsuhn C. Properties of a selective kappa agonist, U-50,488H. Life Sci 1982; 31: 2257-60.
40. Von Voigtlander PF, Lahti RA, Ludens JH. U-50,488H: A selective and structurally novel non-mu (kappa) opioid agonist. J Pharmacol Exp Therap 1982; 224: 7-12.
41. Von Voigtlander PF, Lewis RA. Analgesic and mechanistic evaluation of spiradoline, a potent kappa opioid. J Pharmacol Exp Therap 1988; 246: 259-262.
42. Halfpenny PR, Horwell DC, Hughes J, Hunter JC, Rees DC. Highly selective kappa-opioid analgesics. 3. Synthesis and structure-activity relationships of novel N-[2-(1-pyrrolidinyl)-4- or -5-substituted-cyclohexyl]arylacetamide derivatives. J Med Chem 1990; 33: 286-91.
43. Kunihara M, Ohyama M, Nakano M, Hayashi S. Analgesic activity of spiradoline mesylate (U-62,066E), a kappa opioid agonist in mice, Life Sci 1989; 45: 1191-8.
44. Kunihara M, Ohyama M, Nakano M. Effects of spiradoline mesylate, a selective κ-opioid-receptor agonist, on the central dopamine system with relation to mouse locomotor activity and analgesia. Japan J Pharmacol 1993; 62: 223-30.
45. 3H] U69,593 Binding sites in the rat heart by receptor binding assays. J Mol Cell Cardiol 1991; 23: 1297-1302.
46. Barron BA, Gu H, Gaugl JF, Caffrey JL. Screening for opioids in dog heart. J Mol Cell Cardiol 1992; 24: 67-77.
47. Zhang WM, Jin WQ, Wong TM. Multiplicity of kappa opioid receptor binding in the rat cardiac sarcolemma. J Mol Cell Cardiol 1996; 28: 1547-54.
48. Ventura C, Bastagli L, Bernardi P, Caldarera CM, Guarnieri C. Opioid receptors in rat cardiac sarcolemma: effect of phenylephrine and isoproterenol. Biochim Biophys Acta 1989; 987: 69-74.
49. Ela C, Barg J, Vogel Z, Hasin Y, Eilam Y. Distinct components of morphine effects on cardiac myocytes are mediated by the kappa and delta opioid receptors. J Mol Cell Cardiol 1997; 29: 711-20.
50. Pugsley MK, Penz WP, Walker MJA, Wong T-M. Cardiovascular actions of the kappa receptor agonist, U-50,488H, in the absence and presence of opioid receptor blockade. Br J Pharmacol 1992; 105: 521-6.
51. Pugsley MK, Saint DA, Penz WP, Walker MJA. Electrophysiological and antiarrhythmic actions of the kappa agonist PD129290, and its R,R (+) enantiomer, PD 129289. Br 3 Pharmacol 1993; 110: 1579-85.
52. Pugsley MK, Penz WP, Walker MJA, Wong T-M. Antiarrhythmic effects of U-50,488H in rats subject to coronary artery occlusion. Eur J Pharmacol 1992; 212: 15-19.
53. Hall ED, Wolf DL, McCall RB. Cardiovascular depressant effects of the kappa opioid receptor agonists U-50,488H and spiradoline mesylate. Circ Shock 1988; 26: 409-17.
54. Pugsley MK, Hayes ES, Saint DA, Walker MJA. Do related kappa agonists produce similar effects on cardiac ion channels? Proc West Pharmacol Soc 1995; 38: 25-7.
55. Pugsley MK, Saint DA, Hayes E, Kramer D, Walker MJA. The sodium channel blocking properties of spiradoline, a κ-receptor agonist, are responsible for its antiarrhythmic action in the rat. J Cardiovasc Pharmacol 1988; 32: 863-74.
56. Brasch H. Influence of the optical isomers (+)-and (-)-naloxone on beating frequency, contractile force and action potentials of guinea-pig isolated cardiac preparations. Br J Pharmacol 1986; 88: 733-40.
57. Kaschube M, Brasch H. Negative chronotropic but no antiarrhythmic effect of (+) and (-)-naloxone in rats and guinea pigs. Cardiovasc Res 1991; 25: 230-3.
58. Penz WP, Pugsley MK, Hsieh MZ, Walker MJA. A new ECG measure (RSh) for detecting possible sodium channel blockade in vivo in rats. J Pharmacol Methods 1992; 27: 51-8.
59. Frame LH, Argentieri TM. Naloxone has local anesthetic effects on canine cardiac Purkinje fibres. Circulation 1985; 72: 234.
60. Sarne Y, Flitstein A, Oppenheimer E. Anti-arrhythmic activities of opioid agonists and antagonists and their stereoisomers. Br J Pharmacol 1991; 102: 696-8.
61. Xia Q, Sheng JZ, Tai KK, Wong TM. Effects of chronic U50,488H treatment on binding and mechanical responses of the rat hearts. J Pharmacol Exp Therap 1994; 268: 930-4.
62. Alarcón S, Hernández J, Laorden ML. Cardiac electrophysiological effects of U-50,488H on guinea-pig papillary muscle. Neuropeptides 1993; 24 313-6.
63. Helgesen KG, Refsum H. Arrhythmogenic, antiarrhythmic and inotropic properties of opioids. Effects of piritramide, pethidine and morphine compared on heart muscle isolated from rats. Pharmacology 1987; 35: 121-9.
64. Hicks MN, Oldroyd KG, Cobbe SM. Ischaemia, extracellular potassium accumulation and the cardiac electrophysiological effects of dl and d-naloxone. Eur Heart J 1992; 13(Suppl): SI - SIV.
65. Kasper E, Ventura C, Ziman BD, Lakatta EG, Weisman H, Capogrossi MC. Effect of U-50,488H on the contractile response of cardiomypathic hamster ventricular myocytes. Life Sci 1992; 50: 2029-35.
66. Lakatta EG, Xiao R, Ventura C, Guarnieri C, Spurgeon HA, Capogrossi MC, Gambassi G. Negative feedback of opioid peptide receptor stimulation on α-adrenergic effects in heart cells. J Mol Cell Cardiol 1992; 24: S25.
67. duBell WH, Lakatta EG. The effects of the κ-opioid agonist U50,488H on guinea pig, ventricular myocytes. Biophys J 1991; 59: 465a.
68. Utz J, Eckert R, Trautwein W. Inhibition of L-type calcium currents in guinea pig ventricular myocytes by the kappa-opioid agonist U50488H does not involve binding to opiate receptors. J Pharmacol Exp Ther 1995; 274: 627-33.
69. Wu C, Fry CH, Henry J. The mode of action of several opioids on cardiac muscle. Exp Physiol 1997; 82: 261-72.
70. Ulens C, Daenens P, Tytgat J. Norpropoxyphene-induced cardiotoxicity is associated with changes in ion-selectivity and gating of HERG currents. Cardiovasc Res 1999; 44: 568-78.
71. Hung CF, Tsai CH, Su MJ. Opioid receptor independent effects of morphine on membrane currents in single cardiac myocytes. Br J Anaesth 1998; 81: 925-31.
72. Curtis MJ, Pugsley MK, Walker MJA. Endogenous chemical mediators of ventricular arrhythmias in ischaemic heart disease. Cardiovasc Res 1993; 27: 703-19.
73. Sitsapesan R, Parratt JR. The effects of drugs interacting with opioid receptors in the early ventricular arrhythmias arising from myocardial ischaemia. Br J Pharmacol 1989; 97: 795-800.
74. Fagbemi O, Lepran I, Parratt JR, Szekeres L. Naloxone inhibits early arrhythmias resulting from acute coronary ligation. Br J Pharmacol 1982; 76: 504-6.
75. Holaday JW, Faden AI. Naloxone reversal of endotoxin hypotension suggests a role of endorphins in shock. Nature 1978; 75: 450-1.
76. Holaday JW. Cardiovascular effects of endogenous opiate systems. Ann Rev Pharmacol Toxicol 1983; 23: 541-94.
77. Parratt JR, Sitsapesan R. Stercospecific antiarrhythmic effect of opioid receptor antagonists in myocardial ischaemia. Br J Pharmacol 1986; 87: 621-7.
78. Mackenzie JE, Parratt JR, Sitsapesan R. (1986). The effects of drugs interacting with opioid receptors on ischaemic arrhythmias in anaesthetised rats. Br J Pharmacol 1986: 87: 89A.
79. Murphy DB, Murphy MB. Opioid antagonist modulation of ischaemia-induced ventricular arrhythmias: a peripheral mechanism. J Cardiovasc Pharmacol 1999; 33: 122-5.
80. Lee AYS. Endogenous opioid peptides and cardiac arrhythmias. Int J Cardiol 1990; 27: 145-51.
81. Zhan ZY, Lee AYS, Wong TM. Naloxone blocks the cardiac effects of myocardial ischaemia and reperfusion in the rat isolated heart. Clin Exp Pharmacol Physiol 1985; 12: 373-8.
82. Huang XD, Lee AYS, Wong TM, Zhan CY, Zhao YY. Naloxone inhibits arrhythmias induced by coronary artery occlusion and reperfusion in anaesthetized dogs. Br J Pharmacol 1986; 87: 475-7.
83. Lee AYS. Stereospecific antiarrhythmic effects of naloxone against myocardial ischaemia and reperfusion in the dog. Br J Pharmacol 1992; 107: 1057-60.
84. Wong TM, Lee YS. Cardiac antiarrhythmic evolution of naloxone with or without propranolol using a modified chloroform-hypoxia screening test in the rat. Clin Exp Pharmacol Physiol 1985; 12, 379-85.
85. Lee AYS, Chen YT, Kan MN, P'eng FK, Chai CY, Kuo JS. Consequences of opiate agonist and antagonist in myocardial ischaemia suggest a role of endogenous opioid peptides in ischaemic heart disease, Cardiovasc Res 1992; 24: 392-5.
86. Fagbemi O, Kane KA, Lepran I, Parratt JR, Szekeres L. Antiarrhythmic actions of meptazinol, a partial agonist at opiate receptors, in acute myocardial ischaemia. Br J Pharmacol 1983; 78: 455-60.
87. Sagy M, Shavit G, Oron Y, Vedne BA, Gitter S, Sarne Y. Nonopiate effect of naloxone on cardiac muscle contractility. J Cardiovasc Pharmacol 1987; 9: 682-5.
88. Boachie-Ansah G, Sitsapesan R, Kane KA, Parratt JR. The antiarrhythmic and cardiac electrophysio logical effects of buprenorphine. Br J Pharmacol 1989; 97: 801-8.
89. Bergey JL, Beil ME. Antiarrhythmic evaluation of naloxone against acute coronary occlusion-induced arrhythmias in pigs. Eur J Pharmacol 1983; 90: 427-31.
90. Pruett JK, Blair JR, Adams RJ. In: Estafanous ES Ed, Opioids in Anesthesia. Boston: Butterworth-Heinemann Publishing Co. 1991:61-70.
91. Wong TM, Lee YS, Tai KK. Effects of drugs interacting with opioid receptors during normal perfusion or ischaemia and reperfusion in the isolated rat heart- an attempt to identify cardiac opioid receptor subtype(s) involved in arrhythmogenesis. J Mol Cell Cardiol 1990; 22: 1167-75.
92. Weihe E, McKnight AT, Corbett AD, Kosterlitz HW. Proenkephalin-and prodynorphin-derived opioid peptides in guinea-pig heart. Neuropeptides 1985; 5: 453-6.
93. Yong SL, Abraham S, Pugsley MK, Hayes ES, Zolotoy AB, Walker MJA. SAR evidence that antiarrhythmic activity is unrelated to opioid kappa agonist activity. Br J Pharmacol 1996; 119: P35.
94. + channel blocking actions of the novel class I anti-arrhythmic agent RSD 921. Br J Pharmacol 1999; 127: 9-18.
95. Pugsley MK, Yu EJ, Goldin AL. Potent and use-dependent block of cardiac sodium channels by U-50,488H, a benzeneacetamide kappa opioid receptor agonist. Exp Clin Cardiol 2001; 6: 1-11.
96. Deamer RL, Wilson DR, Clark DS, Pritchard JG. Torsades de pointes associated with high dose levomethadyl acetate (ORLAAM). J Addict Dis 2001; 20: 1-5.
97. Krantz, MJ, Lewkowiez L, Hays H, Woodroffe MA, Robertson AD Mehler PS. Torsades de pointes associated with very-high-dose methadone. Ann Int Med 2002: 137: 142.
98. Berzetei-Gurske IP, White A, Polgar W, DeCosta BR, Pasternak GW, Toll L. The in vitro pharmacological characterization of naloxone benzoylhydrazone. Eur J Pharmacol 1995; 277: 257-63.
99. Curtis MJ, Walker MJA. Quantification of arrhythmias using scoring systems: an examination of seven scores in an in vivo model of regional myocardial ischaemia. Cardiovasc Res 1988; 22: 656-65.
100. Kitts DD, Weiler K. Bioactive proteins and peptides from food sources. Applications of bioprocesses used in isolation and recovery. Curr Pharm Design 2003; 9(16): 1309-23.
101. Teschemacher H. Opioid receptor ligands derived from food proteins. Curr Pharm Design 2003; 9(16): 1331-44.
102. Yoshikawa M, Takahashi M, Yang S. Delta opioid peptides derived from plant proteins. Curr Pharm Design 2003; 9(16): 1325-30.