Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT) 2A and 5-HT2C receptors

Journal of Pharmacology and Experimental Therapeutics

Volumn 321, Issue 3, 2007, Pages 1054-1061

  Moya, Pablo R ^a   Berg, Kelly A ^b   Gutiérrez Hernandez, Manuel A ^a   Sáez Briones, Patricio ^c   Reyes Parada, Miguel ^c   Cassels, Bruce K ^a   Clarke, William P ^b,d  

^a UNIVERSITY OF CHILE   (Chile)

^b Mays Cancer Center at UT Health San Antonio   (United States)

^c UNIVERSIDAD DE SANTIAGO DE CHILE   (Chile)

^d UNIVERSITY OF TEXAS HEALTH SCIENCE CENTER AT SAN ANTONIO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,5 DIMETHOXY 4 NITROPHENETHYLAMINE; 2,5 DIMETHOXYPHENYLISOPROPYLAMINE; AMINE; PARTIAL AGONIST; PHENETHYLAMINE; PHENYLISOPROPYLAMINE DERIVATIVE; PHOSPHOLIPASE A2; PHOSPHOLIPASE C; PSYCHEDELIC AGENT; SEROTONIN 2A RECEPTOR; SEROTONIN 2C RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; ENZYME ASSAY; IN VITRO STUDY; LIGAND BINDING; NONHUMAN; OVARY CELL; PRIORITY JOURNAL; SIGNAL TRANSDUCTION;

2,5-DIMETHOXY-4-METHYLAMPHETAMINE; AMPHETAMINES; ANIMALS; ARACHIDONIC ACID; BEHAVIOR, ANIMAL; CHO CELLS; CRICETINAE; CRICETULUS; HALLUCINOGENS; HUMANS; INOSITOL PHOSPHATES; MALE; MESCALINE; MOTOR ACTIVITY; PHENETHYLAMINES; RATS; RATS, SPRAGUE-DAWLEY; RECEPTOR, SEROTONIN, 5-HT2A; RECEPTOR, SEROTONIN, 5-HT2C; SIGNAL TRANSDUCTION; TRANSFECTION;

EID: 34248583550     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.106.117507     Document Type: Article

References (40)

1. Acuña-Castillo C, Villalobos C, Moya PR, Sáez P, Cassels BK, and Huidobro-Toro JP (2002) Differences in potency and efficacy of a series of phenylisopropylamine/ phenylethylamine pairs at 5-HT(2A) and 5-HT(2C) receptors. Br J Pharmacol 136:510-519.
2. Bedard P and Pycock CJ (1977) "Wet-dog" shake behaviour in the rat: a possible quantitative model of central 5-hydroxytryptamine activity. Neuropharmacology 16:663-670.
3. Berg KA and Clarke WP (2006) Development of functionally selective agonists as novel therapeutic agents. Drug Discov Today 3:421-428.
4. Berg KA, Maayani S, Goldfarb J, Scaramellini C, Leff P, and Clarke WP (1998) Effector pathway-dependent relative efficacy at serotonin type 2A and 2C receptors: evidence for agonist-directed trafficking of receptor stimulus. Mol Pharmacol 54:94-104.
5. Brea J, Masaguer CF, Villazon M, Cadavid MI, Ravina E, Fontaine F, Dezi C, Pastor M, Sanz F, and Loza MI (2003) Conformationally constrained butyrophenones as new pharmacological tools to study 5-HT2A and 5-HT2C receptor behaviours. Eur J Med Chem 38:433-440.
6. Chang M, Zhang LS, Tam JP, and Sanders-Bush E (2000) Dissecting G proteincoupled receptor signaling pathways with membrane-permeable blocking peptides: endogenous 5-HT2C receptors in choroid plexus epithelial cells. J Biol Chem 275:7021-7029.
7. Clarke WP and Bond RA (1998) The elusive nature of intrinsic efficacy. Trends Pharmacol Sci 19:270-276.
8. Egan CT, Herrick-Davis K, Miller K, Glennon RA, and Teitler M (1998) Agonist activity of LSD and lisuride at cloned 5HT2A and 5HT2C receptors. Psychopharmacology (Berl) 136:409-414.
9. 2 and the release of arachidonic acid in hippocampal neurons by a type 2 serotonin receptor that is independent of inositolphospholipid hydrolysis. Proc Natl Acad Sci USA 87:2187-2191.
10. Fitzsimons CP, Gompels UA, Verzijl D, Vischer HF, Mattick C, Leurs R, and Smit MJ (2006) Chemokine-directed trafficking of receptor stimulus to different g proteins: selective inducible and constitutive signaling by human herpesvirus 6-encoded chemokine receptor U51. Mol Pharmacol 69:888-898.
11. Gay EA, Urban JD, Nichols DE, Oxford GS, and Mailman RB (2004) Functional selectivity of D-2 receptor ligands in a Chinese hamster ovary hD(2L) cell line: evidence for induction of ligand-specific receptor states. Mol Pharmacol 66:97-105.
12. Gerhardt CC and van Heerikhuizen H (1997) Functional characteristics of heterologously expressed 5-HT receptors. Eur J Pharmacol 334:1-23.
13. Gewirtz JC and Marek GJ (2000) Behavioral evidence for interactions between a hallucinogenic drug and group II metabotropic glutamate receptors. Neuropsychopharmacology 23:569-576.
14. Glennon RA, Raghupathi R, Bartyzel P, Teitler M, and Leonhardt S (1992) Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J Med Chem 35:734-740.
15. Gray JA and Roth BL (2002) Cell biology. A last GASP for GPCRs? Science (Wash DC) 297:529-531.
16. Grotewiel MS and Sanders-Bush E (1999) Differences in agonist-independent activity of 5-HT2A and 5-HT2C receptors revealed by heterologous expression. Naunyn-Schmiedeberg's Arch Pharmacol 359:21-27.
17. Kenakin T (1995) Agonist-receptor efficacy II: agonist trafficking of receptor signals. Trends Pharmacol Sci 16:232-238.
18. Kenakin T (2001) Inverse, protean, and ligand-selective agonism: matters of receptor conformation. FASEB J 15:598-611.
19. Kenakin T (2003) Ligand-selective receptor conformations revisited: the promise and the problem. Trends Pharmacol Sci 24:346-354.
20. Kenakin T (2004) Principles: receptor theory in pharmacology. Trends Pharmacol Sci 25:186-192.
21. Kennett GA, Wood MD, Bright F, Trail B, Riley G, Holland V, Avenell KY, Stean T, Upton N, Bromidge S, et al. (1997) SB 242084, a selective and brain penetrant 5-HT2C receptor antagonist. Neuropharmacology 36:609-620.
22. Kroeze WK, Kristiansen K, and Roth BL (2002) Molecular biology of serotonin receptors structure and function at the molecular level. Curr Top Med Chem 2:507-528.
23. Kurrasch-Orbaugh DM, Watts VJ, Barker EL, and Nichols DE (2003) Serotonin 5-hydroxytryptamine(2A) receptor-coupled phospholipase C and phospholipase A(2) signaling pathways have different receptor reserves. J Pharmacol Exp Ther 304:229-237.
24. López-Giménez JF, Villazón M, Brea J, Loza MI, Palacios JM, Mengod G, and Vilaró MT (2001) Multiple conformations of native and recombinant human 5-hydroxytryptamine(2a) receptors are labeled by agonists and discriminated by antagonists. Mol Pharmacol 60:690-699.
25. Mailman RB and Gay EA (2004) Novel mechanisms of drug action: functional selectivity at D-2 dopamine receptors (a lesson for drug discovery). Med Chem Res 13:115-126.
26. Meller E, Puza T, Diamond J, Lieu HD, and Bohmaker K (1992) Comparative effects of receptor inactivation, 17β-estradiol and pertussis toxin on dopaminergic inhibition of prolactin secretion in vitro. J Pharmacol Exp Ther 263:462-469.
27. i values. J Pharmacol Exp Ther 251:238-246.
28. Nelson DL, Lucaites VL, Wainscott DB, and Glennon RA (1999) Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors. Naunyn-Schmiedeberg's Arch Pharmacol 359:1-6.
29. Nichols DE (2004) Hallucinogens. Pharmacol Ther 101:131-181.
30. Nichols DE, Frescas S, Marona-Lewicka D, Huang X, Roth BL, Gudelsky GA, and Nash JF (1994) 1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)-2-aminopropane: a potent serotonin 5-HT2A/2C agonist. J Med Chem 37:4346-4351.
31. Niswender CM, Herrick-Davis K, Dilley GE, Meltzer HY, Overholser JC, Stockmeier CA, Emeson RB, and Sanders-Bush E (2001) RNA editing of the human serotonin 5-HT2C receptor alterations in suicide and implications for serotonergic pharmacotherapy. Neuropsychopharmacology 24:478-491.
32. Parrish JC, Braden MR, Gundy E, and Nichols DE (2005) Differential phospholipase C activation by phenylalkylamine serotonin 5-HT 2A receptor agonists. J Neurochem 95:1575-1584.
33. Piñeyro G and Archer-Lahlou E (2007) Ligand-specific receptor states: implications for opiate receptor signalling and regulation. Cell Signal 19:8-19
34. Sáez P, Borges Y, González E, and Cassels BK (1994) Alpha-adrenergic and 5-HT2-serotonergic effects of some beta-phenylethylamines on isolated rat thoracic aorta. Gen Pharmacol 25:211-216.
35. Shapiro DA, Kristiansen K, Kroeze WK, and Roth BL (2000) Differential modes of agonist binding to 5-hydroxytryptamine(2A) serotonin receptors revealed by mutation and molecular modeling of conserved residues in transmembrane region 5. Mol Pharmacol 58:877-886.
36. Shoemaker JL, Ruckle MB, Mayeux PR, and Prather PL (2005) Agonist-directed trafficking of response by endocannabinoids acting at CB2 receptors. J Pharmacol Exp Ther 315:828-838.
37. Skrzydelski D, Lhiaubet AM, Lebeau A, Forgez P, Yamada M, Hermans E, Rostene W, and Pelaprat D (2003) Differential involvement of intracellular domains of the rat NTS1 neurotensin receptor in coupling to G proteins: a molecular basis for agonist-directed trafficking of receptor stimulus. Mol Pharmacol 64:421-429.
38. Stout BD, Clarke WP, and Berg KA (2002) Rapid desensitization of the serotonin(2C) receptor system: effector pathway and agonist dependence. J Pharmacol Exp Ther 302:957-962.
39. Urban JD, Clarke WP, von Zastrow M, Nichols DE, Kobilka BK, Weinstein H, Javitch JA, Roth BL, Christopoulos A, Sexton P, et al. (2007) Functional selectivity and classical concepts of quantitative pharmacology. J Pharmacol Exp Ther 320: 1-13.
40. Yap CY and Taylor DA (1983) Involvement of 5-HT2 receptors in the wet-dog shake behaviour induced by 5-hydroxytryptophan in the rat. Neuropharmacology 22: 801-804.