Pharmacological characterization of 2-methoxy-N-propylnorapomorphine's interactions with D2 and D3 dopamine receptors

Synapse

Volumn 63, Issue 6, 2009, Pages 462-475

  Skinbjerg, Mette ^a,b,c   Namkung, Yoon ^a   Halldin, Christer ^b   Innis, Robert B ^c   Sibley, David R ^a  

^a NATIONAL INSTITUTE OF NEUROLOGICAL DISORDERS AND STROKE   (United States)

^b KAROLINSKA INSTITUTE   (Sweden)

^c NATIONAL INSTITUTE OF MENTAL HEALTH   (United States)

Author keywords

Agonist; Dopamine; Internalization; MNPA; PET; Receptor

Indexed keywords

2 METHOXY N PROPYLNORAPOMORPHINE; 2 METHOXY N PROPYLNORAPOMORPHINE H 3; CYCLIC AMP; DOPAMINE; DOPAMINE 2 RECEPTOR; DOPAMINE 3 RECEPTOR; FORSKOLIN; GUANOSINE TRIPHOSPHATE; MORPHINE DERIVATIVE; PROPYLNORAPOMORPHINE; RADIOLIGAND; RECOMBINANT PROTEIN; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BINDING COMPETITION; CELL MEMBRANE; CELL STRAIN HEK293; CONTROLLED STUDY; DRUG POTENCY; DRUG RECEPTOR BINDING; GENETIC TRANSFECTION; HUMAN; HUMAN CELL; INTERNALIZATION; MEMBRANE BINDING; PRIORITY JOURNAL;

APOMORPHINE; BINDING, COMPETITIVE; CELL LINE, TUMOR; CELL MEMBRANE; DOPAMINE AGONISTS; ENDOCYTOSIS; FORSKOLIN; HUMANS; MICROSCOPY, CONFOCAL; NEURONS; POSITRON-EMISSION TOMOGRAPHY; PROTEIN TRANSPORT; RECEPTORS, DOPAMINE D2; RECEPTORS, DOPAMINE D3;

EID: 66149124054     PISSN: 08874476     EISSN: 10982396     Source Type: Journal    
DOI: 10.1002/syn.20626     Document Type: Article

References (61)

1. Beaulieu JM, Sotnikova TD, Marion S, Lefkowitz RJ, Gainetdinov RR, Caron MG. 2005. An Akt/beta-arrestin 2/PP2A signaling complex mediates dopaminergic neurotransmission and behavior. Cell 122:261-273.
2. Boundy VA, Luedtke RR, Gallitano AL, Smith JE, Filtz TM, Kallen RG, Molinoff PB. 1993. Expression and characterization of the rat D3 dopamine receptor: Pharmacologic properties and development of antibodies. J Pharmacol Exp Ther 264:1002-1011.
3. Bouthenet ML, Souil E, Martres MP, Sokoloff P, Giros B, Schwartz JC. 1991. Localization of dopamine D3 receptor mRNA in the rat brain using in situ hybridization histochemistry: Comparison with dopamine D2 receptor mRNA. Brain Res 564:203-219.
4. Breier JI, Mullani NA, Thomas AB, Wheless JW, Plenger PM, Gould KL, Papanicolaou A, Willmore LJ. 1997. Effects of duration of epilepsy on the uncoupling of metabolism and blood flow in complex partial seizures. Neurology 48:1047-1053.
5. Castro SW, Strange PG. 1993. Coupling of D2 and D3 dopamine receptors to G-proteins. FEBS Lett 315:223-226.
6. Chio CL, Lajiness ME, Huff RM. 1994. Activation of heterologously expressed D3 dopamine receptors: Comparison with D2 dopamine receptors. Mol Pharmacol 45:51-60.
7. Creese I, Sibley DR, Leff SE. 1984. Agonist interactions with dopamine receptors: Focus on radioligand-binding studies. Fed Proc 43:2779-2784.
8. Cumming P, Gillings NM, Jensen SB, Bjarkam C, Gjedde A. 2003. Kinetics of the uptake and distribution of the dopamine D(2,3) agonist (R)-N-[1-(11)C]n- propylnorapomorphine in brain of healthy and MPTP-treated Gottingen miniature pigs. Nucl Med Biol 30:547-553.
9. Cumming P, Wong DF, Gillings N, Hilton J, Scheffel U, Gjedde A. 2002. Specific binding of [(11)C]raclopride and N-[(3)H]propyl-norapomorphine to dopamine receptors in living mouse striatum: Occupancy by endogenous dopamine and guanosine triphosphate-free G protein. J Cereb Blood Flow Metab 22:596-604.
10. De Lean A, Kilpatrick BF, Caron MG. 1982. Dopamine receptor of the porcine anterior pituitary gland. Evidence for two affinity states discriminated by both agonists and antagonists. Mol Pharmacol 22:290-297.
11. Ferguson SS. 2001. Evolving concepts in G protein-coupled receptor endocytosis: The role in receptor desensitization and signaling. Pharmacol Rev 53:1-24.
12. Finnema SJ, Seneca N, Farde L, Shchukin E, Sovago J, Gulyas B, Wikstrom HV, Innis RB, Neumeyer JL, Halldin C. 2005. A preliminary PET evaluation of the new dopamine D2 receptor agonist [11C]MNPA in cynomolgus monkey. Nucl Med Biol 32:353-360.
13. Freedman SB, Patel S, Marwood R, Emms F, Seabrook GR, Knowles MR, McAllister G. 1994. Expression and pharmacological characterization of the human D3 dopamine receptor. J Pharmacol Exp Ther 268:417-426.
14. Gao YG, Baldessarini RJ, Kula NS, Neumeyer JL. 1990. Synthesis and dopamine receptor affinities of enantiomers of 2-substituted apomorphines and their N-n-propyl analogues. J Med Chem 33:1800-1805.
15. Ginovart N, Galineau L, Willeit M, Mizrahi R, Bloomfield PM, Seeman P, Houle S, Kapur S, Wilson AA. 2006. Binding characteristics and sensitivity to endogenous dopamine of [11C]-(+)-PHNO, a new agonist radiotracer for imaging the high-affinity state of D2 receptors in vivo using positron emission tomography. J Neurochem 97:1089-1103.
16. Ginovart N, Wilson AA, Houle S, Kapur S. 2004. Amphetamine pretreatment induces a change in both D2-Receptor density and apparent affinity: A [11C]raclopride positron emission tomography study in cats. Biol Psychiatry 55:1188-1194.
17. Goggi JL, Sardini A, Egerton A, Strange PG, Grasby PM. 2007. Agonist-dependent internalization of D2 receptors: Imaging quantification by confocal microscopy. Synapse 61:231-241.
18. Groer CE, Tidgewell K, Moyer RA, Harding WW, Rothman RB, Prisinzano TE, Bohn LM. 2007. An opioid agonist that does not induce micro-opioid receptor-arrestin interactions or receptor internalization. Mol Pharmacol 71:549-557.
19. Hall DA, Strange PG. 1999. Comparison of the ability of dopamine receptor agonists to inhibit forskolin-stimulated adenosine 3′5′-cyclic monophosphate (cAMP) accumulation via D2L (long isoform) and D3 receptors expressed in Chinese hamster ovary (CHO) cells. Biochem Pharmacol 58:285-289.
20. Hwang DR, Narendran R, Laruelle M. 2005. Positron-labeled dopamine agonists for probing the high affinity states of dopamine subtype 2 receptors. Bioconjug Chem 16:27-31.
21. Insel PA, Mahan LC, Motulsky HJ, Stoolman LM, Koachman AM. 1983. Time-dependent decreases in binding affinity of agonists for beta-adrenergic receptors of intact S49 lymphoma cells. A mechanism of desensitization. J Biol Chem 258:13597-13605.
22. Ito K, Haga T, Lameh J, Sadee W. 1999. Sequestration of dopamine D2 receptors depends on coexpression of G-protein-coupled receptor kinases 2 or 5. Eur J Biochem 260:112-119.
23. Iwata K, Ito K, Fukuzaki A, Inaki K, Haga T. 1999. Dynamin and rab5 regulate GRK2-dependent internalization of dopamine D2 receptors. Eur J Biochem 263:596-602.
24. Kim KM, Valenzano KJ, Robinson SR, Yao WD, Barak LS, Caron MG. 2001. Differential regulation of the dopamine D2 and D3 receptors by G protein-coupled receptor kinases and beta-arrestins. J Biol Chem 276:37409-37414.
25. Kim SJ, Kim MY, Lee EJ, Ahn YS, Baik JH. 2004. Distinct regulation of internalization and mitogen-activated protein kinase activation by two isoforms of the dopamine D2 receptor. Mol Endocrinol 18:640-652.
26. Laruelle M. 2000. Imaging synaptic neurotransmission with in vivo binding competition techniques: A critical review. J Cereb Blood Flow Metab 20:423-451. (Pubitemid 30164887)
27. Laruelle M, Iyer RN, al-Tikriti MS, Zea-Ponce Y, Malison R, Zoghbi SS, Baldwin RM, Kung HF, Charney DS, Hoffer PB, Innis RB, Bradberry CW. 1997. Microdialysis and SPECT measurements of amphetamine-induced dopamine release in nonhuman primates. Synapse 25:1-14.
28. Levesque D, Diaz J, Pilon C, Martres MP, Giros B, Souil E, Schott D, Morgat JL, Schwartz JC, Sokoloff P. 1992. Identification, characterization, and localization of the dopamine D3 receptor in rat brain using 7-[3H]hydroxy-N,N- di-n-propyl-2-aminotetralin. Proc Natl Acad Sci USA 89:8155-8159.
29. Macey TA, Gurevich VV, Neve KA. 2004. Preferential Interaction between the dopamine D2 receptor and Arrestin2 in neostriatal neurons. Mol Pharmacol 66:1635-1642.
30. MacKenzie RG, VanLeeuwen D, Pugsley TA, Shih YH, Demattos S, Tang L, Todd RD, O'Malley KL. 1994. Characterization of the human dopamine D3 receptor expressed in transfected cell lines. Eur J Pharmacol 266:79-85.
31. Marchese A, Paing MM, Temple BR, Trejo J. 2008. G protein-coupled receptor sorting to endosomes and lysosomes. Annu Rev Pharmacol Toxicol 48:601-629.
32. McAllister G, Knowles MR, Ward-Booth SM, Sinclair HA, Patel S, Marwood R, Emms F, Patel S, Smith A, Seabrook GR. 1995. Functional coupling of human D2, D3, and D4 dopamine receptors in HEK293 cells. J Recept Signal Transduct Res 15:267-281.
33. McCarron JA, Zoghbi SS, Shetty HU, Vermeulen ES, Wikstrom HV, Ichise M, Yasuno F, Halldin C, Innis RB, Pike VW. 2007. Synthesis and initial evaluation of [11C](R)-RWAY in monkey-a new, simply labeled antagonist radioligand for imaging brain 5-HT1A receptors with PET. Eur J Nucl Med Mol Imaging 34:1670-1682.
34. McDonald WM, Sibley DR, Kilpatrick BF, Caron MG. 1984. Dopaminergic inhibition of adenylate cyclase correlates with high affinity agonist binding to anterior pituitary D2 dopamine receptors. Mol Cell Endocrinol 36:201-209.
35. Mukherjee J, Narayanan TK, Christian BT, Shi B, Yang ZY. 2004. Binding characteristics of high-affinity dopamine D2/D3 receptor agonists, 11C-PPHT and 11C-ZYY-339 in rodents and imaging in non-human primates by PET. Synapse 54:83-91.
36. Murray AM, Ryoo HL, Gurevich E, Joyce JN. 1994. Localization of dopamine D3 receptors to mesolimbic and D2 receptors to mesostriatal regions of human forebrain. Proc Natl Acad Sci USA 91:11271-11275.
37. Namkung Y, Sibley DR. 2004. Protein kinase C mediates phosphorylation, desensitization, and trafficking of the D2 dopamine receptor. J Biol Chem 279(47):49533-49541.
38. Narendran R, Hwang DR, Slifstein M, Talbot PS, Erritzoe D, Huang Y, Cooper TB, Martinez D, Kegeles LS, Abi-Dargham A, Laruelle M. 2004. In vivo vulnerability to competition by endogenous dopamine: Comparison of the D2 receptor agonist radiotracer (-)-N-[11C]propyl-norapomorphine ([11C]NPA) with the D2 receptor antagonist radiotracer [11C]-raclopride. Synapse 52:188-208.
39. Narendran R, Hwang DR, Slifstein M, Hwang Y, Huang Y, Ekelund J, Guillin O, Scher E, Martinez D, Laruelle M. 2005. Measurement of the proportion of D2 receptors configured in state of high affinity for agonists in vivo: A positron emission tomography study using [11C]N-propyl-norapomorphine and [11C]raclopride in baboons. J Pharmacol Exp Ther 315:80-90.
40. Narendran R, Slifstein M, Guillin O, Hwang Y, Hwang DR, Scher E, Reeder S, Rabiner E, Laruelle M. 2006. Dopamine (D2/3) receptor agonist positron emission tomography radiotracer [11C]-(+)-PHNO is a D3 receptor preferring agonist in vivo. Synapse 60:485-495.
41. Narendran R, Slifstein M, Hwang DR, Hwang Y, Scher E, Reeder S, Martinez D, Laruelle M. 2007. Amphetamine-induced dopamine release: Duration of action as assessed with the D2/3 receptor agonist radiotracer (-)-N-[(11)C]propyl- norapomorphine ([11C]NPA) in an anesthetized nonhuman primate. Synapse 61:106-109.
42. Neumeyer JL, Gao YG, Kula NS, Baldessarini RJ. 1990. Synthesis and dopamine receptor affinity of (R)-(2)-2-fluoro-N-n-propylnorapomorphine: A highly potent and selective dopamine D2 agonist. J Med Chem 33:3122-3124.
43. Oldham WM, Hamm HE. 2008. Heterotrimeric G protein activation by G-protein-coupled receptors. Nat Rev Mol Cell Biol 9(1):60-71.
44. Pilon C, Levesque D, Dimitriadou V, Griffon N, Martres MP, Schwartz JC, Sokoloff P. 1994. Functional coupling of the human dopamine D3 receptor in a transfected NG 108-15 neuroblastomaglioma hybrid cell line. Eur J Pharmacol 268(2):129-139.
45. Robinson SW, Caron MG. 1997. Selective inhibition of adenylyl cyclase type V by the dopamine D3 receptor. Mol Pharmacol 52:508-514.
46. Sedaghat K, Nantel MF, Ginsberg S, Lalonde V, Tiberi M. 2006. Molecular characterization of dopamine D2 receptor isoforms tagged with green fluorescent protein. Mol Biotechnol 34:1-14.
47. Seeman P. 2008. Dopamine D2(High) receptors on intact cells. Synapse 62:314-318.
48. Seneca N, Finnema SJ, Farde L, Gulyas B, Wikstrom HV, Halldin C, Innis RB. 2006. Effect of amphetamine on dopamine D2 receptor binding in nonhuman primate brain: A comparison of the agonist radioligand [11C]MNPA and antagonist [11C]raclopride. Synapse 59:260-269.
49. Sibley DR, De Lean A, Creese I. 1982. Anterior pituitary dopamine receptors. Demonstration of interconvertible high and low affinity states of the D-2 dopamine receptor. J Biol Chem 257:6351-6361.
50. Sibley DR, Mahan LC, Creese I. 1983. Dopamine receptor binding on intact cells. Absence of a high-affinity agonist-receptor binding state. Mol Pharmacol 23:295-302.
51. Slifstein M, Narendran R, Hwang DR, Sudo Y, Talbot PS, Huang Y, Laruelle M. 2004. Effect of amphetamine on [(18)F]fallypride in vivo binding to D(2) receptors in striatal and extrastriatal regions of the primate brain: Single bolus and bolus plus constant infusion studies. Synapse 54:46-63.
52. Sokoloff P, Giros B, Martres MP, Bouthenet ML, Schwartz JC. 1990. Molecular cloning and characterization of a novel dopamine receptor (D3) as a target for neuroleptics. Nature 347:146-151.
53. Toews ML, Harden TK, Perkins JP. 1983. High-affinity binding of agonists to beta-adrenergic receptors on intact cells. Proc Natl Acad Sci USA 80:3553-3557.
54. Urban JD, Vargas GA, von Zastrow M, Mailman RB. 2007. Aripiprazole has functionally selective actions at dopamine D2 receptor-mediated signaling pathways. Neuropsychopharmacology 32:67-77.
55. Vanhauwe JF, Fraeyman N, Francken BJ, Luyten WH, Leysen JE. 1999. Comparison of the ligand binding and signaling properties of human dopamine D(2) and D(3) receptors in Chinese hamster ovary cells. J Pharmacol Exp Ther 290:908-916.
56. Vickery RG, von Zastrow M. 1999. Distinct dynamin-dependent and -independent mechanisms target structurally homologous dopamine receptors to different endocytic membranes. J Cell Biol 144:31-43.
57. Watts VJ, Neve KA. 1996. Sensitization of endogenous and recombinant adenylate cyclase by activation of D2 dopamine receptors. Mol Pharmacol 50:966-976.
58. Willeit M, Ginovart N, Kapur S, Houle S, Hussey D, Seeman P, Wilson AA. 2006. High-affinity states of human brain dopamine D2/3 receptors imaged by the agonist [11C]-(+)-PHNO. Biol Psychiatry 59:389-394.
59. Wilson AA, McCormick P, Kapur S, Willeit M, Garcia A, Hussey D, Houle S, Seeman P, Ginovart N. 2005. Radiosynthesis and evaluation of [11C]-(+)-4-propyl-3,4,4a,5,6,10b-hexahydro-2H-naphtho [1,2-b][1,4]oxazin-9-ol as a potential radiotracer for in vivo imaging of the dopamine D2 high-affinity state with positron emission tomography. J Med Chem 48:4153-4160.
60. Xu ZQ, Zhang X, Scott L. 2007. Regulation of G protein-coupled receptor trafficking. Acta Physiol (Oxf) 190:39-45.
61. Yasuno F, Zoghbi SS, McCarron JA, Hong J, Ichise M, Brown AK, Gladding RL, Bacher JD, Pike VW, Innis RB. 2006. Quantification of serotonin 5-HT1A receptors in monkey brain with [11C](R)-(-)-RWAY. Synapse 60:510-520.