Beyond small-molecule sar: Using the dopamine d3 receptor crystal structure to guide drug design

Advances in Pharmacology

Volumn 69, Issue , 2014, Pages 267-300

  Keck, Thomas M ^a   Burzynski, Caitlin ^a   Shi, Lei ^b   Newman, Amy Hauck ^a  

^a NATIONAL INSTITUTE ON DRUG ABUSE   (United States)

^b WEILL CORNELL MEDICAL COLLEGE   (United States)

Author keywords

Addiction; Crystal structure; Pharmacology; Receptor homology modeling; Structure activity relationships

Indexed keywords

1 PHENYLPIPERAZINE DERIVATIVE; BP 14979; BP 897; BUSPIRONE; CARIPRAZINE; CJB 090; DOPAMINE 2 RECEPTOR; DOPAMINE 3 RECEPTOR; DOPAMINE 3 RECEPTOR BLOCKING AGENT; DOPAMINE 3 RECEPTOR STIMULATING AGENT; GSK 598809; N [4 [2 (6 CYANO 1,2,3,4 TETRAHYDRO 2 ISOQUINOLINYL)ETHYL]CYCLOHEXYL] 4 QUINOLINECARBOXAMIDE; N [4 [2 (8 CYANO 1,3A,4,9B TETRAHYDRO 1 BENZOPYRANO[3,4 C]PYRROL 2(3H) YL)ETHYL]PHENYL]ACETAMIDE; NAXAGOLIDE C 11; NGB 2904; PARTIAL AGONIST; PG 01037; PG 619; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG; YQA 14;

ARTICLE; COMPARATIVE MOLECULAR FIELD ANALYSIS; CRYSTAL STRUCTURE; DRUG DEPENDENCE; DRUG DESIGN; DRUG INDUSTRY; DRUG SCREENING; DRUG SEEKING BEHAVIOR; DRUG TARGETING; ENANTIOSELECTIVITY; HUMAN; IN VIVO STUDY; MOLECULAR DOCKING; NONHUMAN; PHARMACOPHORE; PRIORITY JOURNAL; PROTEIN PROTEIN INTERACTION; RECEPTOR AFFINITY; REINFORCEMENT; STRUCTURE ACTIVITY RELATION;

ADDICTION; CRYSTAL STRUCTURE; PHARMACOLOGY; RECEPTOR HOMOLOGY MODELING; STRUCTURE-ACTIVITY RELATIONSHIPS;

ANIMALS; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; DOPAMINE AGENTS; DRUG DESIGN; HUMANS; PROTEIN BINDING; RECEPTORS, DOPAMINE D3; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTANCE-RELATED DISORDERS;

EID: 84893175454     PISSN: 10543589     EISSN: 15578925     Source Type: Book Series    
DOI: 10.1016/B978-0-12-420118-7.00007-X     Document Type: Chapter

References (131)

1. Achat-Mendes C., Grundt P., Cao J., Platt D.M., Newman A.H., Spealman R.D. Dopamine D3 and D2 receptor mechanisms in the abuse-related behavioral effects of cocaine: Studies with preferential antagonists in squirrel monkeys. Journal of Pharmacology and Experimental Therapeutics 2010, 334:556-565.
2. Achat-Mendes C., Platt D.M., Newman A.H., Spealman R.D. The dopamine D3 receptor partial agonist CJB 090 inhibits the discriminative stimulus but not the reinforcing or priming effects of cocaine in squirrel monkeys. Psychopharmacology 2009, 206:73-84.
3. Agai-Csongor E., Domany G., Nogradi K., Galambos J., Vago I., Keseru G.M., et al. Discovery of cariprazine (RGH-188): A novel antipsychotic acting on dopamine D3/D2 receptors. Bioorganic and Medicinal Chemistry Letters 2012, 22:3437-3440.
4. Arnold J.M., Roberts D.C. A critique of fixed and progressive ratio schedules used to examine the neural substrates of drug reinforcement. Pharmacology, Biochemistry, and Behavior 1997, 57:441-447.
5. Austin N.E., Baldwin S.J., Cutler L., Deeks N., Kelly P.J., Nash M., et al. Pharmacokinetics of the novel, high-affinity and selective dopamine D3 receptor antagonist SB-277011 in rat, dog and monkey: In vitro/in vivo correlation and the role of aldehyde oxidase. Xenobiotica 2001, 31:677-686.
6. Ballesteros J.A., Jensen A.D., Liapakis G., Rasmussen S.G., Shi L., Gether U., et al. Activation of the beta 2-adrenergic receptor involves disruption of an ionic lock between the cytoplasmic ends of transmembrane segments 3 and 6. Journal of Biological Chemistry 2001, 276:29171-29177.
7. Ballesteros J.A., Shi L., Javitch J.A. Structural mimicry in G protein-coupled receptors: Implications of the high-resolution structure of rhodopsin for structure-function analysis of rhodopsin-like receptors. Molecular Pharmacology 2001, 60:1-19.
8. Banala A.K., Levy B.A., Khatri S.S., Furman C.A., Roof R.A., Mishra Y., et al. N-(3-fluoro-4-(4-(2-methoxy or 2,3-dichlorophenyl)piperazine-1-yl)butyl)arylcarboxamides as selective dopamine D3 receptor ligands: Critical role of the carboxamide linker for D3 receptor selectivity. Journal of Medicinal Chemistry 2011, 54:3581-3594.
9. Basile M., Lin R., Kabbani N., Karpa K., Kilimann M., Simpson I., et al. Paralemmin interacts with D3 dopamine receptors: Implications for membrane localization and cAMP signaling. Archives of Biochemistry and Biophysics 2006, 446:60-68.
10. Beninger R.J., Banasikowski T.J. Dopaminergic mechanism of reward-related incentive learning: Focus on the dopamine D(3) receptor. Neurotoxicity Research 2008, 14:57-70.
11. Bergman J., Roof R.A., Furman C.A., Conroy J.L., Mello N.K., Sibley D.R., et al. Modification of cocaine self-administration by buspirone (buspar®): Potential involvement of D3 and D4 dopamine receptors. International Journal of Neuropsychopharmacology 2013, 16:445-458.
12. Blaylock B.L., Gould R.W., Banala A., Grundt P., Luedtke R.R., Newman A.H., et al. Influence of cocaine history on the behavioral effects of dopamine D(3) receptor-selective compounds in monkeys. Neuropsychopharmacology 2011, 36:1104-1113.
13. Boeckler F., Ohnmacht U., Lehmann T., Utz W., Hubner H., Gmeiner P. CoMFA and CoMSIA investigations revealing novel insights into the binding modes of dopamine D3 receptor agonists. Journal of Medicinal Chemistry 2005, 48:2493-2508.
14. Boileau I., Payer D., Houle S., Behzadi A., Rusjan P.M., Tong J., et al. Higher binding of the dopamine D3 receptor-preferring ligand [11C]-(+)-propyl-hexahydro-naphtho-oxazin in methamphetamine polydrug users: A positron emission tomography study. Journal of Neuroscience 2012, 32:1353-1359.
15. Bonanomi G., Braggio S., Capelli A.M., Checchia A., Di Fabio R., Marchioro C., et al. Triazolyl azabicyclo[3.1.0]hexanes: A class of potent and selective dopamine D(3) receptor antagonists. ChemMedChem 2010, 5:705-715.
16. Butini S., Campiani G., Franceschini S., Trotta F., Kumar V., Guarino E., et al. Discovery of bishomo(hetero)arylpiperazines as novel multifunctional ligands targeting dopamine D(3) and serotonin 5-HT(1A) and 5-HT(2A) receptors. Journal of Medicinal Chemistry 2010, 53:4803-4807.
17. Caine S.B., Thomsen M., Barrett A.C., Collins G.T., Grundt P., Newman A.H., et al. Cocaine self-administration in dopamine D(3) receptor knockout mice. Experimental and Clinical Psychopharmacology 2012, 20:352-363.
18. Carlsson J., Coleman R.G., Setola V., Irwin J.J., Fan H., Schlessinger A., et al. Ligand discovery from a dopamine D3 receptor homology model and crystal structure. Nature Chemical Biology 2011, 7:769-778.
19. Chen J., Collins G.T., Levant B., Woods J., Deschamps J.R., Wang S. CJ-1639: A potent and highly selective dopamine D3 receptor full agonist. ACS Medicinal Chemistry Letters 2011, 2:620-625.
20. Cherezov V., Rosenbaum D.M., Hanson M.A., Rasmussen S.G., Thian F.S., Kobilka T.S., et al. High-resolution crystal structure of an engineered human beta2-adrenergic G protein-coupled receptor. Science 2007, 318:1258-1265.
21. Chien E.Y., Liu W., Zhao Q., Katritch V., Han G.W., Hanson M.A., et al. Structure of the human dopamine D3 receptor in complex with a D2/D3 selective antagonist. Science 2010, 330:1091-1095.
22. Cho D.I., Zheng M., Kim K.M. Current perspectives on the selective regulation of dopamine D(2) and D(3) receptors. Archives of Pharmacal Research 2010, 33:1521-1538.
23. Citrome L. Cariprazine: Chemistry, pharmacodynamics, pharmacokinetics, and metabolism, clinical efficacy, safety, and tolerability. Expert Opinion on Drug Metabolism & Toxicology 2013, 9:193-206.
24. Congreve M., Langmead C.J., Mason J.S., Marshall F.H. Progress in structure based drug design for G protein-coupled receptors. Journal of Medicinal Chemistry 2011, 54:4283-4311.
25. de Oliveira Citó M.D.C., da Silva F.C., Silva M.I., Moura B.A., Macedo D.S., Woods D.J., et al. Reversal of cocaine withdrawal-induced anxiety by ondansetron, buspirone and propranolol. Behavioural Brain Research 2012, 231:116-123.
26. Diaz J., Pilon C., Le Foll B., Gros C., Triller A., Schwartz J.C., et al. Dopamine D3 receptors expressed by all mesencephalic dopamine neurons. Journal of Neuroscience 2000, 20:8677-8684.
27. Di Ciano P. Drug seeking under a second-order schedule of reinforcement depends on dopamine D3 receptors in the basolateral amygdala. Behavioral Neuroscience 2008, 122:129-139.
28. Ehrlich K., Gotz A., Bollinger S., Tschammer N., Bettinetti L., Harterich S., et al. Dopamine D2, D3, and D4 selective phenylpiperazines as molecular probes to explore the origins of subtype specific receptor binding. Journal of Medicinal Chemistry 2009, 52:4923-4935.
29. Fiorentini C., Busi C., Gorruso E., Gotti C., Spano P., Missale C. Reciprocal regulation of dopamine D1 and D3 receptor function and trafficking by heterodimerization. Molecular Pharmacology 2008, 74:59-69.
30. Garcia-Ladona F.J., Cox B.F. BP 897, a selective dopamine D3 receptor ligand with therapeutic potential for the treatment of cocaine-addiction. CNS Drug Reviews 2003, 9:141-158.
31. Ginovart N., Willeit M., Rusjan P., Graff A., Bloomfield P.M., Houle S., et al. Positron emission tomography quantification of [11C]-(+)-PHNO binding in the human brain. Journal of Cerebral Blood Flow and Metabolism 2007, 27:857-871.
32. Gleeson M.P. Generation of a set of simple, interpretable ADMET rules of thumb. Journal of Medicinal Chemistry 2008, 51:817-834.
33. Graff-Guerrero A., Mamo D., Shammi C.M., Mizrahi R., Marcon H., Barsoum P., et al. The effect of antipsychotics on the high-affinity state of D2 and D3 receptors: A positron emission tomography study with [11C]-(+)-PHNO. Archives of General Psychiatry 2009, 66:606-615.
34. Graff-Guerrero A., Mizrahi R., Agid O., Marcon H., Barsoum P., Rusjan P., et al. The dopamine D2 receptors in high-affinity state and D3 receptors in schizophrenia: A clinical [11C]-(+)-PHNO PET study. Neuropsychopharmacology 2009, 34:1078-1086.
35. Graff-Guerrero A., Redden L., Abi-Saab W., Katz D.A., Houle S., Barsoum P., et al. Blockade of [11C](+)-PHNO binding in human subjects by the dopamine D3 receptor antagonist ABT-925. International Journal of Neuropsychopharmacology 2010, 13:273-287.
36. Graff-Guerrero A., Willeit M., Ginovart N., Mamo D., Mizrahi R., Rusjan P., et al. Brain region binding of the D2/3 agonist [11C]-(+)-PHNO and the D2/3 antagonist [11C]raclopride in healthy humans. Human Brain Mapping 2008, 29:400-410.
37. Grundt P., Carlson E.E., Cao J., Bennett C.J., McElveen E., Taylor M., et al. Novel heterocyclic trans olefin analogues of N-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl}arylcarboxamides as selective probes with high affinity for the dopamine D3 receptor. Journal of Medicinal Chemistry 2005, 48:839-848.
38. Grundt P., Prevatt K.M., Cao J., Taylor M., Floresca C.Z., Choi J.K., et al. Heterocyclic analogues of N-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butyl)arylcarboxamides with functionalized linking chains as novel dopamine D3 receptor ligands: Potential substance abuse therapeutic agents. Journal of Medicinal Chemistry 2007, 50:4135-4146.
39. Gurevich E.V., Joyce J.N. Distribution of dopamine D3 receptor expressing neurons in the human forebrain: Comparison with D2 receptor expressing neurons. Neuropsychopharmacology 1999, 20:60-80.
40. Hann M.M., Keseru G.M. Finding the sweet spot: The role of nature and nurture in medicinal chemistry. Nature Reviews. Drug Discovery 2012, 11:355-365.
41. Heidbreder C.A., Gardner E.L., Xi Z.X., Thanos P.K., Mugnaini M., Hagan J.J., et al. The role of central dopamine D3 receptors in drug addiction: A review of pharmacological evidence. Brain Research. Brain Research Reviews 2005, 49:77-105.
42. Heidbreder C.A., Newman A.H. Current perspectives on selective dopamine D(3) receptor antagonists as pharmacotherapeutics for addictions and related disorders. Annals of the New York Academy of Sciences 2010, 1187:4-34.
43. Higley A.E., Kiefer S.W., Li X., Gaal J., Xi Z.X., Gardner E.L. Dopamine D(3) receptor antagonist SB277011A inhibits methamphetamine self-administration and methamphetamine-induced reinstatement of drug-seeking in rats. European Journal of Pharmacology 2011, 659:187-192.
44. Higley A.E., Spiller K., Grundt P., Newman A.H., Kiefer S.W., Xi Z.X., et al. PG01037, a novel dopamine D3 receptor antagonist, inhibits the effects of methamphetamine in rats. Journal of Psychopharmacology 2011, 25:263-273.
45. Hill A.P., Young R.J. Getting physical in drug discovery: A contemporary perspective on solubility and hydrophobicity. Drug Discovery Today 2010, 15:648-655.
46. Hobrath J.V., Wang S. Computational elucidation of the structural basis of ligand binding to the dopamine 3 receptor through docking and homology modeling. Journal of Medicinal Chemistry 2006, 49:4470-4476.
47. Horn A.S., Hazelhoff B., Dijkstra D., de Vries J.B., Mulder T.B., Timmermans P., et al. The hydroxy-hexanydronaphthoxazines: A new group of very potent and selective dopamine agonists. Journal of Pharmacy and Pharmacology 1984, 36:639-640.
48. Jean M., Renault J., Levoin N., Danvy D., Calmels T., Berrebi-Bertrand I., et al. Synthesis and evaluation of amides surrogates of dopamine D3 receptor ligands. Bioorganic and Medicinal Chemistry Letters 2010, 20:5376-5379.
49. Johnson M., Antonio T., Reith M.E., Dutta A.K. Structure-activity relationship study of N(6)-(2-(4-(1H-Indol-5-yl)piperazin-1-yl)ethyl)-N(6)-propyl-4,5,6,7-tetrahydroben zo[d]thiazole-2,6-diamine analogues: Development of highly selective D3 dopamine receptor agonists along with a highly potent D2/D3 agonist and their pharmacological characterization. Journal of Medicinal Chemistry 2012, 55:5826-5840.
50. Jorgensen W.L. Efficient drug lead discovery and optimization. Accounts of Chemical Research 2009, 42:724-733.
51. Joyce J.N., Millan M.J. Dopamine D3 receptor antagonists as therapeutic agents. Drug Discovery Today 2005, 10:917-925.
52. Khaled M.A., Farid Araki K., Li B., Coen K.M., Marinelli P.W., Varga J., et al. The selective dopamine D3 receptor antagonist SB 277011-A, but not the partial agonist BP 897, blocks cue-induced reinstatement of nicotine-seeking. International Journal of Neuropsychopharmacology 2010, 13:181-190.
53. Koller W., Herbster G., Gordon J. PHNO, a novel dopamine agonist, in animal models of parkinsonism. Movement Disorders 1987, 2:193-199.
54. Kufareva I., Rueda M., Katritch V., Stevens R.C., Abagyan R., GPCR Dock 2010 participants Status of GPCR modeling and docking as reflected by community-wide GPCR Dock 2010 assessment. Structure 2011, 19:1108-1126.
55. Le Foll B., Boileau I. Repurposing buspirone for drug addiction treatment. International Journal of Neuropsychopharmacology 2013, 16:251-253.
56. Le Foll B., Diaz J., Sokoloff P. Increased dopamine D3 receptor expression accompanying behavioral sensitization to nicotine in rats. Synapse 2003, 47:176-183.
57. Le Foll B., Goldberg S.R., Sokoloff P. The dopamine D3 receptor and drug dependence: Effects on reward or beyond?. Neuropharmacology 2005, 49:525-541.
58. Levant B. The D3 dopamine receptor: Neurobiology and potential clinical relevance. Pharmacological Reviews 1997, 49:231-252.
59. Levesque D., Diaz J., Pilon C., Martres M.P., Giros B., Souil E., et al. Identification, characterization, and localization of the dopamine D3 receptor in rat brain using 7-[3H]hydroxy-N, N-di-n-propyl-2-aminotetralin. Proceedings of the National Academy of Sciences of the United States of America 1992, 89:8155-8159.
60. Levoin N., Calmels T., Krief S., Danvy D., Berrebi-Bertrand I., Lecornte J.M., et al. Homology model versus X-ray structure in receptor-based drug design: A retrospective analysis with the dopamine D3 receptor. ACS Medicinal Chemistry Letters 2011, 2:293-297.
61. Liang J., Zheng X., Chen J., Li Y., Xing X., Bai Y., et al. Roles of BDNF, dopamine D(3) receptors, and their interactions in the expression of morphine-induced context-specific locomotor sensitization. European Neuropsychopharmacology 2011, 21:825-834.
62. Lipinski C.A. Drug-like properties and the causes of poor solubility and poor permeability. Journal of Pharmacological and Toxicological Methods 2000, 44:235-249.
63. Lipinski C.A., Lombardo F., Dominy B.W., Feeney P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Advanced Drug Delivery Reviews 1997, 23:3-25.
64. Liu J., Li Y., Zhang S., Xiao Z., Ai C. Studies of new fused benzazepine as selective dopamine D3 receptor antagonists using 3D-QSAR, molecular docking and molecular dynamics. International Journal of Molecular Sciences 2011, 12:1196-1221.
65. Lopez L., Selent J., Ortega R., Masaguer C.F., Dominguez E., Areias F., et al. Synthesis, 3D-QSAR, and structural modeling of benzolactam derivatives with binding affinity for the D(2) and D(3) receptors. ChemMedChem 2010, 5:1300-1317.
66. Macarron R., Banks M.N., Bojanic D., Burns D.J., Cirovic D.A., Garyantes T., et al. Impact of high-throughput screening in biomedical research. Nature Reviews. Drug Discovery 2011, 10:188-195.
67. Maggio R., Aloisi G., Silvano E., Rossi M., Millan M.J. Heterodimerization of dopamine receptors: New insights into functional and therapeutic significance. Parkinsonism & Related Disorders 2009, 15(Suppl. 4):S2-S7.
68. Marcellino D., Ferre S., Casado V., Cortes A., Le Foll B., Mazzola C., et al. Identification of dopamine D1-D3 receptor heteromers. Indications for a role of synergistic D1-D3 receptor interactions in the striatum. Journal of Biological Chemistry 2008, 283:26016-26025.
69. Martin G.E., Williams M., Pettibone D.J., Zrada M.M., Lotti V.J., Taylor D.A., et al. Selectivity of (+)-4-propyl-9-hydroxynaphthoxazine [(+)-PHNO] for dopamine receptors in vitro and in vivo. Journal of Pharmacology and Experimental Therapeutics 1985, 233:395-401.
70. Mash D.C., Staley J.K. D3 dopamine and kappa opioid receptor alterations in human brain of cocaine-overdose victims. Annals of the New York Academy of Sciences 1999, 877:507-522.
71. Mason C.W., Hassan H.E., Kim K.P., Cao J., Eddington N.D., Newman A.H., et al. Characterization of the transport, metabolism, and pharmacokinetics of the dopamine D3 receptor-selective fluorenyl- and 2-pyridylphenyl amides developed for treatment of psychostimulant abuse. Journal of Pharmacology and Experimental Therapeutics 2010, 333:854-864.
72. Mello N.K., Fivel P.A., Kohut S.J. Effects of chronic buspirone treatment on nicotine and concurrent nicotine+cocaine self-administration. Neuropsychopharmacology 2013, 38:1264-1275.
73. Mello N.K., Fivel P.A., Kohut S.J., Bergman J. Effects of chronic buspirone treatment on cocaine self-administration. Neuropsychopharmacology 2013, 38:455-467.
74. Micheli F. Recent advances in the development of dopamine D3 receptor antagonists: A medicinal chemistry perspective. ChemMedChem 2011, 6:1152-1162.
75. Micheli F., Arista L., Bertani B., Braggio S., Capelli A.M., Cremonesi S., et al. Exploration of the amine terminus in a novel series of 1,2,4-triazolo-3-yl-azabicyclo[3.1.0]hexanes as selective dopamine D3 receptor antagonists. Journal of Medicinal Chemistry 2010, 53:7129-7139.
76. Micheli F., Arista L., Bonanomi G., Blaney F.E., Braggio S., Capelli A.M., et al. 1,2,4-Triazolyl azabicyclo[3.1.0]hexanes: A new series of potent and selective dopamine D(3) receptor antagonists. Journal of Medicinal Chemistry 2010, 53:374-391.
77. Micheli F., Bonanomi G., Blaney F.E., Braggio S., Capelli A.M., Checchia A., et al. 1,2,4-Triazol-3-yl-thiopropyl-tetrahydrobenzazepines: A series of potent and selective dopamine D(3) receptor antagonists. Journal of Medicinal Chemistry 2007, 50:5076-5089.
78. Micheli F., Heidbreder C. Dopamine D3 receptor antagonists: A patent review (2007-2012). Expert Opinion on Therapeutic Patents 2013, 23:363-381.
79. Michino M., Donthamsetti P., Beuming T., Banala A., Duan L., Roux T., et al. A single glycine in extracellular loop 1 is the critical determinant for pharmacological specificity of dopamine D2 and D3 receptors. Molecular Pharmacology 2013, 84:854-864.
80. Millan M.J., Gobert A., Newman-Tancredi A., Lejeune F., Cussac D., Rivet J.M., et al. S33084, a novel, potent, selective, and competitive antagonist at dopamine D(3)-receptors: I. Receptorial, electrophysiological and neurochemical profile compared with GR218,231 and L741,626. Journal of Pharmacology and Experimental Therapeutics 2000, 293:1048-1062.
81. Millan M.J., Loiseau F., Dekeyne A., Gobert A., Flik G., Cremers T.I., et al. S33138 (N-[4-[2-[(3aS,9bR)-8-cyano-1,3a,4,9b-tetrahydro[1] benzopyrano[3,4-c]pyrrol-2(3H)-yl)-ethyl]phenyl-acetamide), a preferential dopamine D3 versus D2 receptor antagonist and potential antipsychotic agent: III. Actions in models of therapeutic activity and induction of side effects. Journal of Pharmacology and Experimental Therapeutics 2008, 324:1212-1226.
82. Millan M.J., Mannoury la Cour C., Novi F., Maggio R., Audinot V., Newman-Tancredi A., et al. S33138 [N-[4-[2-[(3aS,9bR)-8-cyano-1,3a,4,9b-tetrahydro[1]-benzopyrano[3,4-c]pyrrol-2(3H)-yl)-ethyl]phenylacetamide], a preferential dopamine D3 versus D2 receptor antagonist and potential antipsychotic agent: I. Receptor-binding profile and functional actions at G-protein-coupled receptors. Journal of Pharmacology and Experimental Therapeutics 2008, 324:587-599.
83. Millan M.J., Peglion J.L., Vian J., Rivet J.M., Brocco M., Gobert A., et al. Functional correlates of dopamine D3 receptor activation in the rat in vivo and their modulation by the selective antagonist, (+)-S 14297: 1. Activation of postsynaptic D3 receptors mediates hypothermia, whereas blockade of D2 receptors elicits prolactin secretion and catalepsy. Journal of Pharmacology and Experimental Therapeutics 1995, 275:885-898.
84. Millan M.J., Svenningsson P., Ashby C.R., Hill M., Egeland M., Dekeyne A., et al. S33138 [N-[4-[2-[(3aS,9bR)-8-cyano-1,3a,4,9b-tetrahydro[1]-benzopyrano[3,4-c]pyrrol-2(3H)-yl)-ethyl]phenylacetamide], a preferential dopamine D3 versus D2 receptor antagonist and potential antipsychotic agent. II. A neurochemical, electrophysiological and behavioral characterization in vivo. Journal of Pharmacology and Experimental Therapeutics 2008, 324:600-611.
85. Mugnaini M., Iavarone L., Cavallini P., Griffante C., Oliosi B., Savoia C., et al. Occupancy of brain dopamine D3 receptors and drug craving: A translational approach. Neuropsychopharmacology 2013, 38:302-312.
86. Narendran R., Slifstein M., Guillin O., Hwang Y., Hwang D.R., Scher E., et al. Dopamine (D2/3) receptor agonist positron emission tomography radiotracer [11C]-(+)-PHNO is a D3 receptor preferring agonist in vivo. Synapse 2006, 60:485-495.
87. Newman A.H., Beuming T., Banala A.K., Donthamsetti P., Pongetti K., LaBounty A., et al. Molecular determinants of selectivity and efficacy at the dopamine D3 receptor. Journal of Medicinal Chemistry 2012, 55:6689-6699.
88. Newman A.H., Blaylock B.L., Nader M.A., Bergman J., Sibley D.R., Skolnick P. Medication discovery for addiction: Translating the dopamine D3 receptor hypothesis. Biochemical Pharmacology 2012, 84:882-890.
89. Newman A.H., Cao J., Bennett C.J., Robarge M.J., Freeman R.A., Luedtke R.R. N-(4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl, butenyl and butynyl)arylcarboxamides as novel dopamine D(3) receptor antagonists. Bioorganic and Medicinal Chemistry Letters 2003, 13:2179-2183.
90. Newman A.H., Grundt P., Cyriac G., Deschamps J.R., Taylor M., Kumar R., et al. N-(4-(4-(2,3-dichloro- or 2-methoxyphenyl)piperazin-1-yl)butyl)heterobiarylcarboxamides with functionalized linking chains as high affinity and enantioselective D3 receptor antagonists. Journal of Medicinal Chemistry 2009, 52:2559-2570.
91. Newman A.H., Grundt P., Nader M.A. Dopamine D3 receptor partial agonists and antagonists as potential drug abuse therapeutic agents. Journal of Medicinal Chemistry 2005, 48:3663-3679.
92. O'Brien C.P., Gardner E.L. Critical assessment of how to study addiction and its treatment: Human and non-human animal models. Pharmacology & Therapeutics 2005, 108:18-58.
93. Orio L., Wee S., Newman A.H., Pulvirenti L., Koob G.F. The dopamine D3 receptor partial agonist CJB090 and antagonist PG01037 decrease progressive ratio responding for methamphetamine in rats with extended-access. Addiction Biology 2010, 15:312-323.
94. Peng X.Q., Ashby C.R., Spiller K., Li X., Li J., Thomasson N., et al. The preferential dopamine D3 receptor antagonist S33138 inhibits cocaine reward and cocaine-triggered relapse to drug-seeking behavior in rats. Neuropharmacology 2009, 56:752-760.
95. Pilla M., Perachon S., Sautel F., Garrido F., Mann A., Wermuth C.G., et al. Selective inhibition of cocaine-seeking behaviour by a partial dopamine D3 receptor agonist. Nature 1999, 400:371-375.
96. Rasmussen S.G., DeVree B.T., Zou Y., Kruse A.C., Chung K.Y., Kobilka T.S., et al. Crystal structure of the beta2 adrenergic receptor-Gs protein complex. Nature 2011, 477:549-555.
97. Reavill C., Taylor S.G., Wood M.D., Ashmeade T., Austin N.E., Avenell K.Y., et al. Pharmacological actions of a novel, high-affinity, and selective human dopamine D(3) receptor antagonist, SB-277011-A. Journal of Pharmacology and Experimental Therapeutics 2000, 294:1154-1165.
98. Rice O.V., Gardner E.L., Heidbreder C.A., Ashby C.R. The acute administration of the selective dopamine D(3) receptor antagonist SB277011A reverses conditioned place aversion produced by naloxone precipitated withdrawal from acute morphine administration in rats. Synapse 2012, 66:85-87.
99. Rice O.V., Heidbreder C.A., Gardner E.L., Schonhar C.D., Ashby C.R. The selective D3 receptor antagonist SB277011A attenuates morphine-triggered reactivation of expression of cocaine-induced conditioned place preference. Synapse 2013, 67:469-475.
100. Rice O.V., Patrick J., Schonhar C.D., Ning H., Ashby C.R. The effects of the preferential dopamine D(3) receptor antagonist S33138 on ethanol binge drinking in C57BL/6J mice. Synapse 2012, 66:975-978.
101. Richardson N.R., Roberts D.C. Progressive ratio schedules in drug self-administration studies in rats: A method to evaluate reinforcing efficacy. Journal of Neuroscience Methods 1996, 66:1-11.
102. Román V., Gyertyan I., Saghy K., Kiss B., Szombathelyi Z. Cariprazine (RGH-188), a D(3)-preferring dopamine D(3)/D(2) receptor partial agonist antipsychotic candidate demonstrates anti-abuse potential in rats. Psychopharmacology 2013, 226:285-293.
103. Rose F.C., Nashef L. Parkinson's disease: Further steps forward. Gerontology 1987, 33:369-373.
104. Rosenbaum D.M., Rasmussen S.G., Kobilka B.K. The structure and function of G-protein-coupled receptors. Nature 2009, 459:356-363.
105. Salama I., Hocke C., Utz W., Prante O., Boeckler F., Hubner H., et al. Structure-selectivity investigations of D2-like receptor ligands by CoMFA and CoMSIA guiding the discovery of D3 selective PET radioligands. Journal of Medicinal Chemistry 2007, 50:489-500.
106. Searle G., Beaver J.D., Comley R.A., Bani M., Tziortzi A., Slifstein M., et al. Imaging dopamine D3 receptors in the human brain with positron emission tomography, [11C]PHNO, and a selective D3 receptor antagonist. Biological Psychiatry 2010, 68:392-399.
107. Segal D.M., Moraes C.T., Mash D.C. Up-regulation of D3 dopamine receptor mRNA in the nucleus accumbens of human cocaine fatalities. Brain Research. Molecular Brain Research 1997, 45:335-339.
108. Shaham Y., Shalev U., Lu L., De Wit H., Stewart J. The reinstatement model of drug relapse: History, methodology and major findings. Psychopharmacology 2003, 168:3-20.
109. Shelton K.L., Hendrick E.S., Beardsley P.M. Efficacy of buspirone for attenuating cocaine and methamphetamine reinstatement in rats. Drug and Alcohol Dependence 2013, 129:210-216.
110. Shi L., Javitch J.A. The binding site of aminergic G protein-coupled receptors: The transmembrane segments and second extracellular loop. Annual Review of Pharmacology and Toxicology 2002, 42:437-467.
111. Shi L., Liapakis G., Xu R., Guarnieri F., Ballesteros J.A., Javitch J.A. Beta2 adrenergic receptor activation. Modulation of the proline kink in transmembrane 6 by a rotamer toggle switch. Journal of Biological Chemistry 2002, 277:40989-40996.
112. Sokoloff P., Diaz J., Le Foll B., Guillin O., Leriche L., Bezard E., et al. The dopamine D3 receptor: A therapeutic target for the treatment of neuropsychiatric disorders. CNS & Neurological Disorders: Drug Targets 2006, 5:25-43.
113. Sokoloff P., Giros B., Martres M.P., Bouthenet M.L., Schwartz J.C. Molecular cloning and characterization of a novel dopamine receptor (D3) as a target for neuroleptics. Nature 1990, 347:146-151.
114. Song R., Yang R.F., Wu N., Su R.B., Li J., Peng X.Q., et al. YQA14: A novel dopamine D3 receptor antagonist that inhibits cocaine self-administration in rats and mice, but not in D3 receptor-knockout mice. Addiction Biology 2012, 17:259-273.
115. Song R., Zhang H.Y., Peng X.Q., Su R.B., Yang R.F., Li J., et al. Dopamine D3 receptor deletion or blockade attenuates cocaine-induced conditioned place preference in mice. Neuropharmacology 2013, 72:82-87.
116. Spiller K., Xi Z.X., Peng X.Q., Newman A.H., Ashby C.R., Heidbreder C., et al. The selective dopamine D3 receptor antagonists SB277011A and NGB 2904 and the putative partial D3 receptor agonist BP-897 attenuate methamphetamine-enhanced brain stimulation reward in rats. Psychopharmacology 2008, 196:533-542.
117. Staley J.K., Mash D.C. Adaptive increase in D3 dopamine receptors in the brain reward circuits of human cocaine fatalities. Journal of Neuroscience 1996, 16:6100-6106.
118. Stemp G., Ashmeade T., Branch C.L., Hadley M.S., Hunter A.J., Johnson C.N., et al. Design and synthesis of trans-N-[4-[2-(6-cyano-1,2,3, 4-tetrahydroisoquinolin-2-yl)ethyl]cyclohexyl]-4-quinolinecarboxamide (SB-277011): A potent and selective dopamine D(3) receptor antagonist with high oral bioavailability and CNS penetration in the rat. Journal of Medicinal Chemistry 2000, 43:1878-1885.
119. Tschammer N., Elsner J., Goetz A., Ehrlich K., Schuster S., Ruberg M., et al. Highly potent 5-aminotetrahydropyrazolopyridines: Enantioselective dopamine D3 receptor binding, functional selectivity, and analysis of receptor-ligand interactions. Journal of Medicinal Chemistry 2011, 54:2477-2491.
120. Tzschentke T.M. Measuring reward with the conditioned place preference (CPP) paradigm: Update of the last decade. Addiction Biology 2007, 12:227-462.
121. Varady J., Wu X., Fang X., Min J., Hu Z., Levant B., et al. Molecular modeling of the three-dimensional structure of dopamine 3 (D3) subtype receptor: Discovery of novel and potent D3 ligands through a hybrid pharmacophore- and structure-based database searching approach. Journal of Medicinal Chemistry 2003, 46:4377-4392.
122. Wager T.T., Hou X., Verhoest P.R., Villalobos A. Moving beyond rules: The development of a central nervous system multiparameter optimization (CNS MPO) approach to enable alignment of druglike properties. ACS Chemical Neuroscience 2010, 1:435-449.
123. Wang Q., Mach R.H., Luedtke R.R., Reichert D.E. Subtype selectivity of dopamine receptor ligands: Insights from structure and ligand-based methods. Journal of Chemical Information and Modeling 2010, 50:1970-1985.
124. Warne T., Moukhametzianov R., Baker J.G., Nehme R., Edwards P.C., Leslie A.G., et al. The structural basis for agonist and partial agonist action on a beta(1)-adrenergic receptor. Nature 2011, 469:241-244.
125. Willeit M., Ginovart N., Graff A., Rusjan P., Vitcu I., Houle S., et al. First human evidence of d-amphetamine induced displacement of a D2/3 agonist radioligand: A [11C]-(+)-PHNO positron emission tomography study. Neuropsychopharmacology 2008, 33:279-289.
126. Willeit M., Ginovart N., Kapur S., Houle S., Hussey D., Seeman P., et al. High-affinity states of human brain dopamine D2/3 receptors imaged by the agonist [11C]-(+)-PHNO. Biological Psychiatry 2006, 59:389-394.
127. Xi Z.X., Gardner E.L. Pharmacological actions of NGB 2904, a selective dopamine D3 receptor antagonist, in animal models of drug addiction. CNS Drug Reviews 2007, 13:240-259.
128. Xi Z.X., Li X., Li J., Peng X.Q., Song R., Gaal J., et al. Blockade of dopamine D3 receptors in the nucleus accumbens and central amygdala inhibits incubation of cocaine craving in rats. Addiction Biology 2013, 18:665-677.
129. Yan Y., Kong H., Wu E.J., Newman A.H., Xu M. Dopamine D3 receptors regulate reconsolidation of cocaine memory. Neuroscience 2013, 241:32-40.
130. Ye N., Neumeyer J.L., Baldessarini R.J., Zhen X., Zhang A. Update 1 of: Recent progress in development of dopamine receptor subtype-selective agents: Potential therapeutics for neurological and psychiatric disorders. Chemical Reviews 2013, 113:R123-R178.
131. Yuan J., Chen X., Brodbeck R., Primus R., Braun J., Wasley J.W., et al. NGB 2904 and NGB 2849: Two highly selective dopamine D3 receptor antagonists. Bioorganic and Medicinal Chemistry Letters 1998, 8:2715-2718.