Three amino acids in the D2 dopamine receptor regulate selective ligand function and affinity

Journal of Neurochemistry

Volumn 110, Issue 1, 2009, Pages 45-57

  Cummings, David F ^a   Ericksen, Spencer S ^b   Schetz, John A ^a  

^a UNIVERSITY OF NORTH TEXAS HEALTH SCIENCE CENTER   (United States)

^b WEILL CORNELL MEDICAL COLLEGE   (United States)

Author keywords

Attention deficit hyperactivity disorder; Dopamine receptor; Erectile dysfunction; G protein coupled receptor; Schizophrenia; Structure activity relationship

Indexed keywords

1 (4 IODOBENZYL) 4 [N (3 ISOPROPOXY 2 PYRIDINYL) N METHYL]AMINOPIPERIDINE; 2 PHENYL 4 [4 (2 PYRIMIDINYL) 1 PIPERAZINYLMETHYL]IMIDAZOLE; 3 [[4 (4 CHLOROPHENYL) 1 PIPERAZINYL]METHYL] 1H PYRROLO[2,3 B]PYRIDINE; 3 [[4 (4 IODOPHENYL) 1 PIPERAZINYL]METHYL] 1H PYRROLO[2,3 B]PYRIDINE; 3 [[4 (4 IODOPHENYL)PIPERAZIN 1 YL]METHYL] 1H PYRROLO[2,3 B]PYRIDINE; DOPAMINE 2 RECEPTOR; DOPAMINE 2 RECEPTOR BLOCKING AGENT; DOPAMINE 2 RECEPTOR STIMULATING AGENT; FAUC 213; MUTANT PROTEIN; N [4 (2 CYANOPHENYL) 1 PIPERAZINYLMETHYL] 3 METHYLBENZAMIDE; PIPERIDINE DERIVATIVE; PYRROLO[2,3 B]PYRIDINE DERIVATIVE; QUINPIROLE; RBI 257; RO 616270; UNCLASSIFIED DRUG; AMINO ACID; DOPAMINE; DOPAMINE 4 RECEPTOR; DOPAMINE RECEPTOR BLOCKING AGENT; DOPAMINE RECEPTOR STIMULATING AGENT; LIGAND;

AMINO ACID SEQUENCE; ARTICLE; DRUG RECEPTOR BINDING; HUMAN; HUMAN CELL; LIGAND BINDING; MOLECULAR DOCKING; PARTIAL AGONISM; PRIORITY JOURNAL; PROTEIN DOMAIN; RECEPTOR AFFINITY; RECEPTOR BLOCKING; STRUCTURE ANALYSIS; ANIMAL; BINDING COMPETITION; BINDING SITE; CATTLE; CELL FRACTIONATION; CELL LINE; CHEMISTRY; DRUG EFFECT; DRUG POTENTIATION; GENETICS; METABOLISM; MUTATION; NUCLEOTIDE SEQUENCE; PHYSIOLOGY; PROTEIN TERTIARY STRUCTURE; SYNAPTIC TRANSMISSION;

AMINO ACID SEQUENCE; AMINO ACIDS; ANIMALS; BINDING SITES; BINDING, COMPETITIVE; CATTLE; CELL LINE; CONSERVED SEQUENCE; DOPAMINE; DOPAMINE AGONISTS; DOPAMINE ANTAGONISTS; HUMANS; LIGANDS; MUTATION; PROTEIN STRUCTURE, TERTIARY; RECEPTORS, DOPAMINE D2; RECEPTORS, DOPAMINE D4; SUBCELLULAR FRACTIONS; SYNAPTIC TRANSMISSION;

EID: 67449123314     PISSN: 00223042     EISSN: 14714159     Source Type: Journal    
DOI: 10.1111/j.1471-4159.2009.06103.x     Document Type: Article

References (43)

1. Ballesteros J. A. Weinstein H. (1995) Integrated methods for modeling G-protein-coupled receptors. Methods Neurosci. 25, 366 428.
2. Cavasotto C. N., Kovacs J. A. Abagyan R. A. (2005) Representing receptor flexibility in ligand docking through relevant normal modes. J. Am. Chem. Soc. 127, 9632 9640. (Pubitemid 40934775)
3. Chemel B. R., Roth B. L., Armbruster B., Watts V. J. Nichols D. E. (2006) WAY-100635 is a potent dopamine D4 receptor agonist. Psychopharmacology (Berl) 188, 244 251. (Pubitemid 44371162)
4. Cherezov V., Rosenbaum D. M., Hanson M. A. et al. (2007) High-resolution crystal structure of an engineered human beta2-adrenergic G protein-coupled receptor. Science 318, 1258 1265. (Pubitemid 350172884)
5. Corrigan M. H., Gallen C. C., Bonura M. L. Merchant K. M. and Sonepiprazole Study Group (2004) Effectiveness of the selective D4 antagonist sonepiprazole in schizophrenia: a placebo-controlled trial. Biol. Psychiatry 55 : 445 451. (Pubitemid 38338530)
6. Drubbisch V., Lameh J., Philip M., Sharma Y. K. Sadee W. (1992) Mapping the ligand binding pocket of the human muscarinic cholinergic receptor Hm1: contribution of tyrosine-82. Pharm. Res. 9, 1644 1647.
7. Ebersole B. J. Sealfon S. C. (2002) Strategies for mapping the binding site of the serotonin 5-HT2A receptor. Methods Enzymol. 343, 123 136.
8. Ericksen S. S., Cummings D. F., Weinstein H. Schetz J. A. (2009) Ligand selectivity of D2 dopamine receptors is modulated by changes in local dynamics produced by sodium binding. J. Pharmacol. Exp. Ther. 328, 40 54.
9. Floresca C. Z. Schetz J. A. (2004) Dopamine receptor microdomains involved in molecular recognition and the regulation of drug affinity and function. J. Recept. Signal Transduct. Res. 24, 207 239. (Pubitemid 39332217)
10. Floresca C. Z., Chen S., Kortagere S. Schetz J. A. (2005) Reciprocal mutations in TM2/TM3 in a D2 dopamine receptor background confirms the importance of this microdomain as a selective determinant of para-halogenated 1,4-disubstituted aromatic piperazines. Arch. Pharm. (Weinheim) 338, 268 275. (Pubitemid 40957265)
11. Frisch M. J., Trucks G. W., Schlegel H. B. et al. (2004) Gaussian 03 (Revision C.02). Gaussian, Inc., Wallingford, CT.
12. Gazi L., Bobirnac I., Danzeisen M., Schupbach E., Bruinvels A. T., Geisse S., Sommer B., Hoyer D., Tricklebank M. Schoeffter P. (1998) The agonist activities of the putative antipsychotic agents, L-745,870 and U-101958 in HEK293 cells expressing the human dopamine D4.4 receptor. Br. J. Pharmacol. 124, 889 896. (Pubitemid 28312822)
13. Han M., Lin S. W., Smith S. O. Sakmar T. P. (1996) The effects of amino acid replacements of glycine 121 on transmembrane helix 3 of rhodopsin. J. Biol. Chem. 271, 32330 32336. (Pubitemid 26422273)
14. al-Jandal N., Farrar G. J., Kiang A. S., Humphries M. M., Bannon N., Findlay J. B., Humphries P. Kenna P. F. (1999) A novel mutation within the rhodopsin gene (Thr-94-Ile) causing autosomal dominant congenital stationary night blindness. Hum. Mutat. 13, 75 81. (Pubitemid 29014379)
15. Jorgensen W. L., Maxwell D. S. Tirado-Rives J. (1996) Development and testing of the OPLS all-atom force field on conformational energetics and properties of organic liquids. J. Am. Chem. Soc. 118, 11225 11236. (Pubitemid 26399746)
16. Kenakin T. P. (1997) Pharmacologic Analysis of Drug-Receptor Interaction, 3rd edition. Lippincott-Raven Press, Philadelphia, PA.
17. Kortagere S., Gmeiner P., Weinstein H. Schetz J. A. (2004) Certain 1,4-disubstituted aromatic piperidines and piperazines with extreme selectivity for the dopamine D4 receptor interact with a∼common receptor microdomain. Mol. Pharmacol. 66, 1491 1499. (Pubitemid 39564775)
18. Kramer M. S., Last B., Getson A. Reines S. A. (1997) The effects of a selective D4 dopamine receptor antagonist (L-745,870) in acutely psychotic inpatients with schizophrenia. D4 Dopamine Antagonist Group. Arch. Gen. Psychiatry 54, 567 572. (Pubitemid 27258555)
19. Lan H., Durand C. J., Teeter M. M. Neve K. A. (2006) Structural determinants of pharmacological specificity between D(1) and D(2) dopamine receptors. Mol. Pharmacol. 69, 185 194. (Pubitemid 43048905)
20. Lawler C. P., Prioleau C., Lewis M. M., Mak C., Jiang D., Schetz J. A., Gonzalez A. M., Sibley D. R. Mailman R. B. (1999) Interactions of the novel antipsychotic aripiprazole (OPC-14597) with dopamine and serotonin receptor subtypes. Neuropsychopharmacology 20, 612 627. (Pubitemid 29189265)
21. Li J., Edwards P. C., Burghammer M., Villa C. Schertler G. F. (2004) Structure of bovine rhodopsin in a trigonal crystal form. J. Mol. Biol. 343, 1409 1438. (Pubitemid 39387834)
22. Lin S. W. Sakmar T. P. (1996) Specific tryptophan UV-absorbance changes are probes of the transition of rhodopsin to its active state. Biochemistry 35, 11149 11159. (Pubitemid 26298750)
23. Lindahl E. Delarue M. (2005) Refinement of docked protein-ligand and protein-DNA structures using low frequency normal mode amplitude optimization. Nucleic Acids Res. 33, 4496 4506. (Pubitemid 41222564)
24. Lindahl E., Azuara C., Koehl P. Delarue M. (2006) NOMAD-Ref: visualization, deformation and refinement of macromolecular structures based on all-atom normal mode analysis. Nucleic Acids Res. 34 (Web Server issue W52 W56.
25. Lu Z. L. Hulme E. C. (1999) The functional topography of transmembrane domain 3 of the M1 muscarinic acetylcholine receptor, revealed by scanning mutagenesis. J. Biol. Chem. 274, 7309 7315.
26. Matsui H., Lazareno S. Birdsall N. J. (1995) Probing of the location of the allosteric site on m1 muscarinic receptors by site-directed mutagenesis. Mol. Pharmacol. 47, 88 98.
27. Millan J. M., Fuchs S., Paricio N., Wedemann H., Gal A., Najera C. Prieto F. (1995) Gly114Asp mutation of rhodopsin in autosomal dominant retinitis pigmentosa. Mol. Cell. Probes 9 (1 67 69.
28. Morris G. M., Goodsell D. S., Halliday R. S., Huey R., Hart W. E., Belew R. K. Olson A. J. (1998) Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J. Comput. Chem. 19, 1639 1662. (Pubitemid 128590223)
29. Perola E., Walters W. P. Charifson P. S. (2004) A detailed comparison of current docking and scoring methods on systems of pharmaceutical relevance. Proteins 56, 235 249. (Pubitemid 38850158)
30. Ramon E., del Valle L. J. Garriga P. (2003) Unusual thermal and conformational properties of the rhodopsin congenital night blindness mutant Thr-94 -> Ile. J. Biol. Chem. 278, 6427 6432. (Pubitemid 36800901)
31. Sakmar T. P., Franke R. R. Khorana H. G. (1991) The role of the retinylidene Schiff base counterion in rhodopsin in determining wavelength absorbance and Schiff base pKa. Proc. Natl Acad. Sci. USA 88, 3079 3083. (Pubitemid 21916562)
32. Šali A. Blundell T. L. (1993) Comparative protein modelling by satisfaction of spatial restraints. J. Mol. Biol. 234, 779 815.
33. Sanyal S. Van Tol H. H. (1997) Review the role of dopamine D4 receptors in schizophrenia and antipsychotic action. J. Psychiatr. Res. 31, 219 232. (Pubitemid 27317570)
34. Schetz J. A. (2009) Dopamine Receptors: Introduction. IUPHAR database (IUPHAR-DB), http://www.iuphar-b.org/GPCR/IntroductionDisplayForward?chapterID= 1282. Last accessed May 1, 2009.
35. Schetz J. A. Sibley D. (2007) Dopaminergic neurotransmission, in Handbook of Contemporary Neuropharmacology (Sibley D., Hanin I., Kuhar M. J. Skolnick P., eds), pp. 221 256. John Wiley & Sons, Inc, Hoboken, NJ.
36. Schetz J. A., Benjamin P. S. Sibley D. R. (2000) Nonconserved residues in the second transmembrane-spanning domain of the D(4) dopamine receptor are molecular determinants of D(4)-selective pharmacology. Mol. Pharmacol. 57, 144 152. (Pubitemid 30033270)
37. Shapiro D. A., Renock S., Arrington E., Chiodo L. A., Liu L. X., Sibley D. R., Roth B. L. Mailman R. (2003) Aripiprazole, a novel atypical antipsychotic drug with a unique and robust pharmacology. Neuropsychopharmacology 28, 1400 1411. (Pubitemid 41070874)
38. Simpson M. M., Ballesteros J. A., Chiappa V., Chen J., Suehiro M., Hartman D. S., Godel T., Snyder L. A., Sakmar T. P. Javitch J. A. (1999) Dopamine D4/D2 receptor selectivity is determined by a divergent aromatic microdomain contained within the second, third, and seventh membrane-spanning segments. Mol. Pharmacol. 56, 1116 1126.
39. Sousa S. F., Fernandes P. A. Ramos M. J. (2006) Protein-ligand docking: current status and future challenges. Proteins 65, 15 26. (Pubitemid 44320611)
40. Truffinet P., Tamminga C. A., Fabre L. F., Meltzer H. Y., Riviere M. E. Papillon-Downey C. (1999) Placebo-controlled study of the D4/5-HT2A antagonist fananserin in the treatment of schizophrenia. Am. J. Psychiatry 156, 419 425. (Pubitemid 29124164)
41. Ustun T. B., Rehm J., Chatterji S., Saxena S., Trotter R., Room R. Bickenbach J. (1999) Multiple-informant ranking of the disabling effects of different health conditions in 14 countries. WHO/NIH Joint Project CAR Study Group. Lancet 354, 111 115.
42. Van Der Spoel D., Lindahl E., Hess B., Groenhof G., Mark A. E. Berendsen H. J. (2005) GROMACS: fast, flexible, and free. J. Comput. Chem. 26, 1701 1718. (Pubitemid 43076182)
43. Wallace A. C., Laskowski R. A. Thornton J. M. (1995) LIGPLOT: a program to generate schematic diagrams of protein-ligand interactions. Protein Eng. 8, 127 134.