A rhodopsin-based model for melatonin recognition at its G protein-coupled receptor

European Journal of Pharmacology

Volumn 304, Issue 1-3, 1996, Pages 173-183

  Navajas, Cecil ^a   Kokkola, Tarja ^a   Poso, Antti ^a   Honka, Nina ^a   Gynther, Jukka ^a   Laitinen, Jarmo T ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

Author keywords

Austin model 1; binding site; comparative molecular field analysis; G protein coupled receptor; melatonin receptor; quantitative structure activity relationship model

Indexed keywords

2 IODOMELATONIN; GUANINE NUCLEOTIDE BINDING PROTEIN; IODINE 125; MELATONIN; MELATONIN DERIVATIVE; MELATONIN RECEPTOR; RECEPTOR PROTEIN; RHODOPSIN;

ANIMAL TISSUE; ARTICLE; CHEMICAL STRUCTURE; CHICKEN; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; MODEL; NONHUMAN; PRIORITY JOURNAL; PROTEIN DOMAIN; PROTEIN SECONDARY STRUCTURE; PROTEIN STRUCTURE; QUANTUM MECHANICS; RECEPTOR AFFINITY; RETINA; STRUCTURE ACTIVITY RELATION; TECHNIQUE;

EID: 0030598632     PISSN: 00142999     EISSN: None     Source Type: Journal    
DOI: 10.1016/0014-2999(96)00114-8     Document Type: Article

References (38)

1. Baldwin, J.M., 1993, The probable arrangement of the helices in G protein-coupled receptors, EMBO J. 12, 1693.
2. Clark, M., R.D. Cramer III, and N. van Opdenbosch, 1989, Validation of the general purpose Tripos 5.2 Force Field, J. Comput. Chem. 10, 982.
3. Cramer III, R.D., D.E. Patterson, and J.D. Bunce, 1988a, Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins, J. Am. Chem. Soc. 110, 5959.
4. Cramer III, R.D., J.D. Bunce, D.E. Patterson, and I.E. Frank, 1988b, Crossvalidation, bootstrapping, and partial least squares compared with multiple regression in conventional QSAR studies, Quant. Struct.-Act. Relat. 7, 18.
5. Dubocovich, M.L., 1985, Melatonin receptors: are there multiple subtypes?, Trends Pharmacol. Sci. 16, 50.
6. Ebisawa, T., S. Karne, M.R. Lerner, and S.M. Reppert, 1994, Expression cloning of a high affinity melatonin receptor from Xenopus dermal melanophores, Proc. Natl. Acad. Sci. USA 91, 6133.
7. Findlay, J. and E. Eliopoulos, 1990, Three-Dimensional modeling of G protein-linked receptors, Trends Pharmacol. Sci. 11, 492.
8. Garratt, P.G., R. Jones, and D.A. Tocher, 1995, Mapping the melatonin receptor. 3. Design and synthesis of melatonin agonists and antagonists derived from 2-phenyltryptamines, J. Med. Chem. 38, 1132.
9. Guerrero, J.M. and R.J. Reiter, 1992, A brief survey of pineal gland-immune system interrelationships, Endocr. Res. 18, 91.
10. Gynther, J., 1988, EI and CI mass fragmentation of tryptamine, tetrahydro-β-carboline and some of their derivatives, Acta Chem. Scand. B 42, 433.
11. Gynther, J., P. Peura, and S. Salmi, 1985, Electron impact and chemical ionization fragmentation of 5-methoxytryptamine and some of 6-methoxy-β-carbolines, Acta Chem. Scand. B 39, 849.
12. Hibert, M.F., S. Trumpp-Kallmayer, A. Bruinvels, and J. Hoflack, 1991, Three-Dimensional models of neurotransmitter G-binding protein-coupled receptors. Mol. Pharmacol. 40, 8.
13. Hutchins, C., 1994, Three-Dimensional models of the D1 and D2 dopamine receptors, Endocr. J. 2, 7.
14. Jackobson, K.A., P.J.M. Van Galen, and M. Williams, 1992, Adenosine receptors: pharmacology, structure-activity relationships, and therapeutic potential, J. Med. Chem. 35, 407.
15. Kokkola, T., J.M. Hyttinen, and J.T. Laitinen, 1995, Molecular cloning of the G protein-coupled melatonin receptors from chick brain and retina, Soc. Neurosci. Abstr. 21, 183.
16. Krause, D.N. and M.L. Dubocovich, 1991, Melatonin receptors, Annu. Rev. Pharmacol. Toxicol. 31, 549.
17. Laitinen, J.T. and J.M. Saavedra, 1990a, Characterization of melatonin receptors in the rat suprachiasmatic nuclei: modulation of affinity with cations and guanine nucleotides, Endocrinology 126, 2110.
18. Laitinen, J.T. and J.M. Saavedra, 1990b, Differential sensitivity to cations of the melatonin receptors in the rat area postrema and suprachiasmatic nuclei, J. Neurochem. 55, 1450.
19. Laitinen, J.T. and O. Vakkuri, 1993, Intracellular sodium regulates agonist-melatonin receptor interactions in the chick retina, in: Melatonin and the Pineal Gland - From Basic Science to Clinical Application, eds. Y. Touitou, J. Arendt and P. Pevet (Elsevier, Amsterdam) p. 137.
20. Laitinen, J.T., C. Navajas, T. Kokkola, A. Poso, N. Honka, J. Gynther, and K.S.M. Laitinen, 1995, A rhodopsin-based model for melatonin recognition at its G protein-coupled receptor, Soc. Neurosci. Abstr. 21, 183.
21. Lolley, R.N. and R.H. Lee, 1990, Cyclic GMP and photoreceptor function, FASEB J. 4, 3001.
22. Molis, T.M., L.L. Spriggs, Y. Jupiter, and S.M. Hill, 1995, Melatonin modulation of estrogen-regulated proteins, growth factors, and protooncogenes in human breast cancer, J. Pineal Res. 18, 93.
23. Morgan, P.J., L.M. Williams, G. Davidson, W. Lawson, and H.E. Howell, 1989, Melatonin receptors on ovine pars tuberalis: characterization and autoradiographical localization, J. Neuroendocrinol. 1, 1.
24. 2-adrenergic receptor: how structure elucidates function, Annu. Rev. Pharmacol. Toxicol. 32, 167.
25. Reiter, R.J., 1991, Pineal melatonin: cell biology of its synthesis and of its physiological interactions, Endocrine Rev. 12, 151.
26. Reppert, S.M., D.R. Weaver, and T. Ebisawa, 1994, Cloning and characterization of a mammalian melatonin receptor that mediates reproductive and circadian responses, Neuron 13, 1177.
27. Reppert, S.M., D.R. Waever, V.M. Cassone, C. Godson, and L.F. Kolakowski Jr, 1995, Melatonin receptors are for the birds: molecular analysis of two receptor subtypes differentially expressed in chick brain, Neuron 15,1003.
28. Savarese, T.M. and C.M. Fraser, 1992, In vitro mutagenesis and the search for structure-function relationships among G-protein-coupled receptors, Biochem. J. 283, 1.
29. Schertler, G.F.X., C. Villa, and R. Henderson, 1993, Projection structure of rhodopsin, Nature 362, 770.
30. Stankov, B., F. Fraschini, and R.J. Reiter, 1991, Melatonin binding sites in the central nervous system, Brain Res. Rev. 16, 245.
31. Stewart, J.J.P., 1990, MOPAC: A semiempirical molecular orbital program, J. Comp.-Aid. Mol. Des. 4, 1.
32. 125I]iodomelatonin binding sites in chicken brain and sheep pars tuberalis, Brain Res. 539, 151.
33. Sugden, D., N.W.S. Chong, and D.F.V. Lewis, 1995, Structural requirements at the melatonin receptor, Br. J. Pharmacol. 114, 618.
34. Trumpp-Kallmeyer, S., J. Hoflack, A. Bruinvels, and M. Hibert, 1992, Modeling of G-protein-coupled receptors: application to dopamine, adrenaline, serotonin, acetylcholine, and mammalian opsin receptors, J. Med. Chem. 35, 3448.
35. Unger, V.M. and F.X. Schertler, 1995, Low resolution structure of bovine rhodopsin determined by electron cryo-microscopy, Biophys. J. 68, 1776.
36. 3H NMR spectroscopy, Anal. Biochem. 142, 284.
37. Wess, J., D. Gdula, and M.R. Brann, 1991, Site-directed mutagenesis of the m3 muscarinic receptor: identification of a series of threonine and tyrosine residues involved in agonist but not antagonist binding, EMBO J. 10, 3729.
38. Yous, S., J. Andrieux, H.E. Howell, P.J. Morgan, P. Renard, B. Pfeiffer, D. Lesieur, and B. Guardiola-Lemaitre, 1992, Novel naphthalenic ligands with high affinity for the melatonin receptor, J. Med. Chem. 35, 1484.