Molecular tools to study melatonin pathways and actions

Trends in Pharmacological Sciences

Volumn 26, Issue 8, 2005, Pages 412-419

  Boutin, Jean A ^a   Audinot, Valérie ^a   Ferry, Gilles ^a   Delagrange, Philippe ^b  

^a INSTITUT DE RECHERCHES SERVIER   (France)

^b INSTITUT DE RECHERCHES SERVIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 IODOMELATONIN; 4 PHENYL 2 PROPIONAMIDOTETRALIN; 5 METHOXYCARBONYLAMINO N ACETYLTRYPTAMINE; 6 CHLOROMELATONIN; ACYLTRANSFERASE INHIBITOR; AGENTS INTERACTING WITH TRANSMITTER, HORMONE OR DRUG RECEPTORS; AGOMELATINE; BUT 3 ENOIC ACID[2 (7 HYDROXYNAPHTHALEN 1 YL)ETHYL]AMIDE; CHRYSOERIOL; ESTROGEN; G PROTEIN COUPLED RECEPTOR; INDOLEAMINE 2,3 DIOXYGENASE; LUZINDOLE; MELATONIN; MELATONIN 1 RECEPTOR; MELATONIN 2 RECEPTOR; MELATONIN DERIVATIVE; MYELOPEROXIDASE; N 1 ACETYL 5 METHOXYKYNURENINE; N [2 (2 IODO 5 METHOXY 1 METHYL 6 NITROINDOL 3 YL)ETHYL]AMIDE; N [2 (5 HYDROXYBENZO[B]THIOPHEN 3 YL)ETHYL]BROMOACETAMIDE; N BROMOACETYLTRYPTAMINE; N1 [[2 [7 [[8 [2 (ACETYLAMINO)ETHYL] 2 NAPHTHYL]OXY]PROPOXY] 1 NAPHTHYL]ETHYL]ACETAMIDE; RALMETEON; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE); RESVERATROL; S 23823; S 26131; SEROTONIN N ACETYLTRANSFERASE; UNCLASSIFIED DRUG;

ANALGESIA; ANTICONVULSANT ACTIVITY; ANTIHYPERTENSIVE ACTIVITY; BRAIN BLOOD FLOW; BRAIN FUNCTION; CATABOLISM; CELL PROLIFERATION; DEPRESSION; DRUG RECEPTOR BINDING; DRUG TOLERANCE; DUODENUM SECRETION; ESTROGEN ACTIVITY; HEART INFARCTION; HEART PROTECTION; HORMONE ACTION; HORMONE INHIBITION; HORMONE METABOLISM; HORMONE RECEPTOR INTERACTION; HORMONE SYNTHESIS; HUMAN; IC 50; LEUKOCYTE MIGRATION INHIBITION; LEUKOCYTE ROLLING; LYMPHOCYTE PROLIFERATION; NEUROMODULATION; NONHUMAN; NORADRENERGIC SYSTEM; PINEAL BODY; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN PURIFICATION; PROTEIN TARGETING; RECEPTOR AFFINITY; REGULATORY MECHANISM; RENAL PROTECTION; REVIEW; SLEEP DISORDER; SPINAL CORD STIMULATION; SYNAPTIC INHIBITION; VASOCONSTRICTION; VASODILATATION; WEIGHT REDUCTION;

ANIMALS; ANTIOXIDANTS; HUMANS; MELATONIN; MOLECULAR STRUCTURE; RECEPTORS, MELATONIN; SIGNAL TRANSDUCTION; TETRAHYDRONAPHTHALENES; TRYPTAMINES;

EID: 22844439551     PISSN: 01656147     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tips.2005.06.006     Document Type: Review

References (73)

1. P. Delagrange Therapeutic perspectives for melatonin agonists and antagonists J. Neuroendocrinol. 15 2003 442 448
2. H. Loo Determination of the dose of agomelatine, a melatoninergic agonist and selective 5-HT(2C) antagonist, in the treatment of major depressive disorder: a placebo-controlled dose range study Int. Clin. Psychopharmacol. 17 2002 239 247
3. S.V. Anisimov Genetic aspects of melatonin biology Rev. Neurosci. 15 2004 209 230
4. R.J. Reiter Pharmacological actions of melatonin in oxygen radical pathophysiology Life Sci. 60 1997 2255 2271
5. D.C. Klein The melatonin rhythm-generating enzyme: molecular regulation of serotonin N-acetyltransferase in the pineal gland Recent Prog. Horm. Res. 52 1997 482 510
6. R.J. Reiter Neurally-mediated and neurally-independent beneficial actions of melatonin in the gastrointestinal tract J. Physiol Pharmacol. 54 2003 113 125
7. S.L. Coon The human serotonin N-acetyltransferase (EC 2.3.1.87) gene (AANAT): structure, chromosomal localization, and tissues expression Genomics 15 1996 76 84
8. A.B. Hickman Melatonin biosynthesis: the structure of serotonin N-acetyltransferase at 2.5 A resolution suggests a catalytic mechanism Mol. Cell 3 1999 23 32
9. A.B. Hickman The structural basis of ordered substrate binding by serotonin N- acetyltransferase: enzyme complex at 1.8 A resolution with a bisubstrate analog Cell 97 1999 361 369
10. E. Wolf X-ray crystallographic studies of serotonin N-acetyltransferase catalysis and inhibition J. Mol. Biol. 317 2002 215 224
11. G. Ferry Further attempts to purify human serotonin N-acetyltransferase (EC 2.3.1.87). Comparison with other species and implication for its enzymatic behavior Prot. Exp. Purif. 38 2004 84 98
12. G. Ferry Characterization and regulation of a CHO cell line stably expressing the human serotonin N-acetyltransferase (EC 2.3.1.87) Cell. Mol. Life Sci. 59 2002 1395 1405
13. S. Ganguly Control of melatonin synthesis in the mammalian pineal gland: the critical role of serotonin acetylation Cell Tissue Res. 309 2003 127 137
14. E. Garbarino-Pico Retinal ganglion cells are autonomous circadian oscillators synthesizing N-acetylserotonin during the day J. Biol. Chem. 279 2004 51172 51181
15. S. Shen Structure-activity relationships for substrates and inhibitors of pineal 5-hydroxytryptamine-N-acetyltransferase: preliminary studies Eur. J. Pharmacol. 307 1996 133 140
16. G. Ferry Substrate specificity and inhibition studies of human serotonin N-acetyltransferase J. Biol. Chem. 275 2000 8794 8805
17. G. Ferry, and J.A. Boutin High-capacity screening of arylalkylamine N-acetyltransferase inhibitors using a high-performance liquid chromatography system J. Biomol. Screen. 5 2000 361 368
18. W. Zheng, and P.A. Cole Serotonin N-acetyltransferase: mechanism and inhibition Curr. Med. Chem. 9 2002 1187 1199
19. G. Ferry New substrate analogues of human serotonin N-acetyltransferase produce in situ specific and potent inhibitors Eur. J. Biochem. 271 2004 418 428
20. N. Beaurain Design, synthesis and in vitro evaluation of novel derivatives as serotonin N-acetyltransferase inhibitors J. Enz. Inhib. Med. Chem. 17 2002 409 414
21. Y. El-Sherif The actions of a charged melatonin receptor ligand, TMEPI, and an irreversible MT2 receptor agonist, BMNEP, on mouse hippocampal evoked potentials in vitro Life Sci. 75 2004 3147 3156
22. C. von Gall Mammalian melatonin receptors: molecular biology and signal transduction Cell Tissue Res. 309 2002 151 162
23. O. Vakkuri Development and validation of a melatonin radioimmunoassay using radioiodinated melatonin tracer Acta Endocrinol. 106 1984 152 157
24. T. Ebisawa Expression cloning of a high-affinity melatonin receptor from Xenopus dermal melanophores Proc. Natl. Acad. Sci. U. S. A. 91 1994 6133 6137
25. S.M. Reppert Cloning and characterization of a mammalian melatonin receptor that mediates reproductive and circadian responses Neuron 13 1994 1177 1185
26. 1b melatonin receptor Proc. Natl. Acad. Sci. U. S. A. 92 1995 8734 8738
27. 2 receptors Naunyn Schmiedebergs Arch. Pharmacol. 367 2003 553 561
28. F. Gauer Daily variations of melatonin receptor density of rats pars tuberalis and suprachiasmatic nuclei are distinctly regulated Brain Res. 641 1994 92 98
29. C. Liu Molecular dissection of two distinct actions of melatonin on the suprachiasmatic circadian clock Neuron 19 1997 91 102
30. 1b melatonin receptor Mol. Cell. Biol. 23 2003 1054 1060
31. P.A. Witt-Enderby Melatonin receptors and their regulation: biochemical and structural mechanisms Life Sci. 72 2003 2183 2198
32. R.S. MacKenzie Dual coupling of MT(1) and MT(2) melatonin receptors to cyclic AMP and phosphoinositide signal transduction cascades and their regulation following melatonin exposure Biochem Pharmacol. 63 2002 587 595
33. C. Huan Activation of melatonin receptor increases a delayed rectifier K+ current in rat cerebellar granule cells Brain Res. 917 2001 182 190
34. 1 mediated influence of melatonin on cAMP concentration and insulin secretion of rat insulinoma cells INS-1 J. Pineal Res. 33 2002 63 71
35. M.L. Dubocovich Molecular pharmacology, regulation and function of mammalian melatonin receptors Front Biosci. 8 2003 d1093 d1108
36. 2 Biochem. Pharmacol. 67 2004 667 677
37. M.L. Dubocovich Melatonin receptor antagonists that differentiate between the human Mel1a and Mel1b recombinant subtypes are used to assess the pharmacological profile of the rabbit retina ML1 presynaptic heteroreceptor Naunyn Schmiedebergs Arch Pharmacol 355 1997 365 375
38. M. Mor Melatonin Curr. Med. Chem. 6 1999 501 518
39. L.R. Fitzgerald, and J.E. Reed Melatonin agonists for the treatment of sleep disorders and major depression Ann. Rep. Med. Chem. 39 2004 25 37
40. M.J. Duncan 2-[125I]Isodomelatonin binding sites in hamster brain membranes: pharmacological characteristics and regional distribution Endocrinology 122 1988 1825 1833
41. D.S. Pickering, and L.P. Niles Pharmacological characterization of melatonin binding sites in Syrian hamster hypothalamus Eur. J. Pharmacol. 175 1990 71 77
42. A.S. Eison Melatonin binding sites are functionally coupled to phosphoinositide hydrolysis in Syrian hamster RPMI 1846 melanoma cells Life Sci. 53 1993 L393 L398
43. 125I]iodo-5-methoxycarbonylamino-N- acetyltryptamine: a selective radioligand for the characterization of melatonin ML2 binding sites Eur. J. Pharmacol. 301 1996 159 168
44. 125I]iodomelatonin binding sites in Syrian hamster peripheral organs J. Pharmacol. Exp. Ther. 290 1999 334 340
45. O. Nosjean Comparative pharmacological studies at the melatonin receptors MT1, MT2 and MT3/QR2 Biochem. Pharmacol. 61 2001 1369 1379
46. O. Nosjean Identification of the melatonin binding site MT3 as the quinone reductase 2 J. Biol. Chem. 275 2000 31311 31317
47. D.J. Long Disruption of dihydronicotinamide riboside:quinone oxidoreductase 2 (NQO2) leads to myeloid hyperplasia of bone marrow and decreased sensitivity to menadione toxicity J Biol Chem. 277 2002 46131 46139
48. 3 FEBS Lett. 578 2004 116 120
49. V. Leclerc Synthesis of nitroindole derivatives as high affinity and selective MT3 melatonin receptor ligands J. Med. Chem. 45 2002 1853 1859
50. J.A. Boutin Quinone reductase 2 substrate specificity and inhibition pharmacology Chem. Biol. Int. 151 2005 213 228
51. K. Wu Catalytic properties of NAD(P)H: quinone oxidoreductase-2 (NQO2), a dihydro-nicotinamide riboside dependent oxydoreductase Arch. Biochem. Biophys. 347 1997 221 228
52. L. Buryanovskyy Crystal structure of quinone reductase 2 in complex with resveratrol Biochemistry 43 2004 11417 11426
53. D.K. Das Cardioprotection of red wine: role of polyphenolic antioxidants Drugs Exp. Clin. Res. 25 1999 115 120
54. A.M. Leone The isolation, purification, and characterisation of the principal urinary metabolites of melatonin J. Pineal Res. 4 1987 253 266
55. F. Hirata In vitro and in vivo formation of two new metabolites of melatonin J. Biol. Chem. 249 1974 1311 1313
56. T. Shimizu Indoleamine-2,3-dioxygenase. Purification and some properties J. Biol. Chem. 253 1978 4700 4706
57. O. Takikawa Monooxygenase activities of dioxygenases. Benzphetamine demethylation and aniline hydroxylation reactions catalyzed by indoleamine 2,3-dioxygenase J. Biol. Chem. 258 1983 6808 6815
58. S.O. Silva Myeloperoxidase-catalyzed oxidation of melatonin by activated neutrophils Biochem. Biophys. Res. Comm. 279 2000 657 662
59. M. Allegra Mechanism of reaction of melatonin with human myeloperoxidase Biochem. Biophys. Res. Comm. 282 2001 380 386
60. G. Ferry Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan. Investigations on both indoleamine-2,3- dioxygenase and myeloperoxidase Biochem. J. 388 2005 205 215
61. T.W. Stone Kynurenines in the CNS: from endogenous obscurity to therapeutic importance Prog. Neurobiol. 64 2001 185 218
62. C.A. Davey, and R.E. Fenna 2.3 A resolution X-ray crystal structure of the bisubstrate analogue inhibitor salicylhydroxamic acid bound to human myeloperoxidase: a model for a prereaction complex with hydrogen peroxide Biochemistry 35 1996 10967 10973
63. D. Acuna-Castroviejo Characterisation of high affinity melatonin binding sites in purified cell nuclei of rat liver J. Pineal Res. 16 1995 100 112
64. M. Becker-Andre Pineal gland hormone melatonin binds and activates an orphan of the nuclear receptor superfamily J. Biol. Chem. 269 1994 28531 28534
65. D.G. Hazlerigg Are nuclear receptors in pituitary responsiveness to melatonin? Mol. Cell. Endocrinol. 123 1996 53 59
66. M. Becker-Andre Erratum: Pineal gland hormone melatonin binds and activates an orphan of the nuclear receptor superfamily J. Biol. Chem. 272 1994 16707
67. G. Milligan G protein-coupled receptor dimerization: function and ligand pharmacology Mol. Pharmacol. 66 2004 1 7
68. M.A. Ayoub Preferential formation of MT1/MT2 melatonin receptor heterodimers with distinct ligand interaction properties compared with MT2 homodimers Mol. Pharmacol. 66 2004 312 321
69. M.L. Dubocovich Luzindole (N-0774): a novel melatonin receptor antagonist J. Pharmacol. Exp. Therap. 246 1988 902 910
70. 1 melatoninergic ligands J. Med. Chem. 46 2003 1127 1129
71. K. Kato Neurochemical properties of ramelteon (TAK-375), a selective MT1/MT2 receptor agonist Neuropharmacology 48 2005 301 310
72. S. Cady, and M. Sono 1-Methyl-DL-tryptophan, beta-(3-benzofuranyl)-DL- alanine (the oxygen analog of tryptophan), and beta-[3-benzo(b)thienyl]-DL- alanine (the sulfur analog of tryptophan) are competitive inhibitors for indoleamine 2,3-dioxygenase Arch. Biochem. Biophys. 291 1991 326 333
73. J.A. Boutin, and A.L. Fauchère Combinatorial peptide synthesis: statistical evaluation of the peptide distribution and its relation to library size and resin bead quantities Trends Pharmacol. Sci. 17 1996 8 13