Novel bromomelatonin derivatives suppress osteoclastic activity and increase osteoblastic activity: Implications for the treatment of bone diseases

Journal of Pineal Research

Volumn 44, Issue 3, 2008, Pages 326-334

  Suzuki, Nobuo ^a   Somei, Masanori ^a   Kitamura, Kei Ichiro ^a   Reiter, Russel J ^b   Hattori, Atsuhiko ^c  

^a KANAZAWA UNIVERSITY   (Japan)

^b UNIVERSITY OF TEXAS HEALTH SCIENCE CENTER AT SAN ANTONIO   (United States)

^c TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

Author keywords

Bone diseases; Bromomelatonin derivatives; Goldfish; Osteoblasts; Osteoclasts; Scales

Indexed keywords

1 ALLYL 2,4,6 TRIBROMOMELATONIN; 1 BENZYL 2,4,6 TRIBROMOMELATONIN; 1 BROMOMELATONIN; 1 HYDROXYMELATONIN; 1 PROPARGYL 2,4,6 TRIBROMOMELATONIN; 2 BROMOMELATONIN; 2,4 DIBROMOMELATONIN; 2,4,5 TRIBROMOMELATONIN; 2,4,6,7 TETRABROMOMELATONIN; 2,4,7 TRIBROMOMELATONIN; 3,4,7 TRIBROMO 2 OXOMELATONIN; BENZYL TRIBROMOMELATONIN; ESTROGEN RECEPTOR; MELATONIN DERIVATIVE; MELATONIN RECEPTOR; MESSENGER RNA; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BINDING AFFINITY; BONE DISEASE; CELL ACTIVITY; CONTROLLED STUDY; DRUG INHIBITION; DRUG MECHANISM; DRUG STRUCTURE; FEMALE; IN VITRO STUDY; NONHUMAN; OSTEOBLAST; OSTEOCLAST; OSTEOPOROSIS; PROTEIN EXPRESSION;

ANIMALS; CELLS, CULTURED; CONNECTIVE TISSUE; FEMALE; GOLDFISH; MELATONIN; OSTEOBLASTS; OSTEOCLASTS; RECEPTORS, ESTROGEN; RNA, MESSENGER;

EID: 40849131148     PISSN: 07423098     EISSN: 1600079X     Source Type: Journal    
DOI: 10.1111/j.1600-079X.2007.00533.x     Document Type: Article

References (52)

1. Reiter RJ. Melatonin: the chemical expression of darkness. Mol Cell Endocrinol 1991 79 : C153 C158.
2. Reiter RJ. The melatonin rhythm: both a clock and a calendar. Experientia 1993 49 : 654 664.
3. Reiter RJ, Craft CM, Johnson JE JR et al. Age-associated reduction in nocturnal pineal melatonin levels in female rats. Endocrinology 1981 109 : 1295 1297.
4. Sack RL, Lewy AJ, Erb DL et al. Human melatonin production decreases with age. J Pineal Res 1986 3 : 379 388.
5. Reiter RJ. The ageing pineal gland and its physiological consequences. BioEssays 1992 14 : 169 175.
6. Hakanson DO, Bergstrom WH. Phototherapy-induced hypocalcemia in newborn rats: prevention by melatonin. Science 1981 214 : 807 809.
7. Roth JA, Kim B-G, Lin W-L, Cho M-I. Melatonin promotes osteoblast differentiation and bone formation. J Biol Chem 1999 274 : 22041 22047.
8. Nakade O, Koyama H, Ariji H et al. Melatonin stimulates proliferation and type I collagen synthesis in human bone cells in vitro. J Pineal Res 1999 27 : 106 110.
9. Koyama H, Nakde O, Takada Y et al. Melatonin at pharmacologic doses increases bone mass by suppressing resorption through down-regulation of the RANKL-mediated osteoclast formation and activation. J Bone Miner Res 2002 17 : 1219 1229.
10. Suda T, Takahashi N, Udagawa N et al. Modulation of osteoclast differentiation and function by the new members of the tumor necrosis factor receptor and ligand families. Endocr Rev 1999 20 : 345 357.
11. Manolagas SC. Birth and death of bone cells: basic regulatory mechanisms and implications for the pathogenesis and treatment of osteoporosis. Endocr Rev 2000 21 : 115 137.
12. Teitelbaum SL. Bone resorption by osteoclasts. Science 2000 289 : 1504 1508.
13. Yamada J. Studies on the structure and growth of the scales in the goldfish. Mem Fac Fish Hokkaido Univ 1961 9 : 181 226.
14. Yamada J. A fine structural aspect of the development of scales in the chum salmon fry. Bull Jap Soc Sci Fish 1971 37 : 18 29.
15. Bereiter-Hahn J, Zylberberg L. Regeneration of teleost fish scale. Comp Biochem Physiol 1993 105A : 625 641.
16. Zylberberg L, Bonaventure J, Cohen-Solal L et al. Organization and characterization of fibrillar collagens in fish scales in situ and in vitro. J Cell Sci 1992 103 : 273 285.
17. Nishimoto SK, Araki N, Robinson FD, Waite JH. Discovery of bone γ-carboxyglutamic acid protein in mineralized scales. J Biol Chem 1992 267 : 11600 11605.
18. Lehane DB, Mckie N, Russell RGG, Henderson IW. Cloning of a fragment of the osteonectin gene from goldfish, Carassius auratus: its expression and potential regulation by estrogen. Gen Comp Endocrinol 1999 114 : 80 87.
19. Onozato H, Watabe N. Studies on fish scale formation and resorption. III. Fine structure and calcification of the fibrillary plates of the scales in Carassius auratus (Cypriniformes: Cyprinidae). Cell Tissue Res 1979 201 : 409 422.
20. Berg A. Studies on the metabolism of calcium and strontium in freshwater fish. I. Relative contribution of direct and intestinal absorption. Mem Ist Ital Idrobiol 1968 23 : 161 196.
21. Takagi Y, Hirano T, Yamada J. Scale regeneration of tilapia (Oreochromis niloticus) under various ambient and dietary calcium concentrations. Comp Biochem Physiol 1989 92A : 605 608.
22. Persson P, Sundell K, Björnsson BTH, Lundqvist H. Calcium metabolism and osmoregulation during sexual maturation of river running Atlantic salmon. J Fish Biol 1998 52 : 334 349.
23. Suzuki N, Suzuki T, Kurokawa T. Suppression of osteoclastic activities by calcitonin in the scales of goldfish (freshwater teleost) and nibbler fish (seawater teleost). Peptides 2000 21 : 115 124.
24. Suzuki N, Hattori A. Melatonin suppresses osteoclastic and osteoblastic activities in the scales of goldfish. J Pineal Res 2002 33 : 253 258.
25. Vaes G. Cellular biology and biochemical mechanism of bone resorption. Clin Orthop 1988 231 : 239 271.
26. Noda T, Tokuda H, Yoshida M et al. Possible involvement of phosphatidylinositol 3-kinase/Akt pathway in insulin-like growth factor-I-induced alkaline phosphatase activity in osteoblasts. Horm Metab Res 2005 37 : 270 274.
27. Delagrange P, Boutin JA. Therapeutic potential of melatonin ligands. Chronobiol Int 2006 23 : 413 418.
28. Alarma-Estrany P, Pintor J. Melatonin receptors in the eye: location, second messengers and role in ocular physiology. Pharmacol Ther 2007 113 : 507 522.
29. Reiter RJ, Tan DX, Pilar Terron M et al. Melatonin and its metabolies: new findings regarding their production and their radical scavenging actions. Acta Biochim Pol 2007 54 : 1 9.
30. Duranti E, Stankov B, Spadoni G et al. 2-bromomelatonin: synthesis and characterization of a potent melatonin agonist. Life Sci 1992 51 : 479 485.
31. Tarzia G, Diamantini G, Di Giacomo B et al. 1-(2-alkanamidoethyl)-6- methoxyindole derivatives: a new class of potent indole melatonin analogues. J Med Chem 1997 40 : 2003 2010.
32. Nonno R, Pannacci M, Lucini V et al. Ligand efficacy and potency at recombinant human MT2 melatonin receptors: evidence for agonist activity of some mt1-antagonists. Br J Pharmacol 1999 127 : 1288 1294.
33. Okazaki R, Inoue D, Shibata M et al. Estrogen promotes early osteoblast differentiation and inhibits adipocyte differentiation in mouse bone marrow stromal cell lines that express estrogen receptor (ER) α or β. Endocrinology 2002 143 : 2349 2356.
34. Wiren KW, Evans AC, Zhang X-W. Osteoblast differentiation influences androgen and estrogen receptor-α and -β expression. J Endocrinol 2002 175 : 683 694.
35. Mendez-Davila C, Garcia-Moreno C, Turbi C, De La Piedra C. Effects of 17β-estrodiol, tamoxifen and raloxifene on the protein and mRNA expression of interleukin-6, transforming growth factor-β1 and insulin-like growth factor-1 in primary human osteoblast cultures. J Endocrinol Invest 2004 27 : 904 912.
36. Yoshikubo H, Suzuki N, Takemura K et al. Osteoblastic activity and estrogenic response in the regenerating scale of goldfish, a good model of osteogenesis. Life Sci 2005 76 : 2699 2709.
37. Somei M, Yamada F, Morikawa H. Syntheses of serotonin, N-methylserotonin, bufotenine, and melatonin, and the first total synthesis of N-(indol-3-yl)methyl-N-methyl-5-methoxytryptamine from tryptamine through a common intermediate, 1-hydroxytryptamine. Heterocycles 1997 46 : 91 94.
38. Somei M, Fukui Y, Hasegawa M et al. Syntheses of melatonin and its derivatives. Heterocycles 2000 53 : 1725 1736.
39. Somei M, Oshikiri N, Hasegawa M, Yamada F. Preparation of melatonin and 1-hydroxymelatonin, and its novel nucleophilic dimerization to (±)-3a,3a′-bispyrrolo[2,3-b]indoles. Heterocycles 1999 51 : 1237 1242.
40. Ma CH, Dong KW, Yu KL. cDNA cloning and expression of a novel estrogen receptor β-subtype in goldfish (Carassius auratus). Biochim Biophys Acta 2000 1490 : 145 152.
41. Chan K-W, Yu K-L, Rivier J, Chow BK-C. Identification and characterization of a receptor from goldfish specific for a teleost growth hormone-releasing hormone-like peptide. Neuroendocrinology 1998 68 : 44 56.
42. 2-blocker, an inhibitor of blood platelet aggregation, and an anti-osteoporosis agent. Heterocycles 2006 68 : 1565 1569.
43. Barjavel MJ, Mamdouh Z, Raghbate N, Bakouche O. Differential expression of the melatonin receptor in human monocytes. J Immunol 1998 160 : 1191 1197.
44. Zisapel N, Egozi Y, Laudon M. Circadian variations in the inhibition of dopamine release from adult and newborn rat hypothalamus by melatonin. Neuroendocrinology 1985 40 : 102 108.
45. Seeger H, Mueck AO, Lippert TH. Effect of melatonin and metabolites on copper-mediated oxidation of low density lipoprotein. Br J Clin Pharmacol 1997 44 : 283 284.
46. Willis GL, Robertson AD. Recovery of experimental Parkinson's disease with the melatonin analogues ML-23 and S-20928 in a chronic, bilateral 6-OHDA model: a new mechanism involving antagonism of the melatonin receptor. Pharmacol Biochem Behav 2004 79 : 413 429.
47. Ladizesky MG, Boggio V, Albornoz LE et al. Melatonin increases oestradiol-induced bone formation in ovariectomized rats. J Pineal Res 2003 34 : 143 151.
48. Ostrowska Z, Kos-Kudla B, Marek B, Kajdaniuk D. Influence of lighting conditions on daily rhythm of bone metabolism in rats and possible involvement of melatonin and other hormones in this process. Endocr Regul 2003 37 : 163 174.
49. Azria M. Calcitonin in therapeutic use. In : The Calcitonins: Physiology and Pharmacology. Azria M, ed., Karger, Basel, 1989 pp. 133 144.
50. Wimalawansa SJ. Amylin, calcitonin gene-related peptide, calcitonin, and adrenomedullin: a peptide superfamily. Crit Rev Neurobiol 1997 11 : 167 239.
51. Colpan L, Gur A, Cevik R et al. The effect of calcitonin on biochemical markers and zinc excretion in postmenopausal osteoporosis. Maturitas 2005 51 : 246 253.
52. Ladizesky MG, Cutrera RA, Boggio V et al. Effect of melatonin on bone metabolism in ovariectomized rats. Life Sci 2001 70 : 557 565.