LC, a novel estrone-rhein hybrid compound, concurrently stimulates osteoprotegerin and inhibits receptor activator of NF-κB ligand (RANKL) and interleukin-6 production by human osteoblastic cells

Molecular and Cellular Endocrinology

Volumn 337, Issue 1-2, 2011, Pages 43-51

  Wang, Yue ^a,b   Li, Ling Zhi ^a,b   Zhang, Yong Liang ^b   Zhu, Ya Qin ^a   Wu, Jian ^a   Sun, Wei Jia ^a  

^a MEDICAL COLLEGE OF CHINESE PEOPLE'S ARMED POLICE FORCES   (China)

^b Tianjin Key Laboratory for Biomarkers of Occupational and Environmental Hazard   (China)

Author keywords

Estrogen receptor; IL 6; LC; OPG; Osteoblast; RANKL

Indexed keywords

COMPOUND LC; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; ESTRONE DERIVATIVE; FULVESTRANT; INTERLEUKIN 6; MITOGEN ACTIVATED PROTEIN KINASE KINASE; OSTEOCLAST DIFFERENTIATION FACTOR; OSTEOPROTEGERIN; PHOSPHATIDYLINOSITOL 3 KINASE; PROTEIN KINASE B; RAS PROTEIN; SMALL INTERFERING RNA; UNCLASSIFIED DRUG;

ARTICLE; BREAST EPITHELIUM; CELL GROWTH; CELL STIMULATION; CONTROLLED STUDY; CYTOKINE PRODUCTION; DRUG MECHANISM; DRUG SELECTIVITY; ENDOMETRIUM; ESTROGEN ACTIVITY; ESTROGEN RESPONSIVE ELEMENT; HUMAN; HUMAN CELL; OSTEOBLAST; OSTEOLYSIS; OVARIECTOMY; PRIORITY JOURNAL; PROTEIN EXPRESSION; SIGNAL TRANSDUCTION; UTERUS GROWTH;

ANIMALS; ANTHRAQUINONES; CELL LINE; CELL PROLIFERATION; ENDOPLASMIC RETICULUM; ENZYME ACTIVATION; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; ESTRONE; FEMALE; GENE KNOCKDOWN TECHNIQUES; HUMANS; INTERLEUKIN-6; INTRACELLULAR SIGNALING PEPTIDES AND PROTEINS; OSTEOBLASTS; OSTEOPROTEGERIN; PROMOTER REGIONS, GENETIC; RANK LIGAND; RATS; RESPONSE ELEMENTS; RNA INTERFERENCE; SIGNAL TRANSDUCTION;

EID: 79953302575     PISSN: 03037207     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.mce.2011.01.018     Document Type: Article

References (49)

1. Bauss F., Esswein A., Reiff K., Sponer G., Müller-Beckmann B. Effect of 17β-estradiol-bisphosphonate conjugates, potential bone-seeking estrogen pro-drugs, on 17β-estradiol serum kinetics and bone mass in rats. Calcif. Tissue Int. 1996, 59:168-173.
2. Boileau C., Tat S.K., Pelletier J.P., Cheng S., Martel-Pelletier J. Diacerein inhibits the synthesis of resorptive enzymes and reduces osteoclastic differentiation/survival in osteoarthritic subchondral bone: a possible mechanism for a protective effect against subchondral bone remodeling. Arthritis Res. Ther. 2008, 10:R71.
3. Brady H., Doubleday M., Gayo-Fung L.M., Hickman M., Khammungkhune S., Kois A., Lipps S., Pierce S., Richard N., Shevlin G., Sutherland M.K., Anderson D.W., Bhagwat S.S., Stein B. Differential response of estrogen receptors alpha and beta to SP500263, a novel potent selective estrogen receptor modulator. Mol. Pharmacol. 2002, 61:562-568.
4. Compston J.E. Sex steroids and bone. Physiol. Rev. 2001, 81:419-447.
5. Cui Y., Li L.Z., Zhu J. Determination of rhein in mouse bone by HPLC. Chin. J. New Drugs 2008, 17:1154-1156.
6. Dang Z.C., van Bezooijen R.L., Karperien M., Papapoulos S.E., Löwik C.W. Exposure of KS483 cells to estrogen enhances osteogenesis and inhibits adipogenesis. J. Bone Miner. Res. 2002, 17:394-405.
7. Eastell R. Treatment of postmenopausal osteoporosis. N. Engl. J. Med. 1998, 338:736-746.
8. Gennari L., Merlotti D., Valleggi F., Martini G., Nuti R. Selective estrogen receptor modulators for postmenopausal osteoporosis: current state of development. Drugs Aging 2007, 24:361-379.
9. Gori F., Hofbauer L.C., Dunstan C.R., Spelsberg T.C., Khosla S., Riggs B.L. The expression of osteoprotegerin and RANK ligand and the support of osteoclast formation by stromal-osteoblast lineage cells is developmentally regulated. Endocrinology 2000, 141:4768-4776.
10. Hofbauer L.C., Khosla S., Dunstan C.R., Lacey D.L., Spelsberg T.C., Riggs B.L. Estrogen stimulates gene expression and protein production of osteoprotegerin in human osteoblastic cells. Endocrinology 1999, 140:4367-4370.
11. 2+ on rhein-induced apoptosis in A-549 human lung cancer cells. Anticancer Res. 2009, 29:309-318.
12. +2 on rhein-induced apoptosis in human cervical cancer Ca Ski cells. Anticancer Res. 2007, 27:379-389.
13. Kassem M., Harris S.A., Spelsberg T.C., Riggs B.L. Estrogen inhibits interleukin-6 production and gene expression in a human osteoblastic cell line with high levels of estrogen receptors. J. Bone Miner. Res. 1996, 11:193-199.
14. Khosla S. The OPG/RANKL/RANK system. Endocrinology 2001, 142:5050-5055.
15. Kulak Júnior J., Kulak C.A., Taylor H.S. SERMs in the prevention and treatment of postmenopausal osteoporosis: an update. Arq. Bras. Endocrinol. Metabol. 2010, 54:200-205.
16. Lacey D.L., Timms E., Tan H.L., Kelley M.J., Dunstan C.R., Burgess T., Elliott R., Colombero A., Elliott G., Scully S., Hsu H., Sullivan J., Hawkins N., Davy E., Capparelli C., Eli A., Qian Y.X., Kaufman S., Sarosi I., Shalhoub V., Senaldi G., Guo J., Delaney J., Boyle W.J. Osteoprotegerin (OPG) ligand is a cytokine that regulates osteoclast differentiation and activation. Cell 1998, 93:165-176.
17. Lai W.W., Yang J.S., Lai K.C., Kuo C.L., Hsu C.K., Wang C.K., Chang C.Y., Lin J.J., Tang N.Y., Chen P.Y., Huang W.W., Chung J.G. Rhein induced apoptosis through the endoplasmic reticulum stress, caspase- and mitochondria-dependent pathways in SCC-4 human tongue squamous cancer cells. In Vivo 2009, 23:309-316.
18. Li J., Sarosi I., Yan X.Q., Morony S., Capparelli C., Tan H.L., McCabe S., Elliott R., Scully S., Van G., Kaufman S., Juan S.C., Sun Y., Tarpley J., Martin L., Christensen K., McCabe J., Kostenuik P., Hsu H., Fletcher F., Dunstan C.R., Lacey D.L., Boyle W.J. RANK is the intrinsic hematopoietic cell surface receptor that controls osteoclastogenesis and regulation of bone mass and calcium metabolism. Proc. Natl. Acad. Sci. U.S.A. 2000, 97:1566-1571.
19. Li L.Z., Cui Y., Cui Y., Gong H.Y., Zhang Y.L. Synthesis and pharmacological activities of a series of estrogen-rhein hybrid compounds. J. China Pharm. Univ. 2007, 38:6-11.
20. Li, L.Z., Cui, Y., Zhang, Y.L., Cui, Y., 2004. Preparative methods of radix anthraquinone derivatives and active components of these derivatives-based drug combination. Chinese Patent ZL10094131.7.
21. 2+-dependent mitochondrial death pathway in human nasopharyngeal carcinoma cells. Anticancer Res. 2007, 27:3313-3322.
22. Lin Y.J., Huang Y.H., Zhen Y.Z., Liu X.J., Zhen Y.S. Rhein lysinate induces apoptosis in breast cancer SK-Br-3 cells by inhibiting HER-2 signal pathway. Yao Xue Xue Bao 2008, 43:1099-10105.
23. Lin Y.J., Zhen Y.S. Rhein lysinate suppresses the growth of breast cancer cells and potentiates the inhibitory effect of taxol in athymic mice. Anticancer Drugs 2009, 20:65-72.
24. Lin Y.J., Zhen Y.Z., Shang B.Y., Zhen Y.S. Rhein lysinate suppresses the growth of tumor cells and increases the anti-tumor activity of taxol in mice. Am. J. Chin. Med. 2009, 37:923-931.
25. Luo X.H., Liao E.Y. Effects of estriol on the proliferation and differentiation of human osteoblastic MG-63 cells. Endocr. Res. 2003, 29:343-351.
26. Manolagas S.C. Role of cytokines in bone resorption. Bone 1995, 17:63S-67S.
27. Manolagas S.C., Kousteni S., Jilka R.L. Sex steroids and bone. Recent Prog. Horm. Res. 2002, 57:385-409.
28. Neale J.R., Richter N.B., Merten K.E., Taylor K.G., Singh S., Waite L.C., Emery N.K., Smith N.B., Cai J., Pierce W.M. Bone selective effect of an estradiol conjugate with a novel tetracycline-derived bone-targeting agent. Bioorg. Med. Chem. Lett. 2009, 19:680-683.
29. Orme M.W., Labroo V.M. Synthesis of β-estradiol-3-benzoate-17-(succinyl-12A-tetracycline): a potential bone-seeking estrogen. Bioorg. Med. Chem. Lett. 1994, 4:1375-1380.
30. Saika M., Inoue D., Kido S., Matsumoto T. 17β-estradiol stimulates expression of osteoprotegerin by a mouse stromal cell line, ST-2, via estrogen receptor-α. Endocrinology 2001, 142:2205-2212.
31. Schiff R., Massarweh S., Shou J., Osborne C.K. Breast cancer endocrine resistance: how growth factor signaling and estrogen receptor coregulators modulate response. Clin. Cancer Res. 2003, 9:447S-454S.
32. Sezer O., Heider U., Zavrski I., Kuhne C.A., Hofbauer L.C. RANK ligand and osteoprotegerin in myeloma bone disease. Blood 2003, 101:2094-2098.
33. Shi P., Huang Z., Chen G. Rhein induces apoptosis and cell cycle arrest in human hepatocellular carcinoma BEL-7402 cells. Am. J. Chin. Med. 2008, 36:805-813.
34. Simonet W.S., Lacey D.L., Dunstan C.R., Kelley M., Chang M.S., Luthy R., Nguyen H.Q., Wooden S., Bennett L., Boone T., Shimamoto G., DeRose M., Eliott R., Colombero A., Tan H.L., Trail G., Sullivan J., Davy E., Bucay N., Renshaw-Gegg L., Hughes T.M., Hill D., Pattison W., Campbell P., Sander S., Van G., Tarpley J., Derby P., Lee R., Amgen Program E.S.T., Boyle W.J. Osteoprotegerin: a novel secreted protein involved in the regulation of bone density. Cell 1997, 89:309-319.
35. Spelsberg T.C., Subramaniam M., Riggs B.L., Khosla S. The actions and interactions of sex steroids and growth factors/cytokines on the skeleton. Mol. Endocrinol. 1999, 13:819-828.
36. Thirunavukkarasu K., Halladay D.L., Miles R.R., Yang X., Galvin R.J., Chandrasekhar S., Martin T.J., Onyia J.E. The osteoblast-specific transcription factor Cbfa1 contributes to the expression of osteoprotegerin, a potent inhibitor of osteoclast differentiation and function. J. Biol. Chem. 2000, 275:25163-25172.
37. Thirunavukkarasu K., Miles R.R., Halladay D.L., Yang X., Galvin R.J., Chandrasekhar S., Martin T.J., Onyia J.E. Stimulation of osteoprotegerin (OPG) gene expression by transforming growth factor-β (TGF-β): mapping of the OPG promoter region that mediates TGF-β effects. J. Biol. Chem. 2001, 276:36241-36250.
38. Tsushima N., Yabuki M., Harada H., Katsumata T., Kanamaru H., Nakatsuka I., Yamamoto M., Nakatsuka M. Tissue distribution and pharmacological potential of SM-16896, a novel oestrogen-bisphosphonate hybrid compound. J. Pharm. Pharmacol. 2000, 52:27-37.
39. Viereck V., Gründker C., Blaschke S., Niederkleine B., Siggelkow H., Frosch K.H., Raddatz D., Emons G., Hofbauer L.C. Raloxifene concurrently stimulatesosteoprotegerin and inhibits interleukin-6 production by human trabecular osteoblasts. J. Clin. Endocrinol. Metab. 2003, 88:4206-4213.
40. Viereck V., Grundker C., Blaschke S., Siggelkow H., Emons G., Hofbauer L.C. The phytoestrogen genistein stimulates the production of osteoprotegerin by human trabecular osteoblasts. J. Cell. Biochem. 2002, 84:725-735.
41. Wang L., Mao Y.J., Wang W.J. Inhibitory effect of diacerein on osteoclastic bone destruction and its possible mechanism of action. Yao Xue Xue Bao 2006, 41:555-560.
42. Watson C.S., Bulayeva N.N., Wozniak A.L., Finnerty C.C. Signaling from the membrane via membrane estrogen receptor-alpha: estrogens, xenoestrogens, and phytoestrogens. Steroids 2005, 70:364-371.
43. Watson C.S., Gametchu B. Proteins of multiple classes may participate in nongenomic steroid actions. Exp. Biol. Med. (Maywood) 2003, 228:1272-1281.
44. Willson T.M., Charifson P.S., Baxter A.D., Geddie N.G. Bone targeted drugs 1: identification of heterocycles with hydroxyapatite affinity. Bioorg. Med. Chem. Lett. 1996, 6:1043-1046.
45. Writing Group for the Women's Health Initiative Investigators Risks and benefits of estrogen plus progestin in healthy postmenopausal women. Principal results from the women's health initiative randomized controlled trial. JAMA 2002, 288:321-333.
46. Yokogawa K., Miya K., Sekido T., Higashi Y., Nomura M., Fujisawa R., Morito K., Masamune Y., Waki Y., Kasugai S., Miyamoto K. Selective delivery of estradiol to bone by aspartic acid oligopeptide and its effects on ovariectomized mice. Endocrinology 2001, 142:1228-1233.
47. Yokogawa K. Pharmacokinetic advantage of an intranasal preparation of a novel anti-osteoporosis drug, l-asp-hexapeptide-conjugated estradiol. Biol. Pharm. Bull. 2006, 29:1229-1233.
48. Zhang L., Cui Y., Li L.Z. Research on absorbance ability of radix anthraquinone compounds by hydroxyapatite. Acta Academiae Medicinae CPAF 2008, 17:1048-1050.
49. Zhang L., Jin X., Li L.Z., Zhang Y.L., Tang C.G., Wang Y. The effects of rhein-estrone on the bone mineral density and uterus in ovariectomized rats. Acta Academiae Medicinae CPAF 2010, 19:841-843.