Synthesis, evaluation and 3D QSAR analysis of novel estradiol-RGD octapeptide conjugates with oral anti-osteoporosis activity

European Journal of Medicinal Chemistry

Volumn 44, Issue 4, 2009, Pages 1689-1704

  Liu, Jiangyuan ^a   Zhang, Xiaoyi ^b   Zhao, Ming ^b   Peng, Shiqi ^a,b  

^a PEKING UNIVERSITY   (China)

^b CAPITAL MEDICAL UNIVERSITY   (China)

Author keywords

3D QSAR; Anti osteoporosis; Conjugate; Estradiol; RGD octapeptide

Indexed keywords

ALKALINE PHOSPHATASE; ARGINYLGLYCYLASPARTIC ACID; ARGINYLGLYCYLASPARTYLPHENYLALANYLARGINYLGLYCYLASPARTYLPHENYLALANINE; ARGINYLGLYCYLASPARTYLSERYLARGINYLGLYCYLASPARTYLSERINE; ARGINYLGLYCYLASPARTYLVALYLARGINYLGLYCYLASPARTYLVALINE; CALCIUM; ESTRADIOL; ESTRADIOL 17BETA O CARBONYLPROPIONYLARGINYLGLYCYLASPARTYLPHENYLALANINE; ESTRADIOL 17BETA O CARBONYLPROPIONYLARGINYLGLYCYLASPARTYLPHENYLALANYLARGINYLGLYCYL ASPARTYLPHENYLALANINE; ESTRADIOL 17BETA O CARBONYLPROPIONYLARGINYLGLYCYLASPARTYLSERINE; ESTRADIOL 17BETA O CARBONYLPROPIONYLARGINYLGLYCYLASPARTYLSERYLARGINYLGLYCYLASPARTYLASPARTIC ACID; ESTRADIOL 17BETA O CARBONYLPROPIONYLARGINYLGLYCYLASPARTYLVALINE; ESTRADIOL 17BETA O CARBONYLPROPIONYLARGINYLGLYCYLASPARTYLVALYLARGINYLGLYCYLASPARTYLVALINE; ESTRADIOL DERIVATIVE; N (ESTRADIOL 3 OXYACETYL)ARGINYLGLYCYLASPARTYLPHENYLALANINE; N (ESTRADIOL 3 OXYACETYL)ARGINYLGLYCYLASPARTYLPHENYLALANYLARGINYLGLYCYLASPARTYLPHENYLALANINE; N (ESTRADIOL 3 OXYACETYL)ARGINYLGLYCYLASPARTYLSERINE; N (ESTRADIOL 3 OXYACETYL)ARGINYLGLYCYLASPARTYLSERYLARGINYLGLYCYLASPARTYLSERINE; N (ESTRADIOL 3 OXYACETYL)ARGINYLGLYCYLASPARTYLVALINE; N (ESTRADIOL 3 OXYACETYL)ARGINYLGLYCYLASPARTYLVALYLARGINYLGLYCYLASPARTYLVALINE; OCTAPEPTIDE; OLIGOPEPTIDE; PHOSPHORUS; TETRAPEPTIDE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BONE MASS; BONE MINERAL; CALCIUM BLOOD LEVEL; CARDIOVASCULAR RISK; CONTROLLED STUDY; DISEASE MODEL; DRUG ACTIVITY; DRUG CONJUGATION; DRUG DESIGN; DRUG EFFECT; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; ENDOMETRIUM HYPERPLASIA; EXPERIMENTAL MOUSE; FEMALE; FEMUR; HORMONE SUBSTITUTION; MOUSE; NONHUMAN; OSTEOPOROSIS; OVARIECTOMY; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RISK ASSESSMENT; THROMBOGENESIS;

ADMINISTRATION, ORAL; ALKALINE PHOSPHATASE; ANIMALS; BLOOD COAGULATION; CALCIUM; ENDOMETRIAL HYPERPLASIA; ESTRADIOL; FEMALE; FEMUR; MICE; MICE, INBRED ICR; MINERALS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OLIGOPEPTIDES; ORGAN SIZE; OSTEOPOROSIS; PHOSPHORUS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; REFERENCE STANDARDS; THROMBOEMBOLISM; UTERUS;

EID: 61349183756     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2008.09.036     Document Type: Article

References (25)

1. Davidson M., and DeSimone M.E. Confronting osteoporosis: what we know, where we're headed. Clin. Rev. 12 (2002) 76-82
2. Amin S., Zhang Y., Felson D.T., Sawin C.T., Hannan M.T., and Wilson P.W.F. Estradiol, testosterone, and the risk for hip fractures in elderly men from the Framingham study. Am. J. Med. 119 (2006) 426-433
3. Rajzbaum G., and Bézie Y. Postmenopausal osteoporosis and atheroma. Joint Bone Spine 73 (2006) 610-613
4. Michael J.S. Selective estrogen receptor modulators: the ideal estrogen replacement. Primary Care Update OB/GYNS. 8 (2001) 25-30
5. Stevenson J.C. HRT and the primary prevention of cardiovascular disease. Maturitas 57 (2007) 31-34
6. Gebbie A. Hormone replacement therapy. Medicine 35 (2007) 529-532
7. Vestergaard P., Rejnmark L., and Mosekilde L. Fracture reducing potential of hormone replacement therapy on a population level. Maturitas 54 (2006) 285-293
8. Cortés-Prieto J., and Juez-Martel P. Incidences of breast cancer throughout long-term hormone replacement therapy. J. Steroid Biochem. Mol. Biol. 104 (2007) 180-189
9. Brixen K., Abrahamsen B., and Kassem M. Prevention and treatment of osteoporosis in women. Curr. Obstet. Gynaecol. 15 (2005) 251-258
10. Rees M. Unravelling the confusion about HRT in women. J. Mens Health Gend. 2 (2005) 287-291
11. Raza J.A., Reinhart R.A., and Movahed A. Ischemic heart disease in women and the role of hormone therapy. Int. J. Cardiol. 96 (2004) 7-19
12. Sgarabotto M., Baldini M., Dei C.A., Manotti C., Barilli A.L., Rinaldi M., Benassi L., and Modena A.B. Effects of raloxifene and continuous combined hormone therapy on haemostasis variables: a multicenter, randomized, double-blind study. Thromb. Res. 119 (2007) 85-91
13. Wang C., Zhao M., Yang J., and Peng S.Q. Synthesis and analgesic effects of kyotorphin-steroid linkers. Steroids 66 (2001) 811-815
14. Wang C., Zhao M., and Peng S.Q. The synthesis and immunosuppressive activities of steroid-urotoxin linkers. Bioorg. Med. Chem. 12 (2004) 4403-4421
15. Wang C., Cui W.N., Zhao M., Yang J., and Peng S.Q. Studies on the synthesis and anti-osteoporosis of estrogen-GHRPS linkers. Bioorg. Med. Chem. Lett. 13 (2003) 143-146
16. Saintier D., Khanine V., Uzan B., Ea H.K., de Vernejoul M.C., and Cohen-Solal M.E. Estradiol inhibits adhesion and promotes apoptosis in murine osteoclasts in vitro. J. Steroid Biochem. Mol. Biol. 99 (2006) 165-173
17. Gallagher J.C. Advances in bone biology and new treatment for bone loss. Maturitas 60 (2008) 65-69
18. Nakamura T., Imai Y., Matsumoto T., Sato S., Takeuchi K., Igarashi K., et al. Estrogen prevents bone loss via estrogen receptor and induction of Fas ligand in osteoclasts. Cell 130 (2007) 811-823
19. Yan X., and Dong L. The mechanism of RGD-insulin anti-osteoclastic bone resorption. Bone 27 (2000) 32
20. Xiong Y., Zhao M., Wang C., Chang H.W., and Peng S. Improved anti-osteoporosis potency and reduced endometrial membrane hyperplasia during hormone replacement therapy with estrogen-RGD peptide conjugates. J. Med. Chem. 50 (2007) 3340-3353
21. Kurihara H., and Nagamune T. Cell adhesion ability of artificial extracellular matrix proteins containing a long repetitive Arg-Gly-Asp sequence. J. Biosci. Bioeng. 100 (2005) 82-87
22. Shaikh A.R., Ismael M., Carpio C.A.D., Tsuboi H., Koyama M., Endou A., Kubo M., Broclawikc E., and Miyamoto A. Three-dimensional quantitative structure-activity relationship (3D-QSAR) and docking studies on (benzothiazole-2-yl)acetonitrile derivatives as c-Jun N-terminal kinase-3 (JNK3) inhibitors. Bioorg. Med. Chem. Lett. 16 (2006) 5917-5925
23. Doddareddy M.R., Cho Y.S., Koh H.Y., and Pae A.N. CoMFA and CoMSIA 3D QSAR analysis on N1-arylsulfonylindole compounds as 5-HT6 antagonists. Bioorg. Med. Chem. 12 (2004) 3977-3985
24. Maurice P., Pires V., Amant C., Kauskot A., Da Nascimento S., Sonnet P., Rochette J., Legrand C., Fauvel-Lafeve F., and Bonnefoy A. Antithrombotic effect of the type III collagen-related octapeptide (KOGEOGPK) in the mouse. Vasc. Pharmacol. 44 (2006) 42-49
25. William A.S., Steven E.S., Thomas E.S., Anne B.S., Jeffrey S.B., Karen S.H., Eddie C.L., and Martin L.O. Antithrombotic and hemostatic effects of a small molecule factor XIa inhibitor in rats. Eur. J. Pharmacol. 570 (2007) 167-174