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Volumn 35, Issue 5, 2008, Pages 615-622

Syntheses and biological activities of novel 2-methoxyestradiol analogs, 2-fluoroethoxyestradiol and 2-fluoropropanoxyestradiol, and a radiosynthesis of 2-[18F]fluoroethoxyestradiol for positron emission tomography

Author keywords

2 18F Fluoroethoxyestradiol; 2 Fluoroethoxyestradiol; 2 Fluoropropanoxyestradiol; 2 Methoxyestradiol; PET

Indexed keywords

2 FLUOROETHOXYESTRADIOL; 2 FLUOROPROPANOXYESTRADIOL; 2 METHOXYESTRADIOL; FLUORINE 18; FLUOROETHOXYESTRADIOL F 18; TRACER;

EID: 45449100536     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2008.04.003     Document Type: Article
Times cited : (5)

References (20)
  • 1
    • 11144239579 scopus 로고    scopus 로고
    • 2-Methoxyestradiol inhibits hypoxia-inducible factor 1a, tumor growth, and angiogenesis and augments paclitaxel efficacy in head and neck squamous cell carcinoma
    • Ricker J.L., Chen Z., Yang X.P., Pribluda V.S., Swartz G.M., and Van Waes C. 2-Methoxyestradiol inhibits hypoxia-inducible factor 1a, tumor growth, and angiogenesis and augments paclitaxel efficacy in head and neck squamous cell carcinoma. Clin Cancer Res 10 (2004) 8665-8673
    • (2004) Clin Cancer Res , vol.10 , pp. 8665-8673
    • Ricker, J.L.1    Chen, Z.2    Yang, X.P.3    Pribluda, V.S.4    Swartz, G.M.5    Van Waes, C.6
  • 2
    • 33846240027 scopus 로고    scopus 로고
    • Antitumor effect of 2-methoxyestradiol in a rat orthotopic brain tumor model
    • Kang S.H., Cho H.T., Devi S., Zhang Z., Escuin D., Liang Z., et al. Antitumor effect of 2-methoxyestradiol in a rat orthotopic brain tumor model. Cancer Res 66 (2006) 11991-11997
    • (2006) Cancer Res , vol.66 , pp. 11991-11997
    • Kang, S.H.1    Cho, H.T.2    Devi, S.3    Zhang, Z.4    Escuin, D.5    Liang, Z.6
  • 3
    • 33645222234 scopus 로고    scopus 로고
    • Modulation of cell-cycle regulatory signaling network by 2-methoxyestradiol in prostate cancer cells is mediated through multiple signal transduction pathways
    • Ray G., Dhar G., Van Veldhuizen P.J., Banerjee S., Saxena N.K., Sengupta K., et al. Modulation of cell-cycle regulatory signaling network by 2-methoxyestradiol in prostate cancer cells is mediated through multiple signal transduction pathways. Biochemistry 45 (2006) 3703-3713
    • (2006) Biochemistry , vol.45 , pp. 3703-3713
    • Ray, G.1    Dhar, G.2    Van Veldhuizen, P.J.3    Banerjee, S.4    Saxena, N.K.5    Sengupta, K.6
  • 4
    • 33751074452 scopus 로고    scopus 로고
    • Hypoxia-inducible factor-1 in human breast and prostate cancer
    • Kimbro K.S., and Simons J.W. Hypoxia-inducible factor-1 in human breast and prostate cancer. Endocr Relat Cancer 13 (2006) 739-749
    • (2006) Endocr Relat Cancer , vol.13 , pp. 739-749
    • Kimbro, K.S.1    Simons, J.W.2
  • 5
    • 0028331925 scopus 로고
    • 2-Methoxyestradiol, and endogenous mammalian metabolite, inhibits tubulin polymerization by interacting at the colchicine site
    • D'Amato R.J., Lin C.M., Flynn E., Folkman J., and Hamel E. 2-Methoxyestradiol, and endogenous mammalian metabolite, inhibits tubulin polymerization by interacting at the colchicine site. Proc Natl Acad Sci U S A 91 (1994) 3964-3968
    • (1994) Proc Natl Acad Sci U S A , vol.91 , pp. 3964-3968
    • D'Amato, R.J.1    Lin, C.M.2    Flynn, E.3    Folkman, J.4    Hamel, E.5
  • 6
    • 10744231706 scopus 로고    scopus 로고
    • 2ME2 inhibits tumor growth and angiogenesis by disrupting microtubules and dysregulating HIF
    • Mabjeesh N.J., Escuin D., LaVallee T.M., Pribluda V.S., Swartz G.M., Johnson M.S., et al. 2ME2 inhibits tumor growth and angiogenesis by disrupting microtubules and dysregulating HIF. Cancer Cell 3 (2003) 363-375
    • (2003) Cancer Cell , vol.3 , pp. 363-375
    • Mabjeesh, N.J.1    Escuin, D.2    LaVallee, T.M.3    Pribluda, V.S.4    Swartz, G.M.5    Johnson, M.S.6
  • 7
    • 33750483598 scopus 로고    scopus 로고
    • Phase I safety, pharmacokinetic and pharmacodynamic studies of 2-methoxyestradiol alone or in combination with docetaxel in patients with locally recurrent or metastatic breast cancer
    • James J., Murry D.J., Treston A.M., Storniolo A.M., Sledge G.W., Sidor C.M., et al. Phase I safety, pharmacokinetic and pharmacodynamic studies of 2-methoxyestradiol alone or in combination with docetaxel in patients with locally recurrent or metastatic breast cancer. Invest New Drugs 25 (2007) 41-48
    • (2007) Invest New Drugs , vol.25 , pp. 41-48
    • James, J.1    Murry, D.J.2    Treston, A.M.3    Storniolo, A.M.4    Sledge, G.W.5    Sidor, C.M.6
  • 8
    • 0842269204 scopus 로고    scopus 로고
    • Mechanism of action of 2-methoxyestradiol: new developments
    • Mooberry S.L. Mechanism of action of 2-methoxyestradiol: new developments. Drug Resist Updat 6 (2003) 355-361
    • (2003) Drug Resist Updat , vol.6 , pp. 355-361
    • Mooberry, S.L.1
  • 9
    • 0030069601 scopus 로고    scopus 로고
    • Interactions of 2-methoxyestradiol, an endogenous mammalian metabolite, with unpolymerized tubulin and with tubulin polymers
    • Hamel E., Lin C.M., Flynn E., and D'Amato R.J. Interactions of 2-methoxyestradiol, an endogenous mammalian metabolite, with unpolymerized tubulin and with tubulin polymers. Biochemistry 35 (1996) 1304-1310
    • (1996) Biochemistry , vol.35 , pp. 1304-1310
    • Hamel, E.1    Lin, C.M.2    Flynn, E.3    D'Amato, R.J.4
  • 10
    • 33846439416 scopus 로고    scopus 로고
    • 11C]methoxy-3,17β-estradiol to measure the pharmacokinetics of an antitumor drug candidate, 2-methoxy-3,17β-estradiol
    • 11C]methoxy-3,17β-estradiol to measure the pharmacokinetics of an antitumor drug candidate, 2-methoxy-3,17β-estradiol. J Labelled Comp Radioparm 49 (2006) 1117-1124
    • (2006) J Labelled Comp Radioparm , vol.49 , pp. 1117-1124
    • Mun, J.1    Voll, R.J.2    Goodman, M.M.3
  • 11
    • 0029008622 scopus 로고
    • Synthesis, antitubulin and antimitotic activity, and cytotoxicity of analogs of 2-methoxyestradiol, an endogenous mammalian metabolite of estradiol that Inhibits tubulin polymerization by binding the colchicine binding site
    • Cushman M., He H.M., Katzenellenbogen J.A., Lin C.M., and Hamel E. Synthesis, antitubulin and antimitotic activity, and cytotoxicity of analogs of 2-methoxyestradiol, an endogenous mammalian metabolite of estradiol that Inhibits tubulin polymerization by binding the colchicine binding site. J Med Chem 38 (1995) 2041-2049
    • (1995) J Med Chem , vol.38 , pp. 2041-2049
    • Cushman, M.1    He, H.M.2    Katzenellenbogen, J.A.3    Lin, C.M.4    Hamel, E.5
  • 12
    • 0030767873 scopus 로고    scopus 로고
    • Synthesis of analogs of 2-methoxyestradiol with enhanced inhibitory effects on tubulin polymerization and cancer cell growth
    • Cushman M., He H.M., Katzenellenbogen J.A., Varma R.K., Hamel E., Lin C.M., et al. Synthesis of analogs of 2-methoxyestradiol with enhanced inhibitory effects on tubulin polymerization and cancer cell growth. J Med Chem 40 (1997) 2323-2334
    • (1997) J Med Chem , vol.40 , pp. 2323-2334
    • Cushman, M.1    He, H.M.2    Katzenellenbogen, J.A.3    Varma, R.K.4    Hamel, E.5    Lin, C.M.6
  • 13
    • 0037057582 scopus 로고    scopus 로고
    • The effect of exchanging various substituents at the 2-position of 2-methoxyestradiol on cytotoxicity in human cancer cell cultures and inhibition of tubulin polymerization
    • Cushman M., Mohanakrishnan A.K., Hollingshead M., and Hamel E. The effect of exchanging various substituents at the 2-position of 2-methoxyestradiol on cytotoxicity in human cancer cell cultures and inhibition of tubulin polymerization. J Med Chem 45 (2002) 4748-4754
    • (2002) J Med Chem , vol.45 , pp. 4748-4754
    • Cushman, M.1    Mohanakrishnan, A.K.2    Hollingshead, M.3    Hamel, E.4
  • 14
    • 0035955176 scopus 로고    scopus 로고
    • Chemical synthesis and biological evaluation of cis- and trans-12,13-cyclopropyl and 12,13-cyclobutyl epothilones and related pyridine side chain analogues
    • Nicolaou K.C., Namoto K.R., Andreas U.T., Shoji M., Li J., D'Amico G., et al. Chemical synthesis and biological evaluation of cis- and trans-12,13-cyclopropyl and 12,13-cyclobutyl epothilones and related pyridine side chain analogues. J Am Chem Soc 123 (2001) 9313-9323
    • (2001) J Am Chem Soc , vol.123 , pp. 9313-9323
    • Nicolaou, K.C.1    Namoto, K.R.2    Andreas, U.T.3    Shoji, M.4    Li, J.5    D'Amico, G.6
  • 18
    • 0033619983 scopus 로고    scopus 로고
    • Radiosynthesis of carbon-11 labeled N-methyl- 2-(arylthio)benzylamines: potential radiotracers for the serotonin reuptake receptor
    • Wilson A.A., and Houle S. Radiosynthesis of carbon-11 labeled N-methyl- 2-(arylthio)benzylamines: potential radiotracers for the serotonin reuptake receptor. J Labelled Comp Radiopharm 42 (1999) 1277-1288
    • (1999) J Labelled Comp Radiopharm , vol.42 , pp. 1277-1288
    • Wilson, A.A.1    Houle, S.2
  • 19
    • 0028129275 scopus 로고
    • A versatile synthesis of 2-methoxyestradiol, an endogenous metabolite of estradiol which inhibits tubulin polymerization by binding to the colchicine binding site
    • He H.M., and Cushman M. A versatile synthesis of 2-methoxyestradiol, an endogenous metabolite of estradiol which inhibits tubulin polymerization by binding to the colchicine binding site. Bioorg Med Chem Lett 4 (1994) 1725-1728
    • (1994) Bioorg Med Chem Lett , vol.4 , pp. 1725-1728
    • He, H.M.1    Cushman, M.2
  • 20
    • 0031793090 scopus 로고    scopus 로고
    • An optimized synthesis of 2-methoxyestradiol, a naturally occurring human metabolite with anticancer activity
    • Wang Z., and Cushman M. An optimized synthesis of 2-methoxyestradiol, a naturally occurring human metabolite with anticancer activity. Syn Commun 28 (1998) 4431-4437
    • (1998) Syn Commun , vol.28 , pp. 4431-4437
    • Wang, Z.1    Cushman, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.