메뉴 건너뛰기




Volumn 3, Issue 5, 2012, Pages 392-396

Boron-based 4-hydroxytamoxifen bioisosteres for treatment of de novo tamoxifen resistant breast cancer

Author keywords

[No Author keywords available]

Indexed keywords

AFIMOXIFENE; BORON; CYTOCHROME P450 2D6; ESTROGEN RECEPTOR; FULVESTRANT; TAMOXIFEN;

EID: 84861033311     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml3000287     Document Type: Article
Times cited : (34)

References (28)
  • 1
    • 0032896905 scopus 로고    scopus 로고
    • Estrogen receptor status by immunohistochemistry is superior to the ligand-binding assay for predicting response to adjuvant endocrine therapy in breast cancer
    • Harvey, J. M.; Clark, G. M.; Osborne, C. K.; Allred, D. C. Estrogen receptor status by immunohistochemistry is superior to the ligand-binding assay for predicting response to adjuvant endocrine therapy in breast cancer J. Clin. Oncol. 1999, 17, 1474
    • (1999) J. Clin. Oncol. , vol.17 , pp. 1474
    • Harvey, J.M.1    Clark, G.M.2    Osborne, C.K.3    Allred, D.C.4
  • 2
    • 69249137029 scopus 로고    scopus 로고
    • Biological determinants of endocrine resistance in breast cancer
    • Musgrove, E. A.; Sutherland, R. L. Biological determinants of endocrine resistance in breast cancer Nat. Rev. Cancer 2009, 9, 631-643
    • (2009) Nat. Rev. Cancer , vol.9 , pp. 631-643
    • Musgrove, E.A.1    Sutherland, R.L.2
  • 3
    • 67749114265 scopus 로고    scopus 로고
    • CYP2D6 and tamoxifen: DNA matters in breast cancer
    • Hoskins, J. M.; Carey, L. A.; McLeod, H. L. CYP2D6 and tamoxifen: DNA matters in breast cancer Nat. Rev. Cancer 2009, 9, 576-586
    • (2009) Nat. Rev. Cancer , vol.9 , pp. 576-586
    • Hoskins, J.M.1    Carey, L.A.2    McLeod, H.L.3
  • 5
    • 0017665570 scopus 로고
    • A monohydroxylated metabolite of tamoxifen with potent antioestrogenic activity
    • Jordan, V. C.; Collins, M. M.; Rowsby, L.; Prestwich, G. A Monohydroxylated metabolite of tamoxifen with potent antiestrogenic activity J. Endocrinol. 1977, 75, 305-316 (Pubitemid 8219148)
    • (1977) Journal of Endocrinology , vol.75 , Issue.2 , pp. 305-316
    • Jordan, V.C.1    Collins, M.M.2    Rowsby, L.3    Prestwich, G.4
  • 6
    • 0020402019 scopus 로고
    • Metabolites of tamoxifen in animals and man: Identification, pharmacology, and significance
    • DOI 10.1007/BF01806449
    • Jordan, V. C. Metabolites of tamoxifen in animals and man: identification, pharmacology, and significance Breast Cancer Res. Treat. 1982, 2, 123-138 (Pubitemid 13233530)
    • (1982) Breast Cancer Research and Treatment , vol.2 , Issue.2 , pp. 123-138
    • Jordan, V.C.1
  • 7
    • 0020033521 scopus 로고
    • Tamoxifen antiestrogens. A comparison of the activity, pharmacokinetics, and metabolic activation of the cis and trans isomers of tamoxifen
    • Robertson, D. W.; Katzenellenbogen, J. A.; Long, D. J.; Rorke, E. A.; Katzenellenbogen, B. S. Tamoxifen antiestrogens. a comparison of the activity, pharmacokinetics, and metabolic activation of the cis and trans Isomers of tamoxifen J. Steroid Biochem. 1982, 16, 1-13 (Pubitemid 12158097)
    • (1982) Journal of Steroid Biochemistry , vol.16 , Issue.1 , pp. 1-13
    • Robertson, D.W.1    Katzenellenbogen, J.A.2    Long, D.J.3
  • 8
    • 0020003085 scopus 로고
    • 7 cells: Correlation between binding to estrogen receptor and inhibition of cell growth
    • Coezy, E.; Borgna, J.-L.; Rochefort, H. Tamoxifen and metabolites in MCF7 cells: correlation between binding to estrogen receptor and inhibition of cell growth Cancer Res. 1982, 42, 317-323 (Pubitemid 12207285)
    • (1982) Cancer Research , vol.42 , Issue.1 , pp. 317-323
    • Coezy, E.1    Borgna, J.L.2    Rochefort, H.3
  • 9
    • 0021618186 scopus 로고
    • The pharmacology and clinical uses of tamoxifen
    • Furr, B. J. A.; Jordan, V. C. The pharmacology and clinical uses of tamoxifen Pharmacol. Ther. 1984, 25, 127-205 (Pubitemid 14015738)
    • (1984) Pharmacology and Therapeutics , vol.25 , Issue.2 , pp. 127-205
    • Furr, B.J.A.1    Jordan, V.C.2
  • 10
    • 4243063941 scopus 로고    scopus 로고
    • Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: Prominent roles for CYP3A and CYP2D6
    • DOI 10.1124/jpet.104.065607
    • Desta, Z.; Ward, B. A.; Soukhova, N. V.; Flockhart, D. A. Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: Prominent roles for CYP3A and CYP2D6 J. Pharmacol. Exp. Ther. 2004, 310, 1062-1075 (Pubitemid 39108928)
    • (2004) Journal of Pharmacology and Experimental Therapeutics , vol.310 , Issue.3 , pp. 1062-1075
    • Desta, Z.1    Ward, B.A.2    Soukhova, N.V.3    Flockhart, D.A.4
  • 11
    • 0029160910 scopus 로고
    • Phase i study of percutaneous 4-hydroxy-tamoxifen with analyses of 4-hydroxy-tamoxifen concentrations in breast cancer and normal breast tissue
    • Pujol, H.; Girault, J.; Rouanet, P.; Fournier, S.; Grenier, J.; Simony, J.; Fourtillan, J.-B.; Pujol, J.-L. Phase I study of percutaneous 4-hydroxy-tamoxifen with analyses of 4-hydroxy-tamoxifen concentrations in breast cancer and normal breast tissue Cancer Chemother. Pharmacol. 1995, 36, 493-498
    • (1995) Cancer Chemother. Pharmacol. , vol.36 , pp. 493-498
    • Pujol, H.1    Girault, J.2    Rouanet, P.3    Fournier, S.4    Grenier, J.5    Simony, J.6    Fourtillan, J.-B.7    Pujol, J.-L.8
  • 12
    • 21144447743 scopus 로고    scopus 로고
    • Neoadjuvant percutaneous 4-hydroxytamoxifen decreases breast tumoral cell proliferation: A prospective controlled randomized study comparing three doses of 4-hydroxytamoxifen gel to oral tamoxifen
    • DOI 10.1200/JCO.2005.06.064
    • Rouanet, P.; Linares-Cruz, G.; Dravet, F.; Poujol, S.; Gourgou, S.; Simony-Lafontaine, J.; Grenier, J.; Kramar, A.; Girault, J.; Le Nestour, E.; Maudelonde, T. Neoadjuvant percutaneous 4-hydroxytamoxifen decreases breast tumoral cell proliferation: A prospective controlled randomized study comparing three doses of 4-hydroxytamoxifen gel to oral tamoxifen J. Clin. Oncol. 2005, 23, 2980-2987 (Pubitemid 46224117)
    • (2005) Journal of Clinical Oncology , vol.23 , Issue.13 , pp. 2980-2987
    • Rouanet, P.1    Linares-Cruz, G.2    Dravet, F.3    Poujol, S.4    Gourgou, S.5    Simony-Lafontaine, J.6    Grenier, J.7    Kramar, A.8    Girault, J.9    Le Nestour, E.10    Maudelonde, T.11
  • 14
    • 62449153701 scopus 로고    scopus 로고
    • The tamoxifen metabolite, endoxifen, is a potent antiestrogen that targets estrogen receptor α for degradation in breast cancer cells
    • Wu, X.; Hawse, J. R.; Subramaniam, M.; Goetz, M. P.; Ingle, J. N.; Spelsberg, T. C. The tamoxifen metabolite, endoxifen, is a potent antiestrogen that targets estrogen receptor α for degradation in breast cancer cells Cancer Res. 2009, 69, 1722-1727
    • (2009) Cancer Res. , vol.69 , pp. 1722-1727
    • Wu, X.1    Hawse, J.R.2    Subramaniam, M.3    Goetz, M.P.4    Ingle, J.N.5    Spelsberg, T.C.6
  • 15
    • 77955661193 scopus 로고    scopus 로고
    • Orally administered endoxifen is a new therapeutic agent for breast cancer
    • Ahmad, A.; Ali, S.; Ahmad, M.; Sheikh, S.; Ahmad, I. Orally administered endoxifen is a new therapeutic agent for breast cancer Breast Cancer Res. Treat. 2010, 122, 579-584
    • (2010) Breast Cancer Res. Treat. , vol.122 , pp. 579-584
    • Ahmad, A.1    Ali, S.2    Ahmad, M.3    Sheikh, S.4    Ahmad, I.5
  • 16
    • 79952191452 scopus 로고    scopus 로고
    • Boronic acids in medicinal chemistry: Anticancer, antibacterial and antiviral applications
    • Trippier, P. C.; McGuigan, C. Boronic acids in medicinal chemistry: Anticancer, antibacterial and antiviral applications Med. Chem. Commun. 2010, 1, 183-198
    • (2010) Med. Chem. Commun. , vol.1 , pp. 183-198
    • Trippier, P.C.1    McGuigan, C.2
  • 17
    • 37049175526 scopus 로고
    • Studies of the boron-carbon linkage. Part I. The oxidation and nitration of phenylboric acid
    • Ainley, A. D.; Challenger, F. Studies of the boron-carbon linkage. Part I. The oxidation and nitration of phenylboric acid J. Chem. Soc. 1930, 2171-2180
    • (1930) J. Chem. Soc. , pp. 2171-2180
    • Ainley, A.D.1    Challenger, F.2
  • 18
    • 0037724313 scopus 로고
    • Electrophilic displacement reactions. ix. effects of substituents on rates of reactions between hydrogen peroxide and benzeneboronic acid
    • Kuivila, H. G.; Armour, A. G. Electrophilic displacement reactions. ix. effects of substituents on rates of reactions between hydrogen peroxide and benzeneboronic acid J. Am. Chem. Soc. 1957, 79, 5659-5662
    • (1957) J. Am. Chem. Soc. , vol.79 , pp. 5659-5662
    • Kuivila, H.G.1    Armour, A.G.2
  • 20
    • 41649085548 scopus 로고    scopus 로고
    • Rational design of a fluorescent hydrogen peroxide probe based on the umbelliferone fluorophore
    • Du, L.; Li, M.; Zheng, S.; Wang, B. Rational design of a fluorescent hydrogen peroxide probe based on the umbelliferone fluorophore Tetrahedron Lett. 2008, 49, 3045-3048
    • (2008) Tetrahedron Lett. , vol.49 , pp. 3045-3048
    • Du, L.1    Li, M.2    Zheng, S.3    Wang, B.4
  • 21
    • 0026021362 scopus 로고
    • Production of large amounts of hydrogen peroxide by human tumor cells
    • Szatrowski, T. P.; Nathan, C. F. Production of large amounts of hydrogen peroxide by human tumor cells Cancer Res. 1991, 51, 794-798
    • (1991) Cancer Res. , vol.51 , pp. 794-798
    • Szatrowski, T.P.1    Nathan, C.F.2
  • 23
    • 34248396033 scopus 로고    scopus 로고
    • Dual role of hydrogen peroxide in cancer: Possible relevance to cancer chemoprevention and therapy
    • Miguel, L.-L. Dual role of hydrogen peroxide in cancer: Possible relevance to cancer chemoprevention and therapy Cancer Lett. 2007, 252, 1-8
    • (2007) Cancer Lett. , vol.252 , pp. 1-8
    • Miguel, L.-L.1
  • 24
    • 0344391944 scopus 로고    scopus 로고
    • Simple and Efficient Production of (Z)-4-Hydroxytamoxifen, a Potent Estrogen Receptor Modulator
    • DOI 10.1021/jo035164n
    • Yu, D. D.; Forman, B. M. Simple and efficient production of (Z)-4-hydroxytamoxifen, a potent estrogen receptor modulator J. Org. Chem. 2003, 68, 9489-9491 (Pubitemid 37456525)
    • (2003) Journal of Organic Chemistry , vol.68 , Issue.24 , pp. 9489-9491
    • Yu, D.D.1    Forman, B.M.2
  • 25
    • 3142514770 scopus 로고
    • Palladium(0)-catalyzed cross-coupling reaction of alkoxydiboron with haloarenes: A direct procedure for arylboronic esters
    • Ishiyama, T.; Murata, M.; Miyaura, N. Palladium(0)-catalyzed cross-coupling reaction of alkoxydiboron with haloarenes: a direct procedure for arylboronic esters J. Org. Chem. 1995, 60, 7508-7510
    • (1995) J. Org. Chem. , vol.60 , pp. 7508-7510
    • Ishiyama, T.1    Murata, M.2    Miyaura, N.3
  • 26
    • 15444380619 scopus 로고    scopus 로고
    • The conversion of phenols to the corresponding aryl halides under mild conditions
    • DOI 10.1055/s-2005-861791, M05304SS
    • Thompson, A. L. S.; Kabalka, G. W.; Akula, M. R.; Huffman, J. W. The conversion of phenols to the corresponding aryl halides under mild conditions Synthesis 2005, 547-550 (Pubitemid 40396043)
    • (2005) Synthesis , Issue.4 , pp. 547-550
    • Thompson, A.L.S.1    Kabalka, G.W.2    Akula, M.R.3    Huffman, J.W.4
  • 27
    • 26844560825 scopus 로고    scopus 로고
    • Deprotection of pinacolyl boronate esters via hydrolysis of intermediate potassium trifluoroborates
    • DOI 10.1016/j.tetlet.2005.09.101, PII S0040403905020745
    • Yuen, A. K. L.; Hutton, C. A. Deprotection of pinacolyl boronate esters via hydrolysis of intermediate potassium trifluoroborates Tetrahedron Lett. 2005, 46, 7899-7903 (Pubitemid 41455043)
    • (2005) Tetrahedron Letters , vol.46 , Issue.46 , pp. 7899-7903
    • Yuen, A.K.L.1    Hutton, C.A.2
  • 28
    • 77956039906 scopus 로고    scopus 로고
    • Ron receptor tyrosine kinase activation confers resistance to tamoxifen in breast cancer cell lines
    • McClaine, R. J.; Marshall, A. M.; Wagh, P. K.; Waltz, S. E. Ron receptor tyrosine kinase activation confers resistance to tamoxifen in breast cancer cell lines Neoplasia 2010, 12, 650-658
    • (2010) Neoplasia , vol.12 , pp. 650-658
    • McClaine, R.J.1    Marshall, A.M.2    Wagh, P.K.3    Waltz, S.E.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.