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Volumn 87, Issue 1, 2003, Pages 75-83

Structure activity relationship studies on C2 side chain substituted 1,1-bis(4-methoxyphenyl)-2-phenylalkenes and 1,1,2-tris(4-methoxyphenyl)alkenes

Author keywords

Cytotoxicity; MCF 7 and MDA MB 231 breast cancer cells; Triarylalkenes

Indexed keywords

1,1 BIS(4 METHOXYPHENYL) 2 PHENYLPENT 1 ENE; 4 HYDROXYTAMOXIFEN; 4,5,5 TRIS(4 METHOXYPHENYL)PENT 4 ENYL; 5,5 BIS(4 METHOXYPHENYL) 4 PHENYLPENT 4 ENYLAMINE; 5,6,6 TRIS(4 HYDROXYPHENYL)HEX 5 ENOIC ACID; 5,6,6 TRIS(4 METHOXYPHENYL)HEX 5 ENENITRILE; 6,6 BIS(4 METHOXYPHENYL) 5 PHENYLHEX 5 ENENITRILE; 6,6 BIS(4 METHOXYPHENYL) 5 PHENYLHEX 5 ENOIC ACID; ALKENE DERIVATIVE; ANTINEOPLASTIC AGENT; ESTROGEN RECEPTOR; TAMOXIFEN; UNCLASSIFIED DRUG;

EID: 0242662631     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-0760(03)00385-6     Document Type: Article
Times cited : (2)

References (30)
  • 1
    • 0027172047 scopus 로고
    • A current view of tamoxifen for the treatment and prevention of breast cancer
    • Jordan V.C. A current view of tamoxifen for the treatment and prevention of breast cancer. Br. J. Pharmacol. 110:1993;507-517.
    • (1993) Br. J. Pharmacol. , vol.110 , pp. 507-517
    • Jordan, V.C.1
  • 3
    • 0028208456 scopus 로고
    • Endometrial cancer in tamoxifen treated breast cancer patients: Findings from the National Surgical Adjuvant Breast and Bowel Project (NSABP) B-14
    • Fisher B., Costantino J.P., Redmond C.K., Fisher E.R., Wickerham D.L., Cronin W.M. Endometrial cancer in tamoxifen treated breast cancer patients: findings from the National Surgical Adjuvant Breast and Bowel Project (NSABP) B-14. J. Natl. Can. Inst. 86:1994;527-537.
    • (1994) J. Natl. Can. Inst. , vol.86 , pp. 527-537
    • Fisher, B.1    Costantino, J.P.2    Redmond, C.K.3    Fisher, E.R.4    Wickerham, D.L.5    Cronin, W.M.6
  • 5
    • 0028936687 scopus 로고
    • Tamoxifen and tumorigenicity: A predictable concern
    • Jordan V.C. Tamoxifen and tumorigenicity: a predictable concern. J. Natl. Can. Inst. 87:1995;623-626.
    • (1995) J. Natl. Can. Inst. , vol.87 , pp. 623-626
    • Jordan, V.C.1
  • 8
    • 0030199499 scopus 로고    scopus 로고
    • Effect of growth factors on estrogen receptor mediated gene expression
    • Hafner F., Holler E., von Angerer E. Effect of growth factors on estrogen receptor mediated gene expression. J. Steroid Biochem. Mol. Biol. 58:1996;385-393.
    • (1996) J. Steroid Biochem. Mol. Biol. , vol.58 , pp. 385-393
    • Hafner, F.1    Holler, E.2    Von Angerer, E.3
  • 9
    • 0037153283 scopus 로고    scopus 로고
    • Investigations on estrogen receptor binding. The estrogenic, antiestrogenic and cytotoxic properties of C2-alkyl-substituted 1,1-bis(4-hydroxyphenyl)-2-phenylalkenes
    • Lubczyk V., Bachmann H., Gust R. Investigations on estrogen receptor binding. The estrogenic, antiestrogenic and cytotoxic properties of C2-alkyl-substituted 1,1-bis(4-hydroxyphenyl)-2-phenylalkenes. J. Med. Chem. 45:2002;5358-5364.
    • (2002) J. Med. Chem. , vol.45 , pp. 5358-5364
    • Lubczyk, V.1    Bachmann, H.2    Gust, R.3
  • 10
    • 0037431405 scopus 로고    scopus 로고
    • Antiestrogenically active 1,1,2-tris(4-hydroxyphenyl)alkenes without basic side chain: Synthesis and biological activity
    • Lubczyk V., Bachmann H., Gust R. Antiestrogenically active 1,1,2-tris(4-hydroxyphenyl)alkenes without basic side chain: synthesis and biological activity. J. Med. Chem. 46:2003;1484-1491.
    • (2003) J. Med. Chem. , vol.46 , pp. 1484-1491
    • Lubczyk, V.1    Bachmann, H.2    Gust, R.3
  • 11
    • 0041887177 scopus 로고    scopus 로고
    • Investigations on the influence of terminal groups at the C2-propyl side chain of 1,1-bis(4-hydroxyphenyl)-2-phenylpent-1-ene and 1,1,2-tris(4- hydroxyphenyl)pent-1-ene on the estrogen receptor binding and the estrogenic and anti-estrogenic properties
    • Gust R., Lubczyk V. Investigations on the influence of terminal groups at the C2-propyl side chain of 1,1-bis(4-hydroxyphenyl)-2-phenylpent-1-ene and 1,1,2-tris(4-hydroxyphenyl)pent-1-ene on the estrogen receptor binding and the estrogenic and anti-estrogenic properties. J. Steroid Biochem. Mol. Biol. 86:2003;57-70.
    • (2003) J. Steroid Biochem. Mol. Biol. , vol.86 , pp. 57-70
    • Gust, R.1    Lubczyk, V.2
  • 12
    • 0023896334 scopus 로고
    • The seed stock concept and quality control for cell lines
    • Hay R.J. The seed stock concept and quality control for cell lines. Anal. Biochem. 171:1988;225-237.
    • (1988) Anal. Biochem. , vol.171 , pp. 225-237
    • Hay, R.J.1
  • 13
    • 0017184389 scopus 로고
    • A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding
    • Bradford M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72:1976;248-254.
    • (1976) Anal. Biochem. , vol.72 , pp. 248-254
    • Bradford, M.M.1
  • 14
    • 0032921685 scopus 로고    scopus 로고
    • Selective estrogen receptor modulators. A look ahead
    • Mitlak B.H., Cohen F.J. Selective estrogen receptor modulators. A look ahead. Drugs. 57:1999;653-663.
    • (1999) Drugs , vol.57 , pp. 653-663
    • Mitlak, B.H.1    Cohen, F.J.2
  • 15
    • 0026606580 scopus 로고
    • Induction of covalent DNA adducts in rodents by Tamoxifen
    • Han X., Liehr J.G. Induction of covalent DNA adducts in rodents by Tamoxifen. Cancer Res. 52:1992;1360-1363.
    • (1992) Cancer Res. , vol.52 , pp. 1360-1363
    • Han, X.1    Liehr, J.G.2
  • 16
    • 0026319776 scopus 로고
    • Cytochrome P450 mediated action and irreversible binding of the antiestrogen tamoxifen to proteins in rat and human liver: Possible involvement of the flavin-containing monooxygenases in tamoxifen action
    • Mani C., Kupfer D. Cytochrome P450 mediated action and irreversible binding of the antiestrogen tamoxifen to proteins in rat and human liver: possible involvement of the flavin-containing monooxygenases in tamoxifen action. Cancer Res. 51:1991;6052-6058.
    • (1991) Cancer Res. , vol.51 , pp. 6052-6058
    • Mani, C.1    Kupfer, D.2
  • 18
    • 0028172242 scopus 로고
    • Alpha-hydroxytamoxifen, a metabolite of tamoxifen with exceptionally high DNA-binding activity in rat hepatocytes
    • Phillips D.H., Carmichael P.L., Hewer A., Cole K.J., Poon G.K. Alpha-hydroxytamoxifen, a metabolite of tamoxifen with exceptionally high DNA-binding activity in rat hepatocytes. Cancer Res. 54:1994;5518-5522.
    • (1994) Cancer Res. , vol.54 , pp. 5518-5522
    • Phillips, D.H.1    Carmichael, P.L.2    Hewer, A.3    Cole, K.J.4    Poon, G.K.5
  • 19
    • 0032519594 scopus 로고    scopus 로고
    • Alpha-hydroxytamoxifen is a substrate of hydroxysteroid (alcohol) sulfotransferase, resulting in tamoxifen DNA adducts
    • Shibutani S., Dasaradhi L., Terashima I., Banoglu E., Duffel M.W. Alpha-hydroxytamoxifen is a substrate of hydroxysteroid (alcohol) sulfotransferase, resulting in tamoxifen DNA adducts. Cancer Res. 58:1998;647-653.
    • (1998) Cancer Res. , vol.58 , pp. 647-653
    • Shibutani, S.1    Dasaradhi, L.2    Terashima, I.3    Banoglu, E.4    Duffel, M.W.5
  • 21
    • 0033958868 scopus 로고    scopus 로고
    • 4-Hydroxylated metabolites of the antiestrogens tamoxifen and toremifene are metabolized to unusually stable quinone methides
    • Fan P.W., Zhang F., Bolton J.L. 4-Hydroxylated metabolites of the antiestrogens tamoxifen and toremifene are metabolized to unusually stable quinone methides. Chem. Res. Toxicol. 13:2000;45-52.
    • (2000) Chem. Res. Toxicol. , vol.13 , pp. 45-52
    • Fan, P.W.1    Zhang, F.2    Bolton, J.L.3
  • 22
    • 0030008422 scopus 로고    scopus 로고
    • Conformational studies and electronic structures of tamoxifen and toremifen and their allylic carbocations proposed as reactive intermediates leading to DNA adduct formation
    • Kuramochi H. Conformational studies and electronic structures of tamoxifen and toremifen and their allylic carbocations proposed as reactive intermediates leading to DNA adduct formation. J. Med. Chem. 39:1996;2877-2886.
    • (1996) J. Med. Chem. , vol.39 , pp. 2877-2886
    • Kuramochi, H.1
  • 23
    • 0021722622 scopus 로고
    • High affinity cytosol binding site(s) for antiestrogens in two human breast cancer cell lines and in biopsy specimens devoid of estrogen receptors
    • Chouvet C., Saez S. High affinity cytosol binding site(s) for antiestrogens in two human breast cancer cell lines and in biopsy specimens devoid of estrogen receptors. J. Steroid Biochem. Mol. Biol. 21:1984;755-761.
    • (1984) J. Steroid Biochem. Mol. Biol. , vol.21 , pp. 755-761
    • Chouvet, C.1    Saez, S.2
  • 24
    • 0028047373 scopus 로고
    • Effect of tamoxifen on the multidrug-resistant phenotype in human breast cancer cells: Isobologram, drug accumulation, and M(r) 170,000 glycoprotein (gp170) binding studies
    • Leonessa F., Jacobson M., Boyle B., Lippman J., McGarvey M., Clarke R. Effect of tamoxifen on the multidrug-resistant phenotype in human breast cancer cells: isobologram, drug accumulation, and M(r) 170,000 glycoprotein (gp170) binding studies. Cancer Res. 54:1994;441-447.
    • (1994) Cancer Res. , vol.54 , pp. 441-447
    • Leonessa, F.1    Jacobson, M.2    Boyle, B.3    Lippman, J.4    Mcgarvey, M.5    Clarke, R.6
  • 25
    • 0025193824 scopus 로고
    • Ca2(+)-dependent binding of tamoxifen to calmodulin isolated from bovine brain
    • Lopes M.C., Vale M.G., Carvalho A.P. Ca2(+)-dependent binding of tamoxifen to calmodulin isolated from bovine brain. Cancer Res. 50:1990;2753-2758.
    • (1990) Cancer Res. , vol.50 , pp. 2753-2758
    • Lopes, M.C.1    Vale, M.G.2    Carvalho, A.P.3
  • 26
    • 0025781261 scopus 로고
    • Influence of di- and tri-phenylethylene estrogen/antiestrogen structure on the mechanisms of protein kinase C inhibition and activation as revealed by a multivariate analysis
    • Bignon E., Pons M., Dore J.C., Gilbert J., Ojasoo T., Miquel J.F., Raynaud J.P., Crastes de Paulet A. Influence of di- and tri-phenylethylene estrogen/antiestrogen structure on the mechanisms of protein kinase C inhibition and activation as revealed by a multivariate analysis. Biochem. Pharm. 42:1991;1373-1383.
    • (1991) Biochem. Pharm. , vol.42 , pp. 1373-1383
    • Bignon, E.1    Pons, M.2    Dore, J.C.3    Gilbert, J.4    Ojasoo, T.5    Miquel, J.F.6    Raynaud, J.P.7    Crastes De Paulet, A.8
  • 27
    • 0034053818 scopus 로고    scopus 로고
    • Changes in phospholipase D isoform activity and expression in multidrug-resistant human cancer cells
    • Fiucci G., Czarny M., Lavie Y., Zhao D., Berse B., Blusztajn J.K., Liscovitch M. Changes in phospholipase D isoform activity and expression in multidrug-resistant human cancer cells. Int. J. Cancer. 85:2000;882-888.
    • (2000) Int. J. Cancer , vol.85 , pp. 882-888
    • Fiucci, G.1    Czarny, M.2    Lavie, Y.3    Zhao, D.4    Berse, B.5    Blusztajn, J.K.6    Liscovitch, M.7
  • 30
    • 0002453760 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of 1,1-dichloro-2,3- diarylcyclopropanes as antitubulin and anti-breast cancer agents
    • Jonnalagadda S.S., ter Haar E., Hamel E., Lin C.M., Magarian R.A., Day B.W. Synthesis and biological evaluation of 1,1-dichloro-2,3- diarylcyclopropanes as antitubulin and anti-breast cancer agents. Bioorg. Med. Chem. 5:1997;715-722.
    • (1997) Bioorg. Med. Chem. , vol.5 , pp. 715-722
    • Jonnalagadda, S.S.1    Ter Haar, E.2    Hamel, E.3    Lin, C.M.4    Magarian, R.A.5    Day, B.W.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.