메뉴 건너뛰기




Volumn 17, Issue 7, 2004, Pages 879-888

Oxidation of raloxifene to quinoids: Potential toxic pathways via a diquinone methide and o-quinones

Author keywords

[No Author keywords available]

Indexed keywords

7 HYDROXYRALOXIFENE; DIQUINONE METHIDE; GLUTATHIONE; QUINONE DERIVATIVE; RALOXIFENE; RALOXIFENE 2 QUINONE GLUTATHIONE CONJUGATE; RALOXIFENE DIQUINONE METHIDE GLUTHATIONE CONJUGATE; TAMOXIFEN; UNCLASSIFIED DRUG;

EID: 3242703146     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx0342722     Document Type: Article
Times cited : (85)

References (39)
  • 1
    • 0027412216 scopus 로고
    • High-grade endometrial carcinoma in tamoxifen-treated breast cancer patients
    • Magriples, U., Naftolin, F., Schwartz, P. E., and Carcangiu, M. L. (1993) High-grade endometrial carcinoma in tamoxifen-treated breast cancer patients. J. Clin. Oncol. 11, 485-490.
    • (1993) J. Clin. Oncol. , vol.11 , pp. 485-490
    • Magriples, U.1    Naftolin, F.2    Schwartz, P.E.3    Carcangiu, M.L.4
  • 2
    • 0027293895 scopus 로고
    • Gynecologic tumors in tamoxifen-treated women with breast cancer
    • Seoud, M. A., Johnson, J., and Weed, J. C., Jr. (1993) Gynecologic tumors in tamoxifen-treated women with breast cancer. Obstet. Gynecol. 82, 165-169.
    • (1993) Obstet. Gynecol. , vol.82 , pp. 165-169
    • Seoud, M.A.1    Johnson, J.2    Weed Jr., J.C.3
  • 3
    • 0034989609 scopus 로고    scopus 로고
    • Understanding the genotoxicity of tamoxifen?
    • Phillips, D. H. (2001) Understanding the genotoxicity of tamoxifen? Carcinogenesis 22, 839-849.
    • (2001) Carcinogenesis , vol.22 , pp. 839-849
    • Phillips, D.H.1
  • 4
    • 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., Constantino, J. P., Redmond, C. K., Fisher, E. R., Wickerham, D. L., and Cronin, W. M. (1994) Endometrial cancer in tamoxifen-treated breast cancer patients: findings from the National Surgical Adjuvant Breast and Bowel project (NSABP) B-14. J. Natl. Cancer Inst. 86, 527-537.
    • (1994) J. Natl. Cancer Inst. , vol.86 , pp. 527-537
    • Fisher, B.1    Constantino, J.P.2    Redmond, C.K.3    Fisher, E.R.4    Wickerham, D.L.5    Cronin, W.M.6
  • 7
    • 0029964446 scopus 로고    scopus 로고
    • Endometrial carcinoma associated with breast carcinoma: Low incidence with tamoxifen use
    • Cuenca, R. E., Giachino, J., Arredondo, M. A., Hempling, R., and Edge, S. B. (1996) Endometrial carcinoma associated with breast carcinoma: low incidence with tamoxifen use. Cancer 77, 2058-2063.
    • (1996) Cancer , vol.77 , pp. 2058-2063
    • Cuenca, R.E.1    Giachino, J.2    Arredondo, M.A.3    Hempling, R.4    Edge, S.B.5
  • 9
  • 10
    • 0026606580 scopus 로고
    • Induction of covalent DNA adducts in rodents by tamoxifen
    • Han, X. L., and Liehr, J. G. (1992) Induction of covalent DNA adducts in rodents by tamoxifen. Cancer Res. 52, 1360-1363.
    • (1992) Cancer Res. , vol.52 , pp. 1360-1363
    • Han, X.L.1    Liehr, J.G.2
  • 11
    • 0028172454 scopus 로고
    • Tamoxifen: Evidence by 32P-postlabeling and use of metabolic inhibitors for two distinct pathways leading to mouse hepatic DNA adduct formation and identification of 4-hydroxytamoxifen as a proximate metabolite
    • Randerath, K., Moorthy, B., Mabon, N., and Sriram, P. (1994) Tamoxifen: evidence by 32P-postlabeling and use of metabolic inhibitors for two distinct pathways leading to mouse hepatic DNA adduct formation and identification of 4-hydroxytamoxifen as a proximate metabolite. Carcinogenesis 15, 2087-2094.
    • (1994) Carcinogenesis , vol.15 , pp. 2087-2094
    • Randerath, K.1    Moorthy, B.2    Mabon, N.3    Sriram, P.4
  • 13
    • 0032519594 scopus 로고    scopus 로고
    • a-Hydroxytamoxifen is a substrate of hydroxysteroid (alcohol) sulfotransferase, resulting in tamoxifen DNA adducts
    • Shibutani, S., Dasaradhi, L., Terashima, I., Banoglu, E., and Duffel, M. W. (1998) a-Hydroxytamoxifen is a substrate of hydroxysteroid (alcohol) sulfotransferase, resulting in tamoxifen DNA adducts. Cancer. Res. 58, 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
  • 14
    • 0031054835 scopus 로고    scopus 로고
    • Identification of tamoxifen-DNA adducts formed by α-sulfate tamoxifen and α-acetoxy-tamoxifen
    • Dasaradhi, L., and Shibutani, S. (1997) Identification of tamoxifen-DNA adducts formed by α-sulfate tamoxifen and α-acetoxy-tamoxifen. Chem. Res. Toxicol. 10, 189-196.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 189-196
    • Dasaradhi, L.1    Shibutani, S.2
  • 15
    • 0029866506 scopus 로고    scopus 로고
    • Evidence that the catechol 3,4-dihydroxytamoxifen is a proximate intermediate to the reactive species binding covalently to proteins
    • Dehal, S. S., and Kupfer, D. (1996) Evidence that the catechol 3,4-dihydroxytamoxifen is a proximate intermediate to the reactive species binding covalently to proteins. Cancer Res. 56, 1283-1290.
    • (1996) Cancer Res. , vol.56 , pp. 1283-1290
    • Dehal, S.S.1    Kupfer, D.2
  • 16
    • 0033017135 scopus 로고    scopus 로고
    • Cytochrome P450 3A and 2D6 catalyze ortho hydroxylation of 4-hydroxytamoxifen and 3-hy-droxytamoxifen (droloxifene) yielding tamoxifen catechol: Involvement of catechols in covalent binding to hepatic proteins
    • Dehal, S. S., and Kupfer, D. (1999) Cytochrome P450 3A and 2D6 catalyze ortho hydroxylation of 4-hydroxytamoxifen and 3-hy-droxytamoxifen (droloxifene) yielding tamoxifen catechol: involvement of catechols in covalent binding to hepatic proteins. Drug Metab. Dispos. 27, 681-688.
    • (1999) Drug Metab. Dispos. , vol.27 , pp. 681-688
    • Dehal, S.S.1    Kupfer, D.2
  • 17
    • 0033065364 scopus 로고    scopus 로고
    • Comparison of the DNA adducts formed by tamoxifen and 4-hydroxytamoxifen in vivo
    • Beland, F. A., McDaniel, L. P., and Marques, M. M. (1999) Comparison of the DNA adducts formed by tamoxifen and 4-hydroxytamoxifen in vivo. Carcinogenesis 20, 471-477.
    • (1999) Carcinogenesis , vol.20 , pp. 471-477
    • Beland, F.A.1    McDaniel, L.P.2    Marques, M.M.3
  • 18
    • 0032974948 scopus 로고    scopus 로고
    • 4-Hydroxytamoxifen gives DNA adducts by chemical activation, but not in rat liver cells
    • Osborne, M. R., Davis, W., Hewer, A. J., Hardcastle, I. R., and Phillips, D. H. (1999) 4-Hydroxytamoxifen gives DNA adducts by chemical activation, but not in rat liver cells. Chem. Res. Toxicol. 12, 151-158.
    • (1999) Chem. Res. Toxicol. , vol.12 , pp. 151-158
    • Osborne, M.R.1    Davis, W.2    Hewer, A.J.3    Hardcastle, I.R.4    Phillips, D.H.5
  • 19
    • 0031416520 scopus 로고    scopus 로고
    • Identification of tamoxifen-DNA adducts by 4-hydroxytamoxifen quinone methide
    • Marques, M. M., and Beland, F. A. (1997) Identification of tamoxifen-DNA adducts by 4-hydroxytamoxifen quinone methide. Carcinogenesis 18, 1949-1954.
    • (1997) Carcinogenesis , vol.18 , pp. 1949-1954
    • Marques, M.M.1    Beland, F.A.2
  • 20
    • 0021201213 scopus 로고
    • Antiestrogens. 2. Structure-activity studies in a series of 3-aroyl-2-arylbenzo[b]thiophene derivatives leading to [6-hydroxy-2-(4- hydroxyphenyl)benzo[b] thien-3-yl] [4-[2-(1-piperidinyl)ethoxylphenyl]methanone hydrochloride (LY156758), a remarkably effective estrogen antagonist with only minimal intrinsic estrogenicity
    • Jones, C. D., Jevnikar, M. G., Pike, A. J., Peters, M. K., Black, L. J., Thompson, A. R., Falcone, J. F., and Clemens, J. A. (1984) Antiestrogens. 2. Structure-activity studies in a series of 3-aroyl-2-arylbenzo[b]thiophene derivatives leading to [6-hydroxy-2-(4-hydroxyphenyl)benzo[b] thien-3-yl] [4-[2-(1-piperidinyl)ethoxylphenyl]methanone hydrochloride (LY156758), a remarkably effective estrogen antagonist with only minimal intrinsic estrogenicity. J. Med. Chem. 27, 1057-1066.
    • (1984) J. Med. Chem. , vol.27 , pp. 1057-1066
    • Jones, C.D.1    Jevnikar, M.G.2    Pike, A.J.3    Peters, M.K.4    Black, L.J.5    Thompson, A.R.6    Falcone, J.F.7    Clemens, J.A.8
  • 21
    • 0021248131 scopus 로고
    • Nonsteroidal antioestrogens-receptor binding and biological response in rat uterus, rat mammary carcinoma and human breast cancer cells
    • Wakeling, A. E., Valcaccia, B., Newboult, E., and Green, L. R. (1984) Nonsteroidal antioestrogens-receptor binding and biological response in rat uterus, rat mammary carcinoma and human breast cancer cells. J. Steroid Biochem. 20, 111-120.
    • (1984) J. Steroid Biochem. , vol.20 , pp. 111-120
    • Wakeling, A.E.1    Valcaccia, B.2    Newboult, E.3    Green, L.R.4
  • 22
    • 0020582094 scopus 로고
    • Effects of a new antiestrogen, keoxifene (LY156758), on growth of carcinogen-induced mammary tumors and on LH and prolactin levels
    • Clemens, J. A., Bennett, D. R., Black, L. J., and Jones, C. D. (1983) Effects of a new antiestrogen, keoxifene (LY156758), on growth of carcinogen-induced mammary tumors and on LH and prolactin levels. Life Sci. 32, 2869-2875.
    • (1983) Life Sci. , vol.32 , pp. 2869-2875
    • Clemens, J.A.1    Bennett, D.R.2    Black, L.J.3    Jones, C.D.4
  • 23
    • 0036718266 scopus 로고    scopus 로고
    • The Study of Tamoxifen and Raloxifene (STAR trial) for the prevention of breast cancer
    • Kelminski, A. (2002) The Study of Tamoxifen and Raloxifene (STAR trial) for the prevention of breast cancer. Hawaii Med. J. 61, 209-210.
    • (2002) Hawaii Med. J. , vol.61 , pp. 209-210
    • Kelminski, A.1
  • 26
    • 0007522011 scopus 로고
    • Stereochemistry and reactions with hydroxyl ion and with silver oxide of the 2-bromo-4-phenylcyclohexanols and the 1-methyl-2-bromo-4-phenylcyclohexanols
    • Curtin, D. Y., and Harder, R. J. (1960) Stereochemistry and reactions with hydroxyl ion and with silver oxide of the 2-bromo-4-phenylcyclohexanols and the 1-methyl-2-bromo-4-phenylcyclohexanols. J. Am. Chem. Soc. 82, 2357-2368.
    • (1960) J. Am. Chem. Soc. , vol.82 , pp. 2357-2368
    • Curtin, D.Y.1    Harder, R.J.2
  • 28
    • 3042794987 scopus 로고    scopus 로고
    • Quinoids formed from estrogens and antiestrogens
    • Bolton, J. L., Yu, L., and Thatcher, G. R. J. (2004) Quinoids formed from estrogens and antiestrogens. Methods Enzymol. 378, 110-123.
    • (2004) Methods Enzymol. , vol.378 , pp. 110-123
    • Bolton, J.L.1    Yu, L.2    Thatcher, G.R.J.3
  • 29
    • 0027205012 scopus 로고
    • Mass spectrometry in the analysis of glutathione conjugates
    • Baillie, T. A., and Davis, M. R. (1993) Mass spectrometry in the analysis of glutathione conjugates. Biol. Mass Spectrom. 22, 319-325.
    • (1993) Biol. Mass Spectrom. , vol.22 , pp. 319-325
    • Baillie, T.A.1    Davis, M.R.2
  • 30
    • 0142200899 scopus 로고    scopus 로고
    • Nitrosation, nitration, and autoxidation of the selective estrogen receptor modulator raloxifene by nitric oxide, peroxynitrite, and reactive nitrogen/oxygen species
    • Toader, V., Xu, X., Nicolescu, A., Yu, L., Bolton, J. L., and Thatcher, G. R. (2003) Nitrosation, nitration, and autoxidation of the selective estrogen receptor modulator raloxifene by nitric oxide, peroxynitrite, and reactive nitrogen/oxygen species. Chem. Res. Toxicol. 16, 1264-1276.
    • (2003) Chem. Res. Toxicol. , vol.16 , pp. 1264-1276
    • Toader, V.1    Xu, X.2    Nicolescu, A.3    Yu, L.4    Bolton, J.L.5    Thatcher, G.R.6
  • 31
    • 0037255847 scopus 로고    scopus 로고
    • Pharmacokinetics of selective estrogen receptor modulators
    • Morello, K. C., Wurz, G. T., and DeGregorio, M. W. (2003) Pharmacokinetics of selective estrogen receptor modulators. Clin. Pharmacokinet. 42, 361-372.
    • (2003) Clin. Pharmacokinet. , vol.42 , pp. 361-372
    • Morello, K.C.1    Wurz, G.T.2    DeGregorio, M.W.3
  • 33
  • 34
    • 0033046884 scopus 로고    scopus 로고
    • Rapid drug metabolite profiling using fast liquid chromatography, automated multiple-stage mass spectrometry and receptor-binding
    • Lim, H. K., Stellingweif, S., Sisenwine, S., and Chan, K. W. (1999) Rapid drug metabolite profiling using fast liquid chromatography, automated multiple-stage mass spectrometry and receptor-binding. J Chromatogr. A 831, 227-241.
    • (1999) J Chromatogr. A , vol.831 , pp. 227-241
    • Lim, H.K.1    Stellingweif, S.2    Sisenwine, S.3    Chan, K.W.4
  • 36
    • 0028930981 scopus 로고
    • o-Methoxy-4-alkylphenols that form quinone methides of intermediate reactivity are the most toxic in rat liver slices
    • Thompson, D. C., Perera, K., Krol, E. S., and Bolton, J. L. (1995) o-Methoxy-4-alkylphenols that form quinone methides of intermediate reactivity are the most toxic in rat liver slices. Chem. Res. Toxicol. 8, 323-327.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 323-327
    • Thompson, D.C.1    Perera, K.2    Krol, E.S.3    Bolton, J.L.4
  • 38
    • 1642270595 scopus 로고
    • Isomerization of 3-substituted indoles, benzofurans, and benzo[b]thiophenes
    • Kost, A. N., Budylin, V. A., Matveeva, E. D., and Sterligov, D. O. (1970) Isomerization of 3-substituted indoles, benzofurans, and benzo[b]thiophenes. Zh. Org. Khim. 6, 1516-1517.
    • (1970) Zh. Org. Khim. , vol.6 , pp. 1516-1517
    • Kost, A.N.1    Budylin, V.A.2    Matveeva, E.D.3    Sterligov, D.O.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.