Metabolism of exogenous 4- and 2-hydroxyestradiol in the human male☆
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Design and synthesis of selective CYP1B1 inhibitor via dearomatization of α-naphthoflavone
2019, Bioorganic and Medicinal ChemistryCitation Excerpt :such as breast cancer and ovarian cancer (Fig. 1). 2-Hydroxylation of E2 regulated by CYP1A1 and CYP1A2 has been recognized as a major inactivation pathway of E2, which affords 2-hydroxy-E2 (2OHE2) as a metabolite,14,17 and methylation by catechol-O-methyltransferase (COMT) affords an inactivated metabolite.18 On the other hand, CYP1B1 produces 4-hydroxy-E2 (4OHE2).19
Whole flaxseed diet alters estrogen metabolism to promote 2-methoxtestradiol-induced apoptosis in hen ovarian cancer
2017, Journal of Nutritional BiochemistryCitation Excerpt :We have previously established that 15% whole flaxseed-supplemented diet increases the serum 2-hydroxyestradiol/16-hydroxyestradiol ratio, in turn suggesting a reduced risk of cancer [12]. The 2-hydroxy and 4-hydroxy metabolites are oxidized by catechol-o-methyl transferase (COMT) to methoxy-metabolites [13]. 2-hydroxyestradiol is preferentially converted to 2-methoxyestradiol [14], whereas 4-hydroxyestradiol is readily oxidized to the 3,4 quinone, a genotoxic metabolite.
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2011, Biochimica et Biophysica Acta - Reviews on CancerCitation Excerpt :Although neither 2-OH-E2 nor 2-OH-E1 is carcinogenic in vitro or in vivo [42,54,55], both 2-OH-E2 and 2-OH-E1 are capable of producing ROS and undergo metabolic redox cycling like 4-OH-E2. The lack of carcinogenicity of 2-hydroxylated estrogen metabolites in vivo may be due to their rapid inactivation by catechol-O-methyltransferase (COMT)-mediated O-methylation [55–57], rapid clearance [58], and weak estrogenic hormonal activity (compared with 4-OH-E2) [59]. It may also be due to 2-MeO-E2, the major product of COMT-mediated O-methylation of 2-OH-E2 that possesses unique anti-tumorigenic activity.
Selective inhibition of methoxyflavonoids on human CYP1B1 activity
2010, Bioorganic and Medicinal ChemistryA methoxyflavonoid, chrysoeriol, selectively inhibits the formation of a carcinogenic estrogen metabolite in MCF-7 breast cancer cells
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This study was presented in part at the 12th Acta Endocrinologica Congress, Stockholm, Sweden 1983 and at the 30th Symposium of the Deutsche Gesellschaft für Endokrinologie, München, F.R.G., 1986.