hydroxyestrones

Summary

Summary: Estrone derivatives substituted with one or more hydroxyl groups in any position. They are important metabolites of estrone and other estrogens.

Top Publications

  1. Ursin G, London S, Yang D, Tseng C, Pike M, Bernstein L, et al. Urinary 2-hydroxyestrone/16alpha-hydroxyestrone ratio and family history of breast cancer in premenopausal women. Breast Cancer Res Treat. 2002;72:139-43 pubmed
    ..Our data suggest that among premenopausal women, family history is not associated with higher urinary estrogen levels or a lower ratio of urinary 2-OHE1/16alpha-OHE1. ..
  2. Greenlee H, Chen Y, Kabat G, Wang Q, Kibriya M, Gurvich I, et al. Variants in estrogen metabolism and biosynthesis genes and urinary estrogen metabolites in women with a family history of breast cancer. Breast Cancer Res Treat. 2007;102:111-7 pubmed
  3. Atkinson C, Skor H, Dawn Fitzgibbons E, Scholes D, Chen C, Wahala K, et al. Urinary equol excretion in relation to 2-hydroxyestrone and 16alpha-hydroxyestrone concentrations: an observational study of young to middle-aged women. J Steroid Biochem Mol Biol. 2003;86:71-7 pubmed
  4. Lu L, Cree M, Josyula S, Nagamani M, Grady J, Anderson K. Increased urinary excretion of 2-hydroxyestrone but not 16alpha-hydroxyestrone in premenopausal women during a soya diet containing isoflavones. Cancer Res. 2000;60:1299-305 pubmed
  5. Muti P, Westerlind K, Wu T, Grimaldi T, De Berry J, Schunemann H, et al. Urinary estrogen metabolites and prostate cancer: a case-control study in the United States. Cancer Causes Control. 2002;13:947-55 pubmed
    ..61 (95% CI 0.33-1.15, p for linear trend = 0.04). Results of this case-control study suggest that the estrogen metabolic pathway favoring 2-hydroxylation over 16alpha-hydroxylation may reduce risk of clinically evident prostate cancer. ..
  6. Dalessandri K, Firestone G, Fitch M, Bradlow H, Bjeldanes L. Pilot study: effect of 3,3'-diindolylmethane supplements on urinary hormone metabolites in postmenopausal women with a history of early-stage breast cancer. Nutr Cancer. 2004;50:161-7 pubmed
    ..020), DIM (P =0. 045), and cortisol (P = 0.039), and a nonsignificant increase of 47% in the 2-OHE1/16alpha-OHE1 ratio from 1.46 to 2.14 (P=0.059). In this pilot study, DIM increased the 2-hydroxylation of estrogen urinary metabolites. ..
  7. Teas J, Cunningham J, Fowke J, Nitcheva D, Kanwat C, Boulware R, et al. Urinary estrogen metabolites, prostate specific antigen, and body mass index among African-American men in South Carolina. Cancer Detect Prev. 2005;29:494-500 pubmed
    ..Further studies of estrogen metabolites may provide insights into prostate cancer risk factors. ..
  8. Ursin G, London S, Stanczyk F, Gentzschein E, Paganini Hill A, Ross R, et al. A pilot study of urinary estrogen metabolites (16alpha-OHE1 and 2-OHE1) in postmenopausal women with and without breast cancer. Environ Health Perspect. 1997;105 Suppl 3:601-5 pubmed
  9. Meilahn E, De Stavola B, Allen D, Fentiman I, Bradlow H, Sepkovic D, et al. Do urinary oestrogen metabolites predict breast cancer? Guernsey III cohort follow-up. Br J Cancer. 1998;78:1250-5 pubmed

More Information

Publications89

  1. Chan E, Sepkovic D, Yoo Bowne H, Yu G, Schantz S. A hormonal association between estrogen metabolism and proliferative thyroid disease. Otolaryngol Head Neck Surg. 2006;134:893-900 pubmed
    ..Further study of estrogen metabolites in relation to proliferative thyroid disease is warranted and may lead to implications for new treatment modalities for proliferative thyroid disease. B-3b. ..
  2. Arslan A, Shore R, Afanasyeva Y, Koenig K, Toniolo P, Zeleniuch Jacquotte A. Circulating estrogen metabolites and risk for breast cancer in premenopausal women. Cancer Epidemiol Biomarkers Prev. 2009;18:2273-9 pubmed publisher
    ..The association between the 2-hydroxy:16alpha-hydroxyestrone ratio and estrogen receptor-positive breast cancer needs to be explored in future studies. ..
  3. Fuhrman B, Schairer C, Gail M, Boyd Morin J, Xu X, Sue L, et al. Estrogen metabolism and risk of breast cancer in postmenopausal women. J Natl Cancer Inst. 2012;104:326-39 pubmed publisher
    ..More extensive 2-hydroxylation of parent estrogens is associated with lower risk, and less extensive methylation of potentially genotoxic 4-hydroxylation pathway catechols is associated with higher risk of postmenopausal breast cancer. ..
  4. Morimoto Y, Conroy S, Pagano I, Isaki M, Franke A, Nordt F, et al. Urinary estrogen metabolites during a randomized soy trial. Nutr Cancer. 2012;64:307-14 pubmed publisher
    ..13) and nonproducers (P = 0.23). These findings suggest a beneficial influence of soy foods on estrogen metabolism regardless of equol producer status. ..
  5. Nettleton J, Greany K, Thomas W, Wangen K, Adlercreutz H, Kurzer M. The effect of soy consumption on the urinary 2:16-hydroxyestrone ratio in postmenopausal women depends on equol production status but is not influenced by probiotic consumption. J Nutr. 2005;135:603-8 pubmed
    ..These results are consistent with studies that found lower urine 2:16OHE(1) ratios in women with breast cancer and suggest that soy consumption increases this ratio only in women who are equol producers. ..
  6. Wellejus A, Olsen A, Tjonneland A, Thomsen B, Overvad K, Loft S. Urinary hydroxyestrogens and breast cancer risk among postmenopausal women: a prospective study. Cancer Epidemiol Biomarkers Prev. 2005;14:2137-42 pubmed
    ..The risk of breast cancer, in particular the estrogen receptor-positive type, was enhanced among postmenopausal women using estradiol-based HRT and among those who had a high 2-OHE concentration. ..
  7. Lotinun S, Westerlind K, Turner R. Tissue-selective effects of continuous release of 2-hydroxyestrone and 16alpha-hydroxyestrone on bone, uterus and mammary gland in ovariectomized growing rats. J Endocrinol. 2001;170:165-74 pubmed
    ..Furthermore, differences in the route of administration could influence the tissue specificity of estrogen metabolites. ..
  8. Lewis J, Thomas T, Klinge C, Gallo M, Thomas T. Regulation of cell cycle and cyclins by 16alpha-hydroxyestrone in MCF-7 breast cancer cells. J Mol Endocrinol. 2001;27:293-307 pubmed
    ..These results show that 16alpha-OHE(1) is a potent estrogen capable of accelerating cell cycle kinetics and stimulating the expression of cell cycle regulatory proteins. ..
  9. Cauley J, Zmuda J, Danielson M, Ljung B, Bauer D, Cummings S, et al. Estrogen metabolites and the risk of breast cancer in older women. Epidemiology. 2003;14:740-4 pubmed
    ..17 (95% confidence interval = 0.73-1.87). The study results do not support the hypothesis that the ratio of 2-OHE1 to 16alpha-OHE1 predicts breast cancer risk. ..
  10. Hsu I, Jou H, Huang C, Wang T, Wu W. The effects of soygerm extracts on blood lipoproteins, antioxidative capacity and urinary estrogen metabolites in postmenopausal women on hormone therapy. Int J Gynaecol Obstet. 2007;98:29-33 pubmed
    ..Soygerm extracts may improve serum lipid profile in postmenopausal Taiwanese women who receive HT, and probably provide a favorable effect on estrogen metabolism. ..
  11. Terashima I, Suzuki N, Shibutani S. Mutagenic properties of estrogen quinone-derived DNA adducts in simian kidney cells. Biochemistry. 2001;40:166-72 pubmed
    ..Thus, 2-OHE quinone-derived DNA adducts are mutagenic, generating primarily G --> T and A --> T mutations in mammalian cells. The mutational frequency varied depending on the nature of the 2-OHE moiety. ..
  12. White K, Johansen A, Nilsen M, Ciuclan L, Wallace E, Paton L, et al. Activity of the estrogen-metabolizing enzyme cytochrome P450 1B1 influences the development of pulmonary arterial hypertension. Circulation. 2012;126:1087-98 pubmed publisher
    ..Increased CYP1B1-mediated estrogen metabolism promotes the development of PAH, likely via the formation of mitogens, including 16?-hydroxyestrone. Collectively, this study reveals a possible novel therapeutic target in clinical PAH. ..
  13. Kasim Karakas S, Almario R, Gregory L, Todd H, Wong R, Lasley B. Effects of prune consumption on the ratio of 2-hydroxyestrone to 16alpha-hydroxyestrone. Am J Clin Nutr. 2002;76:1422-7 pubmed
    ..The potential significance of the decrease in 16alphaOHE1 excretion, without a change in the 2OHE1-16alphaOHE1 ratio, on the prevention of estrogen-dependent cancers remains to be determined. ..
  14. Spierto F, Gardner F, Smith S. Evaluation of an EIA method for measuring serum levels of the estrogen metabolite 2-hydroxyestrone in adults. Steroids. 2001;66:59-62 pubmed
    ..Because the within-run variability is relatively smaller than the total variability (among run + within run), use of the assay for determining differences among groups could be justified only when measurements were made in a single run. ..
  15. Markushin Y, Gaikwad N, Zhang H, Kapke P, Rogan E, Cavalieri E, et al. Potential biomarker for early risk assessment of prostate cancer. Prostate. 2006;66:1565-71 pubmed
    ..This is the first demonstration that CEQ-derived DNA adducts are present in urine samples from subjects with prostate cancer. ..
  16. Day J, Newman S, Comninos A, Solomon C, Purohit A, Leese M, et al. The effects of 2-substituted oestrogen sulphamates on the growth of prostate and ovarian cancer cells. J Steroid Biochem Mol Biol. 2003;84:317-25 pubmed
  17. Paquette B, Cantin A, Kocsis Bédard S, Barry S, Lemay R, Jay Gerin J. In vitro generation of peroxynitrite by 2- and 4-hydroxyestrogens in the presence of nitric oxide. Chem Res Toxicol. 2001;14:547-54 pubmed
    ..Since the third-order reaction rate for the reaction between 2(*)NO and O(2) is 2 x 10(6) M(-2) s(-1), it can therefore be suggested that the reaction between (*)NO and 4-OHE(2) occurs at a faster rate. ..
  18. Im A, Vogel V, Ahrendt G, Lloyd S, Ragin C, Garte S, et al. Urinary estrogen metabolites in women at high risk for breast cancer. Carcinogenesis. 2009;30:1532-5 pubmed publisher
  19. Cutolo M, Villaggio B, Seriolo B, Montagna P, Capellino S, Straub R, et al. Synovial fluid estrogens in rheumatoid arthritis. Autoimmun Rev. 2004;3:193-8 pubmed
    ..e. SF in RA) of 16alpha-hydroxyestrone or 2-hydroxyestrogens. ..
  20. Maskarinec G, Morimoto Y, Heak S, Isaki M, Steinbrecher A, Custer L, et al. Urinary estrogen metabolites in two soy trials with premenopausal women. Eur J Clin Nutr. 2012;66:1044-9 pubmed publisher
    ..Contrary to our hypothesis and some previous reports, the results from two well-controlled dietary interventions do not support an effect of a high-soy diet on a panel of urinary estrogen metabolites and the 2-OH/16?-OHE(1) ratio. ..
  21. Cheng Z, Huang S, Tan Z, Wang W, Zhou H. Determination of estradiol metabolites in human liver microsome by high performance liquid chromatography-electrochemistry detector. Acta Pharmacol Sin. 2001;22:369-74 pubmed
    ..This method is sensitive enough to detect E1 in a substrate concentration of 1 micromol/L. The method can be used to study the metabolism mechanism of estradiol in liver microsome. ..
  22. Pisha E, Lui X, Constantinou A, Bolton J. Evidence that a metabolite of equine estrogens, 4-hydroxyequilenin, induces cellular transformation in vitro. Chem Res Toxicol. 2001;14:82-90 pubmed
    ..These data suggest that oxidative stress could be partially responsible for the carcinogenic effects caused by 4-OHEN and that 4-OHEN is a more potent transforming agent than 4-OHE in vitro. ..
  23. Bentz A, Schneider C, Westerlind K. The relationship between physical activity and 2-hydroxyestrone, 16alpha-hydroxyestrone, and the 2/16 ratio in premenopausal women (United States). Cancer Causes Control. 2005;16:455-61 pubmed
    ..This alteration in estrogen metabolism may represent one of the mechanisms by which increased physical activity reduces breast cancer risk. ..
  24. Philips B, Ansell P, Newton L, Harada N, Honda S, Ganjam V, et al. Estrogen receptor-independent catechol estrogen binding activity: protein binding studies in wild-type, Estrogen receptor-alpha KO, and aromatase KO mice tissues. Biochemistry. 2004;43:6698-708 pubmed
    ..The extensive biochemical characterization of this binding protein indicates that this protein may be a receptor, and thus may mediate ERalpha/beta-independent effects of catechol estrogens and their metabolites. ..
  25. Lewis J, Thomas T, Pestell R, Albanese C, Gallo M, Thomas T. Differential effects of 16alpha-hydroxyestrone and 2-methoxyestradiol on cyclin D1 involving the transcription factor ATF-2 in MCF-7 breast cancer cells. J Mol Endocrinol. 2005;34:91-105 pubmed
    ..The binding of ATF-2 was inhibited by the presence of 2-ME2. These results show that 2-ME2 can downregulate cyclin D1 and thereby cell cycle progression by a mechanism involving the disruption of ATF-2 binding to cyclin D1 promoter. ..
  26. Naik R, Nixon S, Lopes A, Godfrey K, Hatem M, Monaghan J. A randomized phase II trial of indole-3-carbinol in the treatment of vulvar intraepithelial neoplasia. Int J Gynecol Cancer. 2006;16:786-90 pubmed
    ..This study has shown significant clinical improvement in symptomatology and vulvoscopic appearance of VIN with I3C therapy. Further clinical and scientific investigations are required to support these preliminary findings. ..
  27. Hamilton Reeves J, Rebello S, Thomas W, Slaton J, Kurzer M. Soy protein isolate increases urinary estrogens and the ratio of 2:16alpha-hydroxyestrone in men at high risk of prostate cancer. J Nutr. 2007;137:2258-63 pubmed
  28. Lippert T, Seeger H, Mueck A. Estradiol metabolism during oral and transdermal estradiol replacement therapy in postmenopausal women. Horm Metab Res. 1998;30:598-600 pubmed
    ..Oral estradiol substitution, however, in our study leads to higher metabolite concentrations which may be regarded as hazardous for women with diseases favoring D-ring metabolism. ..
  29. Maskarinec G, Heak S, Morimoto Y, Custer L, Franke A. The relation of urinary estrogen metabolites with mammographic densities in premenopausal women. Cancer Epidemiol. 2012;36:e310-6 pubmed publisher
  30. Jernstrom H, Klug T, Sepkovic D, Bradlow H, Narod S. Predictors of the plasma ratio of 2-hydroxyestrone to 16alpha-hydroxyestrone among pre-menopausal, nulliparous women from four ethnic groups. Carcinogenesis. 2003;24:991-1005 pubmed
    ..The reported elevated risk of early onset breast cancer among young oral contraceptive users could be mediated in part through altered estrogen metabolism induced by synthetic estrogens and progestins. ..
  31. Paracchini V, Pedotti P, Raimondi S, Garte S, Bradlow H, Sepkovic D, et al. A common CYP1B1 polymorphism is associated with 2-OHE1/16-OHE1 urinary estrone ratio. Clin Chem Lab Med. 2005;43:702-6 pubmed
    ..These results suggest that the Leu/Val CYP1B1 polymorphism may modify estradiol metabolism. ..
  32. Ritter J, Chen F, Sheen Y, Lubet R, Owens I. Two human liver cDNAs encode UDP-glucuronosyltransferases with 2 log differences in activity toward parallel substrates including hyodeoxycholic acid and certain estrogen derivatives. Biochemistry. 1992;31:3409-14 pubmed
    ..abstract truncated at 250 words) ..
  33. Weber S, Leuschner P, Kampfer P, Dott W, Hollender J. Degradation of estradiol and ethinyl estradiol by activated sludge and by a defined mixed culture. Appl Microbiol Biotechnol. 2005;67:106-12 pubmed
    ..The turnover rates of E2 were 0.025-0.1 microg h(-1) cfu(-1) and did not depend on the steroid concentration. ..
  34. Salazar E, Mercado E, Sojo I, Salcedo M. Relationship between estradiol 16 alpha-hydroxylation and human papillomavirus infection in cervical cell transformation. Gynecol Endocrinol. 2001;15:335-40 pubmed
    ..05). We considered that the presence of HPV infection probably increased 16 alpha-hydroxylation of estradiol, providing a possible link between the viral and hormonal elements, possibly having a bearing on the etiology of the disease. ..
  35. Hirose Y, Tsutsui T, Ohno M, Barrett J, Tsutsui T. Effects of a catechol-O-methyltransferase inhibitor on catechol estrogen-induced cellular transformation, chromosome aberrations and apoptosis in Syrian hamster embryo cells. Int J Cancer. 2007;120:1627-33 pubmed
  36. Wang L, Hingerty B, Shapiro R, Broyde S. Structural and stereoisomer effects of model estrogen quinone-derived DNA adducts: N6-(2-hydroxyestron-6(alpha,beta)-yl)-2'-deoxyadenosine and N2-(2-hydroxyestron-6(alpha,beta)-yl)-2'-deoxyguanosine. Chem Res Toxicol. 2004;17:311-24 pubmed
    ..Stereochemistry-dependent differences in adduct orientation could be expected to produce different biochemical effects, as has been observed in adducts derived from polycyclic aromatic hydrocarbons. ..
  37. Barba M, Yang L, Schunemann H, Sperati F, Grioni S, Stranges S, et al. Urinary estrogen metabolites and prostate cancer: a case-control study and meta-analysis. J Exp Clin Cancer Res. 2009;28:135 pubmed publisher
    ..first tertile: OR 0.53, 95% CI 0.31-0.90). Our study and the pooled results provide evidence for a differential role of the estrogen hydroxylation pathway in Pca development and encourage further study. ..
  38. Fowke J, Qi D, Bradlow H, Shu X, Gao Y, Cheng J, et al. Urinary estrogen metabolites and breast cancer: differential pattern of risk found with pre- versus post-treatment collection. Steroids. 2003;68:65-72 pubmed
    ..Our case-control analysis using pre-treatment urine samples suggested that a lower 2-OHE/16-OHE ratio was associated with an increased risk of pre-menopausal and post-menopausal breast cancer diagnosis among Chinese women. ..
  39. Schmidt M, Hartung R, Capellino S, Cutolo M, Pfeifer Leeg A, Straub R. Estrone/17beta-estradiol conversion to, and tumor necrosis factor inhibition by, estrogen metabolites in synovial cells of patients with rheumatoid arthritis and patients with osteoarthritis. Arthritis Rheum. 2009;60:2913-22 pubmed publisher
    ..A preponderance of 16alpha-hydroxylated estrogens is an unfavorable sign in synovial inflammation. ..
  40. Wentz M, Shi S, Shi L, Salama S, Harirah H, Fouad H, et al. Treatment with an inhibitor of catechol-O-methyltransferase activity reduces preterm birth and impedes cervical resistance to stretch in pregnant rats. Reproduction. 2007;134:831-9 pubmed
    ..28) when compared with cervical tissues taken from rats treated with vehicle control (0.18). Modulation of COMT activity may play a role in the regulation of myometrial contractility and cervical ripening during pregnancy. ..
  41. Cohen L, Crespin J, Wolper C, Zang E, Pittman B, Zhao Z, et al. Soy isoflavone intake and estrogen excretion patterns in young women: effect of probiotic administration. In Vivo. 2007;21:507-12 pubmed
    ..However, adding concentrated probiotics may alter isoflavone bioavailability. ..
  42. Chen X, Talati M, Fessel J, Hemnes A, Gladson S, French J, et al. Estrogen Metabolite 16α-Hydroxyestrone Exacerbates Bone Morphogenetic Protein Receptor Type II-Associated Pulmonary Arterial Hypertension Through MicroRNA-29-Mediated Modulation of Cellular Metabolism. Circulation. 2016;133:82-97 pubmed publisher
    ..Antagonism of miR-29 improves in vivo and in vitro features of HPAH and reveals a possible novel therapeutic target. ..
  43. Berstein L, Boyarkina M, Vasilyev D, Poroshina T, Kovalenko I, Imyanitov E, et al. Endocrine metabolic disorders in patients with breast cancer, carriers of BRCA1 gene mutations. Bull Exp Biol Med. 2012;152:610-2 pubmed
    ..BRCA1 gene mutations in breast cancer patients were associated with signs of estrogenization and a pro-genotoxic shift in the estrogen and glucose system, which could modulate the disease course and requires correction. ..
  44. Wacker M, Risendal B, Westerlind K, Lezotte D, Byers T. Ethnicity, body size, and estrogen levels in postmenopausal Hispanic and non-Hispanic white women. J Womens Health (Larchmt). 2009;18:487-91 pubmed publisher
  45. Gao W, Zeng C, Cai D, Liu B, Li Y, Wen X, et al. Serum concentrations of selected endogenous estrogen and estrogen metabolites in pre- and post-menopausal Chinese women with osteoarthritis. J Endocrinol Invest. 2010;33:644-9 pubmed publisher
  46. Yagi E, Barrett J, Tsutsui T. The ability of four catechol estrogens of 17beta-estradiol and estrone to induce DNA adducts in Syrian hamster embryo fibroblasts. Carcinogenesis. 2001;22:1505-10 pubmed
    ..E(1)) and four of their catechol estrogens, 2- and 4-hydroxyestradiols (2- and 4-OHE(2)), and 2- and 4-hydroxyestrones (2- and 4-OHE(1)) induce morphological transformation in Syrian hamster embryo (SHE) fibroblasts, and the ..
  47. Mueck A, Seeger H, Graser T, Oettel M, Lippert T. The effects of postmenopausal hormone replacement therapy and oral contraceptives on the endogenous estradiol metabolism. Horm Metab Res. 2001;33:744-7 pubmed
    ..HRT and OC in the estrogen-progestin combinations tested did not impose any negative effects on estradiol metabolism--they did not elicit a higher D-ring metabolism, which is considered to increase breast cancer risk. ..
  48. Napoli N, Vattikuti S, Yarramaneni J, Giri T, Nekkalapu S, Qualls C, et al. Increased 2-hydroxylation of estrogen is associated with lower body fat and increased lean body mass in postmenopausal women. Maturitas. 2012;72:66-71 pubmed publisher
  49. Kulke M, Chan J, Meyerhardt J, Zhu A, Abrams T, Blaszkowsky L, et al. A prospective phase II study of 2-methoxyestradiol administered in combination with bevacizumab in patients with metastatic carcinoid tumors. Cancer Chemother Pharmacol. 2011;68:293-300 pubmed publisher
  50. Kurisu F, Ogura M, Saitoh S, Yamazoe A, Yagi O. Degradation of natural estrogen and identification of the metabolites produced by soil isolates of Rhodococcus sp. and Sphingomonas sp. J Biosci Bioeng. 2010;109:576-82 pubmed publisher
    ..The presence of these compounds implied degradation through a second pathway initiated through an attack of the saturated ring. ..
  51. Murdock G, Chin C, Offord R, Bradshaw R, Warren J. Human placental estradiol 17 beta-dehydrogenase. Identification of a single histidine residue affinity-labeled by both 3-bromoacetoxyestrone and 12 beta-bromoacetoxy-4-estrene-3,17-dione. J Biol Chem. 1983;258:11460-4 pubmed
    ..It is concluded that the steroid-binding site of human placental estradiol 17 beta-dehydrogenase contains a histidine residue which proximates the upper A-ring region of the steroid as it undergoes the reversible binding step. ..
  52. Sowers M, McConnell D, Jannausch M, Randolph J, Brook R, Gold E, et al. Oestrogen metabolites in relation to isoprostanes as a measure of oxidative stress. Clin Endocrinol (Oxf). 2008;68:806-13 pubmed
    ..This study does not support the commonly held hypothesis that levels of endogenous E2 or its oestrone metabolites favourably modify oxidative stress by decreasing F2(a)-isoprostane levels. ..
  53. Stavrakakis C, Colin R, Héquet V, Faur C, Le Cloirec P. Development and statistical validation of a quantitative method for the determination of steroid hormones in environmental water by column liquid chromatography/tandem mass spectrometry. J AOAC Int. 2008;91:237-46 pubmed
    ..The high efficiency of the purification was proved with LOD < 0.3 ng/L from 200 mL sample. Specificity of the entire analytical procedure was shown by repeatable recoveries at low and high levels of the calibration range. ..
  54. Sturgeon S, Volpe S, Puleo E, Bertone Johnson E, Heersink J, Sabelawski S, et al. Effect of flaxseed consumption on urinary levels of estrogen metabolites in postmenopausal women. Nutr Cancer. 2010;62:175-80 pubmed publisher
  55. Sowers M, McConnell D, Jannausch M, Buyuktur A, Hochberg M, Jamadar D. Estradiol and its metabolites and their association with knee osteoarthritis. Arthritis Rheum. 2006;54:2481-7 pubmed
    ..54-0.86 range), after adjustment for other covariates. There were significant associations of lower baseline serum estradiol and urinary 2-hydroxyestrone with developing knee OA in middle-aged women. ..
  56. Cooke D, Blackwell L. Clearing of suspensions of Micrococcus lysodeikticus catalysed by lysozymes from hen, goose, and turkey egg whites, human milk, and phage T4. Assessment of potential as signal generators for homogeneous enzyme immunoassays for urinary steroids. J Immunoassay Immunochem. 2007;28:67-90 pubmed
    ..The apparent K(M) values for hen egg white lysozyme increased with the enzyme concentration. ..
  57. Chen Y, Liu X, Pisha E, Constantinou A, Hua Y, Shen L, et al. A metabolite of equine estrogens, 4-hydroxyequilenin, induces DNA damage and apoptosis in breast cancer cell lines. Chem Res Toxicol. 2000;13:342-50 pubmed
    ..Our data suggest that the cytotoxic effects of 4-OHEN may be related to its ability to induce DNA damage and apoptosis in hormone sensitive cells in vivo, and these effects may be potentiated by the estrogen receptor. ..
  58. Gruber D, Huber J. Conjugated estrogens--the natural SERMs. Gynecol Endocrinol. 1999;13 Suppl 6:9-12 pubmed
    ..Estrone sulfate, the main component in conjugated estrogens, can be activated into estrone and 17 beta-estradiol in a tissue specific manner. This aspect will become of interest in clinical practice with HRT. ..
  59. Markushin Y, Kapke P, Saeed M, Zhang H, Dawoud A, Rogan E, et al. Development of monoclonal antibodies to 4-hydroxyestrogen-2-N-acetylcysteine conjugates: immunoaffinity and spectroscopic studies. Chem Res Toxicol. 2005;18:1520-7 pubmed
    ..Femtomole detection limits have been demonstrated. Future prospects in clinical diagnostics for testing human exposure to CEQ by urine analysis are briefly addressed. ..
  60. Turan V, Sanchez R, Li J, Li S, Reuhl K, Thomas P, et al. The effects of steroidal estrogens in ACI rat mammary carcinogenesis: 17beta-estradiol, 2-hydroxyestradiol, 4-hydroxyestradiol, 16alpha-hydroxyestradiol, and 4-hydroxyestrone. J Endocrinol. 2004;183:91-9 pubmed
    ..In summary, we observed a dose-dependent induction of mammary tumors in female ACI rats treated continuously with E2; however, under these conditions 2-OH E2, 4-OH E2, 16alpha-OH E2, and 4-OH E1 were inactive in inducing mammary tumors...
  61. Lotinun S, Westerlind K, Kennedy A, Turner R. Comparative effects of long-term continuous release of 16 alpha-hydroxyestrone and 17 beta-estradiol on bone, uterus, and serum cholesterol in ovariectomized adult rats. Bone. 2003;33:124-31 pubmed
    ..As a consequence of its skeletal effects, older women who produce high levels of 16alpha-OHE(1) could have a lower risk for developing postmenopausal osteoporosis than women who produce less-active estrogen metabolites. ..
  62. Thompson D, Kirshner M, Klug T, Kastango K, Pollock B. A preliminary study of the effect of fluoxetine treatment on the 2:16-alpha-hydroxyestrone ratio in young women. Ther Drug Monit. 2003;25:125-8 pubmed
    ..08 +/- 0.11; posttreatment, 3.50 +/- 0.46; paired Student's t-test P = 4.72, P = 0.021). ..
  63. Sawicka E, Długosz A. The role of 17?-estradiol metabolites in chromium-induced oxidative stress. Adv Clin Exp Med. 2017;26:215-221 pubmed publisher
    ..The metabolites do not have toxic interactions with CrVI. On the contrary, they exhibited a protective effect. The mechanism of protection varied: 4-OHE2 decreased TBARS and increased SOD activity, while 16?-OHE1 increased GST activity. ..
  64. Matthews C, Fortner R, Xu X, Hankinson S, Eliassen A, Ziegler R. Association between physical activity and urinary estrogens and estrogen metabolites in premenopausal women. J Clin Endocrinol Metab. 2012;97:3724-33 pubmed publisher
  65. Seeger H, Mueck A, Lippert T. Effect of norethisterone acetate on estrogen metabolism in postmenopausal women. Horm Metab Res. 2000;32:436-9 pubmed
    ..In conclusion, transdermal NETA in HRT did not elicit any change in estrogen metabolism after 2 weeks' treatment. However, oral NETA may in some cases have an impact on estradiol metabolism which should be further evaluated. ..
  66. Riza E, Dos Santos Silva I, De Stavola B, Bradlow H, Sepkovic D, Linos D, et al. Urinary estrogen metabolites and mammographic parenchymal patterns in postmenopausal women. Cancer Epidemiol Biomarkers Prev. 2001;10:627-34 pubmed
  67. McAlindon T, Gulin J, Chen T, Klug T, Lahita R, Nuite M. Indole-3-carbinol in women with SLE: effect on estrogen metabolism and disease activity. Lupus. 2001;10:779-83 pubmed
    ..Women with SLE can manifest a metabolic response to I3C and might benefit from its antiestrogenic effects. We did not observe any striking effects on SLE disease activity during the 3-month observational period. ..
  68. Zeleniuch Jacquotte A, Shore R, Afanasyeva Y, Lukanova A, Sieri S, Koenig K, et al. Postmenopausal circulating levels of 2- and 16?-hydroxyestrone and risk of endometrial cancer. Br J Cancer. 2011;105:1458-64 pubmed publisher
    ..Our results do not support the hypothesis that greater metabolism of oestrogen via the 2-OH pathway, relative to the 16?-OH pathway, protects against endometrial cancer. ..
  69. Rinaldi S, Moret C, Kaaks R, Biessy C, Kurzer M, Dechaud H, et al. Reproducibility over time of measurements of androgens, estrogens and hydroxy estrogens in urine samples from post-menopausal women. Eur J Epidemiol. 2003;18:417-24 pubmed
    ..85), acceptable for E2, E1 and ADIOL (r > 0.55), but low for 2(OH)-E, 16alpha(OH)-E1 and their ratio (r < 0.46). The adjustment for creatinine concentrations did not increase these correlations. ..
  70. Mueck A, Seeger H, Lippert T. [Estrogen-dependent neoplasia - what is the significance of estradiol metabolites]. Zentralbl Gynakol. 2003;125:458-66 pubmed
    ..Whether the investigation of gene polymorphism of enzymes, which are involved in estradiol metabolism, may be helpful for the assessment or treatment of risk patients, to our opinion needs further research. ..
  71. Mueck A, Seeger H, Wallwiener D. Endogenous estradiol metabolism during treatment with oral contraceptives. Int J Clin Pharmacol Ther. 2004;42:160-4 pubmed
    ..OCs containing norethisterone acetate, dienogest or levonorgestrel did not have a negative effect on estradiol metabolism, i.e. they did not elicit a higher D-ring metabolism, which is considered to increase breast cancer risk. ..
  72. Matei D, Schilder J, Sutton G, Perkins S, Breen T, Quon C, et al. Activity of 2 methoxyestradiol (Panzem NCD) in advanced, platinum-resistant ovarian cancer and primary peritoneal carcinomatosis: a Hoosier Oncology Group trial. Gynecol Oncol. 2009;115:90-96 pubmed publisher
    ..The NCD formulation of 2ME2 is well tolerated in patients with heavily pretreated EOC. Few of these heavily pretreated patients had sustained stable disease. ..
  73. Capellino S, Montagna P, Villaggio B, Soldano S, Straub R, Cutolo M. Hydroxylated estrogen metabolites influence the proliferation of cultured human monocytes: possible role in synovial tissue hyperplasia. Clin Exp Rheumatol. 2008;26:903-9 pubmed
    ..Therefore, since estrogen metabolite/ratios are altered in the synovial fluid of RA patients, they might play important roles at least in RA synovial tissue hyperplasia. ..
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    ..ionization mass spectrometry method has been developed for measuring endogenous 2- and 4-hydroxyestrones, the main catechol estrogens in human urine...
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    ..These results suggest a mechanism for the decrease in 2-hydroxylation of estradiol that is observed in obese women and the increase in 2-hydroxylation observed in women with depleted fat depots. ..
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  78. Webster K, Taylor A, Gaston K. Oestrogen and progesterone increase the levels of apoptosis induced by the human papillomavirus type 16 E2 and E7 proteins. J Gen Virol. 2001;82:201-13 pubmed
    ..We discuss these results in terms of the origin and progression of cervical cancer. ..
  79. Atkinson C, Newton K, Aiello Bowles E, Lehman C, Stanczyk F, Westerlind K, et al. Daidzein-metabolizing phenotypes in relation to mammographic breast density among premenopausal women in the United States. Breast Cancer Res Treat. 2009;116:587-94 pubmed publisher
    ..In this population of low-soy consuming premenopausal women, there were no associations between daidzein-metabolizing phenotypes and breast density, suggesting that these phenotypes per se do not influence premenopausal breast density. ..
  80. Lee S, Rhee M, Min Y, Kim S. Involvement of peroxiredoxin IV in the 16alpha-hydroxyestrone-induced proliferation of human MCF-7 breast cancer cells. Cell Biol Int. 2008;32:401-5 pubmed publisher
    ..These results suggested that Prx IV involved in the 16alpha-OHE1-induced proliferation of MCF-7 cells has a proliferative effect and may be related to cancer development or progression. ..