2-Hydroxyestradiol (BioDeep_00000405244)
Main id: BioDeep_00000637477
natural product
代谢物信息卡片
化学式: C18H24O3 (288.1725)
中文名称: 2-羟基-17β-雌二醇
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC12CCC3C(C1CCC2O)CCC4=CC(=C(C=C34)O)O
InChI: InChI=1S/C18H24O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,17,19-21H,2-7H2,1H3/t11-,12+,14-,17-,18-/m0/s1
描述信息
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
同义名列表
2 个代谢物同义名
数据库引用编号
16 个数据库交叉引用编号
- ChEBI: CHEBI:28744
- KEGG: C05301
- PubChem: 247304
- DrugBank: DB07706
- ChEMBL: CHEMBL467987
- CAS: 362-05-0
- MoNA: HMDB0000338_ms_ms_544
- MoNA: HMDB0000338_ms_ms_545
- MoNA: HMDB0000338_ms_ms_543
- PubChem: 7685
- LipidMAPS: LMST02010027
- PDB-CCD: ECS
- NIKKAJI: J108.138A
- RefMet: 2-Hydroxyestradiol
- KNApSAcK: 28744
- LOTUS: LTS0096486
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
14 个相关的物种来源信息
- 3708 - Brassica napus: 10.3389/FNUT.2022.822033
- 7711 - Chordata: LTS0096486
- 2759 - Eukaryota: LTS0096486
- 9604 - Hominidae: LTS0096486
- 9605 - Homo: LTS0096486
- 9606 - Homo sapiens:
- 9606 - Homo sapiens: 10.1038/NBT.2488
- 9606 - Homo sapiens: LTS0096486
- 40674 - Mammalia: LTS0096486
- 33208 - Metazoa: LTS0096486
- 10066 - Muridae: LTS0096486
- 10088 - Mus: LTS0096486
- 10090 - Mus musculus: LTS0096486
- 10090 - Mus musculus: NA
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:
- PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。
文献列表
- Nhung Le, Melissa Cregger, Veronica Brown, Julio Loret de Mola, Pamela Bremer, Lyn Nguyen, Kathleen Groesch, Teresa Wilson, Paula Diaz-Sylvester, Andrea Braundmeier-Fleming. Association of microbial dynamics with urinary estrogens and estrogen metabolites in patients with endometriosis.
PloS one.
2021; 16(12):e0261362. doi:
10.1371/journal.pone.0261362
. [PMID: 34914785] - Emil Jakobsen, Sofie C Lange, Jens V Andersen, Claus Desler, Henriette F Kihl, Michaela C Hohnholt, Malin H Stridh, Lene J Rasmussen, Helle S Waagepetersen, Lasse K Bak. The inhibitors of soluble adenylate cyclase 2-OHE, KH7, and bithionol compromise mitochondrial ATP production by distinct mechanisms.
Biochemical pharmacology.
2018 09; 155(?):92-101. doi:
10.1016/j.bcp.2018.06.023
. [PMID: 29940175] - Peter Thomas. Role of G-protein-coupled estrogen receptor (GPER/GPR30) in maintenance of meiotic arrest in fish oocytes.
The Journal of steroid biochemistry and molecular biology.
2017 03; 167(?):153-161. doi:
10.1016/j.jsbmb.2016.12.005
. [PMID: 28007532] - Chieh-Ming Fang, Ming-Chun Ku, Che-Kai Chang, Huei-Chen Liang, Tzu-Fan Wang, Chih-Hsing Wu, Shu-Hui Chen. Identification of Endogenous Site-specific Covalent Binding of Catechol Estrogens to Serum Proteins in Human Blood.
Toxicological sciences : an official journal of the Society of Toxicology.
2015 Dec; 148(2):433-42. doi:
10.1093/toxsci/kfv190
. [PMID: 26342215] - W L Gao, L S Wu, J H Zi, B Wu, Y Z Li, Y C Song, D Z Cai. Measurement of serum estrogen and estrogen metabolites in pre- and postmenopausal women with osteoarthritis using high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry.
Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas.
2015 Feb; 48(2):146-53. doi:
10.1590/1414-431x20144129
. [PMID: 25410577] - Hui-Hui Li, Ying-Jie Zhao, Yan Li, Cai-Feng Dai, Sheikh O Jobe, Xing-Sheng Yang, Xing-Fu Li, Manish S Patankar, Ronald R Magness, Jing Zheng. Estradiol 17β and its metabolites stimulate cell proliferation and antagonize ascorbic acid-suppressed cell proliferation in human ovarian cancer cells.
Reproductive sciences (Thousand Oaks, Calif.).
2014 Jan; 21(1):102-11. doi:
10.1177/1933719113492211
. [PMID: 23757313] - R J Aitken, T B Smith, T Lord, L Kuczera, A J Koppers, N Naumovski, H Connaughton, M A Baker, G N De Iuliis. On methods for the detection of reactive oxygen species generation by human spermatozoa: analysis of the cellular responses to catechol oestrogen, lipid aldehyde, menadione and arachidonic acid.
Andrology.
2013 Mar; 1(2):192-205. doi:
10.1111/j.2047-2927.2012.00056.x
. [PMID: 23316012] - Xin Sun, Jagadeesan Nair, Jakob Linseisen, Robert W Owen, Helmut Bartsch. Lipid peroxidation and DNA adduct formation in lymphocytes of premenopausal women: Role of estrogen metabolites and fatty acid intake.
International journal of cancer.
2012 Nov; 131(9):1983-90. doi:
10.1002/ijc.27479
. [PMID: 22322480] - Sharon Anderson, Terry T Oyama, Jessie N Lindsley, William E Schutzer, Douglas R Beard, Vincent H Gattone, Radko Komers. 2-Hydroxyestradiol slows progression of experimental polycystic kidney disease.
American journal of physiology. Renal physiology.
2012 Mar; 302(5):F636-45. doi:
10.1152/ajprenal.00265.2011
. [PMID: 22160773] - Daniel W Sepkovic, Laura Raucci, Johann Stein, Antoine D Carlisle, Karen Auborn, H Barbara Ksieski, Themba Nyirenda, H Leon Bradlow. 3,3'-Diindolylmethane increases serum interferon-γ levels in the K14-HPV16 transgenic mouse model for cervical cancer.
In vivo (Athens, Greece).
2012 Mar; 26(2):207-11. doi:
NULL
. [PMID: 22351660] - Jiang Huang, Jianghao Sun, Yanhua Chen, Yongmei Song, Lijia Dong, Qinmin Zhan, Ruiping Zhang, Zeper Abliz. Analysis of multiplex endogenous estrogen metabolites in human urine using ultra-fast liquid chromatography-tandem mass spectrometry: a case study for breast cancer.
Analytica chimica acta.
2012 Jan; 711(?):60-8. doi:
10.1016/j.aca.2011.10.058
. [PMID: 22152797] - Nesma A Z Sarhan, Ezzeldein S El-Denshary, Nabila S Hassan, Ferial M Abu-Salem, Mosaad A Abdel-Wahhab. Isoflavones-Enriched Soy Protein Prevents CCL(4)-Induced Hepatotoxicity in Rats.
ISRN pharmacology.
2012; 2012(?):347930. doi:
10.5402/2012/347930
. [PMID: 22530140] - Hala O El Mesallamy, Nadia S Metwally, Mahmoud S Soliman, Kawkab A Ahmed, Mai M Abdel Moaty. The chemopreventive effect of Ginkgo biloba and Silybum marianum extracts on hepatocarcinogenesis in rats.
Cancer cell international.
2011 Oct; 11(1):38. doi:
10.1186/1475-2867-11-38
. [PMID: 22040519] - Nadia Obi, Alina Vrieling, Judith Heinz, Jenny Chang-Claude. Estrogen metabolite ratio: Is the 2-hydroxyestrone to 16α-hydroxyestrone ratio predictive for breast cancer?.
International journal of women's health.
2011 Feb; 3(?):37-51. doi:
10.2147/ijwh.s7595
. [PMID: 21339936] - E Gregoraszczuk, A Ptak. Involvement of caspase-9 but not caspase-8 in the anti-apoptotic effects of estradiol and 4-OH-Estradiol in MCF-7 human breast cancer cells.
Endocrine regulations.
2011 Jan; 45(1):3-8. doi:
. [PMID: 21314204]
- Maggie Laidlaw, Carla A Cockerline, Daniel W Sepkovic. Effects of a breast-health herbal formula supplement on estrogen metabolism in pre- and post-menopausal women not taking hormonal contraceptives or supplements: a randomized controlled trial.
Breast cancer : basic and clinical research.
2010 Dec; 4(?):85-95. doi:
10.4137/bcbcr.s6505
. [PMID: 21234288] - W Gao, C Zeng, D Cai, B Liu, Y Li, X Wen, Y Chen. Serum concentrations of selected endogenous estrogen and estrogen metabolites in pre- and post-menopausal Chinese women with osteoarthritis.
Journal of endocrinological investigation.
2010 Oct; 33(9):644-9. doi:
10.1007/bf03346664
. [PMID: 20339312] - Raghvendra K Dubey, Edwin K Jackson, Delbert G Gillespie, Lefteris C Zacharia, Bruno Imthurn, Marinella Rosselli. Resveratrol, a red wine constituent, blocks the antimitogenic effects of estradiol on human female coronary artery smooth muscle cells.
The Journal of clinical endocrinology and metabolism.
2010 Sep; 95(9):E9-17. doi:
10.1210/jc.2010-0460
. [PMID: 20534756] - Bhupendra Singh, Sarah M Mense, Nimee K Bhat, Sandeep Putty, William A Guthiel, Fabrizio Remotti, Hari K Bhat. Dietary quercetin exacerbates the development of estrogen-induced breast tumors in female ACI rats.
Toxicology and applied pharmacology.
2010 Sep; 247(2):83-90. doi:
10.1016/j.taap.2010.06.011
. [PMID: 20600213] - Ki Sung Kang, Yujing Wen, Noriko Yamabe, Masayuki Fukui, Stephanie C Bishop, Bao Ting Zhu. Dual beneficial effects of (-)-epigallocatechin-3-gallate on levodopa methylation and hippocampal neurodegeneration: in vitro and in vivo studies.
PloS one.
2010 Aug; 5(8):e11951. doi:
10.1371/journal.pone.0011951
. [PMID: 20700524] - Emanuela Taioli, Annie Im, Xia Xu, Timothy D Veenstra, Gretchen Ahrendt, Seymour Garte. Comparison of estrogens and estrogen metabolites in human breast tissue and urine.
Reproductive biology and endocrinology : RB&E.
2010 Aug; 8(?):93. doi:
10.1186/1477-7827-8-93
. [PMID: 20678202] - Jadwiga Piwowarska, Stanisław Radowicki, Jan Pachecka. Simultaneous determination of eight estrogens and their metabolites in serum using liquid chromatography with electrochemical detection.
Talanta.
2010 Apr; 81(1-2):275-80. doi:
10.1016/j.talanta.2009.11.069
. [PMID: 20188920] - P S Tofovic, B M Rosado, K R Dubey, Z Mi, Edwin K Jackson. Effects of estradiol metabolites on cAMP production and degradation.
Prilozi.
2009 Jul; 30(1):5-24. doi:
. [PMID: 19736528]
- Kenneth R Hallows, Huamin Wang, Robert S Edinger, Michael B Butterworth, Nicholas M Oyster, Hui Li, Jochen Buck, Lonny R Levin, John P Johnson, Núria M Pastor-Soler. Regulation of epithelial Na+ transport by soluble adenylyl cyclase in kidney collecting duct cells.
The Journal of biological chemistry.
2009 Feb; 284(9):5774-83. doi:
10.1074/jbc.m805501200
. [PMID: 19126549] - Nilesh W Gaikwad, Li Yang, Sandhya Pruthi, James N Ingle, Nicole Sandhu, Eleanor G Rogan, Ercole L Cavalieri. Urine biomarkers of risk in the molecular etiology of breast cancer.
Breast cancer : basic and clinical research.
2009 Jan; 3(?):1-8. doi:
10.4137/bcbcr.s2112
. [PMID: 21556245] - Mylène Aubertin-Leheudre, Sherwood Gorbach, Margo Woods, Johanna T Dwyer, Barry Goldin, Herman Adlercreutz. Fat/fiber intakes and sex hormones in healthy premenopausal women in USA.
The Journal of steroid biochemistry and molecular biology.
2008 Nov; 112(1-3):32-9. doi:
10.1016/j.jsbmb.2008.08.002
. [PMID: 18761407] - Carina Ankarberg-Lindgren, Ensio Norjavaara. Twenty-four hours secretion pattern of serum estradiol in healthy prepubertal and pubertal boys as determined by a validated ultra-sensitive extraction RIA.
BMC endocrine disorders.
2008 Sep; 8(?):10. doi:
10.1186/1472-6823-8-10
. [PMID: 18817534] - Sarah M Mense, Jaimeet Chhabra, Hari K Bhat. Preferential induction of cytochrome P450 1A1 over cytochrome P450 1B1 in human breast epithelial cells following exposure to quercetin.
The Journal of steroid biochemistry and molecular biology.
2008 May; 110(1-2):157-62. doi:
10.1016/j.jsbmb.2008.03.029
. [PMID: 18456490] - Sarah M Mense, Tom K Hei, Ramesh K Ganju, Hari K Bhat. Phytoestrogens and breast cancer prevention: possible mechanisms of action.
Environmental health perspectives.
2008 Apr; 116(4):426-33. doi:
10.1289/ehp.10538
. [PMID: 18414622] - Xiaoying Qiao, Kristi R McConnell, Raouf A Khalil. Sex steroids and vascular responses in hypertension and aging.
Gender medicine.
2008; 5 Suppl A(?):S46-64. doi:
10.1016/j.genm.2008.03.006
. [PMID: 18395683] - Melissa J Wentz, Shao-Qing Shi, Leili Shi, Salama A Salama, Hassan M Harirah, Hala Fouad, Robert E Garfield, Ayman Al-Hendy. Treatment with an inhibitor of catechol-O-methyltransferase activity reduces preterm birth and impedes cervical resistance to stretch in pregnant rats.
Reproduction (Cambridge, England).
2007 Dec; 134(6):831-9. doi:
10.1530/rep-07-0245
. [PMID: 18042640] - Masatoki Katayama, Kiyoshi Takamatsu, Satoru Kaneko, Keisuke Miyaji, Hiromichi Ishikawa, Yoshifumi Matsuda. HPLC for stress-free screening of potential prostate cancer marker catechol estrogens in urine using a diamond-electrode electrochemical and a fluorescence detector.
Journal of separation science.
2007 Sep; 30(14):2279-85. doi:
10.1002/jssc.200700096
. [PMID: 17668912] - Heather Greenlee, Yu Chen, Geoffrey C Kabat, Qiao Wang, Muhammad G Kibriya, Irina Gurvich, Daniel W Sepkovic, H Leon Bradlow, Ruby T Senie, Regina M Santella, Habibul Ahsan. Variants in estrogen metabolism and biosynthesis genes and urinary estrogen metabolites in women with a family history of breast cancer.
Breast cancer research and treatment.
2007 Mar; 102(1):111-7. doi:
10.1007/s10549-006-9308-7
. [PMID: 16850246] - Xinchen Zhang, Youhong Jia, Edwin K Jackson, Stevan P Tofovic. 2-Methoxyestradiol and 2-ethoxyestradiol retard the progression of renal disease in aged, obese, diabetic ZSF1 rats.
Journal of cardiovascular pharmacology.
2007 Jan; 49(1):56-63. doi:
10.1097/fjc.0b013e31802cb88e
. [PMID: 17261964] - Katherine E Liney, Josephine A Hagger, Charles R Tyler, Michael H Depledge, Tamara S Galloway, Susan Jobling. Health effects in fish of long-term exposure to effluents from wastewater treatment works.
Environmental health perspectives.
2006 Apr; 114 Suppl 1(?):81-9. doi:
10.1289/ehp.8058
. [PMID: 16818251] - Christopher M Masi, Louise C Hawkley, Jarett D Berry, John T Cacioppo. Estrogen metabolites and systolic blood pressure in a population-based sample of postmenopausal women.
The Journal of clinical endocrinology and metabolism.
2006 Mar; 91(3):1015-20. doi:
10.1210/jc.2005-2339
. [PMID: 16384842] - J R Muñoz-Castañeda, I Túnez, M C Muñoz, I Bujalance, J Muntané, P Montilla. Effect of catecholestrogen administration during adriamycin-induced cardiomyopathy in ovariectomized rat.
Free radical research.
2005 Sep; 39(9):943-8. doi:
10.1080/10715760400013805
. [PMID: 16087475] - Stevan P Tofovic, Eman M Salah, Raghvendra K Dubey, Mona F Melhem, Edwin K Jackson. Estradiol metabolites attenuate renal and cardiovascular injury induced by chronic nitric oxide synthase inhibition.
Journal of cardiovascular pharmacology.
2005 Jul; 46(1):25-35. doi:
10.1097/01.fjc.0000162765.89437.ae
. [PMID: 15965351] - Jin Yoshida, Shinji Kumagai, Takeo Tabuchi, Hiroshi Kosaka, Susumu Akasaka, Hajime Oda. Effects of dioxin on metabolism of estrogens in waste incinerator workers.
Archives of environmental & occupational health.
2005 Jul; 60(4):215-22. doi:
10.3200/aeoh.60.4.215-222
. [PMID: 17214292] - C S A Markides, J G Liehr. Specific binding of 4-hydroxyestradiol to mouse uterine protein: evidence of a physiological role for 4-hydroxyestradiol.
The Journal of endocrinology.
2005 May; 185(2):235-42. doi:
10.1677/joe.1.06014
. [PMID: 15845916] - Raghvendra K Dubey, Edwin K Jackson, Delbert G Gillespie, Marinella Rosselli, Federica Barchiesi, Andree Krust, Hansjoerg Keller, Lefteris C Zacharia, Bruno Imthurn. Cytochromes 1A1/1B1- and catechol-O-methyltransferase-derived metabolites mediate estradiol-induced antimitogenesis in human cardiac fibroblast.
The Journal of clinical endocrinology and metabolism.
2005 Jan; 90(1):247-55. doi:
10.1210/jc.2003-032154
. [PMID: 15507517] - V K Turan, R I Sanchez, J J Li, S A Li, K R Reuhl, P E Thomas, A H Conney, M A Gallo, F C Kauffman, S Mesia-Vela. The effects of steroidal estrogens in ACI rat mammary carcinogenesis: 17beta-estradiol, 2-hydroxyestradiol, 4-hydroxyestradiol, 16alpha-hydroxyestradiol, and 4-hydroxyestrone.
The Journal of endocrinology.
2004 Oct; 183(1):91-9. doi:
10.1677/joe.1.05802
. [PMID: 15525577] - P H Roos, S Tschirbs, A Hack, P Welge, M Wilhelm. Different mechanisms of handling ingested polycyclic aromatic hydrocarbons in mammalian species: organ-specific response patterns of CYP1A1-induction after oral intake of PAH-contaminated soils.
Xenobiotica; the fate of foreign compounds in biological systems.
2004 Sep; 34(9):781-95. doi:
10.1080/00498250400010880
. [PMID: 15742974] - Nikhil K Basu, Shigeki Kubota, Meselhy R Meselhy, Marco Ciotti, Bhabadeb Chowdhury, Masao Hartori, Ida S Owens. Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation.
The Journal of biological chemistry.
2004 Jul; 279(27):28320-9. doi:
10.1074/jbc.m401396200
. [PMID: 15117964] - Lefteris C Zacharia, Claude A Piché, Robert M Fielding, Kathleen M Holland, S Dean Allison, Raghvendra K Dubey, Edwin K Jackson. 2-hydroxyestradiol is a prodrug of 2-methoxyestradiol.
The Journal of pharmacology and experimental therapeutics.
2004 Jun; 309(3):1093-7. doi:
10.1124/jpet.103.062505
. [PMID: 14872091] - Lefteris C Zacharia, Raghvendra K Dubey, Edwin K Jackson. A gas chromatography/mass spectrometry assay to measure estradiol, catecholestradiols, and methoxyestradiols in plasma.
Steroids.
2004 Apr; 69(4):255-61. doi:
10.1016/j.steroids.2004.01.005
. [PMID: 15183691] - Lefteris C Zacharia, Joseph A Gogos, Maria Karayiorgou, Edwin K Jackson, Delbert G Gillespie, Federica Barchiesi, Raghvendra K Dubey. Methoxyestradiols mediate the antimitogenic effects of 17beta-estradiol: direct evidence from catechol-O-methyltransferase-knockout mice.
Circulation.
2003 Dec; 108(24):2974-8. doi:
10.1161/01.cir.0000106900.66354.30
. [PMID: 14662705] - Michael Teepker, Norman Anthes, Jürgen-Christian Krieg, Helmut Vedder. 2-OH-estradiol, an endogenous hormone with neuroprotective functions.
Journal of psychiatric research.
2003 Nov; 37(6):517-23. doi:
10.1016/s0022-3956(03)00068-2
. [PMID: 14563383] - Hong Fang, Weida Tong, William S Branham, Carrie L Moland, Stacy L Dial, Huixiao Hong, Qian Xie, Roger Perkins, William Owens, Daniel M Sheehan. Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.
Chemical research in toxicology.
2003 Oct; 16(10):1338-58. doi:
10.1021/tx030011g
. [PMID: 14565775] - Raghvendra K Dubey, Lefteris C Zacharia, Delbert G Gillespie, Bruno Imthurn, Edwin K Jackson. Catecholamines block the antimitogenic effect of estradiol on human glomerular mesangial cells.
Hypertension (Dallas, Tex. : 1979).
2003 Sep; 42(3):349-55. doi:
10.1161/01.hyp.0000088320.81260.26
. [PMID: 12913061] - Kaori Takanashi, Yasunori Osanai, Takahiro Kyo, Itsuo Yoshizawa. Comparison of ex vivo inhibitory effect between 2-hydroxyestradiol and its 17-sulfate on rat hepatic microsomal lipid peroxidation.
Lipids.
2003 Aug; 38(8):847-54. doi:
10.1007/s11745-003-1135-4
. [PMID: 14577664] - Lefteris C Zacharia, Raghvendra K Dubey, Zaichuan Mi, Edwin K Jackson. Methylation of 2-hydroxyestradiol in isolated organs.
Hypertension (Dallas, Tex. : 1979).
2003 Jul; 42(1):82-7. doi:
10.1161/01.hyp.0000074702.06466.27
. [PMID: 12771046] - Kaori Takanashi. [Studies on 2-hydroxyestradiol 17-sulfate derived from fetoplacental unit: the antioxidant as a potential defense substance against preeclampsia].
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.
2003 Jun; 123(6):399-411. doi:
10.1248/yakushi.123.399
. [PMID: 12822484] - Kaori Takanashi, Yoshimi Itoh, Kazuhiro Watanabe, Itsuo Yoshizawa. Metabolism of [6,7-3H, 35S] estradiol 17-sulfate in rats.
Steroids.
2003 Apr; 68(4):383-92. doi:
10.1016/s0039-128x(03)00037-0
. [PMID: 12787901] - Raghvendra K Dubey, Delbert G Gillespie, Lefteris C Zacharia, Federica Barchiesi, Bruno Imthurn, Edwin K Jackson. CYP450- and COMT-derived estradiol metabolites inhibit activity of human coronary artery SMCs.
Hypertension (Dallas, Tex. : 1979).
2003 Mar; 41(3 Pt 2):807-13. doi:
10.1161/01.hyp.0000048862.28501.72
. [PMID: 12624000] - Stevan P Tofovic, Raghvendra Dubey, Eman M Salah, Edwin K Jackson. 2-Hydroxyestradiol attenuates renal disease in chronic puromycin aminonucleoside nephropathy.
Journal of the American Society of Nephrology : JASN.
2002 Nov; 13(11):2737-47. doi:
10.1097/01.asn.0000031804.77546.f5
. [PMID: 12397044] - Sanae Muraoka, Toshiaki Miura. Protection by estrogens of biological damage by 2,2'-azobis(2-amidinopropane) dihydrochloride.
The Journal of steroid biochemistry and molecular biology.
2002 Nov; 82(4-5):343-8. doi:
10.1016/s0960-0760(02)00216-9
. [PMID: 12589941] - N F Boyd, J Stone, L J Martin, R Jong, E Fishell, M Yaffe, G Hammond, S Minkin. The association of breast mitogens with mammographic densities.
British journal of cancer.
2002 Oct; 87(8):876-82. doi:
10.1038/sj.bjc.6600537
. [PMID: 12373602] - Gerald Finking, Christina Lenz, Thomas Schochat, Hartmut Hanke. Reduction of post injury neointima formation due to 17beta-estradiol and phytoestrogen treatment is not influenced by the pure synthetic estrogen receptor antagonist ICI 182,780 in vitro.
BMC cardiovascular disorders.
2002 Aug; 2(?):13. doi:
10.1186/1471-2261-2-13
. [PMID: 12162794] - Rosa Martínez, Kristina Quintana, Rosaura Navarro, César Martín, M Luisa Hernández, Igor Aurrekoetxea, José Ignacio Ruiz-Sanz, Mercedes Lacort, M Begoña Ruiz-Larrea. Pro-oxidant and antioxidant potential of catecholestrogens against ferrylmyoglobin-induced oxidative stress.
Biochimica et biophysica acta.
2002 Jul; 1583(2):167-75. doi:
10.1016/s1388-1981(02)00207-x
. [PMID: 12117560] - Richard S Lord, Bradley Bongiovanni, J Alexander Bralley. Estrogen metabolism and the diet-cancer connection: rationale for assessing the ratio of urinary hydroxylated estrogen metabolites.
Alternative medicine review : a journal of clinical therapeutic.
2002 Apr; 7(2):112-29. doi:
. [PMID: 11991791]
- Raghvendra K Dubey, Delbert G Gillespie, Lefteris C Zacharia, Marinella Rosselli, Bruno Imthurn, Edwin K Jackson. Methoxyestradiols mediate the antimitogenic effects of locally applied estradiol on cardiac fibroblast growth.
Hypertension (Dallas, Tex. : 1979).
2002 Feb; 39(2 Pt 2):412-7. doi:
10.1161/hy0202.102837
. [PMID: 11882582] - Raghvendra K Dubey, Delbert G Gillespie, Paul J Keller, Bruno Imthurn, Lefteris C Zacharia, Edwin K Jackson. Role of methoxyestradiols in the growth inhibitory effects of estradiol on human glomerular mesangial cells.
Hypertension (Dallas, Tex. : 1979).
2002 Feb; 39(2 Pt 2):418-24. doi:
10.1161/hy0202.103297
. [PMID: 11882583] - S P Tofovic, R K Dubey, E K Jackson. 2-Hydroxyestradiol attenuates the development of obesity, the metabolic syndrome, and vascular and renal dysfunction in obese ZSF1 rats.
The Journal of pharmacology and experimental therapeutics.
2001 Dec; 299(3):973-7. doi:
. [PMID: 11714885]
- R K Dubey, E K Jackson, P J Keller, B Imthurn, M Rosselli. Estradiol metabolites inhibit endothelin synthesis by an estrogen receptor-independent mechanism.
Hypertension (Dallas, Tex. : 1979).
2001 Feb; 37(2 Pt 2):640-4. doi:
10.1161/01.hyp.37.2.640
. [PMID: 11230349] - S Xiao, D G Gillespie, C Baylis, E K Jackson, R K Dubey. Effects of estradiol and its metabolites on glomerular endothelial nitric oxide synthesis and mesangial cell growth.
Hypertension (Dallas, Tex. : 1979).
2001 Feb; 37(2 Pt 2):645-50. doi:
10.1161/01.hyp.37.2.645
. [PMID: 11230350] - I Terashima, N Suzuki, S Shibutani. Mutagenic properties of estrogen quinone-derived DNA adducts in simian kidney cells.
Biochemistry.
2001 Jan; 40(1):166-72. doi:
10.1021/bi002273c
. [PMID: 11141067] - A F Badawi, E L Cavalieri, E G Rogan. Effect of chlorinated hydrocarbons on expression of cytochrome P450 1A1, 1A2 and 1B1 and 2- and 4-hydroxylation of 17beta-estradiol in female Sprague-Dawley rats.
Carcinogenesis.
2000 Aug; 21(8):1593-9. doi:
10.1093/carcin/21.8.1593
. [PMID: 10910964] - R R Newbold, J G Liehr. Induction of uterine adenocarcinoma in CD-1 mice by catechol estrogens.
Cancer research.
2000 Jan; 60(2):235-7. doi:
. [PMID: 10667565]
- C E Garner, H B Matthews, L T Burka. Phenolphthalein metabolite inhibits catechol-O-methyltransferase-mediated metabolism of catechol estrogens: a possible mechanism for carcinogenicity.
Toxicology and applied pharmacology.
2000 Jan; 162(2):124-31. doi:
10.1006/taap.1999.8830
. [PMID: 10637136] - A M Leal, M Begoña Ruiz-Larrea, R Martínez, M Lacort. Cytoprotective actions of estrogens against tert-butyl hydroperoxide-induced toxicity in hepatocytes.
Biochemical pharmacology.
1998 Dec; 56(11):1463-9. doi:
10.1016/s0006-2952(98)00248-2
. [PMID: 9827578] - T Miura, S Muraoka, Y Fujimoto. Effect of estrogens on the oxidative damage induced by ferrylmyoglobin.
The Journal of steroid biochemistry and molecular biology.
1998 Oct; 67(1):57-62. doi:
10.1016/s0960-0760(98)00068-5
. [PMID: 9780030] - Z Cheng, G R Rios, C D King, B L Coffman, M D Green, B Mojarrabi, P I Mackenzie, T R Tephly. Glucuronidation of catechol estrogens by expressed human UDP-glucuronosyltransferases (UGTs) 1A1, 1A3, and 2B7.
Toxicological sciences : an official journal of the Society of Toxicology.
1998 Sep; 45(1):52-7. doi:
10.1006/toxs.1998.2494
. [PMID: 9848110] - K Yagi. Female hormones act as natural antioxidants--a survey of our research.
Acta biochimica Polonica.
1997; 44(4):701-9. doi:
10.18388/abp.1997_4372
. [PMID: 9584850] - T Miura, S Muraoka, T Ogiso. Inhibition of lipid peroxidation by estradiol and 2-hydroxyestradiol.
Steroids.
1996 Jun; 61(6):379-83. doi:
10.1016/0039-128x(96)00044-x
. [PMID: 8776801] - B T Zhu, J G Liehr. Inhibition of catechol O-methyltransferase-catalyzed O-methylation of 2- and 4-hydroxyestradiol by quercetin. Possible role in estradiol-induced tumorigenesis.
The Journal of biological chemistry.
1996 Jan; 271(3):1357-63. doi:
10.1074/jbc.271.3.1357
. [PMID: 8576124] - B Ruiz-Larrea, A Leal, C Martín, R Martínez, M Lacort. Effects of estrogens on the redox chemistry of iron: a possible mechanism of the antioxidant action of estrogens.
Steroids.
1995 Nov; 60(11):780-3. doi:
10.1016/0039-128x(95)00119-b
. [PMID: 8585103] - M B Ruiz-Larrea, A Leal, R Martínez, C Martín, M Lacort. Mechanism of inhibition of microsomal lipid peroxidation by estrogens: possible interactions with the cytochrome P450-dependent monooxygenase system.
Biochemical Society transactions.
1995 May; 23(2):256S. doi:
10.1042/bst023256s
. [PMID: 7672280] - S Taniguchi, T Yanase, K Kobayashi, R Takayanagi, M Haji, F Umeda, H Nawata. Catechol estrogens are more potent antioxidants than estrogens for the Cu(2+)-catalyzed oxidation of low or high density lipoprotein: antioxidative effects of steroids on lipoproteins.
Endocrine journal.
1994 Dec; 41(6):605-11. doi:
10.1507/endocrj.41.605
. [PMID: 7704084] - X Han, J G Liehr. 8-Hydroxylation of guanine bases in kidney and liver DNA of hamsters treated with estradiol: role of free radicals in estrogen-induced carcinogenesis.
Cancer research.
1994 Nov; 54(21):5515-7. doi:
NULL
. [PMID: 7923187] - M B Ruiz-Larrea, A M Leal, M Liza, M Lacort, H de Groot. Antioxidant effects of estradiol and 2-hydroxyestradiol on iron-induced lipid peroxidation of rat liver microsomes.
Steroids.
1994 Jun; 59(6):383-8. doi:
10.1016/0039-128x(94)90006-x
. [PMID: 7940617] - F R Tekpetey, D T Armstrong. Catecholestrogen modulation of steroid production by rat luteal cells: mechanism of action.
Molecular and cellular endocrinology.
1994 May; 101(1-2):49-57. doi:
10.1016/0303-7207(94)90218-6
. [PMID: 9397936] - X Han, J G Liehr. DNA single-strand breaks in kidneys of Syrian hamsters treated with steroidal estrogens: hormone-induced free radical damage preceding renal malignancy.
Carcinogenesis.
1994 May; 15(5):997-1000. doi:
10.1093/carcin/15.5.997
. [PMID: 8200107] - K Jankowski, D Kulawiak, M Woźniak. Inhibitory effect of 2-hydroxyestradiol on lipid peroxidation in placental microsomes.
Acta biochimica Polonica.
1994; 41(2):151-2. doi:
10.18388/abp.1994_4742
. [PMID: 7976029] - B T Zhu, J G Liehr. Inhibition of the catechol-O-methyltransferase-catalyzed O-methylation of 2- and 4-hydroxyestradiol by catecholamine: implications for the mechanism of estrogen-induced carcinogenesis.
Archives of biochemistry and biophysics.
1993 Jul; 304(1):248-56. doi:
10.1006/abbi.1993.1346
. [PMID: 8323288] - K Saegusa, E Suzuki, T Anjo, Y Matsuki, T Nambara. Determination of catechol and guaiacol estrogens in urine by capillary gas chromatography/mass spectrometry.
Biomedical chromatography : BMC.
1993 May; 7(3):172-6. doi:
10.1002/bmc.1130070315
. [PMID: 8391354] - C F Rosenkrans, B C Paria, D L Davis, G Milliken. Synthesis of prostaglandins by pig blastocysts cultured in medium containing estradiol or catechol estrogen.
Prostaglandins.
1992 Apr; 43(4):309-19. doi:
10.1016/0090-6980(92)90031-n
. [PMID: 1319081] - D Roy, J G Liehr. Target organ-specific inactivation of drug metabolizing enzymes in kidney of hamsters treated with estradiol.
Molecular and cellular biochemistry.
1992 Mar; 110(1):31-9. doi:
10.1007/bf02385003
. [PMID: 1315925] - J C Seegers, C H van Aswegen, B L Nieuwoudt, W S Joubert. Morphological effects of the catecholestrogens on cells of the seminiferous tubules of Sprague-Dawley rats.
Andrologia.
1991 Sep; 23(5):339-45. doi:
10.1111/j.1439-0272.1991.tb02576.x
. [PMID: 1666271] - F R Tekpetey, D T Armstrong. Steroidogenic response of rat and pig luteal cells to estradiol-17 beta and catecholestrogens in vitro.
Biology of reproduction.
1991 Sep; 45(3):498-505. doi:
10.1095/biolreprod45.3.498
. [PMID: 1664248] - R W Brueggemeier, K Tseng, N E Katlic, M A Beleh, Y C Lin. Estrogen metabolism in primary kidney cell cultures from Syrian hamsters.
Journal of steroid biochemistry.
1990 Jul; 36(4):325-31. doi:
10.1016/0022-4731(90)90225-h
. [PMID: 2391962] - J G Liehr, D Roy, A Ari-Ulubelen, Q D Bui, J Weisz, H W Strobel. Effect of chronic estrogen treatment of Syrian hamsters on microsomal enzymes mediating formation of catecholestrogens and their redox cycling: implications for carcinogenesis.
Journal of steroid biochemistry.
1990 Apr; 35(5):555-60. doi:
10.1016/0022-4731(90)90198-2
. [PMID: 2162450] - D Roy, J Weisz, J G Liehr. The O-methylation of 4-hydroxyestradiol is inhibited by 2-hydroxyestradiol: implications for estrogen-induced carcinogenesis.
Carcinogenesis.
1990 Mar; 11(3):459-62. doi:
10.1093/carcin/11.3.459
. [PMID: 2311190] - D Roy, Q D Bui, J Weisz, J G Liehr. Comparison of assays for catechol estrogen synthase activity: product isolation vs radioenzymatic catechol-O-methyltransferase-coupled procedures.
Journal of steroid biochemistry.
1989 Aug; 33(2):243-9. doi:
10.1016/0022-4731(89)90300-2
. [PMID: 2549304] - J J Fernández-Ruiz, C Alvarez-Sanz, J A Ramos. 2-Hydroxyestradiol is not mediating the effects of estradiol on tuberoinfundibular dopaminergic neurons controlling prolactin secretion in female rats.
Journal of steroid biochemistry.
1989 Jan; 32(1A):71-5. doi:
10.1016/0022-4731(89)90016-2
. [PMID: 2536446] - L J Spicer, J M Hammond. Mechanism of action of 2-hydroxyestradiol on steroidogenesis in ovarian granulosa cells: interactions with catecholamines and gonadotropins involve cyclic adenosine monophosphate.
Biology of reproduction.
1989 Jan; 40(1):87-95. doi:
10.1095/biolreprod40.1.87
. [PMID: 2538165] - G Emons, G R Merriam, D Pfeiffer, D L Loriaux, P Ball, R Knuppen. Metabolism of exogenous 4- and 2-hydroxyestradiol in the human male.
Journal of steroid biochemistry.
1987 Nov; 28(5):499-504. doi:
10.1016/0022-4731(87)90508-5
. [PMID: 2824929] - K E Hudson, E J Wickings, S G Hillier. Effects of 2-hydroxyoestradiol, oestradiol and testosterone on FSH-induction of catecholamine- and gonadotrophin-responsive progesterone biosynthesis in rat granulosa cell cultures.
Journal of steroid biochemistry.
1987 Sep; 28(3):267-72. doi:
10.1016/0022-4731(87)91017-x
. [PMID: 2821323] - S W Lamberts, T Verleun. Differences in the mechanism of the inhibitory actions of catecholestrogens, tamoxifen and high concentrations of estrogens on prolactin release by cultured rat pituitary tumor cells.
European journal of cancer & clinical oncology.
1987 Aug; 23(8):1117-23. doi:
10.1016/0277-5379(87)90143-x
. [PMID: 2820746]