ST 18:3;O3 (BioDeep_00000637477)
Secondary id: BioDeep_00000001748, BioDeep_00000005353, BioDeep_00000009764, BioDeep_00000405244, BioDeep_00001869362
代谢物信息卡片
estra-1,3.5(10)-triene-3,16beta,17beta-triol
化学式: C18H24O3 (288.1725354)
中文名称: 4-羟基雌二醇, 17-环雌三醇, 2-羟基-17β-雌二醇
谱图信息:
最多检出来源 Homo sapiens(urine) 0.12%
分子结构信息
SMILES: C1(O)=CC2[C@@]3([H])CC[C@]4(C)[C@@H](O)CC[C@@]4([H])[C@]3([H])CCC=2C=C1O
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
A 4-hydroxy steroid that consists of 17beta-estradiol having an additional hydroxy group at position 4.
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen
同义名列表
12 个代谢物同义名
estra-1,3,5(10)-triene-2,4,17beta-triol; 4-Hydroxy-17beta-estradiol; 4-hydroxyestradiol; 4-OH-Estradiol; ST 18:3;O3; 17-Epiestriol; 16,17-Epiestriol; estra-1,3,5(10)-triene-3,6beta,17beta-triol; 6beta-Hydroxyestradiol-17beta; estra-1,3,5(10)-triene-2,3,17beta-triol; 2-Hydroxyestradiol; estra-1,3.5(10)-triene-3,16beta,17beta-triol
数据库引用编号
37 个数据库交叉引用编号
- ChEBI: CHEBI:62845
- ChEBI: CHEBI:42156
- ChEBI: CHEBI:16784
- ChEBI: CHEBI:28744
- KEGG: C14209
- KEGG: C03935
- KEGG: C05301
- PubChem: 5282360
- PubChem: 256737
- PubChem: 440168
- PubChem: 247304
- DrugBank: DB07702
- DrugBank: DB07706
- ChEMBL: CHEMBL1412489
- ChEMBL: CHEMBL1232445
- ChEMBL: CHEMBL390714
- ChEMBL: CHEMBL467987
- LipidMAPS: LMST02010028
- LipidMAPS: LMST02010049
- LipidMAPS: LMST02010045
- LipidMAPS: LMST02010031
- LipidMAPS: LMST02010027
- LipidMAPS: LMST02010006
- CAS: 5976-61-4
- CAS: 1228-72-4
- CAS: 3583-03-7
- CAS: 362-05-0
- MetaboLights: MTBLC62845
- PubChem: 6661
- 3DMET: B01701
- NIKKAJI: J824.125B
- PubChem: 7685
- PDB-CCD: ECS
- NIKKAJI: J108.138A
- PubChem: 7847019
- NIKKAJI: J353.576B
- RefMet: ST 18:3;O3
分类词条
相关代谢途径
Reactome(5)
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)
3 个相关的物种来源信息
- 3708 - Brassica napus: 10.3389/FNUT.2022.822033
- 9606 - Homo sapiens:
- 9606 - Homo sapiens: 10.1007/S11306-016-1051-4
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
- Saranya Sedtananun, Kornkanok Promthep. The potential of Mangifera indica Linn. and Musa acuminata extracts to attenuate 4-hydroxyestradiol (4-OHE2 )-induced DNA oxidative damage in MCF-10A cells by upregulating detoxifying and antioxidant enzymes.
Journal of food biochemistry.
2021 06; 45(6):e13754. doi:
10.1111/jfbc.13754. [PMID: 33969512] - 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] - Wahid Ali Khan, Arshi Malik, Mohd Wajid Ali Khan. Estrogenization of insulin by catecholestrogen produced high affinity autoantibodies and altered the normal function of insulin in type 1 diabetes.
Life sciences.
2020 Sep; 256(?):117910. doi:
10.1016/j.lfs.2020.117910. [PMID: 32504753] - Xu Mao, Jian Wang, Qian Wang, Lan Yang, Yilin Li, Hao Lin, Ying Peng, Jiang Zheng. Nitidine Chloride-Induced CYP1 Enzyme Inhibition and Alteration of Estradiol Metabolism.
Drug metabolism and disposition: the biological fate of chemicals.
2019 08; 47(8):919-927. doi:
10.1124/dmd.119.086892. [PMID: 31147316] - Nur Ozten, Katherine Vega, Joachim Liehr, Xi Huang, Lori Horton, Ercole L Cavalieri, Eleanor G Rogan, Maarten C Bosland. Role of Estrogen in Androgen-Induced Prostate Carcinogenesis in NBL Rats.
Hormones & cancer.
2019 06; 10(2-3):77-88. doi:
10.1007/s12672-019-00360-7. [PMID: 30877616] - 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] - Pan Wang, Bao-Ting Zhu. Unique effect of 4-hydroxyestradiol and its methylation metabolites on lipid and cholesterol profiles in ovariectomized female rats.
European journal of pharmacology.
2017 Apr; 800(?):107-117. doi:
10.1016/j.ejphar.2017.02.032. [PMID: 28219710] - 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] - H Zhao, Y Jiang, Y Liu, C Yun, L Li. Endogenous estrogen metabolites as biomarkers for endometrial cancer via a novel method of liquid chromatography-mass spectrometry with hollow fiber liquid-phase microextraction.
Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme.
2015 Feb; 47(2):158-64. doi:
10.1055/s-0034-1371865. [PMID: 24722971] - 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] - Jeyaprakash Jeyabalan, Farrukh Aqil, Lisa Soper, David J Schultz, Ramesh C Gupta. Potent Chemopreventive/Antioxidant Activity Detected in Common Spices of the Apiaceae Family.
Nutrition and cancer.
2015; 67(7):1201-7. doi:
10.1080/01635581.2015.1075051. [PMID: 26381237] - 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] - Shien Zou, Qing Sang, Huan Wang, Ruizhi Feng, Qiaoli Li, Xinzhi Zhao, Qinghe Xing, Li Jin, Lin He, Lei Wang. Common genetic variation in CYP1B1 is associated with concentrations of T₄, FT₃ and FT₄ in the sera of polycystic ovary syndrome patients.
Molecular biology reports.
2013 Apr; 40(4):3315-20. doi:
10.1007/s11033-012-2406-1. [PMID: 23283740] - 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] - Parvin Ataie-Kachoie, David L Morris, Mohammad H Pourgholami. Minocycline suppresses interleukine-6, its receptor system and signaling pathways and impairs migration, invasion and adhesion capacity of ovarian cancer cells: in vitro and in vivo studies.
PloS one.
2013; 8(4):e60817. doi:
10.1371/journal.pone.0060817. [PMID: 23593315] - 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] - Inik Chang, Jan Liu, Shahana Majid, Sharanjot Saini, Mohd S Zaman, Soichiro Yamamura, Varahram Shahryari, Takeshi Chiyomaru, Guoren Deng, Rajvir Dahiya, Yuichiro Tanaka. Catechol-O-methyltransferase-mediated metabolism of 4-hydroxyestradiol inhibits the growth of human renal cancer cells through the apoptotic pathway.
Carcinogenesis.
2012 Feb; 33(2):420-6. doi:
10.1093/carcin/bgr294. [PMID: 22159223] - A Heather Eliassen, Donna Spiegelman, Xia Xu, Larry K Keefer, Timothy D Veenstra, Robert L Barbieri, Walter C Willett, Susan E Hankinson, Regina G Ziegler. Urinary estrogens and estrogen metabolites and subsequent risk of breast cancer among premenopausal women.
Cancer research.
2012 Feb; 72(3):696-706. doi:
10.1158/0008-5472.can-11-2507. [PMID: 22144471] - 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] - Man Ho Choi, Ju-Yeon Moon, Sung-Hee Cho, Bong Chul Chung, Eun Jig Lee. Metabolic alteration of urinary steroids in pre- and post-menopausal women, and men with papillary thyroid carcinoma.
BMC cancer.
2011 Aug; 11(?):342. doi:
10.1186/1471-2407-11-342. [PMID: 21824401] - 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] - Yow-Jiun Jeng, Mikhail Kochukov, Dhananjaya Nauduri, Bhupendra S Kaphalia, Cheryl S Watson. Subchronic exposure to phytoestrogens alone and in combination with diethylstilbestrol - pituitary tumor induction in Fischer 344 rats.
Nutrition & metabolism.
2010 May; 7(?):40. doi:
10.1186/1743-7075-7-40. [PMID: 20459739] - 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:
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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] - Latanya M Scott, Xia Xu, Timothy D Veenstra, Janet A Tooze, Charles E Wood, Thomas C Register, Nancy D Kock, J Mark Cline. Past oral contraceptive use and current dietary soy isoflavones influence estrogen metabolism in postmenopausal monkeys (Macaca fascicularis).
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2008 Oct; 17(10):2594-602. doi:
10.1158/1055-9965.epi-08-0278. [PMID: 18843000] - 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] - Jeanne Farrell, Lavoisier Ramos, Martin Tresguerres, Margarita Kamenetsky, Lonny R Levin, Jochen Buck. Somatic 'soluble' adenylyl cyclase isoforms are unaffected in Sacy tm1Lex/Sacy tm1Lex 'knockout' mice.
PloS one.
2008 Sep; 3(9):e3251. doi:
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Chemical research in toxicology.
2008 Aug; 21(8):1622-30. doi:
10.1021/tx800145w. [PMID: 18582124] - 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] - Harini S Aiyer, Sunita Kichambare, Ramesh C Gupta. Prevention of oxidative DNA damage by bioactive berry components.
Nutrition and cancer.
2008; 60 Suppl 1(?):36-42. doi:
10.1080/01635580802398448. [PMID: 19003579] - 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] - Qingming Fang, Jagadeesan Nair, Xin Sun, Dimiter Hadjiolov, Helmut Bartsch. Etheno-DNA adduct formation in rats gavaged with linoleic acid, oleic acid and coconut oil is organ- and gender specific.
Mutation research.
2007 Nov; 624(1-2):71-9. doi:
10.1016/j.mrfmmm.2007.04.002. [PMID: 17521682] - Xia Xu, John M Roman, Haleem J Issaq, Larry K Keefer, Timothy D Veenstra, Regina G Ziegler. Quantitative measurement of endogenous estrogens and estrogen metabolites in human serum by liquid chromatography-tandem mass spectrometry.
Analytical chemistry.
2007 Oct; 79(20):7813-21. doi:
10.1021/ac070494j. [PMID: 17848096] - 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] - Wahid Ali Khan, Khursheed Alam, Moinuddin. Catechol-estrogen modified DNA: a better antigen for cancer autoantibody.
Archives of biochemistry and biophysics.
2007 Sep; 465(1):293-300. doi:
10.1016/j.abb.2007.06.006. [PMID: 17632072] - 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] - Xia Xu, Larry K Keefer, Regina G Ziegler, Timothy D Veenstra. A liquid chromatography-mass spectrometry method for the quantitative analysis of urinary endogenous estrogen metabolites.
Nature protocols.
2007; 2(6):1350-5. doi:
10.1038/nprot.2007.176. [PMID: 17545972] - 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] - Y Markushin, N Gaikwad, H Zhang, P Kapke, E G Rogan, E L Cavalieri, B J Trock, C Pavlovich, R Jankowiak. Potential biomarker for early risk assessment of prostate cancer.
The Prostate.
2006 Oct; 66(14):1565-71. doi:
10.1002/pros.20484. [PMID: 16894534] - Ercole Cavalieri, Dhubajyoti Chakravarti, Joseph Guttenplan, Elizabeth Hart, James Ingle, Ryszard Jankowiak, Paola Muti, Eleanor Rogan, Jose Russo, Richard Santen, Thomas Sutter. Catechol estrogen quinones as initiators of breast and other human cancers: implications for biomarkers of susceptibility and cancer prevention.
Biochimica et biophysica acta.
2006 Aug; 1766(1):63-78. doi:
10.1016/j.bbcan.2006.03.001. [PMID: 16675129] - 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:
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Chemical research in toxicology.
2005 Oct; 18(10):1520-7. doi:
10.1021/tx050013w. [PMID: 16533015] - Yuki Tsuchiya, Miki Nakajima, Tsuyoshi Yokoi. Cytochrome P450-mediated metabolism of estrogens and its regulation in human.
Cancer letters.
2005 Sep; 227(2):115-24. doi:
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Free radical research.
2005 Sep; 39(9):943-8. doi:
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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] - Brian J Philips, Pete J Ansell, Leslie G Newton, Nobuhiro Harada, Shin-Ichiro Honda, Venkataseshu K Ganjam, George E Rottinghaus, Wade V Welshons, Dennis B Lubahn. Estrogen receptor-independent catechol estrogen binding activity: protein binding studies in wild-type, Estrogen receptor-alpha KO, and aromatase KO mice tissues.
Biochemistry.
2004 Jun; 43(21):6698-708. doi:
10.1021/bi036154j. [PMID: 15157104] - Mime Nagai, Allan H Conney, Bao Ting Zhu. Strong inhibitory effects of common tea catechins and bioflavonoids on the O-methylation of catechol estrogens catalyzed by human liver cytosolic catechol-O-methyltransferase.
Drug metabolism and disposition: the biological fate of chemicals.
2004 May; 32(5):497-504. doi:
10.1124/dmd.32.5.497. [PMID: 15100171] - 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] - Ryszard Jankowiak, Yuri Markushin, Ercole L Cavalieri, Gerald J Small. Spectroscopic characterization of the 4-hydroxy catechol estrogen quinones-derived GSH and N-acetylated Cys conjugates.
Chemical research in toxicology.
2003 Mar; 16(3):304-11. doi:
10.1021/tx020088p. [PMID: 12641430] - 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:
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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:
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Carcinogenesis.
2001 Jun; 22(6):905-11. doi:
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Carcinogenesis.
2001 Mar; 22(3):489-97. doi:
10.1093/carcin/22.3.489. [PMID: 11238191] - 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] - L Muskhelishvili, P A Thompson, D F Kusewitt, C Wang, F F Kadlubar. In situ hybridization and immunohistochemical analysis of cytochrome P450 1B1 expression in human normal tissues.
The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society.
2001 Feb; 49(2):229-36. doi:
10.1177/002215540104900210. [PMID: 11156691] - 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]