4-Hydroxyestradiol (BioDeep_00000009764)

Main id: BioDeep_00000637477

 

human metabolite Endogenous


代谢物信息卡片


(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-5,6,14-triol

化学式: C18H24O3 (288.1725)
中文名称: 4-羟基雌二醇
谱图信息: 最多检出来源 Mus musculus(blood) 27.16%

分子结构信息

SMILES: C1=CC2[C@@]3([H])CC[C@]4(C)[C@@H](O)CC[C@@]4([H])[C@]3([H])CCC=2C(O)=C1O
InChI: InChI=1S/C18H24O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h4,6,11-12,14,16,19-21H,2-3,5,7-9H2,1H3/t11-,12-,14+,16+,18+/m1/s1



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(5)

BioCyc(0)

PlantCyc(0)

代谢反应

47 个相关的代谢反应过程信息。

Reactome(45)

BioCyc(0)

WikiPathways(2)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

2 个相关的物种来源信息

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。

亚细胞结构定位 关联基因列表
Cytoplasm 12 AHR, BRCA1, CAT, CYP1A1, CYP3A4, ESR1, HPGDS, LPO, NFE2L2, NQO1, TYR, VEGFA
Peripheral membrane protein 3 CYP1A1, CYP1B1, ESR1
Endoplasmic reticulum membrane 6 CYP19A1, CYP1A1, CYP1A2, CYP1B1, CYP3A4, HMOX1
Nucleus 8 AHR, BRCA1, ESR1, ESR2, HMOX1, NFE2L2, NQO1, VEGFA
cytosol 8 AHR, CAT, COMT, ESR1, HMOX1, HPGDS, NFE2L2, NQO1
dendrite 2 COMT, NQO1
nuclear body 1 BRCA1
centrosome 1 NFE2L2
nucleoplasm 7 AHR, BRCA1, ESR1, ESR2, HMOX1, HPGDS, NFE2L2
RNA polymerase II transcription regulator complex 1 NFE2L2
Cell membrane 2 COMT, ESR1
Cytoplasmic side 2 ESR1, HMOX1
Multi-pass membrane protein 2 CYP19A1, SLC45A2
Synapse 2 COMT, NQO1
cell surface 1 VEGFA
Golgi apparatus 3 ESR1, NFE2L2, VEGFA
lysosomal membrane 1 EGF
mitochondrial inner membrane 1 CYP1A1
neuronal cell body 1 NQO1
Cytoplasm, cytosol 2 NFE2L2, NQO1
Lysosome 1 TYR
plasma membrane 5 BRCA1, COMT, EGF, ESR1, NFE2L2
Membrane 12 BRCA1, CAT, COMT, CYP19A1, CYP1B1, CYP3A4, EGF, ESR1, HMOX1, NQO1, SLC45A2, VEGFA
axon 1 COMT
basolateral plasma membrane 1 LPO
extracellular exosome 4 CAT, COMT, EGF, LPO
endoplasmic reticulum 3 CYP19A1, HMOX1, VEGFA
extracellular space 4 EGF, HMOX1, LPO, VEGFA
perinuclear region of cytoplasm 2 HMOX1, TYR
adherens junction 1 VEGFA
mitochondrion 4 CAT, CYP1A1, CYP1B1, ESR2
protein-containing complex 4 AHR, BRCA1, CAT, ESR1
intracellular membrane-bounded organelle 9 CAT, COMT, CYP1A1, CYP1A2, CYP1B1, CYP3A4, ESR2, HPGDS, TYR
Microsome membrane 5 CYP19A1, CYP1A1, CYP1A2, CYP1B1, CYP3A4
Single-pass type I membrane protein 1 TYR
Secreted 2 LPO, VEGFA
extracellular region 4 CAT, EGF, LPO, VEGFA
mitochondrial outer membrane 1 HMOX1
mitochondrial matrix 1 CAT
Extracellular side 1 COMT
transcription regulator complex 2 AHR, ESR1
Secreted, extracellular space, extracellular matrix 1 VEGFA
Melanosome membrane 2 SLC45A2, TYR
Golgi-associated vesicle 1 TYR
Single-pass type II membrane protein 1 COMT
Mitochondrion inner membrane 1 CYP1A1
focal adhesion 1 CAT
extracellular matrix 1 VEGFA
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
secretory granule 1 VEGFA
chromatin 4 AHR, ESR1, ESR2, NFE2L2
mediator complex 1 NFE2L2
Chromosome 1 BRCA1
[Isoform 5]: Cytoplasm 1 BRCA1
lateral element 1 BRCA1
aryl hydrocarbon receptor complex 1 AHR
Melanosome 1 TYR
euchromatin 1 ESR1
ubiquitin ligase complex 1 BRCA1
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
male germ cell nucleus 1 BRCA1
platelet alpha granule lumen 2 EGF, VEGFA
XY body 1 BRCA1
Single-pass type IV membrane protein 1 HMOX1
clathrin-coated endocytic vesicle membrane 1 EGF
ribonucleoprotein complex 1 BRCA1
[Isoform 1]: Nucleus 1 ESR1
protein-DNA complex 1 NFE2L2
intracellular non-membrane-bounded organelle 1 BRCA1
DNA repair complex 1 BRCA1
BRCA1-C complex 1 BRCA1
catalase complex 1 CAT
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
[Isoform Soluble]: Cytoplasm 1 COMT
[Isoform Membrane-bound]: Cell membrane 1 COMT
nuclear aryl hydrocarbon receptor complex 1 AHR
cytosolic aryl hydrocarbon receptor complex 1 AHR
BRCA1-A complex 1 BRCA1
BRCA1-B complex 1 BRCA1
BRCA1-BARD1 complex 1 BRCA1
gamma-tubulin ring complex 1 BRCA1
nuclear ubiquitin ligase complex 1 BRCA1


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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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: 10.1371/journal.pone.0003251. [PMID: 18806876]
  • Leslie A Bransfield, Alissa Rennie, Kala Visvanathan, Shelly-Ann Odwin, Thomas W Kensler, James D Yager, Marlin D Friesen, John D Groopman. Formation of two novel estrogen guanine adducts and HPLC/MS detection of 4-hydroxyestradiol-N7-guanine in human urine. 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]
  • 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]
  • 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]
  • 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]
  • Y Markushin, P Kapke, M Saeed, H Zhang, A Dawoud, E G Rogan, E L Cavalieri, R Jankowiak. Development of monoclonal antibodies to 4-hydroxyestrogen-2-N-acetylcysteine conjugates: immunoaffinity and spectroscopic studies. 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: 10.1016/j.canlet.2004.10.007. [PMID: 16112414]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • R Todorovic, P Devanesan, S Higginbotham, J Zhao, M L Gross, E G Rogan, E L Cavalieri. Analysis of potential biomarkers of estrogen-initiated cancer in the urine of Syrian golden hamsters treated with 4-hydroxyestradiol. Carcinogenesis. 2001 Jun; 22(6):905-11. doi: 10.1093/carcin/22.6.905. [PMID: 11375897]
  • P Devanesan, R Todorovic, J Zhao, M L Gross, E G Rogan, E L Cavalieri. Catechol estrogen conjugates and DNA adducts in the kidney of male Syrian golden hamsters treated with 4-hydroxyestradiol: potential biomarkers for estrogen-initiated cancer. Carcinogenesis. 2001 Mar; 22(3):489-97. doi: 10.1093/carcin/22.3.489. [PMID: 11238191]
  • 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]
  • 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]
  • X Xu, A M Duncan, B E Merz-Demlow, W R Phipps, M S Kurzer. Menstrual cycle effects on urinary estrogen metabolites. The Journal of clinical endocrinology and metabolism. 1999 Nov; 84(11):3914-8. doi: 10.1210/jcem.84.11.6134. [PMID: 10566628]
  • 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]
  • G G Kuiper, B Carlsson, K Grandien, E Enmark, J Häggblad, S Nilsson, J A Gustafsson. Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. Endocrinology. 1997 Mar; 138(3):863-70. doi: 10.1210/endo.138.3.4979. [PMID: 9048584]
  • 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]
  • 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 D Green, E M Oturu, T R Tephly. Stable expression of a human liver UDP-glucuronosyltransferase (UGT2B15) with activity toward steroid and xenobiotic substrates. Drug metabolism and disposition: the biological fate of chemicals. 1994 Sep; 22(5):799-805. doi: NULL. [PMID: 7835232]
  • 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]
  • 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]
  • 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]
  • 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]
  • C H van Aswegen, L B Nieuwoudt, R J Hooke, D J du Plessis. A serum oestradiol/4-hydroxyestradiol ratio test as prostatic tumour marker. South African medical journal = Suid-Afrikaanse tydskrif vir geneeskunde. 1991 Jul; 80(1):60. doi: NULL. [PMID: 2063246]
  • 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]
  • K P Nephew, S P Ford, M L Day, W F Pope. Extension of short cycles in postpartum beef cows by intrauterine treatment with catecholestradiol. Domestic animal endocrinology. 1989 Oct; 6(4):363-70. doi: 10.1016/0739-7240(89)90030-1. [PMID: 2620506]
  • 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]
  • 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]
  • L J Spicer, J M Hammond. Catecholestrogens stimulate progestin secretion by cultured porcine granulosa cells. Molecular and cellular endocrinology. 1987 Mar; 50(1-2):139-47. doi: 10.1016/0303-7207(87)90086-4. [PMID: 3034696]
  • G Emons, H Schuppe, M Peter, C Brack, P Ball. Modulation of LH-secretion in ovariectomized ewes by constant infusions of oestradiol and 4-hydroxyoestradiol: effects of varying infusion times and of high oestrogen doses. Acta endocrinologica. 1986 Oct; 113(2):219-25. doi: 10.1530/acta.0.1130219. [PMID: 3776435]
  • J G Liehr, W F Fang, D A Sirbasku, A Ari-Ulubelen. Carcinogenicity of catechol estrogens in Syrian hamsters. Journal of steroid biochemistry. 1986 Jan; 24(1):353-6. doi: 10.1016/0022-4731(86)90080-4. [PMID: 3009986]
  • P Ball, G Emons. Effects of short-term exposure to catecholestrogens on serum concentrations of gonadotrophins and metabolism of catecholestrogens in ovariectomized rats. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme. 1985 Apr; 17(4):184-8. doi: 10.1055/s-2007-1013487. [PMID: 2989139]
  • G Emons, C Brack, R Chatelain, H H Abel, S Isedor, P Ball. Effects of continuous infusions of 4-hydroxyoestradiol and oestradiol on plasma LH-levels in the ovariectomized ewe. Acta endocrinologica. 1984 Nov; 107(3):328-36. doi: 10.1530/acta.0.1070328. [PMID: 6095572]
  • S Miyabo, S Kishida, T Sugiyama, T Hashimoto, Y Fujii, M Teranishi. Effects of 2-hydroxyoestradiol and 4-hydroxyoestradiol on gonadotrophin and prolactin secretion in women. Acta endocrinologica. 1984 Jan; 105(1):1-5. doi: 10.1530/acta.0.1050001. [PMID: 6421038]
  • P Ball, G Emons, H Kayser, J Teichmann. Metabolic clearance rates of catechol estrogens in rats. Endocrinology. 1983 Nov; 113(5):1781-3. doi: 10.1210/endo-113-5-1781. [PMID: 6628326]
  • N J MacLusky, M Riskalla, L Krey, N Parvizi, F Naftolin. Anovulation in female rats induced by neonatal administration of the catechol estrogens, 2-hydroxy-estradiol and 4-hydroxy-estradiol. Neuroendocrinology. 1983 Nov; 37(5):321-7. doi: 10.1159/000123569. [PMID: 6196675]
  • G Emons, R Knuppen, P Ball. 4-Hydroxyestradiol-17 beta and 4-hydroxyestradiol-17 alpha: comparative studies on central and peripheral effects of two epimeric catecholestrogens. Endocrinology. 1981 Nov; 109(5):1799-801. doi: 10.1210/endo-109-5-1799. [PMID: 7297508]
  • S Franks, N J MacLusky, S J Naish, F Naftolin. Actions of catechol oestrogens on concentrations of serum luteinizing hormone in the adult castrated rat: various effects of 4-hydroxyoestradiol and 2-hydroxyoestradiol. The Journal of endocrinology. 1981 May; 89(2):289-95. doi: 10.1677/joe.0.0890289. [PMID: 7241016]
  • P Ball, G Emons, U Gethmann. Effect of low doses of continuously administered catecholoestrogens on peripheral and central target organs. Acta endocrinologica. 1981 Apr; 96(4):470-4. doi: 10.1530/acta.0.0960470. [PMID: 6782789]
  • S Franks, P Ball, F Naftolin, K B Ruf. Effect of catechol oestrogens on induced ovulation in the immature rat. The Journal of endocrinology. 1980 Aug; 86(2):263-8. doi: 10.1677/joe.0.0860263. [PMID: 6253586]
  • G Emons, H O Hoppen, P Ball, R Knuppen. 4-hydroxyestrone, isolation and identification in human urine. Steroids. 1980 Jul; 36(1):73-9. doi: 10.1016/0039-128x(80)90069-0. [PMID: 7414657]