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362-05-0,MFCD00010490
Catalog No.:AA00C0T7

362-05-0 | 2-HYDROXYESTRADIOL

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1mg
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5mg
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10mg
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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00C0T7
Chemical Name:
2-HYDROXYESTRADIOL
CAS Number:
362-05-0
Molecular Formula:
C18H24O3
Molecular Weight:
288.3814
MDL Number:
MFCD00010490
SMILES:
OC1CCC2C1(C)CCC1C2CCc2c1cc(O)c(c2)O
NSC Number:
61711
Properties
Computed Properties
 
Complexity:
411  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
3  
XLogP3:
3.7  

Literature

Title: Catechol estrogens induce proliferation and malignant transformation in prostate epithelial cells.

Journal: Toxicology letters 20130718

Title: Lipid peroxidation and DNA adduct formation in lymphocytes of premenopausal women: Role of estrogen metabolites and fatty acid intake.

Journal: International journal of cancer 20121101

Title: Sexual dimorphisms in the immune system of catechol-O-methyltransferase knockout mice.

Journal: Immunobiology 20120801

Title: Soluble adenylyl cyclase activity is necessary for retinal ganglion cell survival and axon growth.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20120530

Title: Catechol-O-methyltransferase (COMT) single nucleotide polymorphisms and haplotypes are not major risk factors for polycystic ovary syndrome.

Journal: Molecular and cellular endocrinology 20120305

Title: 2-Hydroxyestradiol slows progression of experimental polycystic kidney disease.

Journal: American journal of physiology. Renal physiology 20120301

Title: In vitro effects of 2-hydroxyestradiol-17β on ovarian follicular steroid secretion in the catfish Heteropneustes fossilis and identification of the receptor and signaling mechanisms.

Journal: General and comparative endocrinology 20120201

Title: Analysis of multiplex endogenous estrogen metabolites in human urine using ultra-fast liquid chromatography-tandem mass spectrometry: a case study for breast cancer.

Journal: Analytica chimica acta 20120120

Title: Hydroxylated estrogens (2-OH-E2 AND 4-OH-E2) do not activate cAMP/PKA and ERK1/2 pathways activation in a breast cancer MCF-7 cell line.

Journal: Endocrine regulations 20120101

Title: BMPR2 expression is suppressed by signaling through the estrogen receptor.

Journal: Biology of sex differences 20120101

Title: 3,3'-Diindolylmethane increases serum interferon-γ levels in the K14-HPV16 transgenic mouse model for cervical cancer.

Journal: In vivo (Athens, Greece) 20120101

Title: Isoflavones-Enriched Soy Protein Prevents CCL(4)-Induced Hepatotoxicity in Rats.

Journal: ISRN pharmacology 20120101

Title: Effect of tumour necrosis factor-alpha on estrogen metabolic pathways in breast cancer cells.

Journal: Journal of Cancer 20120101

Title: Chemopreventive activity of vitamin E in breast cancer: a focus on γ- and δ-tocopherol.

Journal: Nutrients 20111101

Title: The effect of tamoxifen and raloxifene on estrogen metabolism and endometrial cancer risk.

Journal: The Journal of steroid biochemistry and molecular biology 20110901

Title: Catechol metabolites of endogenous estrogens induce redox cycling and generate reactive oxygen species in breast epithelial cells.

Journal: Carcinogenesis 20110801

Title: Effect of 2-hydroxyestradiol on binge intake in rats.

Journal: Physiology & behavior 20110706

Title: The ability of hydroxylated estrogens (2-OH-E2 and 4-OH-E2) to increase of SHBG gene, protein expression and intracellular levels in MCF-7 cells line.

Journal: Endocrine regulations 20110701

Title: 2ME and 2OHE2 exhibit growth inhibitory effects and cell cycle arrest at G2/M in RL95-2 human endometrial cancer cells through activation of p53 and Chk1.

Journal: Molecular and cellular biochemistry 20110601

Title: Risk factors and control strategies for the rapidly rising rate of breast cancer in Korea.

Journal: Journal of breast cancer 20110601

Title: Tetra-methoxystilbene modulates ductal growth of the developing murine mammary gland.

Journal: Breast cancer research and treatment 20110401

Title: The effects of estradiol and catecholestrogens on uterine glycogen metabolism in mink (Neovison vison).

Journal: Theriogenology 20110315

Title: Soluble adenylyl cyclase mediates bicarbonate-dependent corneal endothelial cell protection.

Journal: American journal of physiology. Cell physiology 20110201

Title: 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.

Journal: Endocrine regulations 20110101

Title: Estrogen metabolite ratio: Is the 2-hydroxyestrone to 16α-hydroxyestrone ratio predictive for breast cancer?

Journal: International journal of women's health 20110101

Title: Mechanisms of estrogens' dose-dependent neuroprotective and neurodamaging effects in experimental models of cerebral ischemia.

Journal: International journal of molecular sciences 20110101

Title: The chemopreventive effect of Ginkgo biloba and Silybum marianum extracts on hepatocarcinogenesis in rats.

Journal: Cancer cell international 20110101

Title: Raloxifene and desmethylarzoxifene block estrogen-induced malignant transformation of human breast epithelial cells.

Journal: PloS one 20110101

Title: Development of pulmonary arterial hypertension in mice over-expressing S100A4/Mts1 is specific to females.

Journal: Respiratory research 20110101

Title: Influence of 17β-estradiol on gene expression of Paracoccidioides during mycelia-to-yeast transition.

Journal: PloS one 20110101

Title: Estrogens and development of pulmonary hypertension: interaction of estradiol metabolism and pulmonary vascular disease.

Journal: Journal of cardiovascular pharmacology 20101201

Title: Serum concentrations of selected endogenous estrogen and estrogen metabolites in pre- and post-menopausal Chinese women with osteoarthritis.

Journal: Journal of endocrinological investigation 20101001

Title: Resveratrol, a red wine constituent, blocks the antimitogenic effects of estradiol on human female coronary artery smooth muscle cells.

Journal: The Journal of clinical endocrinology and metabolism 20100901

Title: Dietary quercetin exacerbates the development of estrogen-induced breast tumors in female ACI rats.

Journal: Toxicology and applied pharmacology 20100901

Title: Involvement of CFTR in oviductal HCO3- secretion and its effect on soluble adenylate cyclase-dependent early embryo development.

Journal: Human reproduction (Oxford, England) 20100701

Title: Simultaneous determination of eight estrogens and their metabolites in serum using liquid chromatography with electrochemical detection.

Journal: Talanta 20100415

Title: Nongenomic inhibition of coronary constriction by 17ß-estradiol, 2-hydroxyestradiol, and 2-methoxyestradiol.

Journal: Canadian journal of physiology and pharmacology 20100201

Title: A methoxyflavonoid, chrysoeriol, selectively inhibits the formation of a carcinogenic estrogen metabolite in MCF-7 breast cancer cells.

Journal: The Journal of steroid biochemistry and molecular biology 20100101

Title: The normal breast microenvironment of premenopausal women differentially influences the behavior of breast cancer cells in vitro and in vivo.

Journal: BMC medicine 20100101

Title: Comparison of estrogens and estrogen metabolites in human breast tissue and urine.

Journal: Reproductive biology and endocrinology : RB&E 20100101

Title: Dual beneficial effects of (-)-epigallocatechin-3-gallate on levodopa methylation and hippocampal neurodegeneration: in vitro and in vivo studies.

Journal: PloS one 20100101

Title: Redox regulation in cancer: a double-edged sword with therapeutic potential.

Journal: Oxidative medicine and cellular longevity 20100101

Title: Morphologic transformation of human breast epithelial cells MCF-10A: dependence on an oxidative microenvironment and estrogen/epidermal growth factor receptors.

Journal: Cancer cell international 20100101

Title: 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.

Journal: Breast cancer : basic and clinical research 20100101

Title: C2- and C4-position 17beta-estradiol metabolites and their relation to breast cancer.

Journal: Biocell : official journal of the Sociedades Latinoamericanas de Microscopia Electronica ... et. al 20091201

Title: Dietary fat alters body composition, mammary development, and cytochrome p450 induction after maternal TCDD exposure in DBA/2J mice with low-responsive aryl hydrocarbon receptors.

Journal: Environmental health perspectives 20090901

Title: [Oxidative transformation of 17beta-estradiol at the interface of delta-MnO2 and water].

Journal: Huan jing ke xue= Huanjing kexue 20090815

Title: Oxidative transformation of 17beta-estradiol by MnO2) in aqueous solution.

Journal: Archives of environmental contamination and toxicology 20090801

Title: Inhibition of osteoclast formation and function by bicarbonate: role of soluble adenylyl cyclase.

Journal: Journal of cellular physiology 20090801

Title: Vitamin C and alpha-naphthoflavone prevent estrogen-induced mammary tumors and decrease oxidative stress in female ACI rats.

Journal: Carcinogenesis 20090701

Title: Effects of estradiol metabolites on cAMP production and degradation.

Journal: Prilozi 20090701

Title: Regulation of epithelial Na+ transport by soluble adenylyl cyclase in kidney collecting duct cells.

Journal: The Journal of biological chemistry 20090227

Title: Identification of a novel haplotype of the human catechol-O-methyltransferase gene.

Journal: Pharmacogenetics and genomics 20090101

Title: Cytochrome P450 1B1 Val432Leu polymorphism and breast cancer risk in Nigerian women: a case control study.

Journal: Infectious agents and cancer 20090101

Title: Calcium-dependent increases in protein kinase-A activity in mouse retinal ganglion cells are mediated by multiple adenylate cyclases.

Journal: PloS one 20090101

Title: Urine biomarkers of risk in the molecular etiology of breast cancer.

Journal: Breast cancer : basic and clinical research 20090101

Title: Development of a stable dual cell-line GFP expression system to study estrogenic endocrine disruptors.

Journal: Biotechnology and bioengineering 20081215

Title: Characterization of a novel human catechol-O-methyl-transferase mutant with triplet point mutations.

Journal: International journal of molecular medicine 20081201

Title: Fat/fiber intakes and sex hormones in healthy premenopausal women in USA.

Journal: The Journal of steroid biochemistry and molecular biology 20081101

Title: Hydroxyestrogens inhibit angiogenesis in swine ovarian follicles.

Journal: The Journal of endocrinology 20081001

Title: Catecholestrogens induce oxidative stress and malignant transformation in human endometrial glandular cells: protective effect of catechol-O-methyltransferase.

Journal: International journal of cancer 20080915

Title: Titanium dioxide mediated photocatalytic degradation of 17beta-estradiol in aqueous solution.

Journal: Chemosphere 20080901

Title: Structure-based development of novel adenylyl cyclase inhibitors.

Journal: Journal of medicinal chemistry 20080814

Title: 17-Beta estradiol and hydroxyestradiols interact via the NF-kappa B pathway to elevate cyclooxygenase 2 expression and prostaglandin E2 secretion in human bronchial epithelial cells.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20080801

Title: Estradiol and the estradiol metabolite, 2-hydroxyestradiol, activate AMP-activated protein kinase in C2C12 myotubes.

Journal: Obesity (Silver Spring, Md.) 20080601

Title: Impact of estrogenic compounds on DNA integrity in human spermatozoa: evidence for cross-linking and redox cycling activities.

Journal: Mutation research 20080510

Title: Biochemical and computational insights into the anti-aromatase activity of natural catechol estrogens.

Journal: The Journal of steroid biochemistry and molecular biology 20080501

Title: Ovarian P450 aromatase activity in the catfish Heteropneustes fossilis: seasonal changes and effects of catecholestrogens.

Journal: General and comparative endocrinology 20080501

Title: Preferential induction of cytochrome P450 1A1 over cytochrome P450 1B1 in human breast epithelial cells following exposure to quercetin.

Journal: The Journal of steroid biochemistry and molecular biology 20080501

Title: Medroxyprogesterone abrogates the inhibitory effects of estradiol on vascular smooth muscle cells by preventing estradiol metabolism.

Journal: Hypertension (Dallas, Tex. : 1979) 20080401

Title: Phytoestrogens and breast cancer prevention: possible mechanisms of action.

Journal: Environmental health perspectives 20080401

Title: Molecular modelling study of the mechanism of high-potency inhibition of human catechol-O-methyltransferase by (-)-epigallocatechin-3-O-gallate.

Journal: Xenobiotica; the fate of foreign compounds in biological systems 20080201

Title: 2-Ethoxyestradiol is antimitogenic and attenuates monocrotaline-induced pulmonary hypertension and vascular remodeling.

Journal: Vascular pharmacology 20080101

Title: Sex steroids and vascular responses in hypertension and aging.

Journal: Gender medicine 20080101

Title: Phytoestrogens modulate the expression of 17alpha-estradiol metabolizing enzymes in cultured MCF-7 cells.

Journal: Advances in experimental medicine and biology 20080101

Title: Estrogen enhanced cell-cell signalling in breast cancer cells exposed to targeted irradiation.

Journal: BMC cancer 20080101

Title: Twenty-four hours secretion pattern of serum estradiol in healthy prepubertal and pubertal boys as determined by a validated ultra-sensitive extraction RIA.

Journal: BMC endocrine disorders 20080101

Title: Hydroxylated estrogen metabolites influence the proliferation of cultured human monocytes: possible role in synovial tissue hyperplasia.

Journal: Clinical and experimental rheumatology 20080101

Title: Grammatical Immune System Evolution for reverse engineering nonlinear dynamic Bayesian models.

Journal: Cancer informatics 20080101

Title: Catechol-o-methyltransferase and methoxyestradiols participate in the intraoviductal nongenomic pathway through which estradiol accelerates egg transport in cycling rats.

Journal: Biology of reproduction 20071201

Title: External Ca2+ acts upstream of adenylyl cyclase SACY in the bicarbonate signaled activation of sperm motility.

Journal: Developmental biology 20071201

Title: Treatment with an inhibitor of catechol-O-methyltransferase activity reduces preterm birth and impedes cervical resistance to stretch in pregnant rats.

Journal: Reproduction (Cambridge, England) 20071201

Title: Estrogenic activity removal of 17beta-estradiol by ozonation and identification of by-products.

Journal: Chemosphere 20071001

Title: HPLC for stress-free screening of potential prostate cancer marker catechol estrogens in urine using a diamond-electrode electrochemical and a fluorescence detector.

Journal: Journal of separation science 20070901

Title: Porcine follicular fluids: comparison of solid-phase extraction and matrix solid-phase dispersion for the GC-MS determination of hormones during follicular growth.

Journal: Journal of pharmaceutical and biomedical analysis 20070727

Title: Increase of carcinogenic risk via enhancement of cyclooxygenase-2 expression and hydroxyestradiol accumulation in human lung cells as a result of interaction between BaP and 17-beta estradiol.

Journal: Carcinogenesis 20070701

Title: Variants in estrogen metabolism and biosynthesis genes and urinary estrogen metabolites in women with a family history of breast cancer.

Journal: Breast cancer research and treatment 20070301

Title: 2-Methoxyestradiol and 2-ethoxyestradiol retard the progression of renal disease in aged, obese, diabetic ZSF1 rats.

Journal: Journal of cardiovascular pharmacology 20070101

Title: Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.

Journal: Journal of molecular graphics & modelling 20061101

Title: Regioselective 2-hydroxylation of 17beta-estradiol by rat cytochrome P4501B1.

Journal: Toxicology and applied pharmacology 20061101

Title: 2-methoxyestradiol inhibits differentiation and is cytotoxic to osteoclasts.

Journal: Journal of cellular biochemistry 20061001

Title: Inhibition of the human liver microsomal and human cytochrome P450 1A2 and 3A4 metabolism of estradiol by deployment-related and other chemicals.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20060901

Title: Estrogens, enzyme variants, and breast cancer: a risk model.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20060901

Title: Catechol estrogen quinones as initiators of breast and other human cancers: implications for biomarkers of susceptibility and cancer prevention.

Journal: Biochimica et biophysica acta 20060801

Title: 2-Hydroxyestradiol-17beta-induced oocyte maturation in catfish (Heteropneustes fossilis) involves protein kinase C and its interaction with protein phosphatases.

Journal: Comparative biochemistry and physiology. Part A, Molecular & integrative physiology 20060801

Title: Involvement of mitogen-activated protein kinase in 2-hydroxyestradiol-17beta-induced oocyte maturation in the catfish Heteropneustes fossilis and a note on possible interaction with protein phosphatases.

Journal: General and comparative endocrinology 20060701

Title: 2-Hydroxyestradiol-17beta-induced oocyte maturation: involvement of cAMP-protein kinase A and okadaic acid-sensitive protein phosphatases, and their interplay in oocyte maturation in the catfish Heteropneustes fossilis.

Journal: The Journal of experimental biology 20060701

Title: Relative effects of estradiol-17beta (E2), catecholestrogens and clomiphene citrate on in vitro oocyte maturation in the catfish Heteropneustes fossilis (Bloch) and E2 inhibition of 2-hydroxyestradiol-induced maturation.

Journal: General and comparative endocrinology 20060601

Title: Sulfotransferase (SULT) 1A1 polymorphic variants *1, *2, and *3 are associated with altered enzymatic activity, cellular phenotype, and protein degradation.

Journal: Molecular pharmacology 20060601

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Effects of gonadotrophin in vivo and 2-hydroxyoestradiol-17beta in vitro on follicular steroid hormone profile associated with oocyte maturation in the catfish Heteropneustes fossilis.

Journal: The Journal of endocrinology 20060501

Title: Comparison of possible carcinogenic estradiol metabolites: effects on proliferation, apoptosis and metastasis of human breast cancer cells.

Journal: Maturitas 20060420

Title: Estradiol and its metabolites 4-hydroxyestradiol and 2-hydroxyestradiol induce mutations in human breast epithelial cells.

Journal: International journal of cancer 20060415

Title: Health effects in fish of long-term exposure to effluents from wastewater treatment works.

Journal: Environmental health perspectives 20060401

Title: Estrogen metabolites and systolic blood pressure in a population-based sample of postmenopausal women.

Journal: The Journal of clinical endocrinology and metabolism 20060301

Title: Analysis of fifteen estrogen metabolites using packed column supercritical fluid chromatography-mass spectrometry.

Journal: Analytical chemistry 20060301

Title: Mutagenic activity of 4-hydroxyestradiol, but not 2-hydroxyestradiol, in BB rat2 embryonic cells, and the mutational spectrum of 4-hydroxyestradiol.

Journal: Chemical research in toxicology 20060301

Title: The greater reactivity of estradiol-3,4-quinone vs estradiol-2,3-quinone with DNA in the formation of depurinating adducts: implications for tumor-initiating activity.

Journal: Chemical research in toxicology 20060101

Title: Mitogenic estrogen metabolites alter the expression of 17beta-estradiol-regulated proteins including heat shock proteins in human MCF-7 breast cancer cells.

Journal: Molecules and cells 20051231

Title: Regulation of CFTR channels by HCO(3)--sensitive soluble adenylyl cyclase in human airway epithelial cells.

Journal: American journal of physiology. Cell physiology 20051101

Title: Estradiol metabolites attenuate monocrotaline-induced pulmonary hypertension in rats.

Journal: Journal of cardiovascular pharmacology 20051001

Title: Impact of induced fit on ligand binding to the androgen receptor: a multidimensional QSAR study to predict endocrine-disrupting effects of environmental chemicals.

Journal: Journal of medicinal chemistry 20050908

Title: Effect of catecholestrogen administration during adriamycin-induced cardiomyopathy in ovariectomized rat.

Journal: Free radical research 20050901

Title: Tyrosinase-catalyzed oxidation of 17beta-estradiol: structure elucidation of the products formed beyond catechol estrogen quinones.

Journal: Chemical research in toxicology 20050901

Title: Estradiol metabolites attenuate renal and cardiovascular injury induced by chronic nitric oxide synthase inhibition.

Journal: Journal of cardiovascular pharmacology 20050701

Title: Detection of DNA strand breaks and oxidized DNA bases at the single-cell level resulting from exposure to estradiol and hydroxylated metabolites.

Journal: Environmental and molecular mutagenesis 20050501

Title: Specific binding of 4-hydroxyestradiol to mouse uterine protein: evidence of a physiological role for 4-hydroxyestradiol.

Journal: The Journal of endocrinology 20050501

Title: Lycopene and beta-carotene ameliorate catechol estrogen-mediated DNA damage.

Journal: The Japanese journal of veterinary research 20050201

Title: Cytochromes 1A1/1B1- and catechol-O-methyltransferase-derived metabolites mediate estradiol-induced antimitogenesis in human cardiac fibroblast.

Journal: The Journal of clinical endocrinology and metabolism 20050101

Title: Estradiol metabolites are potent mitogenic substances for human ovarian cancer cells.

Journal: European journal of gynaecological oncology 20050101

Title: Genetic polymorphisms in human SULT1A1 and UGT1A1 genes associate with breast tumor characteristics: a case-series study.

Journal: Breast cancer research : BCR 20050101

Title: Effects of dioxin on metabolism of estrogens in waste incinerator workers.

Journal: Archives of environmental & occupational health 20050101

Title: Estradiol metabolites as isoform-specific inhibitors of human glutathione S-transferases.

Journal: Chemico-biological interactions 20041230

Title: 2-Hydroxyestradiol induces oxidative DNA damage and apoptosis in human mammary epithelial cells.

Journal: Journal of toxicology and environmental health. Part A 20041201

Title: Resveratrol inhibits TCDD-induced expression of CYP1A1 and CYP1B1 and catechol estrogen-mediated oxidative DNA damage in cultured human mammary epithelial cells.

Journal: Carcinogenesis 20041001

Title: The effects of steroidal estrogens in ACI rat mammary carcinogenesis: 17beta-estradiol, 2-hydroxyestradiol, 4-hydroxyestradiol, 16alpha-hydroxyestradiol, and 4-hydroxyestrone.

Journal: The Journal of endocrinology 20041001

Title: In vitro model of mammary estrogen metabolism: structural and kinetic differences between catechol estrogens 2- and 4-hydroxyestradiol.

Journal: Chemical research in toxicology 20040901

Title: 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.

Journal: Xenobiotica; the fate of foreign compounds in biological systems 20040901

Title: Catecholamines block the antimitogenic effect of estradiol on human coronary artery smooth muscle cells.

Journal: The Journal of clinical endocrinology and metabolism 20040801

Title: Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation.

Journal: The Journal of biological chemistry 20040702

Title: Rapid yeast estrogen bioassays stably expressing human estrogen receptors alpha and beta, and green fluorescent protein: a comparison of different compounds with both receptor types.

Journal: The Journal of steroid biochemistry and molecular biology 20040701

Title: 2-hydroxyestradiol is a prodrug of 2-methoxyestradiol.

Journal: The Journal of pharmacology and experimental therapeutics 20040601

Title: Differential regulation of estrogen receptor subtypes alpha and beta in human aortic smooth muscle cells by oligonucleotides and estradiol.

Journal: The Journal of clinical endocrinology and metabolism 20040501

Title: 4-Hydroxy estradiol but not 2-hydroxy estradiol induces expression of hypoxia-inducible factor 1alpha and vascular endothelial growth factor A through phosphatidylinositol 3-kinase/Akt/FRAP pathway in OVCAR-3 and A2780-CP70 human ovarian carcinoma cells.

Journal: Toxicology and applied pharmacology 20040401

Title: A gas chromatography/mass spectrometry assay to measure estradiol, catecholestradiols, and methoxyestradiols in plasma.

Journal: Steroids 20040401

Title: Concentration-dependent mitogenic and antiproliferative actions of 2-methoxyestradiol in estrogen receptor-positive human breast cancer cells.

Journal: The Journal of steroid biochemistry and molecular biology 20040301

Title: The functional UGT1A1 promoter polymorphism decreases endometrial cancer risk.

Journal: Cancer research 20040201

Title: Prevention of mammary carcinogenesis by short-term estrogen and progestin treatments.

Journal: Breast cancer research : BCR 20040101

Title: Microsomal estrogen metabolism in channel catfish.

Journal: Marine environmental research 20040101

Title: Methoxyestradiols mediate the antimitogenic effects of 17beta-estradiol: direct evidence from catechol-O-methyltransferase-knockout mice.

Journal: Circulation 20031216

Title: Exposure of bovine oocytes to the endogenous metabolite 2-methoxyestradiol during in vitro maturation inhibits early embryonic development.

Journal: Biology of reproduction 20031201

Title: Sequential action of phase I and II enzymes cytochrome p450 1B1 and glutathione S-transferase P1 in mammary estrogen metabolism.

Journal: Cancer research 20031201

Title: Neuroprotective and neurotoxic effects of estrogens.

Journal: Brain research 20031114

Title: Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.

Journal: Chemical research in toxicology 20031001

Title: Activation of matrix metalloproteinase-2 and -9 by 2- and 4-hydroxyestradiol.

Journal: The Journal of steroid biochemistry and molecular biology 20031001

Title: Catecholamines block the antimitogenic effect of estradiol on human glomerular mesangial cells.

Journal: Hypertension (Dallas, Tex. : 1979) 20030901

Title: Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms.

Journal: Endocrinology 20030801

Title: Comparison of ex vivo inhibitory effect between 2-hydroxyestradiol and its 17-sulfate on rat hepatic microsomal lipid peroxidation.

Journal: Lipids 20030801

Title: Methylation of 2-hydroxyestradiol in isolated organs.

Journal: Hypertension (Dallas, Tex. : 1979) 20030701

Title: Aldehydic DNA lesions induced by catechol estrogens in calf thymus DNA.

Journal: Carcinogenesis 20030601

Title: [Studies on 2-hydroxyestradiol 17-sulfate derived from fetoplacental unit: the antioxidant as a potential defense substance against preeclampsia].

Journal: Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20030601

Title: Investigation of the regio- and stereo-selectivity of deoxyguanosine linkage to deuterated 2-hydroxyestradiol by using liquid chromatography/ESI-ion trap mass spectrometry.

Journal: Journal of the American Society for Mass Spectrometry 20030401

Title: Endogenous estradiol metabolites stimulate the in vitro proliferation of human osteoblastic cells.

Journal: International journal of clinical pharmacology and therapeutics 20030401

Title: Short synthesis of 2-methoxyestradiol and 2-hydroxyestradiol.

Journal: Steroids 20030401

Title: Metabolism of [6,7-3H, 35S] estradiol 17-sulfate in rats.

Journal: Steroids 20030401

Title: Medical hypothesis: hyperhomocysteinemia is a risk factor for estrogen-induced hormonal cancer.

Journal: International journal of oncology 20030301

Title: In vitro effects of catecholamines and catecholestrogens on brain tyrosine hydroxylase activity and kinetics in the female catfish Heteropneustes fossilis.

Journal: Journal of neuroendocrinology 20030301

Title: CYP450- and COMT-derived estradiol metabolites inhibit activity of human coronary artery SMCs.

Journal: Hypertension (Dallas, Tex. : 1979) 20030301

Title: 2-OH-estradiol, an endogenous hormone with neuroprotective functions.

Journal: Journal of psychiatric research 20030101

Title: Crystal structure of human sex hormone-binding globulin in complex with 2-methoxyestradiol reveals the molecular basis for high affinity interactions with C-2 derivatives of estradiol.

Journal: The Journal of biological chemistry 20021122

Title: 2-Hydroxyestradiol attenuates renal disease in chronic puromycin aminonucleoside nephropathy.

Journal: Journal of the American Society of Nephrology : JASN 20021101

Title: Protection by estrogens of biological damage by 2,2'-azobis(2-amidinopropane) dihydrochloride.

Journal: The Journal of steroid biochemistry and molecular biology 20021101

Title: The association of breast mitogens with mammographic densities.

Journal: British journal of cancer 20021007

Title: Tissue content of hydroxyestrogens in relation to survival of breast cancer patients.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20021001

Title: The redox protein thioredoxin-1 regulates the constitutive and inducible expression of the estrogen metabolizing cytochromes P450 1B1 and 1A1 in MCF-7 human breast cancer cells.

Journal: Carcinogenesis 20021001

Title: Catechol estrogen formation in liver microsomes from female ACI and Sprague-Dawley rats: comparison of 2- and 4-hydroxylation revisited.

Journal: Carcinogenesis 20020801

Title: Estradiol enhances and estriol inhibits the expression of CYP1A1 induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin in a mouse ovarian cancer cell line.

Journal: Toxicology 20020715

Title: Pro-oxidant and antioxidant potential of catecholestrogens against ferrylmyoglobin-induced oxidative stress.

Journal: Biochimica et biophysica acta 20020711

Title: Stimulatory effect of cigarette smoking on the 15 alpha-hydroxylation of estradiol by human term placenta.

Journal: Clinical pharmacology and therapeutics 20020501

Title: Reactions of estradiol-2,3-quinone with deoxyribonucleosides: possible insights in the reactivity of estrogen quinones with DNA.

Journal: Chemical research in toxicology 20020501

Title: Catecholamines block 2-hydroxyestradiol-induced antimitogenesis in mesangial cells.

Journal: Hypertension (Dallas, Tex. : 1979) 20020401

Title: Methoxyestradiols mediate estradiol-induced antimitogenesis in human aortic SMCs.

Journal: Hypertension (Dallas, Tex. : 1979) 20020401

Title: Estrogen metabolism and the diet-cancer connection: rationale for assessing the ratio of urinary hydroxylated estrogen metabolites.

Journal: Alternative medicine review : a journal of clinical therapeutic 20020401

Title: Catecholestrogen sulfation: possible role in carcinogenesis.

Journal: Biochemical and biophysical research communications 20020329

Title: 2-methoxyestradiol induces interferon gene expression and apoptosis in osteosarcoma cells.

Journal: Bone 20020201

Title: Methoxyestradiols mediate the antimitogenic effects of locally applied estradiol on cardiac fibroblast growth.

Journal: Hypertension (Dallas, Tex. : 1979) 20020201

Title: Role of methoxyestradiols in the growth inhibitory effects of estradiol on human glomerular mesangial cells.

Journal: Hypertension (Dallas, Tex. : 1979) 20020201

Title: Highly specific anti-estradiol antibodies: structural characterisation and binding diversity.

Journal: Journal of molecular biology 20020125

Title: 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.

Journal: BMC cardiovascular disorders 20020101

Title: 2-Hydroxyestradiol attenuates the development of obesity, the metabolic syndrome, and vascular and renal dysfunction in obese ZSF1 rats.

Journal: The Journal of pharmacology and experimental therapeutics 20011201

Title: Catecholamines abrogate antimitogenic effects of 2-hydroxyestradiol on human aortic vascular smooth muscle cells.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20011101

Title: The ability of four catechol estrogens of 17beta-estradiol and estrone to induce DNA adducts in Syrian hamster embryo fibroblasts.

Journal: Carcinogenesis 20010901

Title: 2-methoxyestradiol does not inhibit superoxide dismutase.

Journal: Archives of biochemistry and biophysics 20010815

Title: Inhibition of large-conductance calcium-activated potassium channel by 2-methoxyestradiol in cultured vascular endothelial (HUV-EC-C) cells.

Journal: The Journal of membrane biology 20010801

Title: Gas chromatographic determination of catecholestrogens following isolation by solid-phase extraction.

Journal: Journal of chromatography. B, Biomedical sciences and applications 20010715

Title: Catechol estrogens induce oxidative DNA damage and estradiol enhances cell proliferation.

Journal: International journal of cancer 20010501

Title: In vitro generation of peroxynitrite by 2- and 4-hydroxyestrogens in the presence of nitric oxide.

Journal: Chemical research in toxicology 20010501

Title: High metabolization of catecholestrogens by type 1 estrogen sulfotransferase (hEST1).

Journal: The Journal of steroid biochemistry and molecular biology 20010401

Title: Determination of estradiol metabolites in human liver microsome by high performance liquid chromatography-electrochemistry detector.

Journal: Acta pharmacologica Sinica 20010401

Title: Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase.

Journal: Molecular pharmacology 20010201

Title: Estradiol metabolites inhibit endothelin synthesis by an estrogen receptor-independent mechanism.

Journal: Hypertension (Dallas, Tex. : 1979) 20010201

Title: Effects of estradiol and its metabolites on glomerular endothelial nitric oxide synthesis and mesangial cell growth.

Journal: Hypertension (Dallas, Tex. : 1979) 20010201

Title: Increased 2-methoxyestradiol production in human coronary versus aortic vascular cells.

Journal: Hypertension (Dallas, Tex. : 1979) 20010201

Title: Role of cytochrome P450 in estradiol metabolism in vitro.

Journal: Acta pharmacologica Sinica 20010201

Title: Mutagenic properties of estrogen quinone-derived DNA adducts in simian kidney cells.

Journal: Biochemistry 20010109

Title: Ratiometric analysis of the ferrocene boronate esters of 2- and 4-hydroxyestradiol by tandem electrospray mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20010101

Title: 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.

Journal: Carcinogenesis 20000801

Title: Involvement of genotoxic effects in the initiation of estrogen-induced cellular transformation: studies using Syrian hamster embryo cells treated with 17beta-estradiol and eight of its metabolites.

Journal: International journal of cancer 20000401

Title: Induction of uterine adenocarcinoma in CD-1 mice by catechol estrogens.

Journal: Cancer research 20000115

Title: Enhanced levels of several mitochondrial mRNA transcripts and mitochondrial superoxide production during ethinyl estradiol-induced hepatocarcinogenesis and after estrogen treatment of HepG2 cells.

Journal: Carcinogenesis 19981201

Title: Estrogenic and antiestrogenic activities of 16alpha- and 2-hydroxy metabolites of 17beta-estradiol in MCF-7 and T47D human breast cancer cells.

Journal: The Journal of steroid biochemistry and molecular biology 19981201

Title: Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta.

Journal: Endocrinology 19970301

Title: Influence of sex steroids and prolactin on haloperidol-induced catalepsy.

Journal: Brain research 19831121

Title: [Metabolism of 2-hydroxyestradiol-(17 beta) and 2-methoxyestradiol-(17 beta)in human and rat tissues].

Journal: Hoppe-Seyler's Zeitschrift fur physiologische Chemie 19610530

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Tags:362-05-0 Molecular Formula|362-05-0 MDL|362-05-0 SMILES|362-05-0 2-HYDROXYESTRADIOL