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5976-61-4,MFCD00063335
Catalog No.:AA00EAIC

5976-61-4 | 4-HYDROXYESTRADIOL

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1mg
≥98%
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$153.00   $107.00
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5mg
≥98%
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10mg
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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00EAIC
Chemical Name:
4-HYDROXYESTRADIOL
CAS Number:
5976-61-4
Molecular Formula:
C18H24O3
Molecular Weight:
288.3814
MDL Number:
MFCD00063335
SMILES:
O[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2O)O
Properties
Properties
 
Form:
Solid  
MP:
>190°C (dec.)  
Storage:
-20 ℃;Keep in dry area;  

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: Fingolimod interrupts the cross talk between estrogen metabolism and sphingolipid metabolism within prostate cancer cells.

Journal: Toxicology letters 20180701

Title: Lack of Cell Proliferative and Tumorigenic Effects of 4-Hydroxyestradiol in the Anterior Pituitary of Rats: Role of Ultrarapid O-Methylation Catalyzed by Pituitary Membrane-Bound Catechol-O-Methyltransferase.

Journal: Chemical research in toxicology 20170717

Title: Leptin induces CYP1B1 expression in MCF-7 cells through ligand-independent activation of the ERα pathway.

Journal: Toxicology and applied pharmacology 20140515

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: Resveratrol suppresses 4-hydroxyestradiol-induced transformation of human breast epithelial cells by blocking IκB kinaseβ-NF-κB signalling.

Journal: Free radical research 20120801

Title: ERα phenotype, estrogen level, and benzo[a]pyrene exposure modulate tumor growth and metabolism of lung adenocarcinoma cells.

Journal: Lung cancer (Amsterdam, Netherlands) 20120301

Title: Biomarker genes for detecting estrogenic activity of endocrine disruptors via estrogen receptors.

Journal: International journal of environmental research and public health 20120301

Title: Catechol-O-methyltransferase-mediated metabolism of 4-hydroxyestradiol inhibits the growth of human renal cancer cells through the apoptotic pathway.

Journal: Carcinogenesis 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: Importance of CYP1A1 polymorphism and its transcriptional regulation in ovarian and endometrial cancer.

Journal: Ginekologia polska 20111201

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

Journal: Nutrients 20111101

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

Journal: Carcinogenesis 20110801

Title: Estrogen metabolism and exposure in a genotypic-phenotypic model for breast cancer risk prediction.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20110701

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: 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: Gender is a risk factor for lung cancer.

Journal: Medical hypotheses 20110301

Title: Immunochemical studies on catechol-estrogen modified plasmid: possible role in rheumatoid arthritis.

Journal: Journal of clinical immunology 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: Platinum resistance in breast and ovarian cancer cell lines.

Journal: Journal of experimental & clinical cancer research : CR 20110101

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

Journal: PloS one 20110101

Title: Hormones and prostate carcinogenesis: Androgens and estrogens.

Journal: Journal of carcinogenesis 20110101

Title: Association of CYP1B1 with hypersensitivity induced by taxane therapy in breast cancer patients.

Journal: Breast cancer research and treatment 20101101

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

Journal: Toxicology and applied pharmacology 20100901

Title: Unexpected hormonal activity of a catechol equine estrogen metabolite reveals reversible glutathione conjugation.

Journal: Chemical research in toxicology 20100816

Title: N-acetylcysteine blocks formation of cancer-initiating estrogen-DNA adducts in cells.

Journal: Free radical biology & medicine 20100801

Title: Degradation of natural estrogen and identification of the metabolites produced by soil isolates of Rhodococcus sp. and Sphingomonas sp.

Journal: Journal of bioscience and bioengineering 20100601

Title: Early changes in gene expression induced by tobacco smoke: Evidence for the importance of estrogen within lung tissue.

Journal: Cancer prevention research (Philadelphia, Pa.) 20100601

Title: Early changes in pulmonary gene expression following tobacco exposure shed light on the role of estrogen metabolism in lung carcinogenesis.

Journal: Cancer prevention research (Philadelphia, Pa.) 20100601

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

Journal: Talanta 20100415

Title: Prostaglandin E2 induces CYP1B1 expression via ligand-independent activation of the ERalpha pathway in human breast cancer cells.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20100401

Title: Estradiol-17beta and its cytochrome P450- and catechol-O-methyltransferase-derived metabolites stimulate proliferation in uterine artery endothelial cells: role of estrogen receptor-alpha versus estrogen receptor-beta.

Journal: Hypertension (Dallas, Tex. : 1979) 20100401

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: Subchronic exposure to phytoestrogens alone and in combination with diethylstilbestrol - pituitary tumor induction in Fischer 344 rats.

Journal: Nutrition & metabolism 20100101

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

Journal: Oxidative medicine and cellular longevity 20100101

Title: A mathematical model for DNA damage and repair.

Journal: Journal of nucleic acids 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: Cytochrome 450 1B1 (CYP1B1) polymorphisms associated with response to docetaxel in Castration-Resistant Prostate Cancer (CRPC) patients.

Journal: BMC cancer 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: Estrogen treatment induces MLL aberrations in human lymphoblastoid cells.

Journal: Leukemia research 20091001

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

Journal: Carcinogenesis 20090701

Title: Effects of 17beta-estradiol, and its metabolite, 4-hydroxyestradiol on fertilization, embryo development and oxidative DNA damage in sand dollar (Dendraster excentricus) sperm.

Journal: The Science of the total environment 20090315

Title: 4-hydroxyestradiol induces anchorage-independent growth of human mammary epithelial cells via activation of IkappaB kinase: potential role of reactive oxygen species.

Journal: Cancer research 20090315

Title: Estrogen mediation of breast tumor formation involves estrogen receptor-dependent, as well as independent, genotoxic effects.

Journal: Annals of the New York Academy of Sciences 20090201

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

Journal: Pharmacogenetics and genomics 20090101

Title: Inhibition of human catechol-O-methyltransferase (COMT)-mediated O-methylation of catechol estrogens by major polyphenolic components present in coffee.

Journal: The Journal of steroid biochemistry and molecular biology 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: Estrogen exposure, metabolism, and enzyme variants in a model for breast cancer risk prediction.

Journal: Cancer informatics 20090101

Title: Modulatory effects of alpha- and gamma-tocopherols on 4-hydroxyestradiol induced oxidative stresses in MCF-10A breast epithelial cells.

Journal: Nutrition research and practice 20090101

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

Journal: Breast cancer : basic and clinical research 20090101

Title: Association of catechol-o-methyl transferase gene polymorphism with prostate cancer and benign prostatic hyperplasia.

Journal: Journal of research in medical sciences : the official journal of Isfahan University of Medical Sciences 20090101

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

Journal: International journal of molecular medicine 20081201

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: CYP1B1 variants are associated with prostate cancer in non-Hispanic and Hispanic Caucasians.

Journal: Carcinogenesis 20080901

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: Formation of two novel estrogen guanine adducts and HPLC/MS detection of 4-hydroxyestradiol-N7-guanine in human urine.

Journal: Chemical research in toxicology 20080801

Title: Prevention of estrogen-DNA adduct formation in MCF-10F cells by resveratrol.

Journal: Free radical biology & medicine 20080715

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

Journal: Environmental health perspectives 20080401

Title: Reduction of estrogen-induced transformation of mouse mammary epithelial cells by N-acetylcysteine.

Journal: The Journal of steroid biochemistry and molecular biology 20080301

Title: Soy isoflavones decrease the catechol-O-methyltransferase-mediated inactivation of 4-hydroxyestradiol in cultured MCF-7 cells.

Journal: Carcinogenesis 20080201

Title: Association of the CYP1B1*3 allele with survival in patients with prostate cancer receiving docetaxel.

Journal: Molecular cancer therapeutics 20080101

Title: Leu432Val polymorphism in CYP1B1 as a susceptible factor towards predisposition to primary open-angle glaucoma.

Journal: Molecular vision 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: Somatic 'soluble' adenylyl cyclase isoforms are unaffected in Sacy tm1Lex/Sacy tm1Lex 'knockout' mice.

Journal: PloS one 20080101

Title: Prevention of oxidative DNA damage by bioactive berry components.

Journal: Nutrition and cancer 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: Inhibition of depurinating estrogen-DNA adduct formation by natural compounds.

Journal: Chemical research in toxicology 20071201

Title: Etheno-DNA adduct formation in rats gavaged with linoleic acid, oleic acid and coconut oil is organ- and gender specific.

Journal: Mutation research 20071101

Title: Absence of uterine tumours in CD-1 mice treated neonatally with subcutaneous tamoxifen or 4-hydroxyoestradiol.

Journal: Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie 20071101

Title: Breast cancer: are estrogen metabolites carcinogenic?

Journal: Climacteric : the journal of the International Menopause Society 20071001

Title: Catechol-estrogen modified DNA: a better antigen for cancer autoantibody.

Journal: Archives of biochemistry and biophysics 20070901

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: Cytochrome P450 isoforms catalyze formation of catechol estrogen quinones that react with DNA.

Journal: Metabolism: clinical and experimental 20070701

Title: Formation of depurinating N3Adenine and N7Guanine adducts by MCF-10F cells cultured in the presence of 4-hydroxyestradiol.

Journal: International journal of cancer 20070415

Title: Binding characteristics of SLE anti-DNA autoantibodies to Catecholestrogen-modified DNA.

Journal: Scandinavian journal of immunology 20061201

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: Potential biomarker for early risk assessment of prostate cancer.

Journal: The Prostate 20061001

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: 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: 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: Is there a causal association between genotoxicity and the imposex effect?

Journal: Environmental health perspectives 20060401

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

Journal: Environmental health perspectives 20060401

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: Characterization of common UGT1A8, UGT1A9, and UGT2B7 variants with different capacities to inactivate mutagenic 4-hydroxylated metabolites of estradiol and estrone.

Journal: Cancer research 20060101

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: 4-Hydroxyestradiol induces oxidative stress and apoptosis in human mammary epithelial cells: possible protection by NF-kappaB and ERK/MAPK.

Journal: Toxicology and applied pharmacology 20051001

Title: Development of monoclonal antibodies to 4-hydroxyestrogen-2-N-acetylcysteine conjugates: immunoaffinity and spectroscopic studies.

Journal: Chemical research in toxicology 20051001

Title: Cytochrome P450-mediated metabolism of estrogens and its regulation in human.

Journal: Cancer letters 20050928

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: Estrogenic and genotoxic potential of equol and two hydroxylated metabolites of Daidzein in cultured human Ishikawa cells.

Journal: Toxicology letters 20050728

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: Nitric oxide enhances catechol estrogen-induced oxidative stress in LNCaP cells.

Journal: Free radical research 20050401

Title: Invasiveness of breast cancer cells MDA-MB-231 through extracellular matrix is increased by the estradiol metabolite 4-hydroxyestradiol.

Journal: International journal of cancer 20050220

Title: The estrogen antagonist ICI-182-780 does not inhibit the transformation phenotypes induced by 17-beta-estradiol and 4-OH estradiol in human breast epithelial cells.

Journal: International journal of oncology 20050201

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

Journal: The Japanese journal of veterinary research 20050201

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: Dietary indole-3-carbinol promotes endometrial adenocarcinoma development in rats initiated with N-ethyl-N'-nitro-N-nitrosoguanidine, with induction of cytochrome P450s in the liver and consequent modulation of estrogen metabolism.

Journal: Carcinogenesis 20041101

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: Phytochemicals inhibit catechol-O-methyltransferase activity in cytosolic fractions from healthy human mammary tissues: implications for catechol estrogen-induced DNA damage.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 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: 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: Equine estrogen metabolite 4-hydroxyequilenin induces anchorage-independent growth of human mammary epithelial MCF-10A cells: differential gene expression.

Journal: Mutation research 20040604

Title: Estrogen receptor-independent catechol estrogen binding activity: protein binding studies in wild-type, Estrogen receptor-alpha KO, and aromatase KO mice tissues.

Journal: Biochemistry 20040601

Title: Strong inhibitory effects of common tea catechins and bioflavonoids on the O-methylation of catechol estrogens catalyzed by human liver cytosolic catechol-O-methyltransferase.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20040501

Title: Extensive chromosomal breaks are induced by tamoxifen and estrogen in DNA repair-deficient cells.

Journal: Cancer research 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: Metabolism and DNA binding studies of 4-hydroxyestradiol and estradiol-3,4-quinone in vitro and in female ACI rat mammary gland in vivo.

Journal: Carcinogenesis 20040201

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: Lack of association of CYP1 B1*3 polymorphism and ovarian cancer in a Caucasian population.

Journal: The International journal of biological markers 20040101

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: Increased estrogen formation and estrogen to androgen ratio in the synovial fluid of patients with rheumatoid arthritis.

Journal: The Journal of rheumatology 20031201

Title: Nrf2, not the estrogen receptor, mediates catechol estrogen-induced activation of the antioxidant responsive element.

Journal: Biochimica et biophysica acta 20031001

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: Spectral characterization of catechol estrogen quinone (CEQ)-derived DNA adducts and their identification in human breast tissue extract.

Journal: Chemical research in toxicology 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: Effect of frying-meat emission particulate on 17beta-estradiol 2- and 4-hydroxylation in human lung adenocarcinoma CL5 cells.

Journal: Journal of toxicology and environmental health. Part A 20030627

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

Journal: Carcinogenesis 20030601

Title: Catechol estrogen 4-hydroxyequilenin is a substrate and an inhibitor of catechol-O-methyltransferase.

Journal: Chemical research in toxicology 20030501

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

Journal: International journal of clinical pharmacology and therapeutics 20030401

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

Journal: International journal of oncology 20030301

Title: Spectroscopic characterization of the 4-hydroxy catechol estrogen quinones-derived GSH and N-acetylated Cys conjugates.

Journal: Chemical research in toxicology 20030301

Title: 2-Methoxyestradiol, a promising anticancer agent.

Journal: Pharmacotherapy 20030201

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: On the structures of hydroxylated metabolites of estradiol 17-sulfate by rat liver microsomes.

Journal: Steroids 20021001

Title: Characterization of human soluble high and low activity catechol-O-methyltransferase catalyzed catechol estrogen methylation.

Journal: Pharmacogenetics 20021001

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: Estradiol metabolism and malignant disease.

Journal: Maturitas 20020930

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: Catecholestrogen sulfation: possible role in carcinogenesis.

Journal: Biochemical and biophysical research communications 20020329

Title: The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYP1B1.

Journal: British journal of cancer 20020304

Title: Catechol estrogen metabolites and conjugates in different regions of the prostate of Noble rats treated with 4-hydroxyestradiol: implications for estrogen-induced initiation of prostate cancer.

Journal: Carcinogenesis 20020201

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

Journal: Journal of molecular biology 20020125

Title: Genetic determinants of mammographic density.

Journal: Breast cancer research : BCR 20020101

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: Selective synthesis of 4-methoxyestrogen from 4-hydroxyestrogen.

Journal: Steroids 20010801

Title: Preferential growth stimulation of mammary glands over uterine endometrium in female rats by a naturally occurring estradiol-17beta-fatty acid ester.

Journal: Cancer research 20010801

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

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

Title: Analysis of potential biomarkers of estrogen-initiated cancer in the urine of Syrian golden hamsters treated with 4-hydroxyestradiol.

Journal: Carcinogenesis 20010601

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: Catechol estrogen conjugates and DNA adducts in the kidney of male Syrian golden hamsters treated with 4-hydroxyestradiol: potential biomarkers for estrogen-initiated cancer.

Journal: Carcinogenesis 20010301

Title: In situ hybridization and immunohistochemical analysis of cytochrome P450 1B1 expression in human normal tissues.

Journal: The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society 20010201

Title: Thiols can either enhance or suppress DNA damage induction by catecholestrogens.

Journal: Free radical biology & medicine 20010101

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: Quantitative analysis of constitutive and 2,3,7,8-tetrachlorodibenzo-p-dioxin-induced cytochrome P450 1B1 expression in human lymphocytes.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 19990201

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: Differential spatiotemporal regulation of lactoferrin and progesterone receptor genes in the mouse uterus by primary estrogen, catechol estrogen, and xenoestrogen.

Journal: Endocrinology 19980601

Title: Estrogenic responses in estrogen receptor-alpha deficient mice reveal a distinct estrogen signaling pathway.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19971125

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

Journal: Endocrinology 19970301

Title: Stable expression of a human liver UDP-glucuronosyltransferase (UGT2B15) with activity toward steroid and xenobiotic substrates.

Journal: Drug metabolism and disposition: the biological fate of chemicals 19940101

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Tags:5976-61-4 Molecular Formula|5976-61-4 MDL|5976-61-4 SMILES|5976-61-4 4-HYDROXYESTRADIOL