DPN
Chemical Name: 2,3-bis(4-Hydroxyphenyl)-propionitrile
Purity: ≥99%
Biological Activity
DPN is a highly potent estrogen ERβ receptor agonist with a 70-fold selectivity over ERα (EC50 values are 0.85 and 66 nM respectively). Relaxes mesenteric arteries in vitro. Shown to regulate expression of GluR1, GluR2 and GluR3 in rat hippocampus.Technical Data
The technical data provided above is for guidance only.
For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Background References
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The role of estrogen signaling in a mouse model of inflammatory bowel disease: a Helicobacter hepaticus model.
Cook L, Hillhouse A, Myles M, Lubahn D, Bryda E, Davis J, Franklin C
PLoS ONE, 2014;9(4):e94209. -
ERbeta-mediated estradiol enhances epithelial mesenchymal transition of lung adenocarcinoma through increasing transcription of midkine.
Mol. Endocrinol., 2012;26(8):1304-15. -
PDZK1 upregulation in estrogen-related hyperpigmentation in melasma.
J. Invest. Dermatol., 2012;132(11):2622-31. -
The DEK oncogene is a target of steroid hormone receptor signaling in breast cancer.
Privette Vinnedge L, Ho S, Wikenheiser-Brokamp K, Wells S
PLoS ONE, 2012;7(10):e46985. -
Estrogen receptor (ER) agonists differentially regulate neuroangiogenesis in peritoneal endometriosis via the repellent factor SLIT3.
Greaves E, Collins F, Esnal-Zufiaurre A, Giakoumelou S, Horne A, Saunders P
Endocrinology, 2014;155(10):4015-26. -
Estrogen prevents oxidative damage to the mitochondria in Friedreich's ataxia skin fibroblasts.
Richardson TE, Yu AE, Wen Y, Yang SH, Simpkins JW
PLoS ONE, 2012;7(4):e34600. -
Loss of estrogen-mediated immunoprotection underlies female gender bias in experimental Crohn's-like ileitis.
Goodman, W A, Garg, R R, Reuter, B K, Mattioli, B, Rissman, E F, Pizarro, T T
Mucosal Immunol, 2014;7(5):1255-65. -
Activities of estrogen receptor alpha- and beta-selective ligands at diverse estrogen responsive gene sites mediating transactivation or transrepression.
Harrington et al.
Mol.Cell.Endocrinol., 2003;206:13 -
Acute effects of oestrogen receptor subtype-specific agonists on vascular contractility.
Montgomery et al.
Br.J.Pharmacol., 2003;139:1249 -
Estrogen receptor-β potency-selective ligands: structure-activity relationship studies of diarylpropionitriles and their acetylene and polar analogues.
Meyers et al.
J.Med.Chem., 2001;44:4230 -
Estrogen receptor alpha and beta specific agonists regulate expression of synaptic proteins in rat hippocampus.
Waters et al.
Brain Res., 2009;1290:1
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Citations for DPN
The citations listed below are publications that use Tocris products. Selected citations for DPN include:
107 Citations: Showing 1 - 10
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Loss of the interaction between E2 and IGF-1 in brain endothelial cells associates to changes in mood homeostasis during peri-menopause in mice.
Authors: Munive Et al.
Aging (Albany NY) 2019;11:174
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ERβ Accelerates Diabetic Wound Healing by Ameliorating Hyperglycemia-Induced Persistent Oxidative Stress.
Authors: Zhou Et al.
Front Endocrinol (Lausanne) 2019;10:499
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Estrogen Promotes Pro-resolving Microglial Behavior and Phagocytic Cell Clearance Through the Actions of Annexin A1.
Authors: Loiola Et al.
Front Endocrinol (Lausanne) 2019;10:420
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17β-estradiol regulates the RNA-binding protein Nova1, which then regulates the alternative splicing of estrogen receptor β in the aging female rat brain.
Authors: Shults Et al.
Neurobiol Aging 2018;61:13
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Estrogen Receptor 1 (ESR1) Enhances Slc2a4/GLUT4 Expression by a SP1 Cooperative Mechanism.
Authors: Barreto-Andrade Et al.
Int J Med Sci 2018;15:1320
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Feedback control of the CXCR7/CXCL11 chemokine axis by estrogen receptor α in ovarian cancer.
Authors: Benhadjeba Et al.
Mol Oncol 2018;12:1689
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Suppression of lymphoma growth by the xenoestrogens bisphenol A and genistein.
Authors: Yakimchuk Et al.
Endocr Connect 2018;
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Estrogen enhances mismatch repair by induction of MLH1 expression via estrogen receptor-β.
Authors: Lu Et al.
Oncotarget 2017;8:38767
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Understanding the dynamics of Toll-like Receptor 5 response to flagellin and its regulation by estradiol.
Authors: Caballero Et al.
Sci Rep 2017;7:40981
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Molecular mechanisms involved in the non-monotonic effect of bisphenol-a on Ca2+ entry in mouse pancreatic β-cells.
Authors: Villar-Pazos Et al.
Sci Rep 2017;7:11770
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Estrogen receptor 1 (ESR1) regulates VEGFA in adipose tissue.
Authors: Fatima
Sci Rep 2017;7(1):16716
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ERβ compensates for the absence of ERα function to promote osteoblast viability by inhibition of SOST signaling.
Authors: Lu Et al.
Exp Ther Med 2017;14:3387
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Identification of Differential ER-Alpha Versus ER-Beta Mediated Activation of eNOS in Ovine Uterine Artery Endothelial Cells.
Authors: Pastore Et al.
Biol Reprod 2016;94:139
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Estrogen replacement therapy-induced neuroprotection against brain ischemia-reperfusion injury involves the activation of astrocytes via estrogen receptor β.
Authors: Ma Et al.
Sci Rep 2016;6:21467
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Pharmacological activation of estrogen receptors-α and -β differentially modulates keratinocyte differentiation with functional impact on wound healing.
Authors: Perželová Et al.
Environ Health Perspect 2016;37:42603
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ERα Mediates Estrogen-Induced Expression of the Breast Cancer Metastasis Suppressor Gene BRMS1.
Authors: Ma
Int J Mol Sci 2016;17
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Mechanisms by Which 17β-OE (E2) Suppress Neuronal cox-2 Gene Expression.
Authors: Stacey Et al.
PLoS One 2016;11:e0161430
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Methoxychlor and its metabolite HPTE inhibit cAMP production and expression of estrogen receptors α and β in the rat granulosa cell in vitro.
Authors: Harvey Et al.
Reprod Toxicol 2015;51:72
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Differential expression of upstream stimulatory factor (USF) 2 variants in eutopic endometria from women with endometriosis: OE regulation.
Authors: Castro Et al.
Biol Res 2015;48:56
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Estrogen receptor subtypes mediate distinct microvascular dilation and reduction in [Ca2+]I in mesenteric microvessels of female rat.
Authors: Mazzuca Et al.
J Pharmacol Exp Ther 2015;352:291
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Biologic roles of estrogen receptor-β and Ins-like growth factor-2 in triple-negative breast cancer.
Authors: Hamilton Et al.
Biomed Res Int 2015;2015:925703
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Classical and membrane-initiated estrogen signaling in an in vitro model of anterior hypothalamic kisspeptin neurons.
Authors: Mittelman-Smith Et al.
Cancer Cell Int 2015;156:2162
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Estrogen mediated expression of nucleophosmin 1 in human endometrial carcinoma clinical stages through estrogen receptor-α signaling.
Authors: Zhou Et al.
Int J Mol Med 2015;14:540
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Rapid responses and mechanism of action for low-dose bisphenol S on ex vivo rat hearts and isolated myocytes: evidence of female-specific proarrhythmic effects.
Authors: Gao Et al.
Endocrinology 2015;123:571
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Gender effect in experimental models of human medulloblastoma: does the estrogen receptor β signaling play a role?
Authors: Ciucci Et al.
J Natl Cancer Inst 2014;9:e101623
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Elevated peritoneal expression and estrogen regulation of nociceptive ion channels in endometriosis.
Authors: Greaves Et al.
J Clin Endocrinol Metab 2014;99:E1738
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Loss of estrogen-mediated immunoprotection underlies female gender bias in experimental Crohn's-like ileitis.
Authors: Goodman Et al.
PLoS One 2014;7:1255
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Rat uterine oxyt. receptor and estrogen receptor α and β mRNA levels are regulated by estrogen through multiple estrogen receptors.
Authors: Murata Et al.
PLoS One 2014;60:55
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IGF-1 gene expression is differentially regulated by estrogen receptors α and β in mouse endometrial stromal cells and ovarian granulosa cells.
Authors: Ogo Et al.
J Reprod Dev 2014;60:216
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Activation of a Gq-coupled membrane estrogen receptor rapidly attenuates α2-adrenoceptor-induced antinociception via an ERK I/II-dependent, non-genomic mechanism in the female rat.
Authors: Nag and Mokha
Am J Physiol Regul Integr Comp Physiol 2014;267:122
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Support of a bi-faceted role of estrogen receptor β (ERβ) in ERα-positive breast cancer cells.
Authors: Jonsson Et al.
Endocr Relat Cancer 2014;21:143
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In vitro chronic administration of ERbeta selective ligands and prostate cancer cell growth: hypotheses on the selective role of 3beta-adiol in AR-positive RV1 cells.
Authors: Colciago Et al.
Biomed Res Int 2014;2014:801473
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Neuroprotection by diarylpropionitrile in mice with spinal cord injury.
Authors: Suwanna Et al.
Am J Physiol Heart Circ Physiol 2014;13:1097
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Estrogen responsiveness of the TFIID subunit TAF4B in the normal mouse ovary and in ovarian tumors.
Authors: Wardell Et al.
Biol Reprod 2013;89:116
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Differential effects of estrogen/androgen on the prevention of nonalcoholic fatty liver disease in the male rat.
Authors: Zhang Et al.
J Lipid Res 2013;54:345
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The memory-enhancing effects of hippocampal estrogen receptor activation involve metabotropic glutamate receptor signaling.
Authors: Boulware Et al.
Cardiovasc Ther 2013;33:15184
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Estrogen mediates neuroprotection and anti-inflammatory effects during EAE through ERα signaling on astrocytes but not through ERβ signaling on astrocytes or neurons.
Authors: Spence Et al.
J Neurosci 2013;33:10924
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Estrogen receptor β does not influence ischemic tolerance in the aged female rat heart.
Authors: Tomicek Et al.
PLoS One 2013;31:32
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ERβ-dependent effects on uterine endothelial cells are cell specific and mediated via Sp1.
Authors: Greaves Et al.
Hum Reprod 2013;28:2490
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△(9)-Tetrahydrocannabinol disrupts estrogen-signaling through up-regulation of estrogen receptor β (ERβ).
Authors: Takeda Et al.
Cancer Res 2013;26:1073
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Estrogens downregulate urocortin 2 expression in rat uterus.
Authors: Watanabe Et al.
J Endocrinol 2013;219:269
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Estrogen Induces Metastatic Potential of Papillary Thyroid Cancer Cells through Estrogen Receptor α and β.
Authors: Dong Et al.
Int J Endocrinol 2013;2013:941568
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Estrogen receptor (ER) β expression in oligodendrocytes is required for attenuation of clinical disease by an ERβ ligand.
Authors: Khalaj Et al.
Proc Natl Acad Sci U S A 2013;110:19125
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Rapid estrogenic effects on TMJ-responsive brainstem neurons.
Authors: Tashiro Et al.
J Dent Res 2012;91:210
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The DEK oncogene is a target of steroid hormone receptor signaling in breast cancer.
Authors: Vinnedge Et al.
Neuroscience 2012;7:e46985
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Estrogen prevents oxidative damage to the mitochondria in Friedreich's ataxia skin fibroblasts.
Authors: Richardson Et al.
Chem Res Toxicol 2012;7:e34600
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Influence of ERβ selective agonism during the neonatal period on the sexual differentiation of the rat hypothalamic-pituitary-gonadal (HPG) axis.
Authors: Patisaul Et al.
Biol Sex Differ 2012;3:2
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Estrogen represses hepatocellular carcinoma (HCC) growth via inhibiting alternative activation of tumor-associated macrophages (TAMs).
Authors: Yang Et al.
J Biol Chem 2012;287:40140
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The rs3743205 SNP is important for the regulation of the dyslexia candidate gene DYX1C1 by estrogen receptor β and DNA methylation.
Authors: Tammimies Et al.
Mol Endocrinol 2012;26:619
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Estrogen-responsive nitroso-proteome in uterine artery endothelial cells: role of endothelial nitric oxide synthase and estrogen receptor-β.
Authors: Zhang Et al.
J Cell Physiol 2012;227:146
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Activation of the G-protein-coupled receptor GPR30 induces anxiogenic effects in mice, similar to oOE.
Authors: Kastenberger Et al.
Psychopharmacology (Berl) 2012;221:527
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Src Inhibition with saracatinib reverses fulves. resistance in ER-positive ovarian cancer models in vitro and in vivo.
Authors: Simpkins Et al.
Clin Cancer Res 2012;18:5911
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OE increases cell growth in human astrocytoma cell lines through ERα activation and its interaction with SRC-1 and SRC-3 coactivators.
Authors: González-Arenas Et al.
Biochim Biophys Acta 2012;1823:379
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OE directly attenuates sodium currents and depolarizing afterpotentials in isolated gonadotropin-releasing hormone neurons.
Authors: Wang and Kuehl-Kovarik
Brain Res 2012;1436:81
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Estrogen receptor β (ERβ) produces autophagy and necroptosis in human seminoma cell line through the binding of the Sp1 on the phosphatase and tensin homolog deleted from chromosome 10 (PTEN) promoter gene.
Authors: Guido Et al.
Endocrinology 2012;11:2911
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Generation of stable reporter breast cancer cell lines for the identification of ER subtype selective ligands.
Authors: Shanle Et al.
Biochem Pharmacol 2011;82:1940
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OE and progesterone strongly inhibit the innate immune response of mononuclear cells in newborns.
Authors: Giannoni Et al.
Infect Immun 2011;79:2690
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17β-OE enhances breast cancer cell motility and invasion via extra-nuclear activation of actin-binding protein ezrin.
Authors: Zheng Et al.
PLoS One 2011;6:e22439
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Specific activation of estrogen receptor α and β enhances male sexual behavior and neuroplasticity in male Japanese quail.
Authors: Seredynski Et al.
Endocrinology 2011;6:e18627
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Estrogen receptor-β ligand treatment modulates dendritic cells in the target organ during autoimmune demyelinating disease.
Authors: Du Et al.
Eur J Immunol 2011;41:140
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Estrogen inhibits NPY secretion through membrane-associated estrogen receptor (ER)-α in clonal, immortalized hypothalamic neurons.
Authors: Dhillon and Belsham
Int J Obes (Lond) 2011;35:198
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Sex hormone control of left ventricular structure/function: mechanistic insights using echocardiography, expression, and DNA methylation analyses in adult mice.
Authors: Sebag Et al.
Am J Pathol 2011;301:H1706
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Crucial role of phospholamban phosphorylation and S-nitrosylation in the negative lusitropism induced by 17β-OE in the male rat heart.
Authors: Filice Et al.
Cell Physiol Biochem 2011;28:41
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The liver receptor homolog-1 (LRH-1) is expressed in human islets and protects {β}-cells against stress-induced apoptosis.
Authors: Baquié Et al.
J Pharmacol Exp Ther 2011;20:2823
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Molecular mechanisms of bladder outlet obstruction in transgenic male mice overexpressing aromatase (Cyp19a1).
Authors: Lin Et al.
Exp Neurol 2011;178:1233
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Estrogen receptor β represses Akt signaling in breast cancer cells via downregulation of HER2/HER3 and upregulation of PTEN: implications for tamox. sensitivity.
Authors: Lindberg Et al.
Breast Cancer Res 2011;13:R43
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Estrogen receptor-mediated enhancement of venous relaxation in female rat: implications in sex-related differences in varicose veins.
Authors: Raffetto Et al.
J Vasc Surg 2010;51:972
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OE selectively stimulates endothelial prostacyclin production through estrogen receptor-{alpha}.
Authors: Sobrino Et al.
J Mol Endocrinol 2010;44:237
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OE-induced desensitization of 5-HT1A receptor signaling in the paraventricular nucleus of the hypothalamus is independent of estrogen receptor-beta.
Authors: Rossi Et al.
Psychoneuroendocrinology 2010;35:1023
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OE acutely potentiates hippocampal excitatory synaptic transmission through a presynaptic mechanism.
Authors: Smejkalova and Woolley
J Neurosci 2010;30:16137
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Estrogen stimulates degradation of β-amyloid peptide by up-regulating neprilysin.
Authors: Liang Et al.
Behav Brain Res 2010;285:935
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Gender-specific reduction in contraction is associated with increased estrogen receptor expression in single vascular smooth muscle cells of female rat.
Authors: Ma Et al.
Cell Physiol Biochem 2010;26:457
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Estrogen promotes cutaneous wound healing via estrogen receptor β independent of its antiinflammatory activities.
Authors: Campbell Et al.
Mol Cell Endocrinol 2010;207:1825
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Phosphorylation of estrogen receptor beta at serine 105 is associated with good prognosis in breast cancer.
Authors: Hamilton-Burke Et al.
Am J Pathol 2010;177:1079
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17β-OE inhibits wound healing in male mice via estrogen receptor-α.
Authors: Gilliver Et al.
Clin Cancer Res 2010;176:2707
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Clomiphene citrate causes aberrant tubal apoptosis and estrogen receptor activation in rat fallopian tube: implications for tubal ectopic pregnancy.
Authors: Shao Et al.
Biol Reprod 2009;80:1262
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Estrogen inhibits ATR signaling to cell cycle checkpoints and DNA repair.
Authors: Pedram Et al.
Mol Biol Cell 2009;20:3374
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Differential involvement of estrogen receptor alpha and estrogen receptor beta in the healing promoting effect of estrogen in human keratinocytes.
Authors: Merlo Et al.
J Endocrinol 2009;200:189
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Neonatal agonism of ERα masculinizes serotonergic (5-HT) projections to the female rat ventromedial nucleus of the hypothalamus (VMN) but does not impair lordosis.
Authors: Patisaul Et al.
Hum Mol Genet 2009;196:317
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Protopanaxadiol and protopanaxatriol bind to glucocorticoid and oestrogen receptors in endothelial cells.
Authors: Leung Et al.
Br J Pharmacol 2009;156:626
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Blockade of estrogen receptor signaling inhibits growth and migration of medulloblastoma.
Authors: Belcher Et al.
Endocrinology 2009;150:1112
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Estrogen rapidly modulates 5-hydroxytrytophan-induced visceral hypersensitivity via GPR30 in rats.
Authors: Lu Et al.
Gastroenterology 2009;137:1040
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Estrogen receptor alpha and beta specific agonists regulate expression of synaptic proteins in rat hippocampus.
Authors: Waters Et al.
Brain Res 2009;1290:43405
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Different roles of estrogen receptors alpha and beta in the regulation of E-cadherin protein levels in a mouse mammary epithelial cell line.
Authors: Helguero Et al.
Cancer Res 2008;68:8695
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Mitochondrial effects of estrogen are mediated by estrogen receptor α in brain endothelial cells.
Authors: Razmara Et al.
FEMS Immunol Med Microbiol 2008;325:782
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Liquiritigenin is a plant-derived highly selective estrogen receptor β agonist.
Authors: Mersereau Et al.
J Biol Chem 2008;283:49
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Roles of estrogen receptor alpha and beta in modulating urothelial cell proliferation.
Authors: Teng Et al.
Endocr Relat Cancer 2008;15:351
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The novel estrogen receptor, G protein-coupled receptor 30, mediates the proliferative effects induced by 17β-OE on mouse spermatogonial GC-1 cell line.
Authors: Sirianni Et al.
J Exp Med 2008;149:5043
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An estrogen receptor-alpha knock-in mutation provides evidence of ligand-independent signaling and allows modulation of ligand-induced pathways in vivo.
Authors: Sinkevicius Et al.
Endocrinology 2008;149:2970
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Estrogen receptor beta protects against acoustic trauma in mice.
Authors: Meltser Et al.
J Clin Invest 2008;118:1563
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Influence of cellular ERalpha/ERbeta ratio on the ERalpha-agonist induced proliferation of human T47D breast cancer cells.
Authors: Sotoca Et al.
Toxicol Sci 2008;105:303
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Estrogen-dependent signaling in a molecularly distinct subclass of aggressive prostate cancer.
Authors: Setlur Et al.
Horm Behav 2008;100:815
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Evidence for the involvement of ERβ and RGS9-2 in 17-β OE enhancement of amphetamine-induced place preference behavior.
Authors: Silverman and Koenig
PLoS One 2007;52:146
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NM23-H2, an estrogen receptor β-associated protein, shows diminished expression with progression of atherosclerosis.
Authors: Rayner Et al.
Endocrinology 2007;292:R743
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Neuroprotection by estrogen against MPP+-induced DA neuron death is mediated by ERα in primary cultures of mouse mesencephalon.
Authors: Bains Et al.
Mucosal Immunol 2007;204:767
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Studies on estrogen receptor (ER) alpha and beta responses on gene regulation in peripheral blood leukocytes in vivo using selective ER agonists.
Authors: Stygar Et al.
J Endocrinol 2007;194:101
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Ins-like growth factor binding proteins IGFBP3, IGFBP4, and IGFBP5 predict endocrine responsiveness in patients with ovarian cancer.
Authors: Walker Et al.
Clin Cancer Res 2007;13:1438
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Differential neuroprotective and antiinflammatory effects of estrogen receptor (ER)alpha and ERbeta ligand treatment.
Authors: Tiwari-Woodruff Et al.
Proc Natl Acad Sci U S A 2007;104:14813
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Tissue- and hormone-dependent progesterone receptor distribution in the rat uterus.
Authors: Sahlin Et al.
Reprod Biol Endocrinol 2006;4:47
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Efficient intracellular multiplication of Legionella pneumophila in human monocytes requires functional host cell L-type calcium channels.
Authors: Wieland Et al.
EXCLI J 2006;47:296
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DAX-1 expression is regulated during mammary epithelial cell differentiation.
Authors: Helguero Et al.
Oncogene 2006;147:3249
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17β-OE induces apoptosis in the developing rodent prostate independently of ERα or ERβ.
Authors: Taylor Et al.
Am J Pathol 2006;147:191
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Biological role of estrogen receptor β in salivary gland adenocarcinoma cells.
Authors: Ohshiro Et al.
J Neurosci 2006;12:5994
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Stimulatory cross-talk between NFAT3 and estrogen receptor in breast cancer cells.
Authors: Zhang Et al.
J Biol Chem 2005;280:43188
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Estrogen receptors alfa (ERα) and β (ERβ) differentially regulate proliferation and apoptosis of the normal murine mammary epithelial cell line HC11.
Authors: Helguero Et al.
Cell Cycle 2005;24:6605
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Estrogen receptor-alpha mediates gene expression changes and growth response in ovarian cancer cells exposed to estrogen.
Authors: O'Donnell Et al.
Endocr Relat Cancer 2005;12:851
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Estrogen receptor beta isoforms exhibit differences in ligand-activated transcriptional activity in an estrogen response element sequence-dependent manner.
Authors: Ramsey Et al.
Endocrinology 2004;145:149
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