DPN

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Cat.No. 1494 - DPN | C15H13NO2 | CAS No. 1428-67-7
Description: Highly potent ERβ agonist
Alternative Names: Diarylpropionitrile
Chemical Name: 2,3-bis(4-Hydroxyphenyl)-propionitrile
Purity: ≥99% (HPLC)
Datasheet
Citations (105)
Reviews
Literature
Pathways

Biological Activity

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

M. Wt 239.27
Formula C15H13NO2
Storage Desiccate at -20°C
Purity ≥99% (HPLC)
CAS Number 1428-67-7
PubChem ID 102614
InChI Key GHZHWDWADLAOIQ-UHFFFAOYSA-N
Smiles OC1=CC=C(CC(C#N)C2=CC=C(O)C=C2)C=C1

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.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
1eq. NaOH 7.18 30
ethanol 23.93 100
DMSO 23.93 100

Preparing Stock Solutions

The following data is based on the product molecular weight 239.27. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 4.18 mL 20.9 mL 41.79 mL
5 mM 0.84 mL 4.18 mL 8.36 mL
10 mM 0.42 mL 2.09 mL 4.18 mL
50 mM 0.08 mL 0.42 mL 0.84 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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References

References are publications that support the biological activity of the product.

Harrington et al (2003) Activities of estrogen receptor alpha- and beta-selective ligands at diverse estrogen responsive gene sites mediating transactivation or transrepression. Mol.Cell.Endocrinol. 206 13 PMID: 12943986

Meyers et al (2001) Estrogen receptor-β potency-selective ligands: structure-activity relationship studies of diarylpropionitriles and their acetylene and polar analogues. J.Med.Chem. 44 4230 PMID: 11708925

Montgomery et al (2003) Acute effects of oestrogen receptor subtype-specific agonists on vascular contractility. Br.J.Pharmacol. 139 1249 PMID: 12890703

Waters et al (2009) Estrogen receptor alpha and beta specific agonists regulate expression of synaptic proteins in rat hippocampus. Brain Res. 1290 1 PMID: 19596275


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Keywords: DPN, DPN supplier, potent, ERβ, ERbeta, agonists, ERb, ERR, Estrogen, Receptors, Diarylpropionitrile, and, Related, 1494, Tocris Bioscience

105 Citations for DPN

Citations are publications that use Tocris products. Selected citations for DPN include:

Munive et al (2019) Loss of the interaction between E2 and IGF-1 in brain endothelial cells associates to changes in mood homeostasis during peri-menopause in mice. Aging (Albany NY) 11 174 PMID: 30636168

Ma (2016) ERα Mediates Estrogen-Induced Expression of the Breast Cancer Metastasis Suppressor Gene BRMS1. Int J Mol Sci 17 PMID: 26821020

Mazzuca et al (2015) Estrogen receptor subtypes mediate distinct microvascular dilation and reduction in [Ca2+]I in mesenteric microvessels of female rat. J Pharmacol Exp Ther 352 291 PMID: 25472954

Wardell et al (2013) Estrogen responsiveness of the TFIID subunit TAF4B in the normal mouse ovary and in ovarian tumors. Biol Reprod 89 116 PMID: 24068106

Greaves et al (2013) ERβ-dependent effects on uterine endothelial cells are cell specific and mediated via Sp1. Hum Reprod 28 2490 PMID: 23756706

Khalaj et al (2013) Estrogen receptor (ER) β expression in oligodendrocytes is required for attenuation of clinical disease by an ERβ ligand. Proc Natl Acad Sci U S A 110 19125 PMID: 24191028

Spence et al (2013) Estrogen mediates neuroprotection and anti-inflammatory effects during EAE through ERα signaling on astrocytes but not through ERβ signaling on astrocytes or neurons. J Neurosci 33 10924 PMID: 23804112

Dong et al (2013) Estrogen Induces Metastatic Potential of Papillary Thyroid Cancer Cells through Estrogen Receptor α and β. Int J Endocrinol 2013 941568 PMID: 24222765

Patisaul et al (2012) Influence of ERβ selective agonism during the neonatal period on the sexual differentiation of the rat hypothalamic-pituitary-gonadal (HPG) axis. Biol Sex Differ 3 2 PMID: 22260364

Tammimies et al (2012) The rs3743205 SNP is important for the regulation of the dyslexia candidate gene DYX1C1 by estrogen receptor β and DNA methylation. Mol Endocrinol 26 619 PMID: 22383464

Zhang et al (2012) Estrogen-responsive nitroso-proteome in uterine artery endothelial cells: role of endothelial nitric oxide synthase and estrogen receptor-β. J Cell Physiol 227 146 PMID: 21374595

Tashiro et al (2012) Rapid estrogenic effects on TMJ-responsive brainstem neurons. J Dent Res 91 210 PMID: 22058119

Kastenberger et al (2012) Activation of the G-protein-coupled receptor GPR30 induces anxiogenic effects in mice, similar to oOE. Psychopharmacology (Berl) 221 527 PMID: 22143579

Shanle et al (2011) Generation of stable reporter breast cancer cell lines for the identification of ER subtype selective ligands. Biochem Pharmacol 82 1940 PMID: 21924251

Filice et al (2011) Crucial role of phospholamban phosphorylation and S-nitrosylation in the negative lusitropism induced by 17β-OE in the male rat heart. Cell Physiol Biochem 28 41 PMID: 21865847

Dhillon and Belsham (2011) Estrogen inhibits NPY secretion through membrane-associated estrogen receptor (ER)-α in clonal, immortalized hypothalamic neurons. Int J Obes (Lond) 35 198 PMID: 20548307

Shao et al (2009) Clomiphene citrate causes aberrant tubal apoptosis and estrogen receptor activation in rat fallopian tube: implications for tubal ectopic pregnancy. Biol Reprod 80 1262 PMID: 19211805

Pedram et al (2009) Estrogen inhibits ATR signaling to cell cycle checkpoints and DNA repair. Mol Biol Cell 20 3374 PMID: 19477925

Merlo et al (2009) Differential involvement of estrogen receptor alpha and estrogen receptor beta in the healing promoting effect of estrogen in human keratinocytes. J Endocrinol 200 189 PMID: 19008331

Murata et al (2014) Rat uterine oxyt. receptor and estrogen receptor α and β mRNA levels are regulated by estrogen through multiple estrogen receptors. PLoS One 60 55 PMID: 24334513

Suwanna et al (2014) Neuroprotection by diarylpropionitrile in mice with spinal cord injury. Am J Physiol Heart Circ Physiol 13 1097 PMID: 26417324

Goodman et al (2014) Loss of estrogen-mediated immunoprotection underlies female gender bias in experimental Crohn's-like ileitis. PLoS One 7 1255 PMID: 24621993

Ciucci et al (2014) Gender effect in experimental models of human medulloblastoma: does the estrogen receptor β signaling play a role? J Natl Cancer Inst 9 e101623 PMID: 25000562

Patisaul et al (2009) Neonatal agonism of ERα masculinizes serotonergic (5-HT) projections to the female rat ventromedial nucleus of the hypothalamus (VMN) but does not impair lordosis. Hum Mol Genet 196 317 PMID: 18950659

Barreto-Andrade et al (2018) Estrogen Receptor 1 (ESR1) Enhances Slc2a4/GLUT4 Expression by a SP1 Cooperative Mechanism. Int J Med Sci 15 1320 PMID: 30275758

Shults et al (2018) 17β-estradiol regulates the RNA-binding protein Nova1, which then regulates the alternative splicing of estrogen receptor β in the aging female rat brain. Neurobiol Aging 61 13 PMID: 29031089

Benhadjeba et al (2018) Feedback control of the CXCR7/CXCL11 chemokine axis by estrogen receptor α in ovarian cancer. Mol Oncol 12 1689 PMID: 30051594

Yakimchuk et al (2018) Suppression of lymphoma growth by the xenoestrogens bisphenol A and genistein. Endocr Connect PMID: 30496125

Lu et al (2017) ERβ compensates for the absence of ERα function to promote osteoblast viability by inhibition of SOST signaling. Exp Ther Med 14 3387 PMID: 29042923

Caballero et al (2017) Understanding the dynamics of Toll-like Receptor 5 response to flagellin and its regulation by estradiol. Sci Rep 7 40981 PMID: 28112187

Villar-Pazos et al (2017) Molecular mechanisms involved in the non-monotonic effect of bisphenol-a on Ca2+ entry in mouse pancreatic β-cells. Sci Rep 7 11770 PMID: 28924161

Hamilton et al (2015) Biologic roles of estrogen receptor-β and Ins-like growth factor-2 in triple-negative breast cancer. Biomed Res Int 2015 925703 PMID: 25874233

Castro et al (2015) Differential expression of upstream stimulatory factor (USF) 2 variants in eutopic endometria from women with endometriosis: OE regulation. Biol Res 48 56 PMID: 26453052

Harvey et al (2015) Methoxychlor and its metabolite HPTE inhibit cAMP production and expression of estrogen receptors α and β in the rat granulosa cell in vitro. Reprod Toxicol 51 72 PMID: 25549949

Boulware et al (2013) The memory-enhancing effects of hippocampal estrogen receptor activation involve metabotropic glutamate receptor signaling. Cardiovasc Ther 33 15184 PMID: 24048848

Tomicek et al (2013) Estrogen receptor β does not influence ischemic tolerance in the aged female rat heart. PLoS One 31 32 PMID: 21884022

Takeda et al (2013) △(9)-Tetrahydrocannabinol disrupts estrogen-signaling through up-regulation of estrogen receptor β (ERβ). Cancer Res 26 1073 PMID: 23718638

Zheng et al (2011) 17β-OE enhances breast cancer cell motility and invasion via extra-nuclear activation of actin-binding protein ezrin. PLoS One 6 e22439 PMID: 21818323

Du et al (2011) Estrogen receptor-β ligand treatment modulates dendritic cells in the target organ during autoimmune demyelinating disease. Eur J Immunol 41 140 PMID: 21182085

Lindberg et al (2011) Estrogen receptor β represses Akt signaling in breast cancer cells via downregulation of HER2/HER3 and upregulation of PTEN: implications for tamox. sensitivity. Breast Cancer Res 13 R43 PMID: 21492444

Giannoni et al (2011) OE and progesterone strongly inhibit the innate immune response of mononuclear cells in newborns. Infect Immun 79 2690 PMID: 21518785

Setlur et al (2008) Estrogen-dependent signaling in a molecularly distinct subclass of aggressive prostate cancer. Horm Behav 100 815 PMID: 18505969

Razmara et al (2008) Mitochondrial effects of estrogen are mediated by estrogen receptor α in brain endothelial cells. FEMS Immunol Med Microbiol 325 782 PMID: 18354059

Mersereau et al (2008) Liquiritigenin is a plant-derived highly selective estrogen receptor β agonist. J Biol Chem 283 49 PMID: 18177995

Sirianni et al (2008) The novel estrogen receptor, G protein-coupled receptor 30, mediates the proliferative effects induced by 17β-OE on mouse spermatogonial GC-1 cell line. J Exp Med 149 5043 PMID: 18566133

Sinkevicius et al (2008) An estrogen receptor-alpha knock-in mutation provides evidence of ligand-independent signaling and allows modulation of ligand-induced pathways in vivo. Endocrinology 149 2970 PMID: 18339713

Helguero et al (2008) Different roles of estrogen receptors alpha and beta in the regulation of E-cadherin protein levels in a mouse mammary epithelial cell line. Cancer Res 68 8695 PMID: 18974111

Sotoca et al (2008) Influence of cellular ERalpha/ERbeta ratio on the ERalpha-agonist induced proliferation of human T47D breast cancer cells. Toxicol Sci 105 303 PMID: 18644836

Teng et al (2008) Roles of estrogen receptor alpha and beta in modulating urothelial cell proliferation. Endocr Relat Cancer 15 351 PMID: 18310301

Perželová et al (2016) Pharmacological activation of estrogen receptors-α and -β differentially modulates keratinocyte differentiation with functional impact on wound healing. Environ Health Perspect 37 42603 PMID: 26397183

Colciago et al (2014) 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. Biomed Res Int 2014 801473 PMID: 24877132

Ogo et al (2014) IGF-1 gene expression is differentially regulated by estrogen receptors α and β in mouse endometrial stromal cells and ovarian granulosa cells. J Reprod Dev 60 216 PMID: 24670778

Baquié et al (2011) The liver receptor homolog-1 (LRH-1) is expressed in human islets and protects {β}-cells against stress-induced apoptosis. J Pharmacol Exp Ther 20 2823 PMID: 21536586

Seredynski et al (2011) Specific activation of estrogen receptor α and β enhances male sexual behavior and neuroplasticity in male Japanese quail. Endocrinology 6 e18627 PMID: 21533185

Sebag et al (2011) Sex hormone control of left ventricular structure/function: mechanistic insights using echocardiography, expression, and DNA methylation analyses in adult mice. Am J Pathol 301 H1706 PMID: 21803942

Lin et al (2011) Molecular mechanisms of bladder outlet obstruction in transgenic male mice overexpressing aromatase (Cyp19a1). Exp Neurol 178 1233 PMID: 21356374

Meltser et al (2008) Estrogen receptor beta protects against acoustic trauma in mice. J Clin Invest 118 1563 PMID: 18317592

Stygar et al (2007) Studies on estrogen receptor (ER) alpha and beta responses on gene regulation in peripheral blood leukocytes in vivo using selective ER agonists. J Endocrinol 194 101 PMID: 17592025

Gao et al (2015) 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. Endocrinology 123 571 PMID: 25723814

Mittelman-Smith et al (2015) Classical and membrane-initiated estrogen signaling in an in vitro model of anterior hypothalamic kisspeptin neurons. Cancer Cell Int 156 2162 PMID: 25730107

Zhou et al (2015) Estrogen mediated expression of nucleophosmin 1 in human endometrial carcinoma clinical stages through estrogen receptor-α signaling. Int J Mol Med 14 540 PMID: 25663821

Greaves et al (2014) Elevated peritoneal expression and estrogen regulation of nociceptive ion channels in endometriosis. J Clin Endocrinol Metab 99 E1738 PMID: 25029427

Jonsson et al (2014) Support of a bi-faceted role of estrogen receptor β (ERβ) in ERα-positive breast cancer cells. Endocr Relat Cancer 21 143 PMID: 24192230

Gilliver et al (2010) 17β-OE inhibits wound healing in male mice via estrogen receptor-α. Clin Cancer Res 176 2707 PMID: 20448060

Liang et al (2010) Estrogen stimulates degradation of β-amyloid peptide by up-regulating neprilysin. Behav Brain Res 285 935 PMID: 19897485

Campbell et al (2010) Estrogen promotes cutaneous wound healing via estrogen receptor β independent of its antiinflammatory activities. Mol Cell Endocrinol 207 1825 PMID: 20733032

Taylor et al (2006) 17β-OE induces apoptosis in the developing rodent prostate independently of ERα or ERβ. Am J Pathol 147 191 PMID: 16223864

Ohshiro et al (2006) Biological role of estrogen receptor β in salivary gland adenocarcinoma cells. J Neurosci 12 5994 PMID: 17062671

Helguero et al (2006) DAX-1 expression is regulated during mammary epithelial cell differentiation. Oncogene 147 3249 PMID: 16627587

Wieland et al (2006) Efficient intracellular multiplication of Legionella pneumophila in human monocytes requires functional host cell L-type calcium channels. EXCLI J 47 296 PMID: 16831218

Lu et al (2017) Estrogen enhances mismatch repair by induction of MLH1 expression via estrogen receptor-β. Oncotarget 8 38767 PMID: 28404976

Pastore et al (2016) Identification of Differential ER-Alpha Versus ER-Beta Mediated Activation of eNOS in Ovine Uterine Artery Endothelial Cells. Biol Reprod 94 139 PMID: 27170438

Stacey et al (2016) Mechanisms by Which 17β-OE (E2) Suppress Neuronal cox-2 Gene Expression. PLoS One 11 e0161430 PMID: 27588681

Ma et al (2016) Estrogen replacement therapy-induced neuroprotection against brain ischemia-reperfusion injury involves the activation of astrocytes via estrogen receptor β. Sci Rep 6 21467 PMID: 26891996

Zhang et al (2013) Differential effects of estrogen/androgen on the prevention of nonalcoholic fatty liver disease in the male rat. J Lipid Res 54 345 PMID: 23175777

Watanabe et al (2013) Estrogens downregulate urocortin 2 expression in rat uterus. J Endocrinol 219 269 PMID: 24109089

Simpkins et al (2012) Src Inhibition with saracatinib reverses fulves. resistance in ER-positive ovarian cancer models in vitro and in vivo. Clin Cancer Res 18 5911 PMID: 22896656

Wang and Kuehl-Kovarik (2012) OE directly attenuates sodium currents and depolarizing afterpotentials in isolated gonadotropin-releasing hormone neurons. Brain Res 1436 81 PMID: 22209345

González-Arenas et al (2012) OE increases cell growth in human astrocytoma cell lines through ERα activation and its interaction with SRC-1 and SRC-3 coactivators. Biochim Biophys Acta 1823 379 PMID: 22142990

Yang et al (2012) Estrogen represses hepatocellular carcinoma (HCC) growth via inhibiting alternative activation of tumor-associated macrophages (TAMs). J Biol Chem 287 40140 PMID: 22908233

Hamilton-Burke et al (2010) Phosphorylation of estrogen receptor beta at serine 105 is associated with good prognosis in breast cancer. Am J Pathol 177 1079 PMID: 20696772

Smejkalova and Woolley (2010) OE acutely potentiates hippocampal excitatory synaptic transmission through a presynaptic mechanism. J Neurosci 30 16137 PMID: 21123560

Sahlin et al (2006) Tissue- and hormone-dependent progesterone receptor distribution in the rat uterus. Reprod Biol Endocrinol 4 47 PMID: 16965620

Zhang et al (2005) Stimulatory cross-talk between NFAT3 and estrogen receptor in breast cancer cells. J Biol Chem 280 43188 PMID: 16219765

O'Donnell et al (2005) Estrogen receptor-alpha mediates gene expression changes and growth response in ovarian cancer cells exposed to estrogen. Endocr Relat Cancer 12 851 PMID: 16322326

Helguero et al (2005) Estrogen receptors alfa (ERα) and β (ERβ) differentially regulate proliferation and apoptosis of the normal murine mammary epithelial cell line HC11. Cell Cycle 24 6605 PMID: 16007178

Fatima (2017) Estrogen receptor 1 (ESR1) regulates VEGFA in adipose tissue. Sci Rep 7 16716 PMID: 29196658

Sobrino et al (2010) OE selectively stimulates endothelial prostacyclin production through estrogen receptor-{alpha}. J Mol Endocrinol 44 237 PMID: 20110403

Rossi et al (2010) OE-induced desensitization of 5-HT1A receptor signaling in the paraventricular nucleus of the hypothalamus is independent of estrogen receptor-beta. Psychoneuroendocrinology 35 1023 PMID: 20138435

Raffetto et al (2010) Estrogen receptor-mediated enhancement of venous relaxation in female rat: implications in sex-related differences in varicose veins. J Vasc Surg 51 972 PMID: 20347696

Ma et al (2010) Gender-specific reduction in contraction is associated with increased estrogen receptor expression in single vascular smooth muscle cells of female rat. Cell Physiol Biochem 26 457 PMID: 20798531

Leung et al (2009) Protopanaxadiol and protopanaxatriol bind to glucocorticoid and oestrogen receptors in endothelial cells. Br J Pharmacol 156 626 PMID: 19226254

Waters et al (2009) Estrogen receptor alpha and beta specific agonists regulate expression of synaptic proteins in rat hippocampus. Brain Res 1290 43405 PMID: 19596275

Belcher et al (2009) Blockade of estrogen receptor signaling inhibits growth and migration of medulloblastoma. Endocrinology 150 1112 PMID: 19008315

Lu et al (2009) Estrogen rapidly modulates 5-hydroxytrytophan-induced visceral hypersensitivity via GPR30 in rats. Gastroenterology 137 1040 PMID: 19344720

Ramsey et al (2004) Estrogen receptor beta isoforms exhibit differences in ligand-activated transcriptional activity in an estrogen response element sequence-dependent manner. Endocrinology 145 149 PMID: 14500565

Nag and Mokha (2014) 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. Am J Physiol Regul Integr Comp Physiol 267 122 PMID: 24613724

Richardson et al (2012) Estrogen prevents oxidative damage to the mitochondria in Friedreich's ataxia skin fibroblasts. Chem Res Toxicol 7 e34600 PMID: 22509330

Vinnedge et al (2012) The DEK oncogene is a target of steroid hormone receptor signaling in breast cancer. Neuroscience 7 e46985 PMID: 23071688

Guido et al (2012) 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. Endocrinology 11 2911 PMID: 22810004

Silverman and Koenig (2007) Evidence for the involvement of ERβ and RGS9-2 in 17-β OE enhancement of amphetamine-induced place preference behavior. PLoS One 52 146 PMID: 17493623

Walker et al (2007) Ins-like growth factor binding proteins IGFBP3, IGFBP4, and IGFBP5 predict endocrine responsiveness in patients with ovarian cancer. Clin Cancer Res 13 1438 PMID: 17332286

Tiwari-Woodruff et al (2007) Differential neuroprotective and antiinflammatory effects of estrogen receptor (ER)alpha and ERbeta ligand treatment. Proc Natl Acad Sci U S A 104 14813 PMID: 17785421

Rayner et al (2007) NM23-H2, an estrogen receptor β-associated protein, shows diminished expression with progression of atherosclerosis. Endocrinology 292 R743 PMID: 17272673

Bains et al (2007) Neuroprotection by estrogen against MPP+-induced DA neuron death is mediated by ERα in primary cultures of mouse mesencephalon. Mucosal Immunol 204 767 PMID: 17320868


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Estrogen

Estrogen Signaling Pathway

Estrogen is a steroid hormone that is responsible for the regulation of growth, differentiation and function of the reproductive system. Estrogen signaling is often dysregulated in breast cancer and osteoporosis.