DPN

Cat. No. 1494

DPN C15H13NO2 [1428-67-7]

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Alternative Name: Diarylpropionitrile

Chemical Name: 2,3-bis(4-Hydroxyphenyl)-propionitrile

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
Solubility:
Soluble to 30 mM in 1eq. NaOH and to 100 mM in ethanol and to 100 mM in DMSO
Purity:
>99 %
Storage:
Desiccate at -20°C
CAS No:
1428-67-7

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
All Tocris products are intended for laboratory research use only.

Certificate of Analysis / Product Datasheet / Safety Data Sheet

Certificate of Analysis / Product Datasheet
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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.

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.

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

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.

If you know of a relevant reference for this product please let us know.

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

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.

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

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.

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

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.

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.

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.

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.

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.

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

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.

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.

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

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

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.

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.

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

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

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.

González-Arenas et al (2012) Estradiol 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.

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.

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

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

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

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

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.

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.

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.

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

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

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 tamoxifen sensitivity. Breast Cancer Res 13 R43. PMID: 21492444.

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.

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.

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

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.

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

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.

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

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

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.

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.

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

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.

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.

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

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

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.

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

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.

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

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.

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

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

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

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.

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

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

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

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

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

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.

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.

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.

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

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.

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Keywords: DPN, supplier, potent, ERβ, ERbeta, agonists, ERb, ERR, Estrogen, Receptors, Tocris Bioscience, Estrogen and Related Receptor Agonist products

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