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DPN | CAS No. 1428-67-7 | Estrogen and Related Receptor Agonists
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Description: Highly potent ERβ agonist
Alternative Names: Diarylpropionitrile

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

Purity: ≥99%

Product Details
Citations (107)

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

Soluble to 30 mM in 1eq. NaOH and to 100 mM in ethanol and to 100 mM in DMSO
Desiccate at -20°C

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.

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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

  1. 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
  2. ERβ Accelerates Diabetic Wound Healing by Ameliorating Hyperglycemia-Induced Persistent Oxidative Stress.
    Authors: Zhou Et al.
    Front Endocrinol (Lausanne)  2019;10:499
  3. 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
  4. 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
  5. 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
  6. Feedback control of the CXCR7/CXCL11 chemokine axis by estrogen receptor α in ovarian cancer.
    Authors: Benhadjeba Et al.
    Mol Oncol  2018;12:1689
  7. Suppression of lymphoma growth by the xenoestrogens bisphenol A and genistein.
    Authors: Yakimchuk Et al.
    Endocr Connect  2018;
  8. Estrogen enhances mismatch repair by induction of MLH1 expression via estrogen receptor-β.
    Authors: Lu Et al.
    Oncotarget  2017;8:38767
  9. 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
  10. 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
  11. Estrogen receptor 1 (ESR1) regulates VEGFA in adipose tissue.
    Authors: Fatima
    Sci Rep  2017;7(1):16716
  12. 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
  13. 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
  14. 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
  15. 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
  16. ERα Mediates Estrogen-Induced Expression of the Breast Cancer Metastasis Suppressor Gene BRMS1.
    Authors: Ma
    Int J Mol Sci  2016;17
  17. Mechanisms by Which 17β-OE (E2) Suppress Neuronal cox-2 Gene Expression.
    Authors: Stacey Et al.
    PLoS One  2016;11:e0161430
  18. 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
  19. 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
  20. 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
  21. 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
  22. 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
  23. 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
  24. 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
  25. 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
  26. Elevated peritoneal expression and estrogen regulation of nociceptive ion channels in endometriosis.
    Authors: Greaves Et al.
    J Clin Endocrinol Metab  2014;99:E1738
  27. Loss of estrogen-mediated immunoprotection underlies female gender bias in experimental Crohn's-like ileitis.
    Authors: Goodman Et al.
    PLoS One  2014;7:1255
  28. 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
  29. 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
  30. 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
  31. 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
  32. 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
  33. Neuroprotection by diarylpropionitrile in mice with spinal cord injury.
    Authors: Suwanna Et al.
    Am J Physiol Heart Circ Physiol  2014;13:1097
  34. 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
  35. 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
  36. The memory-enhancing effects of hippocampal estrogen receptor activation involve metabotropic glutamate receptor signaling.
    Authors: Boulware Et al.
    Cardiovasc Ther  2013;33:15184
  37. 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
  38. Estrogen receptor β does not influence ischemic tolerance in the aged female rat heart.
    Authors: Tomicek Et al.
    PLoS One  2013;31:32
  39. ERβ-dependent effects on uterine endothelial cells are cell specific and mediated via Sp1.
    Authors: Greaves Et al.
    Hum Reprod  2013;28:2490
  40. △(9)-Tetrahydrocannabinol disrupts estrogen-signaling through up-regulation of estrogen receptor β (ERβ).
    Authors: Takeda Et al.
    Cancer Res  2013;26:1073
  41. Estrogens downregulate urocortin 2 expression in rat uterus.
    Authors: Watanabe Et al.
    J Endocrinol  2013;219:269
  42. 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
  43. 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
  44. Rapid estrogenic effects on TMJ-responsive brainstem neurons.
    Authors: Tashiro Et al.
    J Dent Res  2012;91:210
  45. The DEK oncogene is a target of steroid hormone receptor signaling in breast cancer.
    Authors: Vinnedge Et al.
    Neuroscience  2012;7:e46985
  46. Estrogen prevents oxidative damage to the mitochondria in Friedreich's ataxia skin fibroblasts.
    Authors: Richardson Et al.
    Chem Res Toxicol  2012;7:e34600
  47. 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
  48. 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
  49. 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
  50. 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
  51. 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
  52. 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
  53. 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
  54. OE directly attenuates sodium currents and depolarizing afterpotentials in isolated gonadotropin-releasing hormone neurons.
    Authors: Wang and Kuehl-Kovarik
    Brain Res  2012;1436:81
  55. 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
  56. 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
  57. OE and progesterone strongly inhibit the innate immune response of mononuclear cells in newborns.
    Authors: Giannoni Et al.
    Infect Immun  2011;79:2690
  58. 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
  59. 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
  60. 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
  61. 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
  62. 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
  63. 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
  64. 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
  65. Molecular mechanisms of bladder outlet obstruction in transgenic male mice overexpressing aromatase (Cyp19a1).
    Authors: Lin Et al.
    Exp Neurol  2011;178:1233
  66. 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
  67. 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
  68. OE selectively stimulates endothelial prostacyclin production through estrogen receptor-{alpha}.
    Authors: Sobrino Et al.
    J Mol Endocrinol  2010;44:237
  69. 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
  70. OE acutely potentiates hippocampal excitatory synaptic transmission through a presynaptic mechanism.
    Authors: Smejkalova and Woolley
    J Neurosci  2010;30:16137
  71. Estrogen stimulates degradation of β-amyloid peptide by up-regulating neprilysin.
    Authors: Liang Et al.
    Behav Brain Res  2010;285:935
  72. 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
  73. Estrogen promotes cutaneous wound healing via estrogen receptor β independent of its antiinflammatory activities.
    Authors: Campbell Et al.
    Mol Cell Endocrinol  2010;207:1825
  74. 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
  75. 17β-OE inhibits wound healing in male mice via estrogen receptor-α.
    Authors: Gilliver Et al.
    Clin Cancer Res  2010;176:2707
  76. 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
  77. Estrogen inhibits ATR signaling to cell cycle checkpoints and DNA repair.
    Authors: Pedram Et al.
    Mol Biol Cell  2009;20:3374
  78. 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
  79. 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
  80. Protopanaxadiol and protopanaxatriol bind to glucocorticoid and oestrogen receptors in endothelial cells.
    Authors: Leung Et al.
    Br J Pharmacol  2009;156:626
  81. Blockade of estrogen receptor signaling inhibits growth and migration of medulloblastoma.
    Authors: Belcher Et al.
    Endocrinology  2009;150:1112
  82. Estrogen rapidly modulates 5-hydroxytrytophan-induced visceral hypersensitivity via GPR30 in rats.
    Authors: Lu Et al.
    Gastroenterology  2009;137:1040
  83. Estrogen receptor alpha and beta specific agonists regulate expression of synaptic proteins in rat hippocampus.
    Authors: Waters Et al.
    Brain Res  2009;1290:43405
  84. 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
  85. 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
  86. Liquiritigenin is a plant-derived highly selective estrogen receptor β agonist.
    Authors: Mersereau Et al.
    J Biol Chem  2008;283:49
  87. Roles of estrogen receptor alpha and beta in modulating urothelial cell proliferation.
    Authors: Teng Et al.
    Endocr Relat Cancer  2008;15:351
  88. 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
  89. 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
  90. Estrogen receptor beta protects against acoustic trauma in mice.
    Authors: Meltser Et al.
    J Clin Invest  2008;118:1563
  91. 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
  92. Estrogen-dependent signaling in a molecularly distinct subclass of aggressive prostate cancer.
    Authors: Setlur Et al.
    Horm Behav  2008;100:815
  93. 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
  94. NM23-H2, an estrogen receptor β-associated protein, shows diminished expression with progression of atherosclerosis.
    Authors: Rayner Et al.
    Endocrinology  2007;292:R743
  95. 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
  96. 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
  97. 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
  98. 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
  99. Tissue- and hormone-dependent progesterone receptor distribution in the rat uterus.
    Authors: Sahlin Et al.
    Reprod Biol Endocrinol  2006;4:47
  100. 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
  101. DAX-1 expression is regulated during mammary epithelial cell differentiation.
    Authors: Helguero Et al.
    Oncogene  2006;147:3249
  102. 17β-OE induces apoptosis in the developing rodent prostate independently of ERα or ERβ.
    Authors: Taylor Et al.
    Am J Pathol  2006;147:191
  103. Biological role of estrogen receptor β in salivary gland adenocarcinoma cells.
    Authors: Ohshiro Et al.
    J Neurosci  2006;12:5994
  104. Stimulatory cross-talk between NFAT3 and estrogen receptor in breast cancer cells.
    Authors: Zhang Et al.
    J Biol Chem  2005;280:43188
  105. 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
  106. 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
  107. 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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