Catalog Number: 1494
Alternate Names: 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:
  • Formula:
  • Solubility:
    Soluble to 30 mM in 1eq. NaOH and to 100 mM in ethanol and to 100 mM in DMSO
  • Purity:
  • Storage:
    Desiccate at -20°C
  • CAS No:
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.
Background References
  1. Acute effects of oestrogen receptor subtype-specific agonists on vascular contractility.
    Montgomery et al.
    Br.J.Pharmacol., 2003;139:1249
  2. 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
  3. Estrogen receptor alpha and beta specific agonists regulate expression of synaptic proteins in rat hippocampus.
    Waters et al.
    Brain Res., 2009;1290:1
  4. 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

The citations listed below are publications that use Tocris products. Selected citations for DPN include:

Showing Results 1 - 10 of 69

  1. 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
  2. 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
  3. Differential expression of upstream stimulatory factor (USF) 2 variants in eutopic endometria from women with endometriosis: estradiol regulation.
    Authors: Castro Et al.
    Biol Res
  4. Biologic roles of estrogen receptor-β and insulin-like growth factor-2 in triple-negative breast cancer.
    Authors: Hamilton Et al.
    Biomed Res Int
  5. Classical and membrane-initiated estrogen signaling in an in vitro model of anterior hypothalamic kisspeptin neurons.
    Authors: Mittelman-Smith Et al.
    Cancer Cell Int
  6. 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
  7. 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.
  8. 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
  9. Loss of estrogen-mediated immunoprotection underlies female gender bias in experimental Crohn's-like ileitis.
    Authors: Goodman Et al.
    PLoS One
  10. Rat uterine oxytocin receptor and estrogen receptor α and β mRNA levels are regulated by estrogen through multiple estrogen receptors.
    Authors: Murata Et al.
    PLoS One
  11. 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
  12. 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
  13. 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
  14. Neuroprotection by diarylpropionitrile in mice with spinal cord injury.
    Authors: Suwanna Et al.
    Am J Physiol Heart Circ Physiol
  15. Estrogen responsiveness of the TFIID subunit TAF4B in the normal mouse ovary and in ovarian tumors.
    Authors: Wardell Et al.
    Biol Reprod
  16. The memory-enhancing effects of hippocampal estrogen receptor activation involve metabotropic glutamate receptor signaling.
    Authors: Boulware Et al.
    Cardiovasc Ther
  17. 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
  18. Estrogen receptor β does not influence ischemic tolerance in the aged female rat heart.
    Authors: Tomicek Et al.
    PLoS One
  19. ERβ-dependent effects on uterine endothelial cells are cell specific and mediated via Sp1.
    Authors: Greaves Et al.
    Hum Reprod
  20. △(9)-Tetrahydrocannabinol disrupts estrogen-signaling through up-regulation of estrogen receptor β (ERβ).
    Authors: Takeda Et al.
    Cancer Res
  21. Estrogen Induces Metastatic Potential of Papillary Thyroid Cancer Cells through Estrogen Receptor α and β.
    Authors: Dong Et al.
    Int J Endocrinol
  22. 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
  23. The DEK oncogene is a target of steroid hormone receptor signaling in breast cancer.
    Authors: Vinnedge Et al.
  24. Estrogen prevents oxidative damage to the mitochondria in Friedreich's ataxia skin fibroblasts.
    Authors: Richardson Et al.
    Chem Res Toxicol
  25. Estrogen represses hepatocellular carcinoma (HCC) growth via inhibiting alternative activation of tumor-associated macrophages (TAMs).
    Authors: Yang Et al.
    J Biol Chem
  26. Src Inhibition with saracatinib reverses fulvestrant resistance in ER-positive ovarian cancer models in vitro and in vivo.
    Authors: Simpkins Et al.
    Clin Cancer Res
  27. Estradiol 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
  28. Estradiol directly attenuates sodium currents and depolarizing afterpotentials in isolated gonadotropin-releasing hormone neurons.
    Authors: Wang and Kuehl-Kovarik
    Brain Res
  29. 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.
  30. Estradiol and progesterone strongly inhibit the innate immune response of mononuclear cells in newborns.
    Authors: Giannoni Et al.
    Infect Immun
  31. 17β-Estradiol enhances breast cancer cell motility and invasion via extra-nuclear activation of actin-binding protein ezrin.
    Authors: Zheng Et al.
    PLoS One
  32. Specific activation of estrogen receptor α and β enhances male sexual behavior and neuroplasticity in male Japanese quail.
    Authors: Seredynski Et al.
  33. Estrogen receptor-β ligand treatment modulates dendritic cells in the target organ during autoimmune demyelinating disease.
    Authors: Du Et al.
    Eur J Immunol
  34. 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
  35. 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
  36. Molecular mechanisms of bladder outlet obstruction in transgenic male mice overexpressing aromatase (Cyp19a1).
    Authors: Lin Et al.
    Exp Neurol
  37. Estrogen receptor β represses Akt signaling in breast cancer cells via downregulation of HER2/HER3 and upregulation of PTEN: implications for tamoxifen sensitivity.
    Authors: Lindberg Et al.
    Breast Cancer Res
  38. Estradiol acutely potentiates hippocampal excitatory synaptic transmission through a presynaptic mechanism.
    Authors: Smejkalova and Woolley
    J Neurosci
  39. Estrogen stimulates degradation of β-amyloid peptide by up-regulating neprilysin.
    Authors: Liang Et al.
    Behav Brain Res
  40. Estrogen promotes cutaneous wound healing via estrogen receptor β independent of its antiinflammatory activities.
    Authors: Campbell Et al.
    Mol Cell Endocrinol
  41. Phosphorylation of estrogen receptor beta at serine 105 is associated with good prognosis in breast cancer.
    Authors: Hamilton-Burke Et al.
    Am J Pathol
  42. 17β-estradiol inhibits wound healing in male mice via estrogen receptor-α.
    Authors: Gilliver Et al.
    Clin Cancer Res
  43. 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
  44. Estrogen inhibits ATR signaling to cell cycle checkpoints and DNA repair.
    Authors: Pedram Et al.
    Mol Biol Cell
  45. 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
  46. 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
  47. 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
  48. Mitochondrial effects of estrogen are mediated by estrogen receptor α in brain endothelial cells.
    Authors: Razmara Et al.
    FEMS Immunol Med Microbiol
  49. Liquiritigenin is a plant-derived highly selective estrogen receptor β agonist.
    Authors: Mersereau Et al.
    J Biol Chem
  50. Roles of estrogen receptor alpha and beta in modulating urothelial cell proliferation.
    Authors: Teng Et al.
    Endocr Relat Cancer
  51. The novel estrogen receptor, G protein-coupled receptor 30, mediates the proliferative effects induced by 17β-estradiol on mouse spermatogonial GC-1 cell line.
    Authors: Sirianni Et al.
    J Exp Med
  52. 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.
  53. Estrogen receptor beta protects against acoustic trauma in mice.
    Authors: Meltser Et al.
    J Clin Invest
  54. Influence of cellular ERalpha/ERbeta ratio on the ERalpha-agonist induced proliferation of human T47D breast cancer cells.
    Authors: Sotoca Et al.
    Toxicol Sci
  55. Estrogen-dependent signaling in a molecularly distinct subclass of aggressive prostate cancer.
    Authors: Setlur Et al.
    Horm Behav
  56. Evidence for the involvement of ERβ and RGS9-2 in 17-β estradiol enhancement of amphetamine-induced place preference behavior.
    Authors: Silverman and Koenig
    PLoS One
  57. NM23-H2, an estrogen receptor β-associated protein, shows diminished expression with progression of atherosclerosis.
    Authors: Rayner Et al.
  58. Neuroprotection by estrogen against MPP+-induced dopamine neuron death is mediated by ERα in primary cultures of mouse mesencephalon.
    Authors: Bains Et al.
    Mucosal Immunol
  59. Insulin-like growth factor binding proteins IGFBP3, IGFBP4, and IGFBP5 predict endocrine responsiveness in patients with ovarian cancer.
    Authors: Walker Et al.
    Clin Cancer Res
  60. 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
  61. Tissue- and hormone-dependent progesterone receptor distribution in the rat uterus.
    Authors: Sahlin Et al.
    Reprod Biol Endocrinol
  62. Efficient intracellular multiplication of Legionella pneumophila in human monocytes requires functional host cell L-type calcium channels.
    Authors: Wieland Et al.
  63. DAX-1 expression is regulated during mammary epithelial cell differentiation.
    Authors: Helguero Et al.
  64. 17β-estradiol induces apoptosis in the developing rodent prostate independently of ERα or ERβ.
    Authors: Taylor Et al.
    Am J Pathol
  65. Biological role of estrogen receptor β in salivary gland adenocarcinoma cells.
    Authors: Ohshiro Et al.
    J Neurosci
  66. Stimulatory cross-talk between NFAT3 and estrogen receptor in breast cancer cells.
    Authors: Zhang Et al.
    J Biol Chem
  67. 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
  68. 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
  69. Estrogen receptor beta isoforms exhibit differences in ligand-activated transcriptional activity in an estrogen response element sequence-dependent manner.
    Authors: Ramsey Et al.
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