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:
    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.
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
Citations:

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

69 Citations: Showing 1 - 10
Filter your results:

  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 2016;37:42603
  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 2015;51:72
  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 2015;48:56
  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 2015;2015:925703
  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 2015;156:2162
  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 2015;14:540
  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.
    Endocrinology 2015;123:571
  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 2014;9:e101623
  9. Loss of estrogen-mediated immunoprotection underlies female gender bias in experimental Crohn's-like ileitis.
    Authors: Goodman Et al.
    PLoS One 2014;7:1255
  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 2014;60:55
  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 2014;60:216
  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 2014;267:122
  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 2014;2014:801473
  14. Neuroprotection by diarylpropionitrile in mice with spinal cord injury.
    Authors: Suwanna Et al.
    Am J Physiol Heart Circ Physiol 2014;13:1097
  15. 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
  16. The memory-enhancing effects of hippocampal estrogen receptor activation involve metabotropic glutamate receptor signaling.
    Authors: Boulware Et al.
    Cardiovasc Ther 2013;33:15184
  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 2013;33:10924
  18. Estrogen receptor β does not influence ischemic tolerance in the aged female rat heart.
    Authors: Tomicek Et al.
    PLoS One 2013;31:32
  19. ERβ-dependent effects on uterine endothelial cells are cell specific and mediated via Sp1.
    Authors: Greaves Et al.
    Hum Reprod 2013;28:2490
  20. △(9)-Tetrahydrocannabinol disrupts estrogen-signaling through up-regulation of estrogen receptor β (ERβ).
    Authors: Takeda Et al.
    Cancer Res 2013;26:1073
  21. 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
  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 2013;110:19125
  23. The DEK oncogene is a target of steroid hormone receptor signaling in breast cancer.
    Authors: Vinnedge Et al.
    Neuroscience 2012;7:e46985
  24. Estrogen prevents oxidative damage to the mitochondria in Friedreich's ataxia skin fibroblasts.
    Authors: Richardson Et al.
    Chem Res Toxicol 2012;7:e34600
  25. 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
  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 2012;18:5911
  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 2012;1823:379
  28. Estradiol directly attenuates sodium currents and depolarizing afterpotentials in isolated gonadotropin-releasing hormone neurons.
    Authors: Wang and Kuehl-Kovarik
    Brain Res 2012;1436:81
  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.
    Endocrinology 2012;11:2911
  30. Estradiol and progesterone strongly inhibit the innate immune response of mononuclear cells in newborns.
    Authors: Giannoni Et al.
    Infect Immun 2011;79:2690
  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 2011;6:e22439
  32. 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
  33. 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
  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 2011;301:H1706
  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 2011;20:2823
  36. Molecular mechanisms of bladder outlet obstruction in transgenic male mice overexpressing aromatase (Cyp19a1).
    Authors: Lin Et al.
    Exp Neurol 2011;178:1233
  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 2011;13:R43
  38. Estradiol acutely potentiates hippocampal excitatory synaptic transmission through a presynaptic mechanism.
    Authors: Smejkalova and Woolley
    J Neurosci 2010;30:16137
  39. Estrogen stimulates degradation of β-amyloid peptide by up-regulating neprilysin.
    Authors: Liang Et al.
    Behav Brain Res 2010;285:935
  40. Estrogen promotes cutaneous wound healing via estrogen receptor β independent of its antiinflammatory activities.
    Authors: Campbell Et al.
    Mol Cell Endocrinol 2010;207:1825
  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 2010;177:1079
  42. 17β-estradiol inhibits wound healing in male mice via estrogen receptor-α.
    Authors: Gilliver Et al.
    Clin Cancer Res 2010;176:2707
  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 2009;80:1262
  44. Estrogen inhibits ATR signaling to cell cycle checkpoints and DNA repair.
    Authors: Pedram Et al.
    Mol Biol Cell 2009;20:3374
  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 2009;200:189
  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 2009;196:317
  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 2008;68:8695
  48. 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
  49. Liquiritigenin is a plant-derived highly selective estrogen receptor β agonist.
    Authors: Mersereau Et al.
    J Biol Chem 2008;283:49
  50. Roles of estrogen receptor alpha and beta in modulating urothelial cell proliferation.
    Authors: Teng Et al.
    Endocr Relat Cancer 2008;15:351
  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 2008;149:5043
  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.
    Endocrinology 2008;149:2970
  53. Estrogen receptor beta protects against acoustic trauma in mice.
    Authors: Meltser Et al.
    J Clin Invest 2008;118:1563
  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 2008;105:303
  55. Estrogen-dependent signaling in a molecularly distinct subclass of aggressive prostate cancer.
    Authors: Setlur Et al.
    Horm Behav 2008;100:815
  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 2007;52:146
  57. NM23-H2, an estrogen receptor β-associated protein, shows diminished expression with progression of atherosclerosis.
    Authors: Rayner Et al.
    Endocrinology 2007;292:R743
  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 2007;204:767
  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 2007;13:1438
  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 2007;104:14813
  61. Tissue- and hormone-dependent progesterone receptor distribution in the rat uterus.
    Authors: Sahlin Et al.
    Reprod Biol Endocrinol 2006;4:47
  62. 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
  63. DAX-1 expression is regulated during mammary epithelial cell differentiation.
    Authors: Helguero Et al.
    Oncogene 2006;147:3249
  64. 17β-estradiol induces apoptosis in the developing rodent prostate independently of ERα or ERβ.
    Authors: Taylor Et al.
    Am J Pathol 2006;147:191
  65. Biological role of estrogen receptor β in salivary gland adenocarcinoma cells.
    Authors: Ohshiro Et al.
    J Neurosci 2006;12:5994
  66. Stimulatory cross-talk between NFAT3 and estrogen receptor in breast cancer cells.
    Authors: Zhang Et al.
    J Biol Chem 2005;280:43188
  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 2005;24:6605
  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 2005;12:851
  69. 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
Expand to show all 69 Citations
Tocris Small Molecules
Description Application Cat# Citations Images  

(R)-DPN

4494 1  
View Sizes & Prices
Catalog# Size Price Stock Quantity
Loading Information....

Have you used DPN?

Submit a review and receive a $25US/€18/£15/$25CAN amazon gift card if you include an image - $10US/€7/£6/$10CAN Amazon card for reviews without an image. Limited to verified customers in USA, Canada and Europe.

Tocris Bioscience is the leading supplier of novel and exclusive tools for life science research with over 30 years' experience in the industry. Tocris is a Bio-Techne brand.

Order Details

Note:

Contact Information

Calculators

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

R&D Systems Guarantee

or select another batch: 

Feedback

Customer Information