Catalog Number: 1426
Chemical Name: 4,4',4''-(4-Propyl-[1H]-pyrazole-1,3,5-triyl)trisphenol
Biological Activity
Potent, subtype-selective estrogen receptor agonist (EC50 ~ 200 pM); displays 410-fold selectivity for ERα over ERβ. Prevents ovariectomy-induced weight gain and loss of bone mineral density, and induces gene expression in the hypothalamus following systemic administration in vivo.
Technical Data
  • M.Wt:
    386.45
  • Formula:
    C24H22N2O3
  • Solubility:
    Soluble to 5 mM in ethanol and to 100 mM in DMSO
  • Purity:
    >99%
  • Storage:
    Store at +4°C
  • CAS No:
    263717-53-9
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. Conformational changes and coactivator recruitment by novel ligands for estrogen receptor-α and estrogen receptor-β: correlations with biological character and distinct differences among SRC coactivator family members.
    Kraichely et al.
    Endocrinology, 2000;141:3534
  2. Characterization of the biological roles of the estrogen receptors, ERα and ERβ, in estrogen target tissues in vivo through the use of an ERα-selective ligand.
    Harris et al.
    Endocrinology, 2002;143:4172
  3. Pyrazole ligands: structure-affinity/activity relationships and estrogen receptor-α-selective agonists.
    Stauffer et al.
    J.Med.Chem., 2000;43:4934
Citations:

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

59 Citations: Showing 1 - 10
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  1. Pancreatic insulin content regulation by the estrogen receptor ER alpha.
    Authors: Alonso-Magdalena Et al.
    PLoS One ;3:e2069
  2. Pharmacological activation of estrogen receptors-α and -β differentially modulates keratinocyte differentiation with functional impact on wound healing.
    Authors: Perželová Et al.
    Endocrinology 2016;37:42603
  3. Rapid modulation of synaptogenesis and spinogenesis by 17β-estradiol in primary cortical neurons.
    Authors: Sellers Et al.
    Front Cell Neurosci 2015;9:137
  4. Nitrostyrene Derivatives Act as RXRα Ligands to Inhibit TNFα Activation of NF-κB.
    Authors: Zeng Et al.
    J Exp Med 2015;75:2049
  5. Oestrogen receptors interact with the α-catalytic subunit of AMP-activated protein kinase.
    Authors: Lipovka Et al.
    Cancer Res 2015;35
  6. 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
  7. 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
  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. 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
  12. Both GPER and membrane oestrogen receptor-α activation protect ventricular remodelling in 17β oestradiol-treated ovariectomized infarcted rats.
    Authors: Lee Et al.
    J Cell Mol Med 2014;18:2454
  13. 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
  14. The memory-enhancing effects of hippocampal estrogen receptor activation involve metabotropic glutamate receptor signaling.
    Authors: Boulware Et al.
    J Neuroendocrinol 2013;33:15184
  15. The effect of estrogen compounds on human embryoid bodies.
    Authors: Kim Et al.
    Nucl Recept 2013;20:661
  16. 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
  17. Estradiol promotes the development of a fibrotic phenotype and is increased in the serum of patients with systemic sclerosis.
    Authors: Aida-Yasuoka Et al.
    Behav Brain Res 2013;15:R10
  18. The DEK oncogene is a target of steroid hormone receptor signaling in breast cancer.
    Authors: Vinnedge Et al.
    Neuroscience 2012;7:e46985
  19. Estrogen modulates NFκB signaling by enhancing IκBα levels and blocking p65 binding at the promoters of inflammatory genes via estrogen receptor-β.
    Authors: Xing Et al.
    PLoS One 2012;7:e36890
  20. Estrogen prevents oxidative damage to the mitochondria in Friedreich's ataxia skin fibroblasts.
    Authors: Richardson Et al.
    Neuropsychopharmacology 2012;7:e34600
  21. 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
  22. 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
  23. 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
  24. Estradiol directly attenuates sodium currents and depolarizing afterpotentials in isolated gonadotropin-releasing hormone neurons.
    Authors: Wang and Kuehl-Kovarik
    Brain Res 2012;1436:81
  25. Estradiol and progesterone strongly inhibit the innate immune response of mononuclear cells in newborns.
    Authors: Giannoni Et al.
    Infect Immun 2011;79:2690
  26. 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
  27. 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
  28. 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
  29. Oestrogen induces rhythmic expression of the Kisspeptin-1 receptor GPR54 in hypothalamic gonadotrophin-releasing hormone-secreting GT1-7 cells.
    Authors: Tonsfeldt Et al.
    PLoS One 2011;23:823
  30. 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
  31. Molecular mechanisms of bladder outlet obstruction in transgenic male mice overexpressing aromatase (Cyp19a1).
    Authors: Lin Et al.
    Mucosal Immunol 2011;178:1233
  32. Estradiol acutely potentiates hippocampal excitatory synaptic transmission through a presynaptic mechanism.
    Authors: Smejkalova and Woolley
    J Neurosci 2010;30:16137
  33. Estrogen stimulates degradation of β-amyloid peptide by up-regulating neprilysin.
    Authors: Liang Et al.
    Arthritis Res Ther 2010;285:935
  34. Estrogen promotes cutaneous wound healing via estrogen receptor β independent of its antiinflammatory activities.
    Authors: Campbell Et al.
    Mol Cell Endocrinol 2010;207:1825
  35. 17β-estradiol inhibits wound healing in male mice via estrogen receptor-α.
    Authors: Gilliver Et al.
    J Neurosci 2010;176:2707
  36. Neonatal bisphenol-a exposure alters rat reproductive development and ovarian morphology without impairing activation of gonadotropin-releasing hormone neurons.
    Authors: Adewale Et al.
    Biol Reprod 2009;81:690
  37. 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
  38. Estrogen inhibits ATR signaling to cell cycle checkpoints and DNA repair.
    Authors: Pedram Et al.
    Mol Biol Cell 2009;20:3374
  39. 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
  40. Estrogen receptor-beta agonist diarylpropionitrile: biological activities of R- and S-enantiomers on behavior and hormonal response to stress.
    Authors: Weiser Et al.
    Endocrinology 2009;150:1817
  41. 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
  42. Mitochondrial effects of estrogen are mediated by estrogen receptor α in brain endothelial cells.
    Authors: Razmara Et al.
    Am J Physiol Heart Circ Physiol 2008;325:782
  43. Liquiritigenin is a plant-derived highly selective estrogen receptor β agonist.
    Authors: Mersereau Et al.
    J Biol Chem 2008;283:49
  44. Roles of estrogen receptor alpha and beta in modulating urothelial cell proliferation.
    Authors: Teng Et al.
    Endocr Relat Cancer 2008;15:351
  45. 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.
    Biosci Rep 2008;149:5043
  46. 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
  47. Estrogen receptor beta protects against acoustic trauma in mice.
    Authors: Meltser Et al.
    J Clin Invest 2008;118:1563
  48. 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
  49. Estrogen-dependent signaling in a molecularly distinct subclass of aggressive prostate cancer.
    Authors: Setlur Et al.
    Horm Behav 2008;100:815
  50. 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
  51. NM23-H2, an estrogen receptor β-associated protein, shows diminished expression with progression of atherosclerosis.
    Authors: Rayner Et al.
    Reprod Sci 2007;292:R743
  52. 17beta-Estradiol utilizes the estrogen receptor to regulate CD16 expression in monocytes.
    Authors: Kramer Et al.
    Mol Cell Endocrinol 2007;279:16
  53. Tissue- and hormone-dependent progesterone receptor distribution in the rat uterus.
    Authors: Sahlin Et al.
    Reprod Biol Endocrinol 2006;4:47
  54. 17β-estradiol induces apoptosis in the developing rodent prostate independently of ERα or ERβ.
    Authors: Taylor Et al.
    Am J Pathol 2006;147:191
  55. Estrogen receptor alpha pathway is involved in the regulation of Calbindin-D9k in the uterus of immature rats.
    Authors: Lee Et al.
    Toxicol Sci 2005;84:270
  56. Stimulatory cross-talk between NFAT3 and estrogen receptor in breast cancer cells.
    Authors: Zhang Et al.
    J Biol Chem 2005;280:43188
  57. Estrogen modulates endothelial and neuronal nitric oxide synthase expression via an estrogen receptor beta-dependent mechanism in hypothalamic slice cultures.
    Authors: Gingerich and Krukoff
    Endocrinology 2005;146:2933
  58. 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
  59. Estrogen receptor-dependent activation of AP-1 via non-genomic signalling.
    Authors: Björnström and Sjöberg
    Cancer Cell Int 2004;2:3
Expand to show all 59 Citations

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