PPT

Cat. No. 1426

PPT C24H22N2O3 [263717-53-9]

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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.

Certificate of Analysis / Product Datasheet / Safety Data Sheet

Certificate of Analysis / Product Datasheet
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Harris et al (2002) 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. Endocrinology 143 4172. PMID: 12399409.

Kraichely et al (2000) 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. Endocrinology 141 3534. PMID: 11014206.

Stauffer et al (2000) Pyrazole ligands: structure-affinity/activity relationships and estrogen receptor-α-selective agonists. J.Med.Chem. 43 4934. PMID: 11150164.

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

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

Perželová et al (2016) Pharmacological activation of estrogen receptors-α and -β differentially modulates keratinocyte differentiation with functional impact on wound healing. Endocrinology 37 42603. PMID: 26397183.

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.

Lipovka et al (2015) Oestrogen receptors interact with the α-catalytic subunit of AMP-activated protein kinase. Cancer Res 35. PMID: 26374855.

Sellers et al (2015) Rapid modulation of synaptogenesis and spinogenesis by 17β-estradiol in primary cortical neurons. Front Cell Neurosci 9 137. PMID: 25926772.

Zeng et al (2015) Nitrostyrene Derivatives Act as RXRα Ligands to Inhibit TNFα Activation of NF-κB. J Exp Med 75 2049. PMID: 25795708.

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.

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.

Lee et al (2014) Both GPER and membrane oestrogen receptor-α activation protect ventricular remodelling in 17β oestradiol-treated ovariectomized infarcted rats. J Cell Mol Med 18 2454. PMID: 25256868.

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.

Aida-Yasuoka et al (2013) Estradiol promotes the development of a fibrotic phenotype and is increased in the serum of patients with systemic sclerosis. Behav Brain Res 15 R10. PMID: 23305385.

Boulware et al (2013) The memory-enhancing effects of hippocampal estrogen receptor activation involve metabotropic glutamate receptor signaling. J Neuroendocrinol 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.

Kim et al (2013) The effect of estrogen compounds on human embryoid bodies. Nucl Recept 20 661. PMID: 23184660.

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.

Richardson et al (2012) Estrogen prevents oxidative damage to the mitochondria in Friedreich's ataxia skin fibroblasts. Neuropsychopharmacology 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.

Xing et al (2012) Estrogen modulates NFκB signaling by enhancing IκBα levels and blocking p65 binding at the promoters of inflammatory genes via estrogen receptor-β. PLoS One 7 e36890. PMID: 22723832.

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.

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). Mucosal Immunol 178 1233. PMID: 21356374.

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.

Tonsfeldt et al (2011) Oestrogen induces rhythmic expression of the Kisspeptin-1 receptor GPR54 in hypothalamic gonadotrophin-releasing hormone-secreting GT1-7 cells. PLoS One 23 823. PMID: 21756268.

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. J Neurosci 176 2707. PMID: 20448060.

Liang et al (2010) Estrogen stimulates degradation of β-amyloid peptide by up-regulating neprilysin. Arthritis Res Ther 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.

Adewale et al (2009) Neonatal bisphenol-a exposure alters rat reproductive development and ovarian morphology without impairing activation of gonadotropin-releasing hormone neurons. Biol Reprod 81 690. PMID: 19535786.

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.

Weiser et al (2009) Estrogen receptor-beta agonist diarylpropionitrile: biological activities of R- and S-enantiomers on behavior and hormonal response to stress. Endocrinology 150 1817. PMID: 19074580.

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. Am J Physiol Heart Circ Physiol 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. Biosci Rep 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.

Kramer et al (2007) 17beta-Estradiol utilizes the estrogen receptor to regulate CD16 expression in monocytes. Mol Cell Endocrinol 279 16. PMID: 17923257.

Rayner et al (2007) NM23-H2, an estrogen receptor β-associated protein, shows diminished expression with progression of atherosclerosis. Reprod Sci 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.

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.

Gingerich and Krukoff (2005) Estrogen modulates endothelial and neuronal nitric oxide synthase expression via an estrogen receptor beta-dependent mechanism in hypothalamic slice cultures. Endocrinology 146 2933. PMID: 15790731.

Lee et al (2005) Estrogen receptor alpha pathway is involved in the regulation of Calbindin-D9k in the uterus of immature rats. Toxicol Sci 84 270. PMID: 15635152.

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.

Björnström and Sjöberg (2004) Estrogen receptor-dependent activation of AP-1 via non-genomic signalling. Cancer Cell Int 2 3. PMID: 15196329.

Alonso-Magdalena et al Pancreatic insulin content regulation by the estrogen receptor ER alpha. PLoS One 3 e2069. PMID: 18446233.

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Keywords: PPT, supplier, Subtype-selective, ERα, ERalpha, agonists, ERR, Estrogen, Receptors, Tocris Bioscience, Estrogen and Related Receptor Agonist products

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