PPT

Pricing Availability   Qty
Cat.No. 1426 - PPT | C24H22N2O3 | CAS No. 263717-53-9
Description: Subtype-selective ERα agonist
Chemical Name: 4,4',4''-(4-Propyl-[1H]-pyrazole-1,3,5-triyl)trisphenol
Purity: ≥99% (HPLC)
Datasheet
Citations (90)
Reviews
Literature
Pathways

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.

Compound Libraries

PPT is also offered as part of the Tocriscreen Plus. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 386.45
Formula C24H22N2O3
Storage Store at +4°C
Purity ≥99% (HPLC)
CAS Number 263717-53-9
PubChem ID 6095481
InChI Key UOSWGERPQQOSHS-UHFFFAOYSA-N
Smiles CCCC1=C(N(N=C1C1=CC=C(O)C=C1)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1

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.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
ethanol 1.93 5
DMSO 38.65 100

Preparing Stock Solutions

The following data is based on the product molecular weight 386.45. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.59 mL 12.94 mL 25.88 mL
5 mM 0.52 mL 2.59 mL 5.18 mL
10 mM 0.26 mL 1.29 mL 2.59 mL
50 mM 0.05 mL 0.26 mL 0.52 mL

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).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

Product Datasheets

Certificate of Analysis / Product Datasheet
Select another batch:

References

References are publications that support the biological activity of the product.

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 PPT, please let us know.

View Related Products by Target

View Related Products by Product Action

View all Estrogen and Related Receptor Agonists

Keywords: PPT, PPT supplier, Subtype-selective, ERα, ERalpha, agonists, ERR, Estrogen, Receptors, and, Related, 1426, Tocris Bioscience

90 Citations for PPT

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

Munive et al (2019) Loss of the interaction between E2 and IGF-1 in brain endothelial cells associates to changes in mood homeostasis during peri-menopause in mice. Aging (Albany NY) 11 174 PMID: 30636168

Ma (2016) ERα Mediates Estrogen-Induced Expression of the Breast Cancer Metastasis Suppressor Gene BRMS1. Int J Mol Sci 17 PMID: 26821020

Oberlander (2016) 17β-OE Acutely Potentiates Glutamatergic Synaptic Transmission in the Hippocampus through Distinct Mechanisms in Males and Females. J Neurosci 36 2677 PMID: 26937008

Mazzuca et al (2015) Estrogen receptor subtypes mediate distinct microvascular dilation and reduction in [Ca2+]I in mesenteric microvessels of female rat. J Pharmacol Exp Ther 352 291 PMID: 25472954

Zhang et al (2012) Estrogen-responsive nitroso-proteome in uterine artery endothelial cells: role of endothelial nitric oxide synthase and estrogen receptor-β. J Cell Physiol 227 146 PMID: 21374595

Shanle et al (2011) Generation of stable reporter breast cancer cell lines for the identification of ER subtype selective ligands. Biochem Pharmacol 82 1940 PMID: 21924251

Richardson et al (2011) Estrogen protection in Friedreich's ataxia skin fibroblasts. Endocrinology 152 2742 PMID: 21540287

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

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

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

Pedram et al (2009) Estrogen inhibits ATR signaling to cell cycle checkpoints and DNA repair. Mol Biol Cell 20 3374 PMID: 19477925

Murata et al (2014) Rat uterine oxyt. receptor and estrogen receptor α and β mRNA levels are regulated by estrogen through multiple estrogen receptors. PLoS One 60 55 PMID: 24334513

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

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

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

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

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

Huo et al (2018) Tph2-/- female mice restore socio-sexual recognition through upregulating ERα and OTR genes in the amygdala. PLoS One 13 e0193395 PMID: 29470551

Shults et al (2018) 17β-estradiol regulates the RNA-binding protein Nova1, which then regulates the alternative splicing of estrogen receptor β in the aging female rat brain. Neurobiol Aging 61 13 PMID: 29031089

Benhadjeba et al (2018) Feedback control of the CXCR7/CXCL11 chemokine axis by estrogen receptor α in ovarian cancer. Mol Oncol 12 1689 PMID: 30051594

Santos et al (2018) Activation of estrogen receptor alpha induces beiging of adipocytes. Mol Metab 18 51 PMID: 30270132

Meseke et al (2018) Distal Dendritic Enrichment of HCN1 Channels in Hippocampal CA1 Is Promoted by Estrogen, but Does Not Require Reelin. Eneuro 5 PMID: 30406178

Villar-Pazos et al (2017) Molecular mechanisms involved in the non-monotonic effect of bisphenol-a on Ca2+ entry in mouse pancreatic β-cells. Sci Rep 7 11770 PMID: 28924161

Caballero et al (2017) Understanding the dynamics of Toll-like Receptor 5 response to flagellin and its regulation by estradiol. Sci Rep 7 40981 PMID: 28112187

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

Hamilton et al (2015) Biologic roles of estrogen receptor-β and Ins-like growth factor-2 in triple-negative breast cancer. Biomed Res Int 2015 925703 PMID: 25874233

Boulware et al (2013) The memory-enhancing effects of hippocampal estrogen receptor activation involve metabotropic glutamate receptor signaling. J Neuroendocrinol 33 15184 PMID: 24048848

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

Aida-Yasuoka et al (2013) OE 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

Zheng et al (2011) 17β-OE enhances breast cancer cell motility and invasion via extra-nuclear activation of actin-binding protein ezrin. PLoS One 6 e22439 PMID: 21818323

Giannoni et al (2011) OE and progesterone strongly inhibit the innate immune response of mononuclear cells in newborns. Infect Immun 79 2690 PMID: 21518785

Sirianni et al (2008) The novel estrogen receptor, G protein-coupled receptor 30, mediates the proliferative effects induced by 17β-OE on mouse spermatogonial GC-1 cell line. Biosci Rep 149 5043 PMID: 18566133

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

Mersereau et al (2008) Liquiritigenin is a plant-derived highly selective estrogen receptor β agonist. J Biol Chem 283 49 PMID: 18177995

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

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

Meltser et al (2008) Estrogen receptor beta protects against acoustic trauma in mice. J Clin Invest 118 1563 PMID: 18317592

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

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

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

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

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

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

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

Lin et al (2011) Molecular mechanisms of bladder outlet obstruction in transgenic male mice overexpressing aromatase (Cyp19a1). Mucosal Immunol 178 1233 PMID: 21356374

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

Stygar et al (2007) Studies on estrogen receptor (ER) alpha and beta responses on gene regulation in peripheral blood leukocytes in vivo using selective ER agonists. J Endocrinol 194 101 PMID: 17592025

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

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

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

Jonsson et al (2014) Support of a bi-faceted role of estrogen receptor β (ERβ) in ERα-positive breast cancer cells. Endocr Relat Cancer 21 143 PMID: 24192230

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

Liang et al (2010) Estrogen stimulates degradation of β-amyloid peptide by up-regulating neprilysin. Arthritis Res Ther 285 935 PMID: 19897485

Gilliver et al (2010) 17β-OE inhibits wound healing in male mice via estrogen receptor-α. J Neurosci 176 2707 PMID: 20448060

Taylor et al (2006) 17β-OE induces apoptosis in the developing rodent prostate independently of ERα or ERβ. Am J Pathol 147 191 PMID: 16223864

Sahlin et al (2006) Tissue- and hormone-dependent progesterone receptor distribution in the rat uterus. Reprod Biol Endocrinol 4 47 PMID: 16965620

Lu et al (2017) Estrogen enhances mismatch repair by induction of MLH1 expression via estrogen receptor-β. Oncotarget 8 38767 PMID: 28404976

Pastore et al (2016) Identification of Differential ER-Alpha Versus ER-Beta Mediated Activation of eNOS in Ovine Uterine Artery Endothelial Cells. Biol Reprod 94 139 PMID: 27170438

Kleensang et al (2016) Genetic variability in a frozen batch of MCF-7 cells invisible in routine authentication affecting cell function. Sci Rep 6 28994 PMID: 27456714

Stacey et al (2016) Mechanisms by Which 17β-OE (E2) Suppress Neuronal cox-2 Gene Expression. PLoS One 11 e0161430 PMID: 27588681

Ma et al (2016) Estrogen replacement therapy-induced neuroprotection against brain ischemia-reperfusion injury involves the activation of astrocytes via estrogen receptor β. Sci Rep 6 21467 PMID: 26891996

Qu et al (2013) Oestrogen receptor α agonist improved long-term ovariectomy-induced spatial cognition deficit in young rats. Int J Neuropsychopharmacol 16 1071 PMID: 22999489

Smith et al (2013) The membrane estrogen receptor ligand STX rapidly enhances GABAergic signaling in NPY/AgRP neurons: role in mediating the anorexigenic effects of 17β-OE. Am J Physiol Endocrinol Metab 305 E632 PMID: 23820624

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

Wang and Kuehl-Kovarik (2012) OE directly attenuates sodium currents and depolarizing afterpotentials in isolated gonadotropin-releasing hormone neurons. Brain Res 1436 81 PMID: 22209345

Simpkins et al (2012) Src Inhibition with saracatinib reverses fulves. resistance in ER-positive ovarian cancer models in vitro and in vivo. Clin Cancer Res 18 5911 PMID: 22896656

González-Arenas et al (2012) OE 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

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

Smejkalova and Woolley (2010) OE acutely potentiates hippocampal excitatory synaptic transmission through a presynaptic mechanism. J Neurosci 30 16137 PMID: 21123560

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

Zhang et al (2005) Stimulatory cross-talk between NFAT3 and estrogen receptor in breast cancer cells. J Biol Chem 280 43188 PMID: 16219765

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

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

Fatima (2017) Estrogen receptor 1 (ESR1) regulates VEGFA in adipose tissue. Sci Rep 7 16716 PMID: 29196658

Sobrino et al (2010) OE selectively stimulates endothelial prostacyclin production through estrogen receptor-{alpha}. J Mol Endocrinol 44 237 PMID: 20110403

Ma et al (2010) Gender-specific reduction in contraction is associated with increased estrogen receptor expression in single vascular smooth muscle cells of female rat. Cell Physiol Biochem 26 457 PMID: 20798531

Raffetto et al (2010) Estrogen receptor-mediated enhancement of venous relaxation in female rat: implications in sex-related differences in varicose veins. J Vasc Surg 51 972 PMID: 20347696

Leung et al (2009) Protopanaxadiol and protopanaxatriol bind to glucocorticoid and oestrogen receptors in endothelial cells. Br J Pharmacol 156 626 PMID: 19226254

Waters et al (2009) Estrogen receptor alpha and beta specific agonists regulate expression of synaptic proteins in rat hippocampus. Brain Res 1290 43405 PMID: 19596275

Belcher et al (2009) Blockade of estrogen receptor signaling inhibits growth and migration of medulloblastoma. Endocrinology 150 1112 PMID: 19008315

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

Ciucci et al (2016) Multiple direct and indirect mechanisms drive estrogen-induced tumor growth in high grade serous ovarian cancers. Oncotarget 7 8155 PMID: 26797759

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

Vinnedge et al (2012) The DEK oncogene is a target of steroid hormone receptor signaling in breast cancer. Neuroscience 7 e46985 PMID: 23071688

Richardson et al (2012) Estrogen prevents oxidative damage to the mitochondria in Friedreich's ataxia skin fibroblasts. Neuropsychopharmacology 7 e34600 PMID: 22509330

Silverman and Koenig (2007) Evidence for the involvement of ERβ and RGS9-2 in 17-β OE enhancement of amphetamine-induced place preference behavior. PLoS One 52 146 PMID: 17493623

Kramer et al (2007) 17beta-OE 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


Do you know of a great paper that uses PPT from Tocris? Please let us know.

Reviews for PPT

There are currently no reviews for this product. Be the first to review PPT and earn rewards!

Have you used PPT?

Submit a review and receive an Amazon gift card.

$50/€35/£30/$50CAN/¥300 Yuan/¥5000 Yen for first to review with an image

$25/€18/£15/$25CAN/¥75 Yuan/¥1250 Yen for a review with an image

$10/€7/£6/$10 CAD/¥70 Yuan/¥1110 Yen for a review without an image

Submit a Review

Literature in this Area

Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* or download your copy today!

*Please note that Tocris will only send literature to established scientific business / institute addresses.


Cancer

Cancer Research Product Guide

A collection of over 750 products for cancer research, the guide includes research tools for the study of:

  • Cancer Metabolism
  • Epigenetics in Cancer
  • Receptor Signaling
  • Cell Cycle and DNA Damage Repair
  • Angiogenesis
  • Invasion and Metastasis
Nuclear Receptors

Nuclear Receptors Product Listing

A collection of over 150 products for key nuclear receptors, the listing includes research tools for the study of:

  • Androgen Receptors
  • Estrogen Receptors
  • Retinoic Acid Receptors
  • Retinoid X Receptors
  • Vitamin D Receptors

Pathways for PPT

Estrogen

Estrogen Signaling Pathway

Estrogen is a steroid hormone that is responsible for the regulation of growth, differentiation and function of the reproductive system. Estrogen signaling is often dysregulated in breast cancer and osteoporosis.