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PPT

Catalog #: 1426
93 Citations Datasheet
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PPT | CAS No. 263717-53-9 | Estrogen and Related Receptor Agonists
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Description: Subtype-selective ERα agonist

Chemical Name: 4,4',4''-(4-Propyl-[1H]-pyrazole-1,3,5-triyl)trisphenol

Purity: ≥99%

Product Details
Citations (93)
Reviews
Biological Activity Technical Data Background Product Datasheets Calculators

Biological Activity

PPT is a 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.
Tocris products are intended for laboratory research use only, unless stated otherwise.

Background References

  1. Loss of estrogen-mediated immunoprotection underlies female gender bias in experimental Crohn's-like ileitis.
    Goodman, W A, Garg, R R, Reuter, B K, Mattioli, B, Rissman, E F, Pizarro, T T
    Mucosal Immunol, 2014;7(5):1255-65.
  2. Activation of estrogen receptor alpha induces beiging of adipocytes
    RS Santos, AP Frank, LA Fátima, BF Palmer, DJ Clegg
    Mol Metab, 2018;0(0):.
  3. Urocortin suppresses endometrial cancer cell migration via CRFR2 and its system components are differentially modulated by estrogen
    GL Owens, KM Lawrence, TR Jackson, EJ Crosbie, BS Sayan, HC Kitchener, PA Townsend
    Cancer Med, 2017;0(0):.
  4. Estrogen receptor (ER) agonists differentially regulate neuroangiogenesis in peritoneal endometriosis via the repellent factor SLIT3.
    Greaves E, Collins F, Esnal-Zufiaurre A, Giakoumelou S, Horne A, Saunders P
    Endocrinology, 2014;155(10):4015-26.
  5. 17 beta-Estradiol activates GPER- and ESR1-dependent pathways inducing apoptosis in GC-2 cells, a mouse spermatocyte-derived cell line.
    Chimento A, Sirianni R, Casaburi I, Ruggiero C, Maggiolini M, Ando S, Pezzi V
    Mol. Cell. Endocrinol., 2012;355(1):49-59.
  6. The DEK oncogene is a target of steroid hormone receptor signaling in breast cancer.
    Privette Vinnedge L, Ho S, Wikenheiser-Brokamp K, Wells S
    PLoS ONE, 2012;7(10):e46985.
  7. ERbeta-mediated estradiol enhances epithelial mesenchymal transition of lung adenocarcinoma through increasing transcription of midkine.

    Mol. Endocrinol., 2012;26(8):1304-15.
  8. 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
  9. 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
  10. Pyrazole ligands: structure-affinity/activity relationships and estrogen receptor-α-selective agonists.
    Stauffer et al.
    J.Med.Chem., 2000;43:4934

Product Datasheets

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Citations for PPT

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

93 Citations: Showing 1 - 10

  1. Pancreatic Ins content regulation by the estrogen receptor ER alpha.
    Authors: Alonso-Magdalena Et al.
    PLoS One  ;3:e2069
  2. GPER is a mechanoregulator of pancreatic stellate cells and the tumor microenvironment.
    Authors: Cortes Et al.
    EMBO Rep  2019;20
  3. Loss of the interaction between E2 and IGF-1 in brain endothelial cells associates to changes in mood homeostasis during peri-menopause in mice.
    Authors: Munive Et al.
    Aging (Albany NY)  2019;11:174
  4. ERβ Accelerates Diabetic Wound Healing by Ameliorating Hyperglycemia-Induced Persistent Oxidative Stress.
    Authors: Zhou Et al.
    Front Endocrinol (Lausanne)  2019;10:499
  5. Estrogen Promotes Pro-resolving Microglial Behavior and Phagocytic Cell Clearance Through the Actions of Annexin A1.
    Authors: Loiola Et al.
    Front Endocrinol (Lausanne)  2019;10:420
  6. 17β-estradiol regulates the RNA-binding protein Nova1, which then regulates the alternative splicing of estrogen receptor β in the aging female rat brain.
    Authors: Shults Et al.
    Neurobiol Aging  2018;61:13
  7. Distal Dendritic Enrichment of HCN1 Channels in Hippocampal CA1 Is Promoted by Estrogen, but Does Not Require Reelin.
    Authors: Meseke Et al.
    Eneuro  2018;5
  8. Activation of estrogen receptor alpha induces beiging of adipocytes.
    Authors: Santos Et al.
    Mol Metab  2018;18:51
  9. Tph2-/- female mice restore socio-sexual recognition through upregulating ERα and OTR genes in the amygdala.
    Authors: Huo Et al.
    PLoS One  2018;13:e0193395
  10. Feedback control of the CXCR7/CXCL11 chemokine axis by estrogen receptor α in ovarian cancer.
    Authors: Benhadjeba Et al.
    Mol Oncol  2018;12:1689
  11. Estrogen enhances mismatch repair by induction of MLH1 expression via estrogen receptor-β.
    Authors: Lu Et al.
    Oncotarget  2017;8:38767
  12. Understanding the dynamics of Toll-like Receptor 5 response to flagellin and its regulation by estradiol.
    Authors: Caballero Et al.
    Sci Rep  2017;7:40981
  13. Molecular mechanisms involved in the non-monotonic effect of bisphenol-a on Ca2+ entry in mouse pancreatic β-cells.
    Authors: Villar-Pazos Et al.
    Sci Rep  2017;7:11770
  14. Estrogen receptor 1 (ESR1) regulates VEGFA in adipose tissue.
    Authors: Fatima
    Sci Rep  2017;7(1):16716
  15. Identification of Differential ER-Alpha Versus ER-Beta Mediated Activation of eNOS in Ovine Uterine Artery Endothelial Cells.
    Authors: Pastore Et al.
    Biol Reprod  2016;94:139
  16. Multiple direct and indirect mechanisms drive estrogen-induced tumor growth in high grade serous ovarian cancers.
    Authors: Ciucci Et al.
    Oncotarget  2016;7:8155
  17. Genetic variability in a frozen batch of MCF-7 cells invisible in routine authentication affecting cell function.
    Authors: Kleensang Et al.
    Sci Rep  2016;6:28994
  18. Estrogen replacement therapy-induced neuroprotection against brain ischemia-reperfusion injury involves the activation of astrocytes via estrogen receptor β.
    Authors: Ma Et al.
    Sci Rep  2016;6:21467
  19. 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
  20. 17β-OE Acutely Potentiates Glutamatergic Synaptic Transmission in the Hippocampus through Distinct Mechanisms in Males and Females.
    Authors: Oberlander
    J Neurosci  2016;36:2677
  21. ERα Mediates Estrogen-Induced Expression of the Breast Cancer Metastasis Suppressor Gene BRMS1.
    Authors: Ma
    Int J Mol Sci  2016;17
  22. Mechanisms by Which 17β-OE (E2) Suppress Neuronal cox-2 Gene Expression.
    Authors: Stacey Et al.
    PLoS One  2016;11:e0161430
  23. Rapid modulation of synaptogenesis and spinogenesis by 17β-OE in primary cortical neurons.
    Authors: Sellers Et al.
    Front Cell Neurosci  2015;9:137
  24. Nitrostyrene Derivatives Act as RXRα Ligands to Inhibit TNFα Activation of NF-κB.
    Authors: Zeng Et al.
    J Exp Med  2015;75:2049
  25. Estrogen receptor subtypes mediate distinct microvascular dilation and reduction in [Ca2+]I in mesenteric microvessels of female rat.
    Authors: Mazzuca Et al.
    J Pharmacol Exp Ther  2015;352:291
  26. Oestrogen receptors interact with the α-catalytic subunit of AMP-activated protein kinase.
    Authors: Lipovka Et al.
    Cancer Res  2015;35
  27. Biologic roles of estrogen receptor-β and Ins-like growth factor-2 in triple-negative breast cancer.
    Authors: Hamilton Et al.
    Biomed Res Int  2015;2015:925703
  28. 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
  29. 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
  30. Loss of estrogen-mediated immunoprotection underlies female gender bias in experimental Crohn's-like ileitis.
    Authors: Goodman Et al.
    PLoS One  2014;7:1255
  31. Rat uterine oxyt. 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
  32. 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
  33. Support of a bi-faceted role of estrogen receptor β (ERβ) in ERα-positive breast cancer cells.
    Authors: Jonsson Et al.
    Endocr Relat Cancer  2014;21:143
  34. Both GPER and membrane oestrogen receptor-α activation protect ventricular remodelling in 17β oOE-treated ovariectomized infarcted rats.
    Authors: Lee Et al.
    J Cell Mol Med  2014;18:2454
  35. 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
  36. The memory-enhancing effects of hippocampal estrogen receptor activation involve metabotropic glutamate receptor signaling.
    Authors: Boulware Et al.
    J Neuroendocrinol  2013;33:15184
  37. The membrane estrogen receptor ligand STX rapidly enhances GABAergic signaling in NPY/AgRP neurons: role in mediating the anorexigenic effects of 17β-OE.
    Authors: Smith Et al.
    Am J Physiol Endocrinol Metab  2013;305:E632
  38. The effect of estrogen compounds on human embryoid bodies.
    Authors: Kim Et al.
    Nucl Recept  2013;20:661
  39. 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
  40. Oestrogen receptor α agonist improved long-term ovariectomy-induced spatial cognition deficit in young rats.
    Authors: Qu Et al.
    Int J Neuropsychopharmacol  2013;16:1071
  41. OE 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
  42. The DEK oncogene is a target of steroid hormone receptor signaling in breast cancer.
    Authors: Vinnedge Et al.
    Neuroscience  2012;7:e46985
  43. 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
  44. Estrogen prevents oxidative damage to the mitochondria in Friedreich's ataxia skin fibroblasts.
    Authors: Richardson Et al.
    Neuropsychopharmacology  2012;7:e34600
  45. 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
  46. Estrogen-responsive nitroso-proteome in uterine artery endothelial cells: role of endothelial nitric oxide synthase and estrogen receptor-β.
    Authors: Zhang Et al.
    J Cell Physiol  2012;227:146
  47. Src Inhibition with saracatinib reverses fulves. resistance in ER-positive ovarian cancer models in vitro and in vivo.
    Authors: Simpkins Et al.
    Clin Cancer Res  2012;18:5911
  48. OE 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
  49. OE directly attenuates sodium currents and depolarizing afterpotentials in isolated gonadotropin-releasing hormone neurons.
    Authors: Wang and Kuehl-Kovarik
    Brain Res  2012;1436:81
  50. Generation of stable reporter breast cancer cell lines for the identification of ER subtype selective ligands.
    Authors: Shanle Et al.
    Biochem Pharmacol  2011;82:1940
  51. OE and progesterone strongly inhibit the innate immune response of mononuclear cells in newborns.
    Authors: Giannoni Et al.
    Infect Immun  2011;79:2690
  52. 17β-OE 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
  53. 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
  54. 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
  55. Oestrogen induces rhythmic expression of the Kisspeptin-1 receptor GPR54 in hypothalamic gonadotrophin-releasing hormone-Secr.g GT1-7 cells.
    Authors: Tonsfeldt Et al.
    PLoS One  2011;23:823
  56. 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
  57. Molecular mechanisms of bladder outlet obstruction in transgenic male mice overexpressing aromatase (Cyp19a1).
    Authors: Lin Et al.
    Mucosal Immunol  2011;178:1233
  58. Estrogen protection in Friedreich's ataxia skin fibroblasts.
    Authors: Richardson Et al.
    Endocrinology  2011;152:2742
  59. Estrogen receptor-mediated enhancement of venous relaxation in female rat: implications in sex-related differences in varicose veins.
    Authors: Raffetto Et al.
    J Vasc Surg  2010;51:972
  60. OE selectively stimulates endothelial prostacyclin production through estrogen receptor-{alpha}.
    Authors: Sobrino Et al.
    J Mol Endocrinol  2010;44:237
  61. OE acutely potentiates hippocampal excitatory synaptic transmission through a presynaptic mechanism.
    Authors: Smejkalova and Woolley
    J Neurosci  2010;30:16137
  62. Estrogen stimulates degradation of β-amyloid peptide by up-regulating neprilysin.
    Authors: Liang Et al.
    Arthritis Res Ther  2010;285:935
  63. Gender-specific reduction in contraction is associated with increased estrogen receptor expression in single vascular smooth muscle cells of female rat.
    Authors: Ma Et al.
    Cell Physiol Biochem  2010;26:457
  64. Estrogen promotes cutaneous wound healing via estrogen receptor β independent of its antiinflammatory activities.
    Authors: Campbell Et al.
    Mol Cell Endocrinol  2010;207:1825
  65. 17β-OE inhibits wound healing in male mice via estrogen receptor-α.
    Authors: Gilliver Et al.
    J Neurosci  2010;176:2707
  66. 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
  67. 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
  68. Estrogen inhibits ATR signaling to cell cycle checkpoints and DNA repair.
    Authors: Pedram Et al.
    Mol Biol Cell  2009;20:3374
  69. 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
  70. Protopanaxadiol and protopanaxatriol bind to glucocorticoid and oestrogen receptors in endothelial cells.
    Authors: Leung Et al.
    Br J Pharmacol  2009;156:626
  71. 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
  72. Blockade of estrogen receptor signaling inhibits growth and migration of medulloblastoma.
    Authors: Belcher Et al.
    Endocrinology  2009;150:1112
  73. Estrogen receptor alpha and beta specific agonists regulate expression of synaptic proteins in rat hippocampus.
    Authors: Waters Et al.
    Brain Res  2009;1290:43405
  74. 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
  75. 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
  76. Liquiritigenin is a plant-derived highly selective estrogen receptor β agonist.
    Authors: Mersereau Et al.
    J Biol Chem  2008;283:49
  77. Roles of estrogen receptor alpha and beta in modulating urothelial cell proliferation.
    Authors: Teng Et al.
    Endocr Relat Cancer  2008;15:351
  78. The novel estrogen receptor, G protein-coupled receptor 30, mediates the proliferative effects induced by 17β-OE on mouse spermatogonial GC-1 cell line.
    Authors: Sirianni Et al.
    Biosci Rep  2008;149:5043
  79. 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
  80. Estrogen receptor beta protects against acoustic trauma in mice.
    Authors: Meltser Et al.
    J Clin Invest  2008;118:1563
  81. 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
  82. Estrogen-dependent signaling in a molecularly distinct subclass of aggressive prostate cancer.
    Authors: Setlur Et al.
    Horm Behav  2008;100:815
  83. Evidence for the involvement of ERβ and RGS9-2 in 17-β OE enhancement of amphetamine-induced place preference behavior.
    Authors: Silverman and Koenig
    PLoS One  2007;52:146
  84. NM23-H2, an estrogen receptor β-associated protein, shows diminished expression with progression of atherosclerosis.
    Authors: Rayner Et al.
    Reprod Sci  2007;292:R743
  85. 17beta-OE utilizes the estrogen receptor to regulate CD16 expression in monocytes.
    Authors: Kramer Et al.
    Mol Cell Endocrinol  2007;279:16
  86. Studies on estrogen receptor (ER) alpha and beta responses on gene regulation in peripheral blood leukocytes in vivo using selective ER agonists.
    Authors: Stygar Et al.
    J Endocrinol  2007;194:101
  87. Tissue- and hormone-dependent progesterone receptor distribution in the rat uterus.
    Authors: Sahlin Et al.
    Reprod Biol Endocrinol  2006;4:47
  88. 17β-OE induces apoptosis in the developing rodent prostate independently of ERα or ERβ.
    Authors: Taylor Et al.
    Am J Pathol  2006;147:191
  89. 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
  90. Stimulatory cross-talk between NFAT3 and estrogen receptor in breast cancer cells.
    Authors: Zhang Et al.
    J Biol Chem  2005;280:43188
  91. 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
  92. 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
  93. Estrogen receptor-dependent activation of AP-1 via non-genomic signalling.
    Authors: Björnström and Sjöberg
    Cancer Cell Int  2004;2:3

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