PHTPP

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Cat.No. 2662 - PHTPP | C20H11F6N3O | CAS No. 805239-56-9
Description: Selective ERβ antagonist
Chemical Name: 4-[2-Phenyl-5,7-bis(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl]phenol
Purity: ≥99% (HPLC)
Datasheet
Citations (37)
Reviews
Literature (2)
Pathways (1)

Biological Activity

Selective estrogen ERβ receptor antagonist that displays 36-fold selectivity over ERα. Exhibits full antagonism at ERβ in a cotransfection assay in human endometrial cancer cells (HEC-1), with minimal effects on ERα.

Compound Libraries

PHTPP is also offered as part of the Tocriscreen 2.0 Max. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 423.31
Formula C20H11F6N3O
Storage Store at RT
Purity ≥99% (HPLC)
CAS Number 805239-56-9
PubChem ID 11201035
InChI Key AEZPAUSGTAHLOQ-UHFFFAOYSA-N
Smiles OC1=CC=C(C=C1)C1=C2N=C(C=C(N2N=C1C1=CC=CC=C1)C(F)(F)F)C(F)(F)F

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
DMSO 13.96 33
ethanol 42.33 100

Preparing Stock Solutions

The following data is based on the product molecular weight 423.31. 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.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.36 mL 11.81 mL 23.62 mL
5 mM 0.47 mL 2.36 mL 4.72 mL
10 mM 0.24 mL 1.18 mL 2.36 mL
50 mM 0.05 mL 0.24 mL 0.47 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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References

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

Compton et al (2004) Pyrazolo[1,5-a]pyrimidines: estrogen receptor ligands possessing estrogen receptor β antagonist activity. J.Med.Chem. 47 5872 PMID: 15537344

Compton et al (2005) Erratum. J.Med.Chem. 48 2724


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View all Estrogen and Related Receptor Antagonists

Keywords: PHTPP, PHTPP supplier, Selective, ERβ, ERbeta, antagonists, Estrogen, Receptors, and, Related, 2662, Tocris Bioscience

37 Citations for PHTPP

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

Zhou et al (2019) ERβ Accelerates Diabetic Wound Healing by Ameliorating Hyperglycemia-Induced Persistent Oxidative Stress. Front Endocrinol (Lausanne) 10 499 PMID: 31396159

Al-Khyatt (2018) Selective oestrogen receptor antagonists inhibit oesophageal cancer cell proliferation in vitro. BMC Cancer 18 121 PMID: 29390981

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

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

Aguirre et al (2010) Progesterone inhibits estrogen-mediated neuroprotection against excitotoxicity by down-regulating estrogen receptor-β. J Neurochem 115 1277 PMID: 20977477

Loiola et al (2019) Estrogen Promotes Pro-resolving Microglial Behavior and Phagocytic Cell Clearance Through the Actions of Annexin A1. Front Endocrinol (Lausanne) 10 420 PMID: 31297095

Wojtowicz et al (2017) Dibutyl Phthalate (DBP)-Induced Apoptosis and Neurotoxicity are Mediated via the Aryl Hydrocarbon Receptor (AhR) but not by Estrogen Receptor Alpha (ERα), Estrogen Receptor Beta (ERβ), or Peroxisome Proliferator-Activated Receptor Gamma (PPAR Neurotox Res 31 77 PMID: 27581038

Lou et al (2017) OE Suppresses TLR4-triggered Apoptosis of Decidual Stromal Cells and Drives an Anti-inflammatory TH2 Shift by Activating SGK1. Int J Biol Sci 13 434 PMID: 28529452

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

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

Giordano et al (2013) Gender differences in brain susceptibility to oxidative stress are mediated by levels of paraoxonase-2 expression. Free Radic Biol Med 58 98 PMID: 23376469

Samanta et al (2012) Regulation of IMP3 by EGFR signaling and repression by ERβ: implications for triple-negative breast cancer. Oncogene 31 4689 PMID: 22266872

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

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

Luo et al (2017) 17β-OE lowers triglycerides in adipocytes via estrogen receptor α and it may be attenuated by inflammation. Lipids Health Dis 16 182 PMID: 28946914

Kim et al (2013) Effects of 17β-OE and estrogen receptor antagonists on the proliferation of gastric cancer cell lines. J Gastric Cancer 13 172 PMID: 24156037

Adams et al (2012) Soy isoflavones genistein and daidzein exert anti-apoptotic actions via a selective ER-mediated mechanism in neurons following HIV-1 Tat(1-86) exposure. PLoS One 7 e37540 PMID: 22629415

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

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

Harvey et al (2015) Methoxychlor and its metabolite HPTE inhibit cAMP production and expression of estrogen receptors α and β in the rat granulosa cell in vitro. Reprod Toxicol 51 72 PMID: 25549949

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

Liu et al (2011) Spinal synthesis of estrogen and concomitant signaling by membrane estrogen receptors regulate spinal κ- and μ-opioid receptor heterodimerization and female-specific spinal mor. antinociception. J Neurosci 31 11836 PMID: 21849544

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

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

Takeda et al (2013) △(9)-Tetrahydrocannabinol disrupts estrogen-signaling through up-regulation of estrogen receptor β (ERβ). Oncotarget 26 1073 PMID: 23718638

Ivanova et al (2011) Tamoxifen increases nuclear respiratory factor 1 transcription by activating estrogen receptor beta and AP-1 recruitment to adjacent promoter binding sites. FASEB J 25 1402 PMID: 21233487

Bertrand et al (2015) HIV-1 Tat and cocaine mediated synaptopathy in cortical and midbrain neurons is prevented by the isoflavone Equol. Environ Health Perspect 6 894 PMID: 26441850

Gao et al (2015) 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. Biosci Rep 123 571 PMID: 25723814

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

Ogo et al (2014) IGF-1 gene expression is differentially regulated by estrogen receptors α and β in mouse endometrial stromal cells and ovarian granulosa cells. J Reprod Dev 60 216 PMID: 24670778

Koong and Watson (2014) Direct OE and diethylstilbestrol actions on early- versus late-stage prostate cancer cells. Prostate 74 1589 PMID: 25213831

Gorelick et al (2014) Transgenic zebrafish reveal tissue-specific differences in estrogen signaling in response to environmental water samples. Environ Health Perspect 122 356 PMID: 24425189

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

Zuloaga et al (2012) Estrogen receptor β dependent attenuation of cytokine-induced cyclooxygenase-2 by androgens in human brain vascular smooth muscle cells and rat mesenteric arteries. Chem Res Toxicol 77 835 PMID: 22542504

Liang et al (2014) Cellular mechanism of the nonmonotonic dose response of bisphenol A in rat cardiac myocytes. Environ Health Perspect 122 601 PMID: 24569941

LaPensee et al (2010) Bisphenol A and OE are equipotent in antagonizing cisplatin-induced cytotoxicity in breast cancer cells. Steroids 290 167 PMID: 19796866


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Literature in this Area

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Cancer

Cancer Research Product Guide

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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
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Pathways for PHTPP

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.