PHTPP

Pricing Availability Delivery Time Qty
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 (18)
Literature
Pathways

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 Plus. 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.

All Tocris products are intended for laboratory research use only.

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 solvent 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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Safety Datasheet

References

References are publications that support the products' biological activity.

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 PMID:


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View all Estrogen and Related Receptor Antagonists

Keywords: Selective ERβ ERbeta antagonists Estrogen Receptors Estrogen and Related Receptors

18 Citations for PHTPP

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

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

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

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

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

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 insulin-like growth factor-2 in triple-negative breast cancer. Biomed Res Int 2015 925703 PMID: 25874233

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

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

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

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

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

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 fulvestrant resistance in ER-positive ovarian cancer models in vitro and in vivo. Clin Cancer Res 18 5911 PMID: 22896656


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Reviews

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Literature in this Area

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

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.

Protocols

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