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SML1355

Sigma-Aldrich

PHTPP

≥98% (HPLC)

Synonyme(s) :

2-Phenyl-3-(4-hydroxyphenyl)-5,7-bis(trifluoromethyl)-pyrazolo[1,5-a]pyrimidine, 4-[2-Phenyl-5,7-bis(trifluoromethyl)pyrazolo[1,5-a]-pyrimidin-3-yl]phenol

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About This Item

Formule empirique (notation de Hill):
C20H11F6N3O
Numéro CAS:
805239-56-9
Poids moléculaire :
423.31
Numéro MDL:
MFCD09971112
Code UNSPSC :
51111800
ID de substance PubChem :
329825810
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Couleur

yellow to orange

Solubilité

DMSO: 5 mg/mL, clear (warmed)

Température de stockage

2-8°C

Chaîne SMILES 

OC(C=C1)=CC=C1C(C(C2=CC=CC=C2)=N3)=C4N3C(C(F)(F)F)=CC(C(F)(F)F)=N4

InChI

1S/C20H11F6N3O/c21-19(22,23)14-10-15(20(24,25)26)29-18(27-14)16(11-6-8-13(30)9-7-11)17(28-29)12-4-2-1-3-5-12/h1-10,30H

Clé InChI

AEZPAUSGTAHLOQ-UHFFFAOYSA-N

Actions biochimiques/physiologiques

PHTPP is a selective estrogen receptor β (ERβ) full antagonist with 36-fold selectivity for ERβ over ERα. PHTPP has been used to distinguish the various activites of the two estrogen receptors. Estrogen can have opposite effects in some tumors expressing ERα compared to Erβ, with Erα enhancing and Erβ suppressing tumor cell growth. PHTPP, a selective ERβ antagonist, significantly enhanced cell growth in ovarian cancer cell lines SKOV3 and OV2008 that express both receptors.
PHTPP is also termed as 4-[2–phenyl-5,7–bis (trifluoromethyl) pyrazolo [1,5-a]-pyrimidin-3-yl] phenol (PHTPP). It blocks hypoglycemic augmentation of norepinephrine (NE) in the hypothalamic arcuate (ARH).

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301

Classification des risques

Acute Tox. 3 Oral

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Hindbrain estrogen receptor-beta antagonism normalizes reproductive and counter-regulatory hormone secretion in hypoglycemic steroid-primed ovariectomized female rats.
Briski KP and Shrestha PK
Neuroscience, 331, 62-71 (2016)
Masayo Hirao-Suzuki et al.
Molecular pharmacology, 95(3), 260-268 (2018-12-16)
Bisphenol A (BPA), recognized as an endocrine disruptor, is thought to exert its activity through a mechanism involving the activation of estrogen receptors (ERs) α/β However, a major problem is that very high concentrations of BPA are required (i.e., those
Cheng Xu et al.
Environmental science and pollution research international, 24(15), 13414-13423 (2017-04-08)
Perfluorooctane sulfonate (PFOS), an artificial fluorosurfactant and global contaminant, is used widely in various consumer products. In this study, we investigated the function of estrogen receptor β (ERβ) in PFOS-induced bile acid and cholesterol metabolism disorders and gut microbiome using
Chin-Hee Song et al.
PloS one, 14(8), e0221650-e0221650 (2019-08-24)
Several reports indicate crosstalk between the transcription factor nuclear factor erythroid 2-related factor 2 (Nrf2) and estrogen, which has a protective effect in colorectal cancer (CRC). The aim of this study was to investigate the role of Nrf2 signaling in
Qinghai Meng et al.
Journal of advanced research, 28, 149-164 (2020-12-29)
Excessive inflammation and the pyroptosis of vascular endothelial cells caused by estrogen deficiency is one cause of atherosclerosis in post-menopausal women. Because autophagy is highly regulated by estrogen, we hypothesized that estrogen can reduce vascular endothelial cell pyroptosis through estrogen
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