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Key Documents

SML0232

Sigma-Aldrich

TPSF

≥98% (HPLC)

Synonym(s):

8-[[4-(4-Fluorophenyl)-4-oxobutyl]thio]-1,3,6,9-tetrahydro-1,3-dimethyl-6-thioxo-2H-purin-2-one

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About This Item

Empirical Formula (Hill Notation):
C17H17FN4O2S2
CAS Number:
6505-98-2
Molecular Weight:
392.47
UNSPSC Code:
51111800
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

light yellow to yellow

solubility

DMSO: ≥10 mg/mL at warmed to 60 °C

storage temp.

2-8°C

InChI

1S/C17H17FN4O2S2/c1-21-14-13(15(25)22(2)17(21)24)19-16(20-14)26-9-3-4-12(23)10-5-7-11(18)8-6-10/h5-8H,3-4,9H2,1-2H3,(H,19,20)

InChI key

BEBDNAPSDUYCHM-UHFFFAOYSA-N

Biochem/physiol Actions

TPSF is a noncompetitive, potent inhibitor of estrogen receptor α, that does not compete with estrogen for binding to Erα. The compound has low toxicity and selectively targets E2-ERα-dependent cell growth. TPSF is effective in cells that become tamoxifen-resistant. It appears that down-regulation of ERα by TPSF is at list partially dependent to enhancement of proteasome-dependent degradation of ERα.
TPSF is a potent inhibitor of estrogen receptor α, that does not compete with estrogen for binding to Erα

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
012M4613V

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Chengjian Mao et al.
The Journal of biological chemistry, 283(19), 12819-12830 (2008-03-14)
Estrogen receptor alpha (ERalpha) plays an important role in several human cancers. Most current ERalpha antagonists bind in the receptor ligand binding pocket and compete for binding with estrogenic ligands. Instead of the traditional approach of targeting estrogen binding to
Nicole M Kretzer et al.
The Journal of biological chemistry, 285(53), 41863-41873 (2010-11-03)
The mechanisms responsible for 17β-estradiol (E(2))-stimulated breast cancer growth and development of resistance to tamoxifen and other estrogen receptor α (ERα) antagonists are not fully understood. We describe a new tool for dissecting ERα action in breast cancer, p-fluoro-4-(1,2,3,6,-tetrahydro-1,3-dimethyl-2-oxo-6-thionpurin-8-ylthio) (TPSF)

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