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Merck
CN

T5202

TPBM

≥98% (HPLC), solid

Synonym(s):

8-Benzylsulfanylmethyl-1,3-dimethyl-3,7-dihydro-purine-2,6-dione, 8-[(Benzylthio)methyl]theophylline, Theophylline, 8-[(benzylthio)methyl]

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About This Item

Empirical Formula (Hill Notation):
C15H16N4O2S
CAS Number:
Molecular Weight:
316.38
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
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InChI

1S/C15H16N4O2S/c1-18-13-12(14(20)19(2)15(18)21)16-11(17-13)9-22-8-10-6-4-3-5-7-10/h3-7H,8-9H2,1-2H3,(H,16,17)

SMILES string

CN1C(=O)N(C)c2nc(CSCc3ccccc3)[nH]c2C1=O

InChI key

FEHAMBYTUPDFJE-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

solid

color

white to off-white

solubility

DMSO: >5 mg/mL

Quality Level

Biochem/physiol Actions

TPBM is a potent inhibitor of estrogen receptor α via blocking ERα binding to consensus estrogen response element (cERE) DNA.
TPBM is a potent inhibitor of estrogen receptor α via blocking ERα binding to consensus estrogen response element (cERE) DNA. Estrogen receptor α (ERα) plays an important role in several human cancers. Current ERα antagonists bind in the receptor ligand binding pocket and compete for binding with estrogenic ligands. TPBM instead inhibits ERα via binding to consensus estrogen response element (cERE) DNA. TPBM is not toxic to cells and does not effect estrogen-independent cell growth. TPBM does not act by chelating the zinc in ERs zinc fingers and differs from known ERα inhibitors.

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.

Preparation Note

TPBM is soluble in DMSO at a concentration that is greater than 5 mg/ml.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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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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