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Key Documents

SML3119

Sigma-Aldrich

SHP1 Inhibitor, TPI-1

≥98% (HPLC)

Synonym(s):

2-(2,5-Dichloro-phenyl)-[1,4]benzoquinone; 2-(2?,5?-Dichlorophenyl)-1,4-benzoquinone, 2-(2,5-Dichlorophenyl)-2,5-cyclohexadiene-1,4-dione, TPI 1, TPI-1, TPI1

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About This Item

Empirical Formula (Hill Notation):
C12H6Cl2O2
CAS Number:
Molecular Weight:
253.08
MDL number:
UNSPSC Code:
12352200

Quality Level

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C1C=CC(C(C2=C(C=CC(Cl)=C2)Cl)=C1)=O

InChI

1S/C12H6Cl2O2/c13-7-1-3-11(14)9(5-7)10-6-8(15)2-4-12(10)16/h1-6H

InChI key

ZKHFYORNAYYOTM-UHFFFAOYSA-N

Biochem/physiol Actions

TPI-1 is an orally bioavailable, noncytotoxic benzoquinone compound that acts as a potent irreversible inhibitor of SHP-1 (Src homology region 2 domain-containing phosphatase 1) catalytic domain (IC50 ~ 40 nM or 0.01 μg/ml) with selectivity over SHP-2 (IC50 ~ 0.1 μg/ml), MKP1 (IC50 > 1 μg/ml) and CD45. TPI-1 potently induces mouse and human primary IFN-g+ cells both in vitro and in vivo. Effectively inhibits B16 melanoma tumors in mice (1 or 3 mg/kg, s.c., daily) and prolong the survival. TPI-1 is shown to be 50-fold more effective than sodium stibogluconate in cell-based assays and may non-specifically react with cysteine residues.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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