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T182

Sigma-Aldrich

Tyrphostin A9

solid

Synonym(s):

Malonoben, [[3,5-bis(1,1-Dimethylethyl)-4-hydroxyphenyl]methylene]propanedinitrile

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About This Item

Empirical Formula (Hill Notation):
C18H22N2O
CAS Number:
10537-47-0
Molecular Weight:
282.38
MDL number:
MFCD00209853
UNSPSC Code:
51111800
PubChem Substance ID:
24278069
NACRES:
NA.77

biological source

synthetic (organic)

Assay

≥98% (HPLC)

form

solid

color

yellow

mp

139-140 °C

solubility

ethanol: 20 mg/mL
DMSO: <25 mg/mL
H2O: insoluble

SMILES string

CC(C)(C)c1cc(\C=C(\C#N)C#N)cc(c1O)C(C)(C)C

InChI

1S/C18H22N2O/c1-17(2,3)14-8-12(7-13(10-19)11-20)9-15(16(14)21)18(4,5)6/h7-9,21H,1-6H3

InChI key

MZOPWQKISXCCTP-UHFFFAOYSA-N

Gene Information

human ... EGFR(1956) , ORAI1(84876) , PDGFRA(5156) , PDGFRB(5159)
mouse ... Eef2k(13631) , Prkaca(18747) , Prkca(18750) , Src(20779)

Application

Tyrphostin A9 can be used for inhibiting tyrosine kinase functions in C2C12 cells. It has also been used to disrupt membrane potential in mammalian cells.

Biochem/physiol Actions

Tyrphostin A9 is a PDGF receptor tyrosine kinase inhibitor that can induce apoptosis in cancer cells, inhibit the growth of vascular smooth cells and block calcium release-dependent phosphorylations.

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Preparation Note

Tyrphostin A9 is soluble in ethanol at 20 mg/ml, in DMSO at a concentration less than 25 mg/ml. It is insoluble in water.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301 + H311

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Oral

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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J Thyberg
European journal of cell biology, 76(1), 33-42 (1998-07-03)
To proliferate, vascular smooth muscle cells first convert from a contractile to a synthetic phenotype. Earlier studies indicate that this process is supported by fibronectin and accelerated by platelet-derived growth factor (PDGF). Here, the mechanisms in this transition were further
So Jung Park et al.
Biochemical and biophysical research communications, 408(3), 465-470 (2011-04-30)
Mitochondria dynamics controls not only their morphology but also functions of mitochondria. Therefore, an imbalance of the dynamics eventually leads to mitochondria disruption and cell death. To identify specific regulators of mitochondria dynamics, we screened a bioactive chemical compound library
Naveen Kumar et al.
Journal of virology, 85(6), 2818-2827 (2011-01-07)
Host signaling pathways play important roles in the replication of influenza virus, but their functional effects remain to be characterized at the molecular level. Here we identify two receptor tyrosine kinase inhibitors (RTKIs) of the tyrphostin class that exhibit robust
Naveen Kumar et al.
Antimicrobial agents and chemotherapy, 55(12), 5553-5559 (2011-09-21)
We have previously reported that two receptor tyrosine kinase inhibitors (RTKIs), called AG879 and tyrphostin A9 (A9), can each block the replication of influenza A virus in cultured cells. In this study, we further characterized the in vitro antiviral efficacies
Manuel Fischer et al.
Molecular biology of the cell, 24(14), 2160-2170 (2013-05-17)
Oxidation of cysteine residues to disulfides drives import of many proteins into the intermembrane space of mitochondria. Recent studies in yeast unraveled the basic principles of mitochondrial protein oxidation, but the kinetics under physiological conditions is unknown. We developed assays
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