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Key Documents

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T182

Sigma-Aldrich

Tyrphostin A9

solid

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C18H22N2O
Número de CAS:
10537-47-0
Peso molecular:
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

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Oral

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
Tyrphostins as molecular tools and potential antiproliferative drugs.
A Levitzki et al.
Trends in pharmacological sciences, 12(5), 171-174 (1991-05-01)
Yan-Jun Xu et al.
Journal of cellular and molecular medicine, 12(3), 942-954 (2008-05-23)
Although lysophosphatidic acid (LPA) is known to increase intracellularfree calcium concentration ([Ca(2+)](i)) in different cell types, the effect of LPA on the skeletal muscle cells is not known. The present study was therefore undertaken to examine the effect of LPA
G E Bilder et al.
The American journal of physiology, 260(4 Pt 1), C721-C730 (1991-04-01)
Tyrphostins are low-molecular-weight synthetic inhibitors of protein tyrosine kinase, which block cell proliferation. Since platelet-derived growth factor (PDGF) is thought to figure prominently in disorders of vascular smooth muscle cells (VSMC), such as atherosclerosis, hypertension, and restenosis, we examined whether
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