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T3434

Sigma-Aldrich

Tyrphostin AG 490

solid

Synonym(s):

2-Cyano-3-(3,4-dihydroxyphenyl)-N-(benzyl)-2-propenamide, 2-Cyano-3-(3,4-dihydroxyphenyl)-N-(phenylmethyl)-2-propenamide

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About This Item

Empirical Formula (Hill Notation):
C17H14N2O3
CAS Number:
133550-30-8
Molecular Weight:
294.30
MDL number:
MFCD00236452
UNSPSC Code:
12352200
PubChem Substance ID:
24278732
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

assay

≥98% (HPLC)

form

solid

color

yellow

solubility

DMSO: soluble 10 mg/ml, clear, yellow
ethanol: 5 mg/mL
H2O: insoluble

storage temp.

−20°C

SMILES string

Oc1ccc(cc1O)\C=C(/C#N)C(=O)NCc2ccccc2

InChI

1S/C17H14N2O3/c18-10-14(8-13-6-7-15(20)16(21)9-13)17(22)19-11-12-4-2-1-3-5-12/h1-9,20-21H,11H2,(H,19,22)/b14-8+

InChI key

TUCIOBMMDDOEMM-RIYZIHGNSA-N

Gene Information

human ... EGFR(1956) , ERBB2(2064) , IL2(3558) , JAK2(3717)

Application

Tyrphostin AG has been used to block IL-6 cytokine signaling to study its effects on glial cell reactivity5. AG 490 has also been used as a JAK2 inhibitor in human umbilical vein endothelial cells6.

Biochem/physiol Actions

Jak-2 protein tyrosine kinase (PTK) inhibitor. Inhibits interleukin 2 (IL-2) driven mitogenesis and triggers apoptosis of tumor cells in Sezary syndrome, a leukemic variant of cutaneous T cell lymphoma.

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.
This compound is featured on the JAKs page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Caution

Photosensitive

Preparation Note

Tyrphostin AG 490 is soluble in ethanol at 5 mg/ml and is insoluble in water. It is also soluble in DMSO at 10 mg/ml and yields a clear, yellow solution.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

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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K W Eriksen et al.
Leukemia, 15(5), 787-793 (2001-05-23)
Interleukin-2 (IL-2) is a growth factor which upon binding to high-affinity receptors (IL-2Ralphabetagamma) triggers mitogenesis in T cells. IL-2Ralpha expression is restricted to T cells which have recently encountered antigen, and in healthy individuals the majority (>95%) of peripheral T
Tao Geng et al.
Gene, 595(1), 69-76 (2016-10-04)
Innate immunity was critical in insects defensive system and able to be induced by Janus kinase/signal transducer and activator of transcription cascade transduction (JAK/STAT) signaling pathway. Currently, it had been identified many JAK/STAT signaling pathway-related genes in silkworm, but little
J Abe et al.
The Journal of biological chemistry, 274(30), 21003-21010 (1999-07-20)
Reactive oxygen species (ROS) activate Ras and the extracellular signal-regulated kinase (ERK) cascade. Because JAK2 is a critical mediator for Ras/Raf/ERK activation by several hormones, we examined the role of JAK2 in ROS signal events. H(2)O(2) stimulated JAK2 activity in
Mengqi Jiang et al.
Oxidative medicine and cellular longevity, 2021, 7385160-7385160 (2021-08-31)
Obesity is considered as a risk factor of osteoarthritis (OA), but the precise relationship is still poorly understood. Leptin, one of the most relevant factors secreted by adipose tissues, plays an important role in the pathogenesis of OA. Our aim
Pei-Ju Sung et al.
Cancer research, 79(14), 3651-3661 (2019-05-16)
Netrin-1 is upregulated in a large fraction of human neoplasms. In multiple animal models, interference with netrin-1 is associated with inhibition of tumor growth and metastasis. Although netrin-1 upregulation was initially described in cancer cells, we report here that in
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