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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

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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)

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This Item
SML1065SML1193658401
Tyrphostin AG 490 solid

Sigma-Aldrich

T3434

Tyrphostin AG 490

TR100 ≥98% (HPLC)

Sigma-Aldrich

SML1065

TR100

SU1498 ≥98% (HPLC)

Sigma-Aldrich

SML1193

SU1498

AG 490 A cell-permeable, reversible, substrate competitive, and potent inhibitor of epidermal growth factor receptor kinase autophosphorylation (IC50 = 100 nM).

Sigma-Aldrich

658401

AG 490

form

solid

form

powder

form

powder

form

solid

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

100

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

solubility

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

solubility

DMSO: 5 mg/mL, clear (warmed)

solubility

DMSO: 10 mg/mL, clear

solubility

DMSO: 100 mg/mL

color

yellow

color

white to beige

color

white to beige

color

yellow

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.

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.

Disclaimer

Photosensitive

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

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Certificates of Analysis (COA)

Lot/Batch Number
SLCP3805
SLCP6656
SLCB7237
SLBX7052
SLBV2800

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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
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
Zaniar Ghazizadeh et al.
iScience, 25(4), 104153-104153 (2022-04-19)
The sinoatrial node (SAN) is the primary pacemaker of the heart. The human SAN is poorly understood due to limited primary tissue access and limitations in robust in vitro derivation methods. We developed a dual SHOX2:GFP; MYH6:mCherry knockin human embryonic stem
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