Tyrphostin A1

Names

[ Name ]:
Tyrphostin A1

[Synonym ]:
AG 9
(4-Methoxybenzylidene)malonitrile
Tyrphostin A1
Tyrphostin 1
2-(4-Methoxybenzylidene)malononitrile
(4-Methoxybenzylidene)malononitrile
2-[(4-methoxyphenyl)methylidene]malononitrile
2-[(4-methoxyphenyl)methylene]malononitrile
p-methoxybenzylidenemalononitrile
(4-methoxyphenylmethylene)methane-1,1-dicarbonitrile
MFCD00019787

Biological Activity

[Description]:

Tyrphostin A1(AG9) inhibits CD40L-stimulated IL-12 production in macrophage cultures and antigen-induced generation of Th1 cells.IC50 value: Target: IL-12 production inhibitorAddition of increasing concentration of A1 resulted in a dose dependent decrease of IL-12 p40, with maximal inhibition (62.5%) occurring at a dose of 10 μM. tyrphostin A1 blocks CD40L-induced translocation of NF-κB to the nucleus, and reduces the activation of IL-12 p40 gene. In vivo therapy with A1 leads to decrease in generation of myelin basic protein (MBP) specific encephalitogenic T cells. In addition, treatment of SJL/J mice with A1 results in attenuation of experimental allergic encephalomyelitis (EAE) [1]. Tyrphostin A1 is a much weaker inhibitor of TK than other tyrphostins (IC50>1250 μM for epidermal growth factor receptor (EGFR) kinase), and therefore often used to differentiate TK-mediated effects of tyrphostins from other non-specific effects [2].

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> Interleukin Related

Research Areas >> Inflammation/Immunology

[References]

[1]. Du C, et al. Inhibition of CD40 signaling pathway by tyrphostin A1 reduces secretion of IL-12 in macrophage, Th1 cell development and experimental allergic encephalomyelitis in SJL/J mice. J Neuroimmunol. 2001 Mar 1;114(1-2):69-79.

[2]. Ogura T, et al. Activation of background membrane conductance by the tyrosine kinase inhibitor tyrphostin A23 and its inactive analog tyrphostin A1 in guinea pig ventricular myocytes. Jpn J Pharmacol. 2001 Nov;87(3):235-9.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.169g/cm3

[ Boiling Point ]:
352.4ºC at 760mmHg

[ Melting Point ]:
113-116ºC(lit.)

[ Molecular Formula ]:
C₁₁H₈N₂O

[ Molecular Weight ]:
184.19400

[ Flash Point ]:
148.8ºC

[ Exact Mass ]:
184.06400

[ PSA ]:
56.81000

[ LogP ]:
2.12576

[ Vapour Pressure ]:
3.85E-05mmHg at 25°C

[ Index of Refraction ]:
1.589

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
chloroform: soluble50mg/mL, clear, light yellow

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
20/21/22

[ Safety Phrases ]:
36/37

[ RIDADR ]:
UN 3439 6.1/PG III

[ WGK Germany ]:
3

[ Packaging Group ]:
III

[ HS Code ]:
2926909090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2926909090

[ Summary ]:
HS:2926909090 other nitrile-function compounds VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

Articles

Tyrphostins I: synthesis and biological activity of protein tyrosine kinase inhibitors.

J. Med. Chem. 32 , 2344, (1989)

A novel class of low molecular weight protein tyrosine kinase inhibitors is described. These compounds constitute a systematic series of molecules with a progressive increase in affinity toward the su...

Blocking of EGF-dependent cell proliferation by EGF receptor kinase inhibitors.

Science 242(4880) , 933-5, (1988)

A systematic series of low molecular weight protein tyrosine kinase inhibitors were synthesized; they had progressively increasing affinity over a 2500-fold range toward the substrate site of epiderma...

Human fibroblast growth factor receptor 1 is a co-receptor for infection by adeno-associated virus 2.

Nat. Med. 5(1) , 71-7, (1999)

Adeno-associated virus 2 (AAV)-based vectors have gained attention as a potentially useful alternative to the more commonly used retroviral and adenoviral vectors for human gene therapy. Although AAV ...

Related Compounds

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