AG-1024

Names

[ Name ]:
AG-1024

[Synonym ]:
(3-bromo-5-tert-butyl-4-hydroxybenzylidene)malononitrile
3-bromo-5-t-butyl-4-hydroxy-benzylidene-malononitrile
propanedinitrile, [[3-bromo-5-(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-
3-Bromo-5-t-butyl-4-hydroxy-benzylidenemalonitrile
2-(3-bromo-5-tert-butyl-4-hydroxybenzylidene)malononitrile
[3-Bromo-4-hydroxy-5-(2-methyl-2-propanyl)benzylidene]malononitrile
2-[(3-bromo-4-hydroxy-5-tert-butyl-phenyl)methylidene]propanedinitrile
Propanedinitrile, 2-[[3-bromo-5-(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-
Tyrphostin AG 1024
ag1024
propanedinitrile,[[3-bromo-5-(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]
AG-1024

Biological Activity

[Description]:

AG-1024 (Tyrphostin) inhibits IGF-1R autophosphorylation with IC50 of 7 μM, less potent to IR with IC50 of 57 μM.IC50 value: 7 uM (IGF-1R autophosphorylation); 57 uM (IR) [1]Target: IGF-1R; IRin vitro: AG-1024 blocks the IGF-1 receptor and IR autophosphorylation with IC50 of 7 μM and 57 μM, respectively. AG-1024 also inhibits the receptor tyrosine kinase activity towards exogenous substrates (TKA) with IC50 values of 18 μM and 80 μM, respectively [1]. Human breast cancer cell line MCF-7 exposure to Tyrphostin AG 1024 inhibited proliferation and induced apoptosis in a time-dependent manner, and the degree of growth inhibition for IC20 plus irradiation (4 Gy) was up to 50% compared to the control. Examination of Tyrphostin AG 1024 effects on radiation response demonstrated a marked enhancement in radiosensitivity and amplification of radiation-induced apoptosis [2]. AG-1024 significantly inhibits melanoma cell proliferation with an IC50 of <50 nM in the absence of serum, by blocking MAPK/ERK2 signaling, subsequently rapidly inducing pRb dephosphorylation and activation, and eventually the formation of growth suppressive pRb-E2F complexes [3].in vivo: Administration of AG-1024 at a dose of 30 μg for 10 days significantly inhibits the tumor growth of Ba/F3-p210 xenograft in mice [4].

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Protein Tyrosine Kinase/RTK >> IGF-1R

Research Areas >> Cancer

[References]

[1]. Párrizas M, et al. Specific inhibition of insulin-like growth factor-1 and insulin receptor tyrosine kinase activity and biological function by tyrphostins. Endocrinology. 1997 Apr;138(4):1427-33.

[2]. Wen B, et al. Tyrphostin AG 1024 modulates radiosensitivity in human breast cancer cells. Br J Cancer. 2001 Dec 14;85(12):2017-21.

[3]. von Willebrand M, et al. The tyrphostin AG1024 accelerates the degradation of phosphorylated forms of retinoblastoma protein (pRb) and restores pRb tumor suppressive function in melanoma cells. Cancer Res. 2003 Mar 15;63(6):1420-9.

[4]. Deutsch E, et al. Tyrosine kinase inhibitor AG1024 exerts antileukaemic effects on STI571-resistant Bcr-Abl expressing cells and decreases AKT phosphorylation. Br J Cancer. 2004 Nov 1;91(9):1735-41.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
379.8±42.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₄H₁₃BrN₂O

[ Molecular Weight ]:
305.170

[ Flash Point ]:
183.5±27.9 °C

[ Exact Mass ]:
304.021118

[ PSA ]:
67.81000

[ LogP ]:
4.18

[ Appearance of Characters ]:
solid | yellow

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.609

[ Storage condition ]:
−20°C

[ Water Solubility ]:
DMSO: soluble

Safety Information

[ Safety Phrases ]:
22-24/25

[ WGK Germany ]:
3

[ HS Code ]:
2926909090

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%