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| Product Name: | AG 490 | | Synonyms: | AG 490;TYRPHOSTIN AG 490;AG490;ZINC02557947;AG-490 (TYRPHOSTIN B42);CS-316;AG 490 - CAS 133550-30-8 - Calbiochem;2-CYANO-3-[3,4-DIHYDROXYPHENYL]-N-[PHENYLMETHYL]-2-PROPENAMIDE;N-BENZYL-3,4-DIHYDROXY-ALPHA-CYANOCINNAMIDE;N-BENZYL-3,4-DIHYDROXY-BENZYLIDENECYANOACETAMIDE;TYROPHOSTIN AG490;TYRPHOSTIN AG 490 | | CAS: | 133550-30-8 | | MF: | C17H14N2O3 | | MW: | 294.3 | | EINECS: | | | Product Categories: | Intracellular Signaling;Inhibitors;Protein Kinase;Inhibitor | | Mol File: | 133550-30-8.mol |  |
| | AG 490 Chemical Properties |
| Melting point | 215°C(lit.) | | Boiling point | 615.2±55.0 °C(Predicted) | | density | 1.337 | | storage temp. | -20°C | | solubility | ethanol: 5 mg/mL | | form | solid | | pka | 8.75±0.10(Predicted) | | color | yellow | | Stability: | Stable for 1 year from date of purchase as supplied. Solutions in DMSO, DMF, or ethanol may be stored at -20°C for up to 1 month. | | InChIKey | TUCIOBMMDDOEMM-ZSOIEALJSA-N |
| Hazard Codes | Xi,N,T | | Risk Statements | 36/37/38-50-25 | | Safety Statements | 26-36-61-45 | | RIDADR | UN2811 - class 6.1 - PG 3 - EHS - Toxic solids, organic, n.o.s., HI: all | | WGK Germany | 1 | | RTECS | UC6316197 | | HazardClass | 6.1 | | PackingGroup | III | | HS Code | 29269090 |
| | AG 490 Usage And Synthesis |
| Description | AG-490 (133550-30-8) is a potent inhibitor of the JAK2 tyrosine kinase. In acute lymphoblastic leukemia (ALL) cells, which abundantly express JAK-2, AG-490 dose-dependently blocked cell growth, induced apoptosis and inhibited DNA synthesis. Blocks the growth of all pre-B ALL cells with no effect on normal B or T cells. Does not significantly inhibit other kinases such as Lck, Lyn, Btk, Syk and Src. Reduces liver injury in LPS-induced shock.3 AG-490 is a useful tool for exploring the role of JAK2/STAT3 pathway in physiologic processes.4 | | Uses | AG 490 is a potent epidermal growth factor receptor kinase autophosphorylation inhibitor with an IC50 of 100 nM and 56.8 μM for EGFR and JAK, respectively. | | Uses | 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. | | Definition | ChEBI: Tyrphostin B42 is a monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2E)-2-cyano-3-(3,4-dihydroxyphenyl)prop-2-enoic acid with the amino group of benzylamine. It has a role as an EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor, an antioxidant, a STAT3 inhibitor, an anti-inflammatory agent, an apoptosis inducer and a geroprotector. It is an enamide, a monocarboxylic acid amide, a nitrile, a member of catechols and a secondary carboxamide. | | Biological Activity | Selective inhibitor of EGF receptor tyrosine kinase (IC 50 values are 2 and 13.5 μ M for EGFR and ErbB2 respectively). Inhibitor of JAK2, JAK3/STAT, JAK3/AP-1 and JAK3/MAPK pathways and potently inhibits cytokine-independent cell growth in vitro and tumor cell invasion in vivo . | | 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. | | storage | Room temperature | | References | References/Citations
1) Wang et al. (1999), JAK3, STAT, and MAPK signaling pathways as novel molecular targets for the tyrphostin AG-490 regulation of IL-2-mediated T cell response; J. Immunol. 162 3897
2) Meydan et al. (1996), Inhibition of acute lymphoblastic leukaemia by Jak-2 inhibitor; Nature, 379 645
3) Gyurkovska and Ivanovaska (2015), Tyrosine kinase inhibitor tyrphostin AG490 reduces liver injury in LPS-induced shock; Eur. J. Pharmacol., 751 118
4) Wu et al. (2015), ROS generated during early reperfusion contribute to intermittent hypobaric hypoxia-afforded cardioprotection against postischemia-induced Ca(+2) overload and contractile dysfunction via the JAK2/STAT3 pathway; J. Mol. Cell. Cardiol., 81 150 |
| | AG 490 Preparation Products And Raw materials |
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