AG 555 (Tyrphostin AG 555) is a potent antiretroviral active molecule and a potent and specific EGFR inhibitor that blocks Cdk2 activation.

Physicochemical Properties

Molecular Formula	C19H18N2O3
Molecular Weight	322.364
Exact Mass	322.132
Elemental Analysis	C, 70.79; H, 5.63; N, 8.69; O, 14.89
CAS #	133550-34-2
Related CAS #	133550-34-2
PubChem CID	5328770
Appearance	Light yellow to yellow solid powder
Density	1.273g/cm3
Boiling Point	621.1ºC at 760mmHg
Flash Point	329.4ºC
Vapour Pressure	5.09E-16mmHg at 25°C
Index of Refraction	1.649
LogP	3.144
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	6
Heavy Atom Count	24
Complexity	488
Defined Atom Stereocenter Count	0
SMILES	O=C(/C(/C#N)=C(\[H])/C1C([H])=C([H])C(=C(C=1[H])O[H])O[H])N([H])C([H])([H])C([H])([H])C([H])([H])C1C([H])=C([H])C([H])=C([H])C=1[H]
InChi Key	GSQOBTOAOGXIFL-LFIBNONCSA-N
InChi Code	InChI=1S/C19H18N2O3/c20-13-16(11-15-8-9-17(22)18(23)12-15)19(24)21-10-4-7-14-5-2-1-3-6-14/h1-3,5-6,8-9,11-12,22-23H,4,7,10H2,(H,21,24)/b16-11+
Chemical Name	(E)-2-cyano-3-(3,4-dihydroxyphenyl)-N-(3-phenylpropyl)prop-2-enamide
Synonyms	AG555; AG 555; AG-555
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	EGFR (IC50 = 0.7 μM)
ln Vitro	AG 555 (100 μM) inhibits the virus's ability to integrate and synthesise viral proteins at both early and late stages of its life cycle[1]. Tyrphostins AG555 are very effective at stopping the growth of EGFR overexpressor cells because they block Cdk2 activation, which causes growth arrest of immortalized cells at G1-S and early S[2]. Tyrphostin AG 555 can bind phosphorylated Jun/ATF-2 at a novel intragenic regulatory sequence and activate the MAP kinase pathway to selectively suppress BPV-1 transcription[3].
Cell Assay	Cell Line: NIH/3T3 uninfected cells and NIH/3T3-Mo-MuLV chronically infected cells. Concentration: 100 μM. Incubation Time: 1 hour. Result: Inhibited Mo-MuLV proviral DNA integration.
References	[1]. Tyrphostin AG-555 inhibits early and late stages of Moloney murine leukemia virus replication cycle. International Journal of Oncology. 1997. [2]. Tyrphostin AG494 blocks Cdk2 activation Nir Osherov. FEBS Letters 410 (1997) 187-190. [3]. Tyrphostin AG 555 Inhibits Bovine Papillomavirus Transcription by Changing the Ratio between E2 Transactivator/Repressor Function. Vol. 278, No. 39, Issue of September 26, pp. 37306–37313, 2003.
Additional Infomation	Tyrphostin B46 is a potent inhibitor of epidermal growth factor receptor kinase autophosphorylation. (NCI)

Solubility Data

Solubility (In Vitro)

DMSO: ~64 mg/mL (~198.5 mM) Ethanol: ~64 mg/mL (~198.5 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (7.76 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.76 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.1021 mL	15.5106 mL	31.0212 mL
	5 mM	0.6204 mL	3.1021 mL	6.2042 mL
	10 mM	0.3102 mL	1.5511 mL	3.1021 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.