AG-556 | CAS# 133550-41-1 | EGFR kinase inhibitor

MedKoo Cat#: 574551 | Name: AG-556

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

AG-556 is an epidermal growth factor receptor (EGFR) kinase inhibitor.

Chemical Structure

AG-556

CAS#133550-41-1

Theoretical Analysis

MedKoo Cat#: 574551

Name: AG-556

CAS#: 133550-41-1

Chemical Formula: C20H20N2O3

Exact Mass: 336.1474

Molecular Weight: 336.39

Elemental Analysis: C, 71.41; H, 5.99; N, 8.33; O, 14.27

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 450.00	2 Weeks
250mg	USD 850.00	2 Weeks

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Related CAS #

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Synonym

AG-556, AG556, AG 556, Tyrphostin AG 556

IUPAC/Chemical Name

(E)-2-Cyano-3-(3,4-dihydroxyphenyl)-N-(4-phenylbutyl)-2-propenamide

InChi Key

GWCNJMUSWLTSCW-SFQUDFHCSA-N

InChi Code

InChI=1S/C20H20N2O3/c21-14-17(12-16-9-10-18(23)19(24)13-16)20(25)22-11-5-4-8-15-6-2-1-3-7-15/h1-3,6-7,9-10,12-13,23-24H,4-5,8,11H2,(H,22,25)/b17-12+

SMILES Code

OC1=C(O)C=C(\C=C(/C#N)C(=O)NCCCCC2=CC=CC=C2)C=C1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

An EGFR inhibitor.

In vitro activity:

To determine whether EGFR tyrosine kinase is involved in genistein‐induced increase of BK current, AG556, a tyrphostin which selectively inhibited EGFR tyrosine kinase, was tested in BK‐HEK 293 cells. AG556 (10 μM) reversibly increased the voltage‐dependent BK current (Fig. 3A), and the effect was antagonized by co‐application of 1 mM orthovanadate (Fig. 3B). The mean percent value of BK current at +70 mV was increased to 151.8% of control by AG556, and the increase was reversed by washout or application of orthovanadate (Fig. 3C). These results indicate that EGFR tyrosine kinase inhibition may contribute to the increase of BK current by AG556 and genistein. Reference: J Cell Mol Med. 2017 Sep; 21(9): 1826–1834. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5571560/

In vivo activity:

Rat testis tissues from all groups were examined under light microscopy during analysis of histopathological findings. Johnsen MTBS scores for both testes in all groups are shown in Table 1. Distribution of Johnsen's scores for the left testis are shown in Fig. 2. On the basis of these results, distinct histopathological injury developed in association with I/R reperfusion when T/D was applied (group 1 vs. group 2; p = 0.004). Group 4 (DMSO + AG556) and group 3 exhibited a protective effect against I/R injury compared with group 2 (group 2 vs. group 4, group 2 vs. group 3, p = 0.002). Although group 4 and group 3 showed significant difference compared with group 1 (group 4 vs. group 1, p < 0.05; group 3 vs. group 1, p < 0.05), AG 556 had a significant superior effect compared with DMSO (group 4 vs. group 3, p = 0.004). Reference: J Pediatr Urol. 2014 Apr;10(2):223-9. https://pubmed.ncbi.nlm.nih.gov/24070787/

	Solvent	mg/mL	mM
Solubility
	DMSO	30.0	89.18
	DMF	30.0	89.18

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 336.39 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Wang Y, Sun HY, Liu YG, Song Z, She G, Xiao GS, Wang Y, Li GR, Deng XL. Tyrphostin AG556 increases the activity of large conductance Ca2+ -activated K+ channels by inhibiting epidermal growth factor receptor tyrosine kinase. J Cell Mol Med. 2017 Sep;21(9):1826-1834. doi: 10.1111/jcmm.13103. Epub 2017 Mar 14. PMID: 28294531; PMCID: PMC5571560. 2. Karaguzel E, Sivrikaya A, Mentese A, Yulug E, Turkmen S, Kutlu O, Guler Y, Us D, Turedi S, Alver A, Kazaz IO. Investigation of tyrphostin AG 556 for testicular torsion-induced ischemia reperfusion injury in rat. J Pediatr Urol. 2014 Apr;10(2):223-9. doi: 10.1016/j.jpurol.2013.08.007. Epub 2013 Sep 11. PMID: 24070787. 3. Feng M, Xiang JZ, Ming ZY, Fu Q, Ma R, Zhang QF, Dun YY, Yang L, Liu H. Activation of epidermal growth factor receptor mediates reperfusion arrhythmias in anaesthetized rats. Cardiovasc Res. 2012 Jan 1;93(1):60-8. doi: 10.1093/cvr/cvr281. Epub 2011 Oct 25. PMID: 22028338.

In vitro protocol:

In vivo protocol:

1. Karaguzel E, Sivrikaya A, Mentese A, Yulug E, Turkmen S, Kutlu O, Guler Y, Us D, Turedi S, Alver A, Kazaz IO. Investigation of tyrphostin AG 556 for testicular torsion-induced ischemia reperfusion injury in rat. J Pediatr Urol. 2014 Apr;10(2):223-9. doi: 10.1016/j.jpurol.2013.08.007. Epub 2013 Sep 11. PMID: 24070787. 2. Feng M, Xiang JZ, Ming ZY, Fu Q, Ma R, Zhang QF, Dun YY, Yang L, Liu H. Activation of epidermal growth factor receptor mediates reperfusion arrhythmias in anaesthetized rats. Cardiovasc Res. 2012 Jan 1;93(1):60-8. doi: 10.1093/cvr/cvr281. Epub 2011 Oct 25. PMID: 22028338.

1: Karaguzel E, Sivrikaya A, Mentese A, Yulug E, Turkmen S, Kutlu O, Guler Y, Us D, Turedi S, Alver A, Kazaz IO. Investigation of tyrphostin AG 556 for testicular torsion-induced ischemia reperfusion injury in rat. J Pediatr Urol. 2014 Apr;10(2):223-9. doi: 10.1016/j.jpurol.2013.08.007. Epub 2013 Sep 11. PMID: 24070787. 2: George J, Biner S, Keren P, Barshack I, Goldberg I, Sherez J, Levitzki A, Keren G, Roth A. Tyrphostin AG-556 reduces myocardial infarct size and improves cardiac performance in the rat. Exp Mol Pathol. 2003 Jun;74(3):314-8. doi: 10.1016/s0014-4800(03)00022-4. PMID: 12782020. 3: Sevransky JE, Shaked G, Novogrodsky A, Levitzki A, Gazit A, Hoffman A, Elin RJ, Quezado ZM, Freeman BD, Eichacker PQ, Danner RL, Banks SM, Bacher J, Thomas ML 3rd, Natanson C. Tyrphostin AG 556 improves survival and reduces multiorgan failure in canine Escherichia coli peritonitis. J Clin Invest. 1997 Apr 15;99(8):1966-73. doi: 10.1172/JCI119364. PMID: 9109441; PMCID: PMC508021. 4: George J, Barshack I, Keren P, Gazit A, Levitzki A, Keren G, Roth A. The effect of tyrphostin AG-556 on intimal thickening in a mouse model of arterial injury. Exp Mol Pathol. 2005 Jun;78(3):233-8. doi: 10.1016/j.yexmp.2004.11.003. Epub 2005 Feb 8. PMID: 15924877. 5: George J, Barshack I, Goldberg I, Keren P, Gazit A, Levitzki A, Keren G, Roth A. The effect of early and late treatment with the tyrphostin AG-556 on the progression of experimental autoimmune myocarditis. Exp Mol Pathol. 2004 Jun;76(3):234-41. doi: 10.1016/j.yexmp.2003.12.011. PMID: 15126106. 6: Usul H, Cakir E, Cobanoglu U, Alver A, Peksoylu B, Topbas M, Baykal S. The effects of tyrphostine Ag 556 on experimental spinal cord ischemia reperfusion injury. Surg Neurol. 2004 Jan;61(1):45-54; discussion 54. doi: 10.1016/s0090-3019(03)00539-1. PMID: 14706378. 7: Brenner T, Poradosu E, Soffer D, Sicsic C, Gazit A, Levitzki A. Suppression of experimental autoimmune encephalomyelitis by tyrphostin AG-556. Exp Neurol. 1998 Dec;154(2):489-98. doi: 10.1006/exnr.1998.6971. PMID: 9878184. 8: Chiang CE, Luk HN, Wang TM, Sheu JR, Ding PY. Genistein and tyrphostin AG 556 block the action potential shortening in septic shock. Zhonghua Yi Xue Za Zhi (Taipei). 2002 Dec;65(12):570-9. PMID: 12636202. 9: Altavilla D, Squadrito F, Campo GM, Saitta A, Squadrito G, Quartarone C, Deodato B, Arlotta M, Ferlito M, Minutoli L, Tringali M, Urna G, Sardella A, Caputi AP. The reduction of myocardial damage and leukocyte polymorphonuclear accumulation following coronary artery occlusion by the tyrosine kinase inhibitor tyrphostin AG 556. Life Sci. 2000 Oct 13;67(21):2615-29. doi: 10.1016/s0024-3205(00)00845-6. PMID: 11104363. 10: Alhan E, Cicek R, Erçin C, Orem A, Vanizor B, Cinel A. Effects of the tyrosine kinase inhibitor tyrphostin AG 556 on acute necrotising pancreatitis in rats. Eur J Surg. 2002;168(10):557-62. PMID: 12666696. 11: Ogura S, Umegaki O, Genovese F, Fernando LP, Cochran JB, Romeo CM, Cook JA. Protective effect of tyrphostin AG-556 on shock induced by endotoxin or gram positive bacteria. Shock. 1999 Aug;12(2):105-10. doi: 10.1097/00024382-199908000-00003. PMID: 10446890. 12: Wu W, Sun HY, Deng XL, Li GR. EGFR tyrosine kinase regulates human small- conductance Ca2+-activated K+ (hSKCa1) channels expressed in HEK-293 cells. Biochem J. 2013 May 15;452(1):121-9. doi: 10.1042/BJ20121324. PMID: 23496660. 13: Balachandra S, Genovese T, Mazzon E, Di Paola R, Thiemerman C, Siriwardena AK, Cuzzocrea S. Inhibition of tyrosine-kinase-mediated cellular signaling by tyrphostins AG 126 and AG556 modulates murine experimental acute pancreatitis. Surgery. 2005 Nov;138(5):913-23. doi: 10.1016/j.surg.2005.05.021. PMID: 16291393. 14: Jarrar D, Wang P, Song GY, Cioffi WG, Bland KI, Chaudry IH. Inhibition of tyrosine kinase signaling after trauma-hemorrhage: a novel approach for improving organ function and decreasing susceptibility to subsequent sepsis. Ann Surg. 2000 Mar;231(3):399-407. doi: 10.1097/00000658-200003000-00013. PMID: 10714633; PMCID: PMC1421011. 15: Lockhart BP, Cressey KC, Lepagnol JM. Suppression of nitric oxide formation by tyrosine kinase inhibitors in murine N9 microglia. Br J Pharmacol. 1998 Mar;123(5):879-89. doi: 10.1038/sj.bjp.0701664. PMID: 9535016; PMCID: PMC1565224. 16: Du XL, Gao Z, Lau CP, Chiu SW, Tse HF, Baumgarten CM, Li GR. Differential effects of tyrosine kinase inhibitors on volume-sensitive chloride current in human atrial myocytes: evidence for dual regulation by Src and EGFR kinases. J Gen Physiol. 2004 Apr;123(4):427-39. doi: 10.1085/jgp.200409013. Epub 2004 Mar 15. PMID: 15024039; PMCID: PMC2217456. 17: Dong MQ, Sun HY, Tang Q, Tse HF, Lau CP, Li GR. Regulation of human cardiac KCNQ1/KCNE1 channel by epidermal growth factor receptor kinase. Biochim Biophys Acta. 2010 May;1798(5):995-1001. doi: 10.1016/j.bbamem.2010.01.010. Epub 2010 Jan 18. PMID: 20085748. 18: Wu W, Dong MQ, Wu XG, Sun HY, Tse HF, Lau CP, Li GR. Human ether-à-go-go gene potassium channels are regulated by EGFR tyrosine kinase. Biochim Biophys Acta. 2012 Feb;1823(2):282-9. doi: 10.1016/j.bbamcr.2011.10.010. Epub 2011 Oct 28. PMID: 22061963. 19: Feng M, Xiang JZ, Ming ZY, Fu Q, Ma R, Zhang QF, Dun YY, Yang L, Liu H. Activation of epidermal growth factor receptor mediates reperfusion arrhythmias in anaesthetized rats. Cardiovasc Res. 2012 Jan 1;93(1):60-8. doi: 10.1093/cvr/cvr281. Epub 2011 Oct 25. PMID: 22028338. 20: Kang W, Saito H, Fukatsu K, Hidemura A, Koyama H, Sakamoto T, Maekawa K. Effects of tyrosine kinase signaling inhibition on survival after cecal ligation and puncture in diet-restricted mice. JPEN J Parenter Enteral Nutr. 2001 Nov- Dec;25(6):291-7; discussion 298. doi: 10.1177/0148607101025006291. PMID: 11688932.