Tyrphostin 51

• CAT Number: I037674
• CAS Number: 126433-07-6
• Molecular Formula: C13H8N4O3
• Molecular Weight: 268.232
• Purity: 98%
• Synonyms: Tyrphostin 51; Tyrphostin A 51; Tyrphostin A-51; Tyrphostin A51.
• Target: Protein Tyrosine Kinase/RTK
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: 2-Amino-1,1,3-tricyano-4-(3',4',5'-trihydroxyphenyl)butadiene
• InChI: InChI=1S/C13H8N4O3/c14-4-8(12(17)9(5-15)6-16)1-7-2-10(18)13(20)11(19)3-7/h1-3,18-20H,17H2/b8-1+
• InChIKey: JKNOYWVMHPMBEL-UNXLUWIOSA-N
• SMILES: c1c(cc(c(c1O)O)O)/C=C(C#N)/C(=C(C#N)C#N)N

Tyrphostin 51 is a potent inhibitor of EGFR (EGF receptor) kinase activity

Reference

1: Chung FY, Song HJ, Park SY, Jang HS, Kim DS, Sim SS, Sohn UD. Signaling mechanisms of sphingosine 1-phosphate-induced ERK1/2 activation in cultured feline esophageal smooth muscle cells. Arch Pharm Res. 2008 Nov;31(11):1437-45. doi: 10.1007/s12272-001-2128-8. Epub 2008 Nov 21. PubMed PMID: 19023540.
2: Ikeda M, Gunji Y, Sonoda H, Oshikawa S, Shimono M, Horie A, Ito K, Yamasaki S. Inhibitory effect of tyrphostin 47 on Shiga toxin-induced cell death. Eur J Pharmacol. 2006 Sep 28;546(1-3):36-9. Epub 2006 Jul 26. PubMed PMID: 16919262.
3: Lee TS, Song HJ, Jeong JH, Min YS, Shin CY, Sohn UD. IL-1beta activates p44/42 and p38 mitogen-activated protein kinases via different pathways in cat esophageal smooth muscle cells. World J Gastroenterol. 2006 Feb 7;12(5):716-22. PubMed PMID: 16521184; PubMed Central PMCID: PMC4066121.
4: Khan SM, Oliver RH, Yeh J. Epidermal growth factor receptor inhibition by tyrphostin 51 induces apoptosis in luteinized granulosa cells. J Clin Endocrinol Metab. 2005 Jan;90(1):469-73. Epub 2004 Oct 19. PubMed PMID: 15494464.
5: Song HJ, Lee TS, Jeong JH, Min YS, Shin CY, Sohn UD. Hydrogen peroxide-induced extracellular signal-regulated kinase activation in cultured feline ileal smooth muscle cells. J Pharmacol Exp Ther. 2005 Jan;312(1):391-8. Epub 2004 Aug 24. PubMed PMID: 15328380.
6: Chao JC, Peng WL, Chen SH. Effects of epidermal growth factor and its signal transduction inhibitors on apoptosis in human colorectal cancer cells. World J Gastroenterol. 2004 Feb 15;10(4):540-4. PubMed PMID: 14966913; PubMed Central PMCID: PMC4716976.
7: Mergler S, Dannowski H, Bednarz J, Engelmann K, Hartmann C, Pleyer U. Calcium influx induced by activation of receptor tyrosine kinases in SV40-transfected human corneal endothelial cells. Exp Eye Res. 2003 Oct;77(4):485-95. PubMed PMID: 12957147.
8: Chiang CE, Luk HN, Chen LL, Wang TM, Ding PY. Genistein inhibits the inward rectifying potassium current in guinea pig ventricular myocytes. J Biomed Sci. 2002 Jul-Aug;9(4):321-6. PubMed PMID: 12145529.
9: Mergler S, Strauss O. Stimulation of L-type Ca(2+) channels by increase of intracellular InsP3 in rat retinal pigment epithelial cells. Exp Eye Res. 2002 Jan;74(1):29-40. PubMed PMID: 11878816.
10: Zeng J, Zheng Q, Zhang W. [Protein tyrosine kinase activation in the repair of rat gastric mucosa after damage]. Zhonghua Yi Xue Za Zhi. 1999 Dec;79(12):934-7. Chinese. PubMed PMID: 11715511.
11: Safronova VG, Gabdoulkhakova AG, Miller AV, Kosarev IV, Vasilenko RN. Variations of the effect of insulin on neutrophil respiratory burst. The role of tyrosine kinases and phosphatases. Biochemistry (Mosc). 2001 Aug;66(8):840-9. PubMed PMID: 11566053.
12: Eude I, Dallot E, Vacher-Lavenu MC, Chapron C, Ferre F, Breuiller-Fouche M. Potentiation response of cultured human uterine leiomyoma cells to various growth factors by endothelin-1: role of protein kinase C. Eur J Endocrinol. 2001 May;144(5):543-8. PubMed PMID: 11331222.
13: Jin N, Hatton ND, Harrington MA, Xia X, Larsen SH, Rhoades RA. H(2)O(2)-induced egr-1, fra-1, and c-jun gene expression is mediated by tyrosine kinase in aortic smooth muscle cells. Free Radic Biol Med. 2000 Oct 15;29(8):736-46. PubMed PMID: 11053775.
14: Tedeschi A, Lorini M, Galbiati S, Gibelli S, Miadonna A. Inhibition of basophil histamine release by tyrosine kinase and phosphatidylinositol 3-kinase inhibitors. Int J Immunopharmacol. 2000 Oct;22(10):797-808. PubMed PMID: 10963852.
15: Aoki K, Zubkov AY, Parent AD, Zhang JH. Mechanism of ATP-induced [Ca(2+)](i) mobilization in rat basilar smooth muscle cells. Stroke. 2000 Jun;31(6):1377-84; discussion 1384-5. PubMed PMID: 10835460.
16: Jiang MJ, Yu YJ, Chen YL, Lee YM, Hung LS. Cyclic strain stimulates monocyte chemotactic protein-1 mRNA expression in smooth muscle cells. J Cell Biochem. 1999 Dec;76(2):303-10. PubMed PMID: 10618646.
17: Stumpff F, Que Y, Boxberger M, Strauss O, Wiederholt M. Stimulation of maxi-K channels in trabecular meshwork by tyrosine kinase inhibitors. Invest Ophthalmol Vis Sci. 1999 Jun;40(7):1404-17. PubMed PMID: 10359322.
18: Nichols MR, Morimoto BH. Tyrosine kinase-independent inhibition of cyclic-AMP phosphodiesterase by genistein and tyrphostin 51. Arch Biochem Biophys. 1999 Jun 15;366(2):224-30. PubMed PMID: 10356287.
19: Strauss O, Steinhausen K, Mergler S, Stumpff F, Wiederholt M. Involvement of protein tyrosine kinase in the InsP3-induced activation of Ca2+-dependent Cl- currents in cultured cells of the rat retinal pigment epithelium. J Membr Biol. 1999 Jun 1;169(3):141-53. PubMed PMID: 10354461.
20: Tertrin-Clary C, Eude I, Fournier T, Paris B, Breuiller-Fouché M, Ferré F. Contribution of protein kinase C to ET-1-induced proliferation in human myometrial cells. Am J Physiol. 1999 Mar;276(3 Pt 1):E503-11. PubMed PMID: 10070017.