For research use only. Not for therapeutic Use.
Lavendustin A, also known as RG 14355, is a potent, cell-permeable inhibitor of epidermal growth factor receptor (EGFR) tyrosine kinase (IC50 = 11 nM). Lavendustin A shows cytotoxic effects on tumor cell lines. Lavendustin A enhances axon elongation in VHL gene-transfected neural stem cells.
| Catalog Number | R000157 |
| CAS Number | 125697-92-9 |
| Synonyms | 5-[[(2,5-Dihydroxyphenyl)methyl][(2-hydroxyphenyl)methyl]amino]-2-hydroxy-benzoic Acid; NSC 678027 |
| Molecular Formula | C21H19NO6 |
| Purity | ≥95% |
| Target | Protein Tyrosine Kinase/RTK |
| Solubility | Soluble in DMSO > 10 mM |
| Storage | Desiccate at -20C |
| IUPAC Name | 5-[(2,5-dihydroxyphenyl)methyl-[(2-hydroxyphenyl)methyl]amino]-2-hydroxybenzoic acid |
| InChI | InChI=1S/C21H19NO6/c23-16-6-8-19(25)14(9-16)12-22(11-13-3-1-2-4-18(13)24)15-5-7-20(26)17(10-15)21(27)28/h1-10,23-26H,11-12H2,(H,27,28) |
| InChIKey | ULTTYPMRMMDONC-UHFFFAOYSA-N |
| SMILES | C1=CC=C(C(=C1)CN(CC2=C(C=CC(=C2)O)O)C3=CC(=C(C=C3)O)C(=O)O)O |
| Reference | </br>1:Synthesis and anticancer activity of chromone-based analogs of lavendustin A. Nam DH, Lee KY, Moon CS, Lee YS.Eur J Med Chem. 2010 Sep;45(9):4288-92. doi: 10.1016/j.ejmech.2010.06.030. Epub 2010 Jun 25. PMID: 20630626 </br>2:Structure-activity relationship studies on a novel class of antiproliferative agents derived from Lavendustin A. Part I: Ring A modifications. Nussbaumer P, Winiski AP.Bioorg Med Chem. 2008 Aug 15;16(16):7552-60. doi: 10.1016/j.bmc.2008.07.039. Epub 2008 Jul 20. PMID: 18678497 </br>3:Influence of the tyrosine kinase inhibitors STI571 (Glivec), lavendustin A and genistein on human mast cell line (HMC-1(560)) activation. Löber K, Alfonso A, Escribano L, Botana LM.J Cell Biochem. 2008 Mar 1;103(4):1076-88. PMID: 17661356 </br>4:Synthesis and anticancer activity of lavendustin A derivatives containing arylethenylchromone substituents. Lee KY, Nam DH, Moon CS, Seo SH, Lee JY, Lee YS.Eur J Med Chem. 2006 Aug;41(8):991-6. Epub 2006 Jun 9. PMID: 16762460 </br>5:4-Anilinoquinazolines with Lavendustin A subunit as inhibitors of epidermal growth factor receptor tyrosine kinase: syntheses, chemical and pharmacological properties. Albuschat R, Löwe W, Weber M, Luger P, Jendrossek V.Eur J Med Chem. 2004 Dec;39(12):1001-11. PMID: 15571862 </br>6:Lavendustin A enhances axon elongation in VHL gene-transfected neural stem cells. Murakami K, Kanno H, Yamamoto I, Saito T.Neuroreport. 2004 Mar 22;15(4):611-4. PMID: 15094462 </br>7:Synthesis, anticancer activity, and inhibition of tubulin polymerization by conformationally restricted analogues of lavendustin A. Mu F, Hamel E, Lee DJ, Pryor DE, Cushman M.J Med Chem. 2003 Apr 24;46(9):1670-82. PMID: 12699385 </br>8:Synthesis and investigation of conformationally restricted analogues of lavendustin A as cytotoxic inhibitors of tubulin polymerization. Mu F, Lee DJ, Pryor DE, Hamel E, Cushman M.J Med Chem. 2002 Oct 10;45(21):4774-85. PMID: 12361405 </br>9:Acute and chronic effects of genistein, tyrphostin and lavendustin A on steroid synthesis in luteinized human granulosa cells. Whitehead SA, Cross JE, Burden C, Lacey M.Hum Reprod. 2002 Mar;17(3):589-94. PMID: 11870108 </br>10:Design, synthesis, and biological evaluation of a series of lavendustin A analogues that inhibit EGFR and Syk tyrosine kinases, as well as tubulin polymerization. Mu F, Coffing SL, Riese DJ 2nd, Geahlen RL, Verdier-Pinard P, Hamel TE, Johnson J, Cushman M.J Med Chem. 2001 Feb 1;44(3):441-52. PMID: 11462983 |
