125697-92-9

Basic information

• Product Name: LAVENDUSTIN A
• Synonyms: RG14355;LAVENDUSTIN A;5-AMINO-[(N-2,5-DIHYDROXYBENZYL)-N'-2-HYDROXYBENZYL]SALICYLIC ACID;5-[[(2,5-DIHYDROXYPHENYL)METHYL][(2-HYDROXYPHENYL)METHYL]AMINO]-2-HYDROXYBENZOIC ACID;5-[(2,5-Dihydroxybenzyl)(2-hydroxybenzyl)amino]-2-hydroxybenzoic acid;Lavendustin A,98%;NSC 678027;Benzoic acid,5-[[(2,5-dihydroxyphenyl)methyl][(2-hydroxyphenyl)methyl]amino]-2-hydroxy-
• CAS NO: 125697-92-9
• Molecular Formula: C21H19NO6
• Molecular Weight: 381.38
• Product Categories: Miscellaneous Natural Products;All Inhibitors;Inhibitors;Tyrosine Kinase Inhibitors
• Mol File: 125697-92-9.mol
• Article Data: 0

Chemical Properties

• Melting Point: 205-215 °C
• Boiling Point: 741.7°C at 760 mmHg
• Flash Point: 402.4°C
• Appearance: Yellow to brown/crystalline
• Density: 1.495±0.06 g/cm3(Predicted)
• Vapor Pressure: 4.23E-23mmHg at 25°C
• Storage Temp.: −20°C
• Solubility: DMSO: soluble
• PKA: 2.31±0.10(Predicted)
• Sensitive: Air Sensitive
• Stability: Moisture Sensitive: Hygroscopic
• CAS DataBase Reference: LAVENDUSTIN A(CAS DataBase Reference)
• NIST Chemistry Reference: LAVENDUSTIN A(125697-92-9)
• EPA Substance Registry System: LAVENDUSTIN A(125697-92-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• RTECS: DG8578950
• Hazardous Substances Data: 125697-92-9(Hazardous Substances Data)

Usage

Description

Lavendustin A is a selective inhibitor of epidermal growth factor (EGF) receptor-associated tyrosine kinase, first isolated from a Streptomyces culture filtrate. It is an off-white solid that does not inhibit protein kinase A (PKA), PKC, or PI3K. Lavendustin A has been used for various applications, including differentiating rat mesenchymal stem cells, inhibiting NMDA-stimulated cGMP production, and inhibiting VEGF-induced angiogenesis.

Uses

Used in Pharmaceutical Industry:
Lavendustin A is used as a potent tyrosine kinase inhibitor for its competitive inhibition with ATP and noncompetitive inhibition with the peptide. This selective inhibition makes it a valuable compound in the development of targeted therapies for various diseases.
Used in Stem Cell Research:
Lavendustin A is used as a differentiating agent for rat mesenchymal stem cells, aiding in the study of stem cell behavior and potential applications in regenerative medicine.
Used in Neurobiology Research:
Lavendustin A is used to inhibit NMDA-stimulated cGMP production, which helps researchers understand the role of this signaling pathway in neuronal function and related disorders.
Used in Angiogenesis Research:
Lavendustin A is used to inhibit VEGF-induced angiogenesis, a process critical for the growth of new blood vessels. This application is important for studying and potentially treating diseases where abnormal blood vessel growth contributes to the pathology, such as cancer.

Biological Activity

Potent, cell-permeable inhibitor of epidermal growth factor receptor (EGFR) tyrosine kinase (IC 50 = 11 nM). Inhibits p60 c-src with an IC 50 of 500 nM and is selective over PKA, PKC and PI 3-kinase (IC 50 > 100 μ M).

InChI:InChI=1/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)/p-1