LAVENDUSTIN A Chemical Properties

Melting point:

205-215 °C

Boiling point:

741.7±60.0 °C(Predicted)

Density 

1.495±0.06 g/cm3(Predicted)

RTECS 

DG8578950

storage temp. 

−20°C

solubility 

DMSO: soluble

form 

crystalline

pka

2.31±0.10(Predicted)

color 

Yellow to brown

Sensitive 

Air Sensitive

Stability:

Moisture Sensitive: Hygroscopic

CAS DataBase Reference

125697-92-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26

WGK Germany 

3

HS Code 

29225000

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

LAVENDUSTIN A Usage And Synthesis

Description

Lavendustin A is a selective inhibitor of epidermal growth factor (EGF) receptor-associated tyrosine kinase (IC₅₀ = 11 nM) that was first isolated from a Streptomyces culture filtrate. It does not inhibit protein kinase A (PKA), PKC, or PI3K (IC₅₀s > 100 μM). It has been used to differentiate rat mesenchymal stem cells, to inhibit NMDA-stimulated cGMP production, and to inhibit VEGF-induced angiogenesis.

Chemical Properties

Off-White Solid

Uses

A potent tyrosine kinase inhibitor. Inhibition is competitive with ATP and is noncompetitive with the peptide.

Definition

ChEBI: 5-[(2,5-dihydroxyphenyl)methyl-[(2-hydroxyphenyl)methyl]amino]-2-hydroxybenzoic acid is an aromatic amine.

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).

target

EGFR | PKC | PI3K | Calcium Channel

References

[1] TOSHIHIKO ONODA. Isolation of a Novel Tyrosine Kinase Inhibitor, Lavendustin A, from Streptomyces griseolavendus[J]. Journal of Natural Products , 1989, 52 6: 1252-1257. DOI: 10.1021/np50066a009
[2] C Y HSU. Kinetic analysis of the inhibition of the epidermal growth factor receptor tyrosine kinase by Lavendustin-A and its analogue.[J]. The Journal of Biological Chemistry, 1991, 266 31: 21105-21112.
[3] KI-CHUL HWANG. Chemicals that modulate stem cell differentiation.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2008: 7467-7471. DOI: 10.1073/pnas.0802825105
[4] THOMAS J. O’’DELL  Seth G N G  Eric R Kandel. Long-term potentiation in the hippocampus is blocked by tyrosine kinase inhibitors[J]. Nature, 1991, 353 6344: 558-560. DOI: 10.1038/353558a0
[5] T P FAN  R B  R Jaggar. Controlling the vasculature: angiogenesis, anti-angiogenesis and vascular targeting of gene therapy.[J]. Trends in pharmacological sciences, 1995, 16 2: 57-66. DOI: 10.1016/s0165-6147(00)88979-8

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