LAVENDUSTIN A

LAVENDUSTIN A Property

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

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26

WGK Germany 

3

HS Code 

29225000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

LAVENDUSTIN A Chemical Properties,Usage,Production

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