A selective inhibitor of EGF receptor-associated tyrosine kinase
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Lavendustin A

Item No. 10010268

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-[[(2,5-dihydroxyphenyl)methyl][(2-hydroxyphenyl)methyl]amino]-2-hydroxy-benzoic acid
CAS Number
125697-92-9
Synonyms
  • NSC 678027
  • RG-14355
Molecular Formula
C21H19NO6
Formula Weight
381.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 15 mg/mlEthanol: 10 mg/ml
SMILES
OC1=CC(CN(C2=CC=C(O)C(C(O)=O)=C2)CC3=CC=CC=C3O)=C(O)C=C1
InChi Code
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)
InChi Key
ULTTYPMRMMDONC-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $90

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    5 mg

    $197

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    10 mg

    $349

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    Product 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.1,2 It does not inhibit protein kinase A (PKA), PKC, or PI3K (IC50s > 100 µM).2 It has been used to differentiate rat mesenchymal stem cells, to inhibit NMDA-stimulated cGMP production, and to inhibit VEGF-induced angiogenesis.3,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Onoda, T., Iinuma, H., Sasaki, Y., et al. Isolation of a novel tyrosine kinase inhibitor, lavendustin A, from Streptomyces griseolavendus. J. Nat. Prod. 52(6), 1252-1257 (1989).

    2. Hsu, C.-Y.J., Persons, P.E., Spada, A.P., et al. Kinetic analysis of the inhibition of the epidermal growth factor receptor tyrosine kinase by lavendustin-A and its analogue. The Journal of Biological Chemisty 266(31), 21105-21112 (1991).

    3. Hwang, K.C., Kim, J.Y., Chang, W., et al. Chemicals that modulate stem cell differentiation. Proc. Natl. Acad. Sci. USA 105(21), 7467-7471 (2008).

    4. O'Dell, T.J., Kandel, E.R., and Grant, S.G.N. Long-term potentiation in the hippocampus is blocked by tyrosine kinase inhibitors. Nature 353(6344), 558-560 (1991).

    5. Fan, T.P.D., Jaggar, R., and Bicknell, R. Controlling the vasculature: Angiogenesis, anti-angiogenesis and vascular targeting of gene therapy. Trends Pharmacol. Sci. 16(2), 57-66 (1995).