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Merck

251650

Damnacanthal

A cell-permeable, potent, reversible, and selective inhibitor of p56lck tyrosine kinase.

Synonym(s):

Damnacanthal, 3-Hydroxy-1-methoxyanthraquinone-2-aldehyde

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About This Item

Empirical Formula (Hill Notation):
C16H10O5
CAS Number:
477-84-9
Molecular Weight:
282.25
MDL number:
MFCD00674209
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥95% (HPLC)
Form:
solid
Quality level:
100
Storage condition:
OK to freeze, protect from light

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SMILES string

O(C)c1c2c(cc(c1C=O)O)C(=O)c3c(cccc3)C2=O

InChI

1S/C16H10O5/c1-21-16-11(7-17)12(18)6-10-13(16)15(20)9-5-3-2-4-8(9)14(10)19/h2-7,18H,1H3

InChI key

IPDMWUNUULAXLU-UHFFFAOYSA-N

assay

≥95% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze, protect from light

color

orange-yellow

solubility

DMSO: 5 mg/mL

shipped in

ambient

storage temp.

−20°C

Quality Level

100

Related Categories

General description

A cell-permeable, potent, reversible, and selective inhibitor of p56lck tyrosine kinase. Inhibits p56lck autophosphorylation (IC50 = 17 nM) and phosphorylation of an exogenous peptide by p56lck (IC50 = 620 nM). Exhibits over 100-fold greater selectivity for p56lck over PKA and PKC, 40-fold greater selectivity for p56lck over EGF receptor kinase, c-ErbB2, insulin receptor kinase, and PDGF receptor kinase, and 7 - 20-fold greater selectivity for p56lck over p60src and p59fyn. Inhibition of p56lck is not significantly affected by the presence of sulfhydryl reagents. Also known to have antimalarial properties and to reverse the phenotype of ras-transformed cells.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
p56lck autophosphorylation
Product does not compete with ATP.
Reversible: yes
Target IC50: 17 nM against p56lck autophosphorylation

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C.

Other Notes

Faltynek, C.R., et al. 1995. Biochemistry34, 12404.
Hiramatsu, T., et al. 1993. Cancer Lett.73, 161.
Koumaglo, K., et al. 1992. Planta Med.58, 533.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Storage Class

11 - Combustible Solids

wgk

WGK 1

Certificates of Analysis (COA)

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