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DAMNACANTHAL

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DAMNACANTHAL Basic information

Product Name:
DAMNACANTHAL
Synonyms:
  • DAMNACANTHAL
  • DAMNACANTAL
  • 1-Methoxy-2-formyl-3-hydroxy-9,10-anthraquinone
  • 1-Methoxy-3-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde
  • 3-HYDROXY-1-METHOXYANTHRAQUINONE-2-ALDEHYDE
  • 9,10-Dihydroxy-3-hydroxy-1-methoxy-9,10-dioxo-2-anthracenecarboxaldehyde
  • 1-Methoxy-3-hydroxy-9,10-dioxoanthracene-2-carbaldehyde
  • 9,10-Dihydro-3-hydroxy-1-methoxy-9,10-dioxo-2-anthracenecarbaldehyde
CAS:
477-84-9
MF:
C16H10O5
MW:
282.25
Mol File:
477-84-9.mol
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DAMNACANTHAL Chemical Properties

Melting point:
218～219℃
Boiling point:
531.9±50.0 °C(Predicted)
Density 
1.461±0.06 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
Soluble in DMSO (up to 7 mg/ml)
pka
5.26±0.20(Predicted)
form 
Pale orange solid.
color 
Yellow
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
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
InChIKey
IPDMWUNUULAXLU-UHFFFAOYSA-N
SMILES
O(C)c1c2c(cc(c1C=O)O)C(=O)c3c(cccc3)C2=O
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Safety Information

WGK Germany 
WGK 1
Storage Class
11 - Combustible Solids
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DAMNACANTHAL Usage And Synthesis

Description

Damnacanthal (477-84-9) is a potent inhibitor of p56lck?tyrosine kinase activity (IC50?= 17 nM for inhibition of autophosphorylation). Displays 7- to 20-fold selectivity over p59fyn?and p60src?tyrosine kinases and > 40-fold to 100-fold selectivity over other kinases.1?Mobilizes intracellular Ca2+?in dermal fibroblasts.2?Inhibits LIM-kinase, impairing cell migration and invasion.3?A potent inhibitor of angiogenesis.4?Inhibits mast cell activation.5

Uses

Damnacanthal-induced anti-inflammation is associated with inhibition of NF-κB activity. Damnacanthal is used in the treatment of inflammatory-related diseases.

Definition

ChEBI: 3-hydroxy-1-methoxy-9,10-dioxo-2-anthracenecarboxaldehyde is a monohydroxyanthraquinone and an aldehyde.

in vivo

Damnacanthal (10-100 mg/kg; oral administration; for 10-300 minutes; male ddY mice) treatment exhibits a significant antinociceptive effect in a dose-dependent manner in the formalin test. Administration of damnacanthal (100 mg/kg) shows significant inhibition of histamine-induced paw edema[4].

Animal Model:Male ddY mice (5-6 weeks) injected with formalin or Histamine[4]
Dosage:10 mg/kg, 30 mg/kg and 100 mg/kg
Administration:Oral administration; for 10 minutes, 30 minutes, 60 minutes or 300 minutes
Result:Significantly reduced the growth of human lung tumor without acute toxicity.

target

Syk | Akt | IL Receptor | TNF-α | Caspase | NF-kB | p53 | p21 | p38MAPK | Bcl-2/Bax | Histamine Receptor

References

[1] CONNIE R. FALTYNEK. Damnacanthal Is a Highly Potent, Selective Inhibitor of p56lck Tyrosine Kinase Activity[J]. Biochemistry Biochemistry, 1995, 34 38: 12404-12410. DOI:10.1021/bi00038a038
[2] KAZUYA AOKI  John Z  Andrew Parent. Mechanism of damnacanthal-induced [Ca2+]i elevation in human dermal fibroblasts[J]. European journal of pharmacology, 2000, 387 2: Pages 119-124. DOI:10.1016/s0014-2999(99)00811-0
[3] KAZUMASA OHASHI. Damnacanthal, an effective inhibitor of LIM-kinase, inhibits cell migration and invasion.[J]. Molecular Biology of the Cell, 2014, 25 6: 828-840. DOI:10.1091/mbc.e13-09-0540
[4] JAVIER A. GARCÍA-VILAS . The noni anthraquinone damnacanthal is a multi-kinase inhibitor with potent anti-angiogenic effects[J]. Cancer letters, 2017, 385: Pages 1-11. DOI:10.1016/j.canlet.2016.10.037
[5] JAVIER A. GARCIA-VILAS . Damnacanthal inhibits IgE receptor-mediated activation of mast cells[J]. Molecular immunology, 2015, 65 1: Pages 86-93. DOI:10.1016/j.molimm.2015.01.008

DAMNACANTHALSupplier

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+49 5662 408730
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