477-84-9

Basic information

• Product Name: DAMNACANTHAL
• Synonyms: DAMNACANTHAL;3-HYDROXY-1-METHOXYANTHRAQUINONE-2-ALDEHYDE;DAMNACANTAL;1-Methoxy-2-formyl-3-hydroxy-9,10-anthraquinone;1-Methoxy-3-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde;1-Methoxy-3-hydroxy-9,10-dioxoanthracene-2-carbaldehyde;9,10-Dihydro-3-hydroxy-1-methoxy-9,10-dioxo-2-anthracenecarbaldehyde;3-hydroxy-1-methoxy-9,10-dioxo-anthracene-2-carbaldehyde
• CAS NO: 477-84-9
• Molecular Formula: C₁₆H₁₀O₅
• Molecular Weight: 282.25
• Mol File: 477-84-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 218～219℃
• Boiling Point: 531.9°Cat760mmHg
• Flash Point: 204.9°C
• Appearance: /
• Density: 1.461g/cm³
• Vapor Pressure: 6.29E-12mmHg at 25°C
• Refractive Index: 1.691
• Storage Temp.: -20°C
• Solubility: Soluble in DMSO (up to 7 mg/ml)
• PKA: 5.26±0.20(Predicted)
• 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.
• CAS DataBase Reference: DAMNACANTHAL(CAS DataBase Reference)
• NIST Chemistry Reference: DAMNACANTHAL(477-84-9)
• EPA Substance Registry System: DAMNACANTHAL(477-84-9)

Safety Data

• Hazardous Substances Data: 477-84-9(Hazardous Substances Data)

Usage

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.

References

1) Faltynek?et al.?(1995),?Damnacanthal is a highly potent, selective inhibitor of p56lck tyrosine kinase activity; Biochemistry,?34?12404 2) Aoki?et al.?(2000),?Mechanism of damnacanthal-induced ;Ca(2+)](i) elevation in human dermal fibroblasts; Eur. J. Pharmacol.,?387?119 3) Ohashi?et al.?(2014),?Damnacanthal, an effective inhibitor of LIM-kinase, inhibits cell migration and invasion; Mol. Biol. Cell,?25?828 4) Garcia-Vilas?et al.?(2017),?The noni anthraquinone damnacanthal is a multi-kinase inhibitor with potent anti-angiogenic effects; Cancer Letters,?385?1 5) Garcia-Vilas?et al.?(2015),?Damnacanthal inhibits IgE receptor-mediated activation of mast cells; Mol. Immunol.,?65?86

InChI:InChI=1/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

Upstream product

• 85-44-9 phthalic anhydride 

Downstream Products

• 3736-59-2 nordamnacanthal 
• 477-83-8 damnacanthol 

Relevant articles and documents

Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines

Damnacanthal and nordamnacanthal, two naturally occurring 9,10-anthraquinones, and their analogues were synthesized. Cytotoxic activity against five cancer cell lines was evaluated using MTT assay. 2-Bromomethyl-1,3-dimethoxyanthraquinone was found to display the highest activity against all cell lines with IC50 range of 2-8 μM. Structure-activity relationship (SAR) assessment was considered to rationalise the cytotoxic effect. Bromomethyl group at position C-2 of the anthraquinone was found to be important in exerting cytotoxic activity of this class of compounds. The presence of the flanking methoxyl or hydroxyl groups at C-1 and C-3 also contributes to this activity. Finally, the antioxidant effect of these compounds was evaluated. MTT assay was used to measure the cytotoxicity against different cancer cell lines. Antioxidant activity was measured by FTC and TBA methods. Only two anthraquinones, damnacanthal and nordamnacanthal, were found to be antioxidative.