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, with an IC50 of 17 nM for inhibition of autophosphorylation. It exhibits selectivity over other kinases, such as p59fyn and p60src, and has been found to mobilize intracellular Ca2+ in dermal fibroblasts. Damnacanthal also inhibits LIM-kinase, which impairs cell migration and invasion, and acts as a potent inhibitor of angiogenesis. Additionally, it inhibits mast cell activation and is associated with anti-inflammatory effects through the inhibition of NF-κB activity.

Uses

Used in Pharmaceutical Industry:
Damnacanthal is used as an anti-inflammatory agent for the treatment of inflammatory-related diseases. Its ability to inhibit NF-κB activity contributes to its potential therapeutic applications in this area.
Used in Oncology:
Damnacanthal is used as an inhibitor of various tyrosine kinases, such as p56lck, p59fyn, and p60src, which play a role in cancer cell proliferation and survival. Its selectivity for these kinases makes it a promising candidate for targeted cancer therapies.
Used in Cell Migration and Invasion Inhibition:
Damnacanthal is used as an inhibitor of LIM-kinase, which impairs cell migration and invasion. This property makes it a potential therapeutic agent for preventing the spread of cancer cells in the body.
Used in Angiogenesis Inhibition:
Damnacanthal is used as a potent inhibitor of angiogenesis, the process through which new blood vessels form. This property can be utilized in the development of anti-cancer drugs, as angiogenesis is a critical factor in tumor growth and metastasis.
Used in Mast Cell Activation Inhibition:
Damnacanthal is used as an inhibitor of mast cell activation, which can contribute to allergic reactions and inflammation. This application suggests its potential use in the treatment of allergic diseases and conditions involving excessive inflammation.

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.