477-84-9 Hazards Identification
Pictogram(s):
Signal:
Warning
GHS Hazard Statements:
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
Precautionary Statement Codes:
P264, P270, P301+P317, P330, and P501
Hazard Classes and Categories:
Acute Tox. 4 (100%)
477-84-9 Usage
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
Check Digit Verification of cas no
The CAS Registry Mumber 477-84-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,7 and 7 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 477-84:
(5*4)+(4*7)+(3*7)+(2*8)+(1*4)=89
89 % 10 = 9
So 477-84-9 is a valid CAS Registry Number.
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
477-84-9Relevant academic research and scientific papers
Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines
Saha, Koushik,Lam, Kok Wai,Abas, Faridah,Sazali Hamzah,Stanslas, Johnson,Hui, Lim Siang,Lajis, Nordin H.
, p. 2093 - 2104 (2013/07/26)
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.
Total synthesis, cytotoxic effects of damnacanthal, nordamnacanthal and related anthraquinone analogues
Akhtar, Muhammad Nadeem,Zareen, Seema,Yeap, Swee Keong,Ho, Wan Yong,Lo, Kong Mun,Hasan, Aurangzeb,Alitheen, Noorjahan Banu
, p. 10042 - 10055 (2013/09/23)
Naturally occurring anthraquinones, damnacanthal (1) and nordamnacanthal (2) were synthesized with modified reaction steps and investigated for their cytotoxicity against the MCF-7 and K-562 cancer cell lines, respectively. Intermediate analogues 2-bromomethyl-1,3-dimethoxyanthraquinone (5, IC 50 = 5.70 ± 0.21 and 8.50 ± 1.18 μg/mL), 2-hydroxymethyl-1,3-dimethoxyanthraquinone (6, IC50 = 12.10 ± 0.14 and 14.00 ± 2.13), 2-formyl-1,3-dimethoxyantharquinone (7, IC 50 = 13.10 ± 1.02 and 14.80 ± 0.74), 1,3-dimethoxy-2-methylanthraquinone (4, IC50 = 9.40 ± 3.51 and 28.40 ± 2.33), and 1,3-dihydroxy-2-methylanthraquinone (3, IC 50 = 25.60 ± 0.42 and 28.40 ± 0.79) also exhibited moderate cytotoxicity against MCF-7 and K-562 cancer cell lines, respectively. Other structurally related compounds like 1,3-dihydroxyanthraquinone (13a, IC50 = 19.70 ± 0.35 and 14.50 ± 1.28), 1,3-dimethoxyanthraquinone (13b, IC50 = 6.50 ± 0.66 and 5.90 ± 0.95) were also showed good cytotoxicity. The target compound damnacanthal (1) was found to be the most cytotoxic against the MCF-7 and K-562 cancer cell lines, with IC50 values of 3.80 ± 0.57 and 5.50 ± 1.26, respectively. The structures of all compounds were elucidated with the help of detailed spectroscopic techniques.
