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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 | | EINECS: | | | Product Categories: | | | Mol File: | 477-84-9.mol |  |
| | 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) | | form | Pale orange solid. | | pka | 5.26±0.20(Predicted) | | 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 |
| WGK Germany | WGK 1 | | Storage Class | 11 - Combustible Solids |
| | DAMNACANTHAL Usage And Synthesis |
| Description | Damnacanthal (477-84-9) is a potent inhibitor of p56lcktyrosine kinase activity (IC50= 17 nM for inhibition of autophosphorylation). Displays 7- to 20-fold selectivity over p59fynand p60srctyrosine kinases and > 40-fold to 100-fold selectivity over other kinases.1Mobilizes intracellular Ca2+in dermal fibroblasts.2Inhibits LIM-kinase, impairing cell migration and invasion.3A potent inhibitor of angiogenesis.4Inhibits 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.
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| | 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 |
| | DAMNACANTHAL Preparation Products And Raw materials |
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