Damnacanthal
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MedKoo CAT#: 574648

CAS#: 477-84-9

Description: Damnacanthal is an inhibitor of p56lck tyrosine kinase activity that mobilizes intracellular Ca2+ in dermal fibroblasts and inhibits Ras function. Damnacanthal also inhibits LIMK1/2 as well as migration and invasion of breast cancer cells in vitro.


Chemical Structure

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Damnacanthal
CAS# 477-84-9

Theoretical Analysis

MedKoo Cat#: 574648
Name: Damnacanthal
CAS#: 477-84-9
Chemical Formula: C16H10O5
Exact Mass: 282.0528
Molecular Weight: 282.25
Elemental Analysis: C, 68.09; H, 3.57; O, 28.34

Price and Availability

Size Price Availability Quantity
1.0mg USD 355.0 2 Weeks
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Synonym: Damnacanthal

IUPAC/Chemical Name: 3-hydroxy-1-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde

InChi Key: IPDMWUNUULAXLU-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: O=CC(C(OC)=C1C2=O)=C(O)C=C1C(C3=C2C=CC=C3)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Product Data:

Biological target: Damnacanthal is an anthraquinone isolated from the root of Morinda citrifolia that inhibits p56 lck autophosphorylation and phosphorylation of exogenous substrates with IC50s of 46 nM and 220 nM, respectively.
In vitro activity: In the present study, the effect of damnacanthal on MCF-7 cell growth regulation was investigated. Treatment of MCF-7 cells with damnacanthal for 72 h indicated an antiproliferative activity. The MTT method confirmed that damnacanthal inhibited the growth of MCF-7 cells at the concentration of 8.2 μg/ml for 72 h. In addition, the drug was found to induce cell cycle arrest at the G1 checkpoint in MCF-7 cells by cell cycle analysis. Damnacanthal induced apoptosis, determined by Annexin V-fluorescein isothiocyanate/propidium iodide (PI) dual-labeling, acridine-orange/PI dyeing and caspase-7 expression. Furthermore, damnacanthalmediated apoptosis involves the sustained activation of p21, leading to the transcription of p53 and the Bax gene. Overall, the present study provided significant evidence demonstrating that p53-mediated damnacanthal induced apoptosis through the activation of p21 and caspase-7. Reference: Oncol Lett. 2014 May;7(5):1479-1484. https://pubmed.ncbi.nlm.nih.gov/24765160/
In vivo activity: It was investigated if the MeOH-, CHCl(3)- and BuOH-soluble phase and its main active component, damnacanthal, isolated from the Noni root, have antinociceptive and anti-inflammatory actions in mice. Damnacanthal (10—100 mg/kg) did not reduce pain response time in the first phase, but significantly suppressed pain-related behavior in the second phase (p0.01). Damnacanthal (30—100 mg/kg) also exhibited a significant antinociceptive effect in a dose-dependent manner. Damnacanthal displaced [3H]-pyrilamine binding to human HEK293 cells in a concentration-dependent manner. In conclusion, the effects of damnacanthal isolated from the Noni root is mediated in part by the histamine H(1) receptor. Reference: Biol Pharm Bull. 2011;34(1):103-7. https://pubmed.ncbi.nlm.nih.gov/21212526/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 7.06 25.0

Preparing Stock Solutions

The following data is based on the product molecular weight 282.25 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Aziz MY, Omar AR, Subramani T, Yeap SK, Ho WY, Ismail NH, Ahmad S, Alitheen NB. Damnacanthal is a potent inducer of apoptosis with anticancer activity by stimulating p53 and p21 genes in MCF-7 breast cancer cells. Oncol Lett. 2014 May;7(5):14791484. doi: 10.3892/ol.2014.1898. Epub 2014 Feb 20. PMID: 24765160; PMCID: PMC3997671. 2. García-Vilas JA, Quesada AR, Medina MA. Damnacanthal, a noni anthraquinone, inhibits c-Met and is a potent antitumor compound against Hep G2 human hepatocellular carcinoma cells. Sci Rep. 2015 Jan 26;5:8021. doi: 10.1038/srep08021. PMID: 25620570; PMCID: PMC4306130. 3. Okusada K, Nakamoto K, Nishida M, Fujita-Hamabe W, Kamiya K, Mizushina Y, Satake T, Tokuyama S. The antinociceptive and anti-inflammatory action of the CHCl3-soluble phase and its main active component, damnacanthal, isolated from the root of Morinda citrifolia. Biol Pharm Bull. 2011;34(1):103-7. doi: 10.1248/bpb.34.103. PMID: 21212526.
In vitro protocol: 1. Aziz MY, Omar AR, Subramani T, Yeap SK, Ho WY, Ismail NH, Ahmad S, Alitheen NB. Damnacanthal is a potent inducer of apoptosis with anticancer activity by stimulating p53 and p21 genes in MCF-7 breast cancer cells. Oncol Lett. 2014 May;7(5):14791484. doi: 10.3892/ol.2014.1898. Epub 2014 Feb 20. PMID: 24765160; PMCID: PMC3997671. 2. García-Vilas JA, Quesada AR, Medina MA. Damnacanthal, a noni anthraquinone, inhibits c-Met and is a potent antitumor compound against Hep G2 human hepatocellular carcinoma cells. Sci Rep. 2015 Jan 26;5:8021. doi: 10.1038/srep08021. PMID: 25620570; PMCID: PMC4306130.
In vivo protocol: 1. Okusada K, Nakamoto K, Nishida M, Fujita-Hamabe W, Kamiya K, Mizushina Y, Satake T, Tokuyama S. The antinociceptive and anti-inflammatory action of the CHCl3-soluble phase and its main active component, damnacanthal, isolated from the root of Morinda citrifolia. Biol Pharm Bull. 2011;34(1):103-7. doi: 10.1248/bpb.34.103. PMID: 21212526.

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1. Hiramatsu et al (1993) Induction of normal phenotypes in ras-transformed cells by damnacanthal from Morinda citrifolia. Cancer Lett. 73 161 PMID: 7693328

2. Faltynek et al (1995) Damnacanthal is a highly potent, selective inhibitor fo p56lck tyrosine kinase activity. Biochemistry 34 12404 PMID: 7547985

3. Aoki et al (2000) Mechanism of damnacanthal-induced [Ca2+]i elevation in human dermal fibroblasts. Eur.J.Pharmacol. 387 119 PMID: 10650151