Damnacanthal | CAS# 477-84-9 | p56lck tyrosine kinase inhibitor

MedKoo Cat#: 574648 | Name: Damnacanthal

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

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

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1mg	USD 550.00	Back order

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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

>95% (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

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Product Data

Product Data

Instruction

View handling instruction

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/

	Solvent	mg/mL	mM
Solubility
	DMSO	7.1	25.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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:

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.

1: Abu N, Ali NM, Ho WY, Yeap SK, Aziz MY, Alitheen NB. Damnacanthal: a promising compound as a medicinal anthraquinone. Anticancer Agents Med Chem. 2014 Jun;14(5):750-5. doi: 10.2174/18715206113136660366. PMID: 24164045. 2: Li R, Li H, Lan J, Yang D, Lin X, Xu H, Han B, Yang M, Su B, Liu F, Jiang W. Damnacanthal isolated from morinda species inhibited ovarian cancer cell proliferation and migration through activating autophagy. Phytomedicine. 2022 Jun;100:154084. doi: 10.1016/j.phymed.2022.154084. Epub 2022 Mar 29. PMID: 35421676. 3: Woradulayapinij W, Pothiluk A, Nualsanit T, Yimsoo T, Yingmema W, Rojanapanthu P, Hong Y, Baek SJ, Treesuppharat W. Acute oral toxicity of damnacanthal and its anticancer activity against colorectal tumorigenesis. Toxicol Rep. 2022 Oct 29;9:1968-1976. doi: 10.1016/j.toxrep.2022.10.015. PMID: 36518435; PMCID: PMC9742955. 4: Sukamporn P, Rojanapanthu P, Silva G, Zhang X, Gritsanapan W, Baek SJ. Damnacanthal and its nanoformulation exhibit anti-cancer activity via cyclin D1 down-regulation. Life Sci. 2016 May 1;152:60-6. doi: 10.1016/j.lfs.2016.03.038. Epub 2016 Mar 24. PMID: 27018445. 5: Kim MH, Jeong HJ. Damnacanthal inhibits the NF-κB/RIP-2/caspase-1 signal pathway by inhibiting p56lck tyrosine kinase. Immunopharmacol Immunotoxicol. 2014 Oct;36(5):355-63. doi: 10.3109/08923973.2014.952819. Epub 2014 Aug 20. PMID: 25139491. 6: Garcia-Vilas JA, Medina MA, Melo FR, Pejler G, Garcia-Faroldi G. Damnacanthal inhibits IgE receptor-mediated activation of mast cells. Mol Immunol. 2015 May;65(1):86-93. doi: 10.1016/j.molimm.2015.01.008. Epub 2015 Feb 2. PMID: 25656801. 7: Nualsanit T, Rojanapanthu P, Gritsanapan W, Lee SH, Lawson D, Baek SJ. Damnacanthal, a noni component, exhibits antitumorigenic activity in human colorectal cancer cells. J Nutr Biochem. 2012 Aug;23(8):915-23. doi: 10.1016/j.jnutbio.2011.04.017. Epub 2011 Aug 17. PMID: 21852088; PMCID: PMC3222750. 8: Latifah SY, Gopalsamy B, Abdul Rahim R, Manaf Ali A, Haji Lajis N. Anticancer Potential of Damnacanthal and Nordamnacanthal from Morinda elliptica Roots on T-lymphoblastic Leukemia Cells. Molecules. 2021 Mar 12;26(6):1554. doi: 10.3390/molecules26061554. PMID: 33808969; PMCID: PMC7998966. 9: García-Vilas JA, Pino-Ángeles A, Martínez-Poveda B, Quesada AR, Medina MÁ. The noni anthraquinone damnacanthal is a multi-kinase inhibitor with potent anti-angiogenic effects. Cancer Lett. 2017 Jan 28;385:1-11. doi: 10.1016/j.canlet.2016.10.037. Epub 2016 Nov 2. PMID: 27816491. 10: 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. 11: Faltynek CR, Schroeder J, Mauvais P, Miller D, Wang S, Murphy D, Lehr R, Kelley M, Maycock A, Michne W, et al. Damnacanthal is a highly potent, selective inhibitor of p56lck tyrosine kinase activity. Biochemistry. 1995 Sep 26;34(38):12404-10. doi: 10.1021/bi00038a038. PMID: 7547985. 12: Nualsanit T, Rojanapanthu P, Gritsanapan W, Kwankitpraniti T, Min KW, Baek SJ. Damnacanthal-induced anti-inflammation is associated with inhibition of NF- κB activity. Inflamm Allergy Drug Targets. 2011 Dec;10(6):455-63. doi: 10.2174/187152811798104908. PMID: 21999179. 13: 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):1479-1484. doi: 10.3892/ol.2014.1898. Epub 2014 Feb 20. PMID: 24765160; PMCID: PMC3997671. 14: Zhang X, Fang P, Zhao Z, Ding X, Xie F, Wang Y, Li C. Antitumorigenic effect of damnacanthal on melanoma cell viability through p53 and NF-κB/caspase-3 signaling pathways. Oncol Lett. 2018 Nov;16(5):6039-6044. doi: 10.3892/ol.2018.9379. Epub 2018 Sep 3. PMID: 30333875; PMCID: PMC6176422. 15: Aoki K, Parent A, Zhang J. Mechanism of damnacanthal-induced [Ca(2+)](i) elevation in human dermal fibroblasts. Eur J Pharmacol. 2000 Jan 10;387(2):119-24. doi: 10.1016/s0014-2999(99)00811-0. PMID: 10650151. 16: Chaichanasak N, Rojanapanthu P, Yoon Y, Gritsanapan W, Chirachanchai S, Sathirakul K, Nualsanit T, Seong JK, Baek SJ. Chitosan-based nanoparticles with damnacanthal suppress CRM1 expression. Oncol Lett. 2018 Dec;16(6):7029-7034. doi: 10.3892/ol.2018.9507. Epub 2018 Sep 26. PMID: 30546436; PMCID: PMC6256335. 17: Lin FL, Hsu JL, Chou CH, Wu WJ, Chang CI, Liu HJ. Activation of p38 MAPK by damnacanthal mediates apoptosis in SKHep 1 cells through the DR5/TRAIL and TNFR1/TNF-α and p53 pathways. Eur J Pharmacol. 2011 Jan 10;650(1):120-9. doi: 10.1016/j.ejphar.2010.10.005. Epub 2010 Oct 14. PMID: 20951126. 18: Mohd MR, Ariff TM, Mohamad N, Abdul Latif AZ, Wan Nik WMN, Mohamed A, Suffian IFM. Development of biodegradable sustained-release damnacanthal nanocapsules for potential application in in-vitro breast cancer studies. Pak J Pharm Sci. 2019 Sep;32(5):2155-2162. PMID: 31813882. 19: Alitheen NB, Manaf AA, Yeap SK, Shuhaimi M, Nordin L, Mashitoh AR. Immunomodulatory effects of damnacanthal isolated from roots of Morinda elliptica. Pharm Biol. 2010 Apr;48(4):446-52. doi: 10.3109/13880200903168031. PMID: 20645725. 20: Ohashi K, Sampei K, Nakagawa M, Uchiumi N, Amanuma T, Aiba S, Oikawa M, Mizuno K. Damnacanthal, an effective inhibitor of LIM-kinase, inhibits cell migration and invasion. Mol Biol Cell. 2014 Mar;25(6):828-40. doi: 10.1091/mbc.E13-09-0540. Epub 2014 Jan 29. PMID: 24478456; PMCID: PMC3952852.