Alizarin

Biological stain CAS# 72-48-0

Alizarin

Catalog No. BCN3479----Order now to get a substantial discount!

Product Name & Size Price Stock
Alizarin:100mg $69.00 In stock
Alizarin:200mg $117.00 In stock
Alizarin:500mg $276.00 In stock
Alizarin:1000mg $483.00 In stock
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Chemical structure

Alizarin

3D structure

Chemical Properties of Alizarin

Cas No. 72-48-0 SDF Download SDF
PubChem ID 6293 Appearance Orange-brown powder
Formula C14H8O4 M.Wt 240.2
Type of Compound Anthraquinones Storage Desiccate at -20°C
Synonyms 1,2-Dihydroxyanthraquinone;
Solubility Soluble to 48 mg/mL (199.82 mM) in DMSO
Chemical Name 1,2-dihydroxyanthracene-9,10-dione
SMILES C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C(=C(C=C3)O)O
Standard InChIKey RGCKGOZRHPZPFP-UHFFFAOYSA-N
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Alizarin

The roots of Rubia cordifolia

Biological Activity of Alizarin

DescriptionAlizarin has a selective and effective inhibitory activity towards cancerous cells, it acts through the inhibition of ERK phosphorylation and cell cycle arrest in the S-phase. Alizarin has antigenotoxic activity, which can be explained by inhibition of CYP activities responsible for activating the mutagens.
TargetsERK | P450 (e.g. CYP17) | NADPH-oxidase
In vitro

The natural compound Alizarin as an osteotropic drug for the treatment of bone tumors.[Pubmed: 22411621]

J Orthop Res. 2012 Sep;30(9):1486-92.

Despite significant clinical improvements, conventional therapies for bone cancer treatment are limited by significant systemic toxicity and lack of specific targeting. In this study, we considered Alizarin, a natural hydroxyanthraquinone derived from madder root with high affinity to calcium and remarkable osteotropic features, as a novel approach for bone cancer treatment. Due to its antitumor properties, as demostrated in colon cancer cells, and to its tropism to bone, Alizarin may be an ideal drug to reduce bone tumor growth.
METHODS AND RESULTS:
We demonstrated that low dosages of Alizarin strongly inhibited the osteosarcoma (IC(50) for Saos-2, MG-63, and U-2 OS cells, 27.5, 29.0, and 69.9 µg/ml, respectively) and breast carcinoma (IC(50) for MDA-MB-231 cells, 62.1 µg/ml) cell proliferation in vitro. Importantly, Alizarin had a significantly lower inhibitory activity on normal cells (IC(50) for MSC, 828.6 µg/ml), thereby revealing a selective activity towards malignant cells. Furthermore, we found that Alizarin acted through the inhibition of ERK phosphorylation and cell cycle arrest in the S-phase. Finally, Alizarin significantly and strongly impaired both osteosarcoma and breast cancer tumorigenesis.
CONCLUSIONS:
Our results highlight a selective and effective inhibitory activity of Alizarin towards cancerous cells, laying the basis for further studies to investigate its application in bone cancer therapy.

Protocol of Alizarin

Kinase Assay

Inhibition of human cytochrome P450 1B1, 1A1 and 1A2 by antigenotoxic compounds, purpurin and alizarin.[Pubmed: 12379470]

Mutat Res. 2002 Oct 31;508(1-2):147-56.

Recently we have shown that anthraquinone food pigments such as purpurin and Alizarin suppress the genotoxic activities of several mutagens including heterocyclic amines and polycyclic aromatic hydrocarbons in the Drosophila DNA repair test and in the Ames test.
METHODS AND RESULTS:
To investigate the mechanism of this inhibition, we have now examined the effects of these anthraquinone pigments on enzymes that metabolize xenobiotics. The activities of eight human recombinant cytochrome P450 (CYP) isozymes were measured in the presence of purpurin, Alizarin or carminic acid. Purpurin and Alizarin strongly inhibited the activities of CYP1A1, CYP1A2 and CYP1B1, and weakly suppressed those of CYP2A6 and CYP2E1 in a dose-dependent manner, but did not inhibit those of CYP2C19, CYP3A4 and CYP3A5. Carminic acid did not affect the activities of any CYPs tested. CYP1B1 was the most strongly affected CYP molecule by purpurin and Alizarin among CYPs examined in this study. From kinetic analysis, it was shown that the inhibition by purpurin on CYP1B1 was both competitive and non-competitive, and that by Alizarin was competitive. The values of slopes obtained from Lineweaver-Burk plots are proportional to the square of purpurin concentration. This observation suggests that two molecules of purpurin are interacting with one molecule of CYP1B1. The K(m) value of CYP1B1 was 11 microM, and the K(i) value of purpurin and Alizarin against CYP1B1 was 0.7 microM(2) and 0.5 microM, respectively. We also examined the effects of these pigments on the mutagenicities of MeIQx and B[a]P in the Ames test, using Salmonella typhimurium TA1538 co-expressing each form of human CYP and NADPH-cytochrome P450 reductase (OR). The mutagenicity of MeIQx in TA1538 1A2/OR or 1B1/OR was suppressed by purpurin and Alizarin but not by carminic acid. Purpurin also reduced the mutagenicity of B[a]P in TA1538 1A1/OR or 1B1/OR.
CONCLUSIONS:
These results suggest that the antigenotoxic activities of purpurin and Alizarin can be explained by inhibition of CYP activities responsible for activating the mutagens.

Alizarin Dilution Calculator

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Alizarin Molarity Calculator

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Preparing Stock Solutions of Alizarin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.1632 mL 20.816 mL 41.632 mL 83.2639 mL 104.0799 mL
5 mM 0.8326 mL 4.1632 mL 8.3264 mL 16.6528 mL 20.816 mL
10 mM 0.4163 mL 2.0816 mL 4.1632 mL 8.3264 mL 10.408 mL
50 mM 0.0833 mL 0.4163 mL 0.8326 mL 1.6653 mL 2.0816 mL
100 mM 0.0416 mL 0.2082 mL 0.4163 mL 0.8326 mL 1.0408 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Alizarin

Alizarin is an anthraquinone dye for detecting the presence of calcium salts [1].

Alizarin belongs to the anthraquinone group. It is a chelator for calcium and is commonly used to stain the calcifying or calcio-receptive zone of the collagenous matrix where calcium salts are being deposited. On the other hand, the Alizarin complexone is used for bone staining in vivo to study bone remodeling [1].

Alizarin is proved to have anti-tumor efficacy. It suppresses the cell growth of the prostate cancer, breast cancer and osteosarcoma cell lines in vitro. Among these, the osteosarcoma cells appear to be most sensitive. The IC50 values of Alizarin against three osteosarcoma cell lines Saos-2, MG-63 and U-2 OS are 27.5, 29 and 69.9μg/ml, respectively. Alizarin inhibits the cell growth through cell proliferation blockade rather than induction of apoptosis. It inhibits the phosphorylation of ERK. In addition, Alizarin is also found to induce S-phase arrest as well as a decrease of the G0/G1 and G2/M phases [1].

References:
[1] Fotia C, Avnet S, Granchi D, Baldini N. The natural compound Alizarin as an osteotropic drug for the treatment of bone tumors. J Orthop Res. 2012 Sep;30(9):1486-92.

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References on Alizarin

The natural compound Alizarin as an osteotropic drug for the treatment of bone tumors.[Pubmed:22411621]

J Orthop Res. 2012 Sep;30(9):1486-92.

Despite significant clinical improvements, conventional therapies for bone cancer treatment are limited by significant systemic toxicity and lack of specific targeting. In this study, we considered Alizarin, a natural hydroxyanthraquinone derived from madder root with high affinity to calcium and remarkable osteotropic features, as a novel approach for bone cancer treatment. Due to its antitumor properties, as demostrated in colon cancer cells, and to its tropism to bone, Alizarin may be an ideal drug to reduce bone tumor growth. We demonstrated that low dosages of Alizarin strongly inhibited the osteosarcoma (IC(50) for Saos-2, MG-63, and U-2 OS cells, 27.5, 29.0, and 69.9 microg/ml, respectively) and breast carcinoma (IC(50) for MDA-MB-231 cells, 62.1 microg/ml) cell proliferation in vitro. Importantly, Alizarin had a significantly lower inhibitory activity on normal cells (IC(50) for MSC, 828.6 microg/ml), thereby revealing a selective activity towards malignant cells. Furthermore, we found that Alizarin acted through the inhibition of ERK phosphorylation and cell cycle arrest in the S-phase. Finally, Alizarin significantly and strongly impaired both osteosarcoma and breast cancer tumorigenesis. Our results highlight a selective and effective inhibitory activity of Alizarin towards cancerous cells, laying the basis for further studies to investigate its application in bone cancer therapy.

Inhibition of human cytochrome P450 1B1, 1A1 and 1A2 by antigenotoxic compounds, purpurin and alizarin.[Pubmed:12379470]

Mutat Res. 2002 Oct 31;508(1-2):147-56.

Recently we have shown that anthraquinone food pigments such as purpurin and Alizarin suppress the genotoxic activities of several mutagens including heterocyclic amines and polycyclic aromatic hydrocarbons in the Drosophila DNA repair test and in the Ames test. To investigate the mechanism of this inhibition, we have now examined the effects of these anthraquinone pigments on enzymes that metabolize xenobiotics. The activities of eight human recombinant cytochrome P450 (CYP) isozymes were measured in the presence of purpurin, Alizarin or carminic acid. Purpurin and Alizarin strongly inhibited the activities of CYP1A1, CYP1A2 and CYP1B1, and weakly suppressed those of CYP2A6 and CYP2E1 in a dose-dependent manner, but did not inhibit those of CYP2C19, CYP3A4 and CYP3A5. Carminic acid did not affect the activities of any CYPs tested. CYP1B1 was the most strongly affected CYP molecule by purpurin and Alizarin among CYPs examined in this study. From kinetic analysis, it was shown that the inhibition by purpurin on CYP1B1 was both competitive and non-competitive, and that by Alizarin was competitive. The values of slopes obtained from Lineweaver-Burk plots are proportional to the square of purpurin concentration. This observation suggests that two molecules of purpurin are interacting with one molecule of CYP1B1. The K(m) value of CYP1B1 was 11 microM, and the K(i) value of purpurin and Alizarin against CYP1B1 was 0.7 microM(2) and 0.5 microM, respectively. We also examined the effects of these pigments on the mutagenicities of MeIQx and B[a]P in the Ames test, using Salmonella typhimurium TA1538 co-expressing each form of human CYP and NADPH-cytochrome P450 reductase (OR). The mutagenicity of MeIQx in TA1538 1A2/OR or 1B1/OR was suppressed by purpurin and Alizarin but not by carminic acid. Purpurin also reduced the mutagenicity of B[a]P in TA1538 1A1/OR or 1B1/OR. These results suggest that the antigenotoxic activities of purpurin and Alizarin can be explained by inhibition of CYP activities responsible for activating the mutagens.

Description

Alizarin is a natural dye extracted from the roots of madder plant and has been widely used as a pigment in textile fabrics and paintings.

Keywords:

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