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| 5g |
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| 10g |
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| 25g | |||
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Purity: ≥98%
Alizarin is a naturally occuring and anthraquinone-based dye extracted from the roots of madder plant. It has been widely used as a pigment in textile fabrics and paintings. Alizarin also exhibits antioxidant activity. It can be used for detecting the presence of calcium salts. 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. 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.
| Targets |
Human cytochrome P450 enzymes: CYP1A1 (IC50 = 6.2 μM), CYP1A2 (IC50 = 10.0 μM), CYP1B1 (IC50 = 2.7 μM; Ki = 0.5 μM, competitive inhibition).[1]
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| ln Vitro |
In vitro activity: Alizarin weakly inhibits CYP2A6 and CYP2E1. Alizarin shows competitive inhibition against CYP1B1 with Ki of 0.5 μM. Alizarin reduces the mutagenicity of MeIQx, which induced by each CYP1A2 or CYP1B1, while does not effectively reduce the mutation induced by B[a]P. Alizarin exhibits antioxidants against iodophenol-derived phenoxyl radicals, superoxide anion radicals and lipid peroxidation in rat liver microsomes. Alizarin strongly inhibited the activities of human recombinant CYP1A1, CYP1A2 and CYP1B1 in a dose-dependent manner, and weakly suppressed CYP2A6 and CYP2E1, but did not inhibit CYP2C19, CYP3A4 or CYP3A5. Carminic acid showed no inhibition.[1] For CYP1B1-mediated 7-ethoxycoumarin O-deethylation, alizarin exhibited competitive inhibition with a Ki value of 0.5 μM. The Lineweaver-Burk plots showed that k values (slopes) were proportional to alizarin concentration, suggesting one molecule of alizarin interacts with one molecule of CYP1B1. The Km of CYP1B1 was 11 μM.[1] In the Ames test using S. typhimurium TA1538 co-expressing human CYP and NADPH-cytochrome P450 reductase, alizarin suppressed the mutagenicity of MeIQx (activated by CYP1A2 or CYP1B1) in a dose-dependent manner, but did not effectively reduce the mutagenicity of B[a]P (activated by CYP1A1 or CYP1B1). Alizarin did not suppress AFB1 mutagenicity (activated by CYP3A4).[1] |
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| ln Vivo |
Alizarin also reduces the hepatic content of thiobarbituric acid-reactive substances and the serum level of alanine aminotransferase in poisoned animals
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| Enzyme Assay |
Enzyme activities of human recombinant CYPs (CYP1A1, CYP1A2, CYP1B1, CYP2A6, CYP2C19, CYP2E1, CYP3A4, CYP3A5) co-expressed with NADPH-cytochrome P450 reductase in E. coli membrane fractions were measured. For CYP1A1 and CYP1B1, activity was determined by 7-ethoxycoumarin O-deethylation using 40 μM and 20 μM substrate respectively, and fluorescence quantification. For CYP1A2, activity was measured by 7-ethoxyresorufin O-deethylation. For CYP2A6, activity was measured by coumarin 7-hydroxylation. For CYP2C19, CYP2E1, CYP3A4 and CYP3A5, metabolite quantification was performed by HPLC with UV detection: CYP2C19 by 4'-hydroxylation of (S)-mephenytoin, CYP2E1 by 6-hydroxylation of chlorzoxazone, and CYP3A4/3A5 by 1'-hydroxylation of midazolam (20 μM for CYP3A4, 7 μM for CYP3A5) using diazepam as internal standard. To evaluate Ki of alizarin against CYP1B1, enzyme activities were measured in the presence of 0.2-1.6 μM alizarin at substrate doses from 2.5 to 40 μM.[1]
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| Cell Assay |
The Ames test was performed using S. typhimurium TA1538 strains co-expressing human CYP and NADPH-cytochrome P450 reductase (TA1538 1A1/OR, 1A2/OR, 1B1/OR, or 3A4/OR). Bacteria were cultured in modified Terrific Broth at 30°C for 8 h (except TA1538 1A2/OR at 25°C), then induced with 1.5 mM IPTG for 18 h. Cells were collected by centrifugation and resuspended in 0.1 M sodium phosphate buffer (pH 7.4) to a concentration of 1-2×10^9 cells/ml. Bacterial suspension (~10^8 cells) was incubated with mutagen (0.1 μM MeIQx for CYP1A2, 0.5 μM MeIQx for CYP1B1, 1.5 μM B[a]P for CYP1A1/CYP1B1, or 25 μM AFB1 for CYP3A4) in the absence or presence of alizarin (10^-3 to 10^-7 M) at 37°C for 20 min without S9 mix. After two days, His+ revertant colonies were counted.[1]
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| Animal Protocol |
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| References |
Mutat Res.2002 Oct 31;508(1-2):147-56.
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| Additional Infomation |
Alizarin is a dihydroxyanthraquinone, namely anthracene-9,10-dione, with the two hydroxyl groups located at positions 1 and 2, respectively. It can be used as a chromophore, dye, and plant metabolite. Alizarin has been reported in Rubia lanceolata, Rubia argyi, and other organisms with relevant data. See also: Root (part) of Rubia tinctorum.
Alizarin has one fewer hydroxyl group than purpurin (lacking the 4-position hydroxy group), which may account for differences in antigenotoxic effects and CYP inhibition potency. Alizarin was less effective than purpurin at inhibiting CYP1A2 and at reducing B[a]P mutagenicity. It is a competitive-type inhibitor of CYP1B1, whereas purpurin shows mixed-type inhibition. The antigenotoxic activity of alizarin is at least partially attributable to suppression of CYP-mediated bioactivation of mutagens. These anthraquinone compounds may be beneficial chemopreventive agents at appropriate doses.[1] |
| Molecular Formula |
C14H8O4
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| Molecular Weight |
240.21
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| Exact Mass |
240.042
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| CAS # |
72-48-0
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| Related CAS # |
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| PubChem CID |
6293
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| Appearance |
Yellow to brown solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
430.0±40.0 °C at 760 mmHg
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| Melting Point |
287 °C
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| Flash Point |
228.0±23.8 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.733
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| LogP |
4.09
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
18
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| Complexity |
378
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
RGCKGOZRHPZPFP-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C14H8O4/c15-10-6-5-9-11(14(10)18)13(17)8-4-2-1-3-7(8)12(9)16/h1-6,15,18H
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| Chemical Name |
1,2-dihydroxyanthracene-9,10-dione
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| Synonyms |
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (10.41 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.5 mg/mL (10.41 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.1630 mL | 20.8151 mL | 41.6302 mL | |
| 5 mM | 0.8326 mL | 4.1630 mL | 8.3260 mL | |
| 10 mM | 0.4163 mL | 2.0815 mL | 4.1630 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT02329548 | Completed | Other: Alizarin Red | Postural Tachycardia Syndrome Syncope |
Nationwide Children's Hospital | December 2014 | Not Applicable |
| NCT03104166 | Completed | Device: Medium Cut-Off (MCO) dialysis membrane |
Vascular Calcification | Charite University, Berlin, Germany | January 22, 2018 | Not Applicable |
| NCT02676921 | Completed | Sinus; Empyema, Maxillary (Chronic) | BERBERI ANTOINE | March 2014 | ||
| NCT03105284 | Completed | Procedure: Liposuction | Mesenchymal Stem Cells | University of Aarhus | September 1, 2016 | Not Applicable |
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