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Anthraflavic acid

Cat No.:V29125 Purity: ≥98%
Anthraflavic acid is a flavonoid and a potent inhibitor of IQ mutagenicity that can inhibit microsomal and cytosolic activation pathways.
Anthraflavic acid
Anthraflavic acid Chemical Structure CAS No.: 84-60-6
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
250mg
500mg
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Product Description
Anthraflavic acid is a flavonoid and a potent inhibitor of IQ mutagenicity that can inhibit microsomal and cytosolic activation pathways. Anthraflavic acid is also a potent and specific inhibitor of cytochrome P-448, an enzyme system closely involved in the activation of many chemical carcinogens.
Anthraflavic acid (CAS 84-60-6), also known as 2,6-Dihydroxyanthraquinone, is a flavonoid and a potent inhibitor of IQ mutagenicity. It inhibits both microsomal and cytosolic activation pathways of IQ. Anthraflavic acid is a potent and specific inhibitor of cytochrome P-448, an enzyme system closely associated with the activation of many chemical carcinogens. It effectively inhibits cytosolic metabolic pathways, obstructs the microsomal and cytosolic activation of IQ, and decreases the metabolic activation of Glu-P-I. It demonstrates no significant impact on phenobarbital-induced cytochrome P-450 or NADPH-dependent cytochrome c reduction.
Biological Activity I Assay Protocols (From Reference)
Targets
Anthraflavic acid targets cytochrome P-448, a specific isoform of cytochrome P450 involved in the activation of chemical carcinogens. It also inhibits the microsomal and cytosolic activation pathways of IQ mutagenicity. By inhibiting these pathways, it acts as a potent inhibitor of IQ mutagenicity. It demonstrates selectivity for cytochrome P-448 over phenobarbital-induced cytochrome P-450.
ln Vitro
In vitro, Anthraflavic acid is a potent inhibitor of IQ mutagenicity. It inhibits both microsomal and cytosolic activation pathways of IQ. It is a potent and specific inhibitor of cytochrome P-448 activity. It effectively inhibits cytosolic metabolic pathways, obstructs the microsomal and cytosolic activation of IQ, and decreases the metabolic activation of Glu-P-I. It demonstrates no significant impact on phenobarbital-induced cytochrome P-450 or NADPH-dependent cytochrome c reduction.
ln Vivo
In vivo activity data for Anthraflavic acid is limited in publicly available literature. As a potent inhibitor of IQ mutagenicity and cytochrome P-448 in vitro, it is hypothesized to exhibit similar effects in vivo. However, specific in vivo efficacy studies, including pharmacokinetic and pharmacodynamic parameters, have not been detailed in the available sources. Further research is needed to fully characterize its in vivo activity and potential as a chemopreventive agent.
Enzyme Assay
For cell-free assays, the inhibitory activity of Anthraflavic acid against cytochrome P-448 can be measured using standard cytochrome P450 activity assays. Microsomal preparations containing cytochrome P-448 are incubated with a specific substrate (e.g., aflatoxin B1 or other carcinogens) and varying concentrations of Anthraflavic acid. The formation of metabolites is measured by HPLC or LC-MS. Its inhibition of IQ mutagenicity can be assessed using Ames test (Salmonella mutagenicity assay) with metabolic activation.
Cell Assay
Anthraflavic acid is not typically used in cell-based pharmacological assays as a test compound. Its primary application is as an inhibitor of mutagenicity and cytochrome P-448 in biochemical and toxicological studies. It can be used in cell-based mutagenicity assays such as the Ames test.
Animal Protocol
Anthraflavic acid could be used in vivo to study its chemopreventive potential against carcinogen-induced mutagenesis. It could be administered orally or intraperitoneally in animal models of chemical carcinogenesis. Endpoints include reduction in DNA adduct formation, mutation frequency, and tumor incidence.
ADME/Pharmacokinetics
Anthraflavic acid (CAS 84-60-6) has a molecular formula of C14H8O4 and a molecular weight of 240.21 g/mol. It is also known as 2,6-Dihydroxyanthraquinone. Appearance: typically a solid. Solubility: DMSO and other organic solvents. Storage: typical for flavonoids (desiccated, protected from light, -20°C). Purity: typically >98% for research use.
Toxicity/Toxicokinetics
No detailed toxicity data is publicly available. As a flavonoid and inhibitor of mutagenicity, it is generally considered to have low toxicity, but standard toxicological studies would be required for drug development.
Additional Infomation
Anthraflavic is a dihydroxyAnthraflavic with the structure anthracene, where hydroxyl groups are substituted at C-3 and C-7, and carbonyl groups are substituted at C-9 and C-10. It has antimutagenic and anti-metabolite effects. It is derived from the hydride of anthracene. 2,6-DihydroxyAnthraflavic has been reported in senna (Senna obtusifolia) and madder (Rubia tinctorum), and relevant data are available.
Anthraflavic acid is a research-grade compound and is not approved for therapeutic use. It serves primarily as a pharmacological tool for studying cytochrome P-448 function, mutagenicity, and chemoprevention. Its mechanism of action involves selective inhibition of cytochrome P-448 and inhibition of IQ mutagenicity. No clinical trials have been reported.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C14H8O4
Molecular Weight
240.2109
Exact Mass
240.042
CAS #
84-60-6
PubChem CID
6776
Appearance
Yellow to green solid powder
Density
1.5±0.1 g/cm3
Boiling Point
442.1±35.0 °C at 760 mmHg
Melting Point
>320 °C(lit.)
Flash Point
235.3±22.4 °C
Vapour Pressure
0.0±1.1 mmHg at 25°C
Index of Refraction
1.733
LogP
3.36
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
0
Heavy Atom Count
18
Complexity
342
Defined Atom Stereocenter Count
0
SMILES
O=C1C2C(=CC=C(C=2)O)C(=O)C2C1=CC=C(C=2)O
InChi Key
APAJFZPFBHMFQR-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H8O4/c15-7-1-3-9-11(5-7)14(18)10-4-2-8(16)6-12(10)13(9)17/h1-6,15-16H
Chemical Name
2,6-dihydroxyanthracene-9,10-dione
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~16.67 mg/mL (~69.40 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 1.67 mg/mL (6.95 mM) in 10% DMSO + 40% PEG300 +5% Tween-80 + 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 16.7 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.

 (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.

Calculator

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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.

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