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Helioxanthin

Alias: HE-145 HE145. Helioxanthin HE 145
Cat No.:V6901 Purity: ≥98%
Helioxanthin (ACH126447) has in vitro anti-viral effect with EC50 of 1 μM against HBV (hepatitis B virus) and is also anti-flavivirus.
Helioxanthin
Helioxanthin Chemical Structure CAS No.: 18920-47-3
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
Other Sizes

Other Forms of Helioxanthin:

  • Helioxanthin derivative 5-4-2
  • Helioxanthin 8-1
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Helioxanthin (ACH126447) has in vitro anti-viral effect with EC50 of 1 μM against HBV (hepatitis B virus) and is also anti-flavivirus.
Helioxanthin (ACH126447) (CAS#: 18920-47-3) is a natural product with significant in vitro antiviral activity, particularly against hepatitis B virus (HBV) and flaviviruses. It has a molecular weight of 348.31 g/mol and a molecular formula of C20H12O6. Helioxanthin exhibits an EC50 of 1 μM against HBV in cell-based assays. It has been studied for its potential as an anti-infective agent. The compound is a research tool and is not approved for any clinical or therapeutic use. Its analogues also exhibit significant antiviral activity, suggesting a class effect. Helioxanthin is typically stored as a powder at -20°C.
Biological Activity I Assay Protocols (From Reference)
Targets
Helioxanthin's primary target is the hepatitis B virus (HBV), although its exact molecular target is not fully elucidated. It exhibits antiviral activity against HBV and flaviviruses. The compound's mechanism of action is believed to involve inhibition of viral replication, but the specific viral or host proteins it interacts with have not been definitively identified. Its activity against flaviviruses suggests a broad-spectrum antiviral potential. Further research is needed to identify its precise molecular target and to understand its mechanism of action in detail.
ln Vitro
In vitro, Helioxanthin demonstrates potent antiviral activity against hepatitis B virus (HBV) with an EC50 of 1 μM. It is also active against flaviviruses. The compound's activity is typically measured using cell-based assays, such as HBV replicon assays, where the reduction in viral DNA or antigen levels is quantified. Its analogues have been shown to exhibit significant in vitro antiviral activity, suggesting that the core structure is important for its antiviral properties. These in vitro findings establish Helioxanthin as a potent antiviral agent against HBV and flaviviruses.
ln Vivo
In vivo activity data for Helioxanthin is limited, as the compound is primarily used as a research tool in in vitro studies. While it has shown potent in vitro antiviral activity, its in vivo efficacy and pharmacokinetic properties have not been extensively characterized in standard product descriptions. The compound could potentially be evaluated in animal models of HBV infection, such as the hydrodynamic injection mouse model or the humanized liver mouse model. However, specific in vivo protocols and results are not detailed in the available literature. Its use remains confined to in vitro research.
Enzyme Assay
The in vitro assays for Helioxanthin measure its antiviral activity against HBV and flaviviruses. For HBV, the most common assay is the HBV replicon assay. In this assay, human hepatoma cells (e.g., HepG2.2.15) that stably replicate HBV are treated with varying concentrations of Helioxanthin. After incubation, the levels of HBV DNA or the secretion of HBV surface antigen (HBsAg) and e antigen (HBeAg) are measured. The EC50, which is the concentration that inhibits 50% of viral replication or antigen production, is determined from dose-response curves. For flaviviruses, similar cell-based assays using virus-infected cells are employed.
Cell Assay
In vitro cell-based assays for Helioxanthin are conducted using HBV-replicating cell lines, such as HepG2.2.15 cells. In a typical assay, cells are seeded in multi-well plates and treated with Helioxanthin at various concentrations. After a defined incubation period (e.g., 3-5 days), the culture supernatant is collected to measure the levels of HBsAg and HBeAg by ELISA. Intracellular HBV DNA can also be quantified by real-time PCR. The EC50 is determined from the dose-response curve. For flavivirus studies, cells are infected with the virus and then treated with Helioxanthin. Viral replication is quantified by measuring viral titers or by detecting viral proteins via immunofluorescence.
Animal Protocol
In vivo animal experiments for Helioxanthin are not extensively described in the available literature. As a research compound with in vitro antiviral activity, it could be evaluated in animal models of HBV infection. For example, the hydrodynamic injection mouse model, where HBV DNA is injected into the tail vein of mice to establish transient infection, could be used. Helioxanthin would be administered orally or by injection, and viral load in the blood and liver would be measured over time. However, specific protocols for Helioxanthin are not detailed. Its use is limited to research applications.
ADME/Pharmacokinetics
Helioxanthin has a molecular weight of 348.31 g/mol and a molecular formula of C20H12O6. It is a solid compound. For storage, it is recommended to keep the powder at -20°C for up to 3 years or at 4°C for up to 2 years. The compound is soluble in DMSO and other organic solvents. Detailed pharmacokinetic properties such as absorption, distribution, metabolism, and excretion (ADME) have not been extensively characterized. As a research compound, its stability under various conditions is primarily managed through proper storage as a dry powder.
Toxicity/Toxicokinetics
Detailed toxicity data for Helioxanthin is not provided in standard product descriptions. As a research compound with antiviral activity, its toxicity profile has not been extensively characterized. In vitro studies have not reported significant cytotoxicity at concentrations that are effective against HBV, but comprehensive toxicological studies are lacking. As with all research chemicals, standard laboratory safety precautions should be followed when handling Helioxanthin. Its use is limited to research applications and it is not intended for human or veterinary use.
References

[1]. Synthesis and antiviral activity of helioxanthin analogues. J Med Chem. 2005 Jan 27;48(2):534-46.

[2]. Cheng, Y. C.; Chou, C. K.; Fu, L.; Kuo, Y. H.; Yeh, S. F.; Zhu, J.; Zhu, Y. Inhibition and treatment of hepatitis B virus and flavivirus by helioxanthin and its analogues. U.S. Patent 6306899 B1, 2001.

[3]. Helioxanthin analogue 8-1 inhibits duck hepatitis B virus replication in cell culture. Antivir Chem Chemother. 2010;21(2):97-103.

Additional Infomation
Helioxanthin is a furan-naphthodioxane compound with the structure furano[3',4':6,7]naphtho[1,2-d][1,3]dioxanthin-7(9H)-one, where the 10-position is substituted with a 1,3-benzodioxanthin-5-yl group. It can inhibit the activity of hepatitis B virus (HBV), hepatitis C virus (HCV), and herpes simplex virus type 1 (HSV-1). Helioxanthin can be used as an anti-hepatitis B virus drug, a plant metabolite, and an antitumor drug. It belongs to the benzodioxanthin, furan-naphthodioxanthin, and lignan classes of compounds. It has been reported that helioxanthin exists in Hypoestes purpurea, Phoebe formosana, and other organisms with relevant data.
Helioxanthin (ACH126447) is a research compound and is not approved for any clinical or therapeutic use. It is a natural product with significant in vitro antiviral activity against hepatitis B virus (HBV), with an EC50 of 1 μM, and is also active against flaviviruses. It is used as a research tool to study the replication of HBV and flaviviruses and to explore potential antiviral strategies. Its mechanism of action is not fully elucidated, but it inhibits viral replication. Helioxanthin and its analogues represent a class of compounds with potential for development as antiviral agents. However, it is not a drug and has not undergone clinical trials.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H12O6
Molecular Weight
348.31
Exact Mass
348.063
CAS #
18920-47-3
Related CAS #
Helioxanthin derivative 5-4-2;203935-39-1;Helioxanthin 8-1;840529-13-7
PubChem CID
177023
Appearance
Light yellow to yellow solid powder
Density
1.5±0.1 g/cm3
Boiling Point
622.5±55.0 °C at 760 mmHg
Flash Point
277.1±31.5 °C
Vapour Pressure
0.0±1.8 mmHg at 25°C
Index of Refraction
1.723
LogP
3.7
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
1
Heavy Atom Count
26
Complexity
581
Defined Atom Stereocenter Count
0
InChi Key
JUBRYHUFFFYTGR-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H12O6/c21-20-12-5-10-2-4-15-19(26-9-24-15)18(10)17(13(12)7-22-20)11-1-3-14-16(6-11)25-8-23-14/h1-6H,7-9H2
Chemical Name
10-(1,3-benzodioxol-5-yl)-9H-[2]benzofuro[6,5-g][1,3]benzodioxol-7-one
Synonyms
HE-145 HE145. Helioxanthin HE 145
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

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)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.8710 mL 14.3550 mL 28.7101 mL
5 mM 0.5742 mL 2.8710 mL 5.7420 mL
10 mM 0.2871 mL 1.4355 mL 2.8710 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

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
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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