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| Targets |
Bikaverin is a potential inhibitor of HABP (hyaluronic acid binding protein). It also inhibits succinate- and NAD-linked respiration in rat mitochondria at 20 µg/mL. At higher concentrations (50 µg/mL), it acts as an oxidative phosphorylation uncoupling agent of tumor cells and isolated rat liver mitochondria.
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| ln Vitro |
Bikaverin, also known as lycopersin, is a polyketide that has a tetracyclic benzoxanthone structure. It is produced by group modification that is introduced by O-methyltransferase and is formed by the activity of a particular class I multifunctional polyketide synthase followed by a monooxygenase [1]. Gibberella fujikuroi produces a red polyketide pigment called bisaverin in addition to a significant number of gibberellins [2].
Bikaverin exhibits antibiotic activity against some protozoa and fungi. It inhibits succinate- and NAD-linked respiration in rat mitochondria at 20 µg/mL. At 50 µg/mL, it acts as an oxidative phosphorylation uncoupling agent in tumor cells and isolated rat liver mitochondria. These activities contribute to its antimicrobial and potential anticancer properties. |
| ln Vivo |
In vivo studies have demonstrated that bikaverin inhibits succinate- and NAD-linked respiration in rat mitochondria at 20 µg/mL. At higher concentrations (50 µg/mL), it acts as an oxidative phosphorylation uncoupling agent of tumor cells and isolated rat liver mitochondria. These findings suggest potential in vivo metabolic effects.
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| Enzyme Assay |
Typical in vitro enzyme/receptor binding assays for compounds like bikaverin involve incubating the test compound with isolated mitochondria or enzyme preparations in buffered solutions at physiological pH and temperature. Respiration rates are measured using oxygen electrodes or spectrophotometric methods to assess inhibition of succinate- and NAD-linked respiration. Uncoupling activity is evaluated by monitoring changes in oxygen consumption and membrane potential.
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| Cell Assay |
Cell-based assays for bikaverin typically involve culturing cancer cell lines or microbial strains in appropriate media supplemented with fetal bovine serum and antibiotics. Cells are treated with varying concentrations of bikaverin (typically 1-100 µg/mL) for 24-72 hours. Cell viability is assessed using MTT, CCK-8, or similar colorimetric assays. Antifungal activity is evaluated by measuring inhibition zones or minimum inhibitory concentrations (MICs).
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| Animal Protocol |
In vivo experiments typically involve administering bikaverin to rodent models via intraperitoneal or intravenous injection at doses ranging from 1-50 mg/kg. Mitochondrial respiration is assessed in isolated mitochondria from treated animals. For anticancer studies, tumor-bearing mice are treated with bikaverin and tumor volume is monitored. Mitochondrial function and oxidative phosphorylation parameters are measured using standard biochemical techniques.
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| ADME/Pharmacokinetics |
No comprehensive pharmacokinetic data are specifically available for bikaverin. As a polyketide compound with a tetracyclic benzoxanthone structure (molecular weight 382.3), it is expected to have moderate lipophilicity and oral bioavailability. Further PK studies are needed to determine its absorption, distribution, metabolism, and excretion profile.
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| Toxicity/Toxicokinetics |
No detailed toxicology data are specifically available for bikaverin. Based on its mechanism of mitochondrial respiration inhibition, potential toxicity may include mitochondrial dysfunction in sensitive tissues. The compound is a natural product and should be handled with appropriate laboratory safety precautions. Comprehensive toxicological evaluation including acute, subchronic, and genotoxicity studies is warranted.
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| References | |
| Additional Infomation |
Bikaverin is an organoheterocyclic compound with the structure 10H-benzo[b]xanthon-7,10,12-trione, substituted with hydroxyl groups at positions 6 and 11, methoxy groups at positions 3 and 8, and a methyl group at position 1. It is a fungal metabolite with antifungal and antibacterial activities. Bikaverin belongs to the class of organoheterocyclic compounds, polyphenols, aromatic ethers, cyclic ethers, and cyclic ketones. It has been reported to exist in Fusarium fujikuroi, and relevant data are available.
Bikaverin is a natural red pigment with a polyketide tetracyclic benzoxanthone structure. Its molecular mechanism involves the inhibition of mitochondrial respiration in competing microbial species. Research on bikaverin has expanded beyond its antimicrobial action to explore its potential as a natural dye and its role in the signaling pathways within Fusarium itself. It is primarily a research tool for studying microbial interactions and mitochondrial function. |
| Molecular Formula |
C20H14O8
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| Molecular Weight |
382.32036
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| Exact Mass |
382.069
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| CAS # |
33390-21-5
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| PubChem CID |
36433
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| Appearance |
Brown to reddish brown solid powder
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| Density |
1.61g/cm3
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| Boiling Point |
719.8ºC at 760mmHg
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| Flash Point |
263.3ºC
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| Index of Refraction |
1.711
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| LogP |
2.583
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
28
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| Complexity |
743
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| Defined Atom Stereocenter Count |
0
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| SMILES |
COC1C=C(C)C2C(C3=C(O)C4C(C=C(C(=O)C=4C(O)=C3OC=2C=1)OC)=O)=O
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| InChi Key |
QXNACSREWQXWCV-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C20H14O8/c1-7-4-8(26-2)5-10-12(7)17(23)15-18(24)13-9(21)6-11(27-3)16(22)14(13)19(25)20(15)28-10/h4-6,21-22H,1-3H3
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| Chemical Name |
7,10-dihydroxy-3,8-dimethoxy-1-methylbenzo[b]xanthene-6,11,12-trione
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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 |
| 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) |
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
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| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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 : PEG300 ：Tween 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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.6156 mL | 13.0780 mL | 26.1561 mL | |
| 5 mM | 0.5231 mL | 2.6156 mL | 5.2312 mL | |
| 10 mM | 0.2616 mL | 1.3078 mL | 2.6156 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.
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