| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
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| 50mg |
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| 100mg |
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| 250mg | |||
| Other Sizes |
| Targets |
HIV-1 integrase (IC50 for 3'-processing = 5.9 ± 1.9 μM; IC50 for strand transfer/integration = 1.6 ± 0.7 μM) [1]
Bacterial DNA and RNA synthesis [2] |
|---|---|
| ln Vitro |
In a dose-dependent manner, robinetin (0.1-10 μM; 1 hour) inhibits HIV integrase cleavage and integration [1]. In Proteus vulgaris, reinocetin inhibits DNA synthesis, but in Staphylococcus aureus, it inhibits RNA synthesis [2]. Hemoglobin A (HbA) glycosylation and egg yolk phosphatidylcholine (EYPC) membrane lipid peroxidation are both efficiently inhibited by robinetin (100–200 or 25 μM; 1 or 72 hours) [3]. The "dual-color" (in the "blue-violet" and "yellow-green") fluorescence properties of flavonols are caused by photoinduced excited-state intramolecular proton transfer exhibited by robinetin. The relative contribution between the two colors is strongly modulated locally by the fluorophore environment[3].
Inhibited HIV-1 integrase catalyzed reactions. In assays using a 21-mer blunt-end oligonucleotide substrate corresponding to the U-5 end of HIV-1 proviral DNA, Robinetin inhibited the 3'-processing (cleavage) reaction with an IC50 of 5.9 ± 1.9 μM and the strand transfer (integration) reaction with an IC50 of 1.6 ± 0.7 μM. The ratio of IC50 for cleavage to IC50 for integration was 3.7 [1]. Showed antibacterial activity by inhibiting nucleic acid synthesis. In studies with Proteus vulgaris and Staphylococcus aureus, Robinetin strongly inhibited DNA and RNA synthesis [2]. |
| Enzyme Assay |
HIV-1 integrase inhibition assays were performed. Purified HIV-1 integrase protein was reacted with a 5' end-labeled 21-mer blunt-end double-stranded oligonucleotide substrate corresponding to the U-5 end of the HIV-1 proviral DNA. The reaction was carried out for 1 hour at 30°C in a buffer containing 50 mM NaCl, 1 mM HEPES, 50 µM EDTA, 50 µM dithiothreitol, 10% glycerol, 7.5 mM MnCl2, 0.1 mg/mL BSA, 10 mM β-mercaptoethanol, and 25 mM MOPS at pH 7.2, with 10% DMSO. The reaction was stopped by adding an equal volume of loading buffer. The products (21-mer substrate, 19-mer cleavage product, and larger integration products) were separated on a 20% denaturing polyacrylamide gel and quantitated using a β-emissions detector. The IC50 for inhibiting both the 3'-processing (cleavage) and strand transfer (integration) reactions was calculated [1].
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| References | |
| Additional Infomation |
Robinin is a 5-hydroxyflavonoid with a structure in which flavonoids are substituted with hydroxyl groups at the 3, 7, 3', 4', and 5' positions. It is a plant metabolite. Robinin is both a 5-hydroxyflavonoid and a 7-hydroxyflavonol. It has been reported to exist in Intsia bijuga, Burkea africana, and other organisms with relevant data.
Structure-Activity Relationship (SAR): Robinetin (pentahydroxyflavone) has three hydroxyl groups on adjacent carbons of its B-ring (positions 3', 4', 5'), which contributes to its potent inhibition of HIV-1 integrase. The presence of at least one ortho pair of phenolic hydroxyl groups and at least one or two additional hydroxyl groups was generally required for inhibition by flavones. Potency was enhanced by the presence of three adjacent hydroxyls, as seen in Robinetin [1]. Mechanism of Action: The inhibition of HIV-1 integrase by flavones like Robinetin is suggested to involve interaction with the enzyme's active site, potentially through stacking with DNA bases, chelation of divalent metal ions (Mn2+ > Mg2+), or redox chemistry involving the ortho hydroxyl groups. The inhibition is not dependent on the zinc-finger domain of the integrase [1]. Comparison with other enzymes: The SAR for Robinetin and related flavones inhibiting HIV-1 integrase is similar to that for inhibiting topoisomerase II and reverse transcriptase [1]. |
| Molecular Formula |
C15H10O7
|
|---|---|
| Molecular Weight |
302.23
|
| Exact Mass |
302.042
|
| CAS # |
490-31-3
|
| PubChem CID |
5281692
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.8±0.1 g/cm3
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| Boiling Point |
669.9±55.0 °C at 760 mmHg
|
| Melting Point |
326-328ºC
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| Flash Point |
258.6±25.0 °C
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| Vapour Pressure |
0.0±2.2 mmHg at 25°C
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| Index of Refraction |
1.823
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| LogP |
2.55
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| Hydrogen Bond Donor Count |
5
|
| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
1
|
| Heavy Atom Count |
22
|
| Complexity |
476
|
| Defined Atom Stereocenter Count |
0
|
| InChi Key |
SOEDEYVDCDYMMH-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C15H10O7/c16-7-1-2-8-11(5-7)22-15(14(21)12(8)19)6-3-9(17)13(20)10(18)4-6/h1-5,16-18,20-21H
|
| Chemical Name |
3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one
|
| Synonyms |
Norkanugin Robinetin
|
| 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 Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). 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 (In Vitro) |
DMSO : ~120 mg/mL (~397.04 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 3 mg/mL (9.93 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 30.0 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: ≥ 3 mg/mL (9.93 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 30.0 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 | 3.3087 mL | 16.5437 mL | 33.0874 mL | |
| 5 mM | 0.6617 mL | 3.3087 mL | 6.6175 mL | |
| 10 mM | 0.3309 mL | 1.6544 mL | 3.3087 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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