| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
COX-2
Inducible nitric oxide synthase (iNOS) and Cyclooxygenase-2 (COX-2). Phenyl beta-D-glucopyranoside inhibits the expression of iNOS and COX-2 at the transcriptional level, and also inhibits the nuclear translocation of NF-kappaB, a key transcription factor regulating the expression of pro-inflammatory mediators. |
|---|---|
| ln Vitro |
In vitro, Phenyl beta-D-glucopyranoside inhibits nitric oxide (NO) production and significantly suppresses the expression of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2) without inducing cytotoxicity. It also inhibits the nuclear translocation of NF-kappaB, preventing the transcription of pro-inflammatory genes. It exhibits anti-cancer and anti-inflammatory activities.
|
| ln Vivo |
No detailed in vivo studies for Phenyl beta-D-glucopyranoside alone are publicly available. Based on its in vitro activity, it would be expected to reduce inflammation and tumor growth in animal models. Its inhibition of NO and PGE2 production suggests potential efficacy in LPS-induced endotoxemia, carrageenan-induced paw edema, or xenograft tumor models.
|
| Enzyme Assay |
A direct biochemical assay for beta-D-glucosidase activity is performed using Phenyl beta-D-glucopyranoside as a chromogenic substrate. The compound is incubated with beta-D-glucosidase enzyme in assay buffer (pH 5.0-6.0) at 37degC. The release of phenol is measured by absorbance at 270 nm or by colorimetric detection using chromogenic reagents, providing a readout of enzyme activity. The kinetic parameters (Km, Vmax) are calculated.
|
| Cell Assay |
For in vitro cellular assays, murine macrophages (RAW 264.7) are stimulated with lipopolysaccharide (LPS, 1 ug/mL) in the presence of serially diluted Phenyl beta-D-glucopyranoside (1-1000 uM) for 24 hours. Nitric oxide (NO) in the supernatant is measured using the Griess reagent. iNOS and COX-2 protein expression are assessed by Western blot. NF-kappaB nuclear translocation is assessed by immunofluorescence or by preparing nuclear and cytoplasmic extracts for Western blot analysis. Cell viability is assessed using an MTT assay.
|
| Animal Protocol |
No published in vivo animal studies are available for this compound. For general research use, a mouse model of LPS-induced systemic inflammation can be used. C57BL/6 mice are injected intraperitoneally with LPS (5 mg/kg). Phenyl beta-D-glucopyranoside is administered orally or intraperitoneally at doses of 10-100 mg/kg, 1 hour before LPS injection. After 4-6 hours, blood is collected for serum NO and cytokine (TNF-alpha, IL-1beta) measurement. Lung and liver tissues are harvested for qPCR and Western blot analysis of iNOS and COX-2 expression.
|
| ADME/Pharmacokinetics |
Phenyl beta-D-glucopyranoside has a molecular weight of 256.25 g/mol and a formula of C12H16O6. It is a small, polar glycoside with high water solubility. Detailed in vivo PK parameters are not publicly available. As a glucoside, it may be hydrolyzed by intestinal beta-glucosidases before absorption, potentially limiting its oral bioavailability. The aglycone phenol is further metabolized and conjugated prior to excretion.
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| Toxicity/Toxicokinetics |
Detailed toxicological data for Phenyl beta-D-glucopyranoside are not publicly available. Based on its use as a chromogenic substrate and its natural occurrence in plants, it is expected to be relatively non-toxic at moderate concentrations. No significant adverse effects have been reported in cell-based assays, where it does not induce cytotoxicity at concentrations up to 1000 uM. Long-term toxicity studies have not been conducted.
|
| References | |
| Additional Infomation |
Phenylo-β-D-glucopyranoside is a glycoside. It has been reported to be found in both Goniophlebium niponicum and Gymnadenia conopsea, and relevant data are available for reference.
Phenyl beta-D-glucopyranoside is a research-grade compound not approved for clinical use. It is used as a chromogenic substrate for the determination of beta-D-glucosidase activity in biochemical assays. It also serves as a natural product tool to study the anti-inflammatory mechanisms mediated by NF-kappaB inhibition and suppression of iNOS and COX-2 expression. This product is for laboratory research purposes only. |
| Molecular Formula |
C12H16O6
|
|---|---|
| Molecular Weight |
256.25
|
| Exact Mass |
256.094
|
| CAS # |
1464-44-4
|
| PubChem CID |
65080
|
| Appearance |
White to off-white solid powder
|
| Density |
1.5±0.1 g/cm3
|
| Boiling Point |
482.1±45.0 °C at 760 mmHg
|
| Melting Point |
176-178ºC(lit.)
|
| Flash Point |
245.4±28.7 °C
|
| Vapour Pressure |
0.0±1.3 mmHg at 25°C
|
| Index of Refraction |
1.619
|
| LogP |
-0.67
|
| Hydrogen Bond Donor Count |
4
|
| Hydrogen Bond Acceptor Count |
6
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
18
|
| Complexity |
255
|
| Defined Atom Stereocenter Count |
5
|
| SMILES |
C1=CC=C(C=C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
|
| InChi Key |
NEZJDVYDSZTRFS-RMPHRYRLSA-N
|
| InChi Code |
InChI=1S/C12H16O6/c13-6-8-9(14)10(15)11(16)12(18-8)17-7-4-2-1-3-5-7/h1-5,8-16H,6H2/t8-,9-,10+,11-,12-/m1/s1
|
| Chemical Name |
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-phenoxyoxane-3,4,5-triol
|
| 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, 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: 100 mg/mL (390.24 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.76 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 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 (9.76 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 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (9.76 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.9024 mL | 19.5122 mL | 39.0244 mL | |
| 5 mM | 0.7805 mL | 3.9024 mL | 7.8049 mL | |
| 10 mM | 0.3902 mL | 1.9512 mL | 3.9024 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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