| Size | Price | Stock | Qty |
|---|---|---|---|
| 100mg |
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| 500mg |
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| Other Sizes |
Purity: =99.86%
| Targets |
α-glucosidase
The primary target of 4-Nitrophenyl aD-glucopyranoside is α-glucosidase, an enzyme that catalyzes the hydrolysis of terminal α-1,4-linked glucose residues. The compound serves as a substrate for this enzyme, and its hydrolysis results in the release of 4-nitrophenol, which can be detected colorimetrically. By measuring the production of 4-nitrophenol, researchers can quantify α-glucosidase activity. The compound is also used to detect glucansucrases. |
|---|---|
| ln Vitro |
P-nitrophenol is released by 4-Nitrophenyl aD-glucopyranoside by enzymatic cleavage. By using colorimetric detection at 405 nm, p-nitrophenol can be measured[2].
In vitro, 4-Nitrophenyl aD-glucopyranoside is used as a chromogenic substrate to measure α-glucosidase activity. The enzyme catalyzes the hydrolysis of the glycosidic bond, releasing 4-nitrophenol, which produces a yellow color in alkaline solution. The absorbance is measured at 400 nm, and the enzyme activity is calculated based on the rate of 4-nitrophenol release. The compound is also used in the detection of glucansucrases and for yeast α-glucosidase. |
| ln Vivo |
4-Nitrophenyl aD-glucopyranoside does not have specific in vivo biological activity as it is used as a substrate for in vitro enzyme assays. However, the compound may be used in ex vivo studies to measure α-glucosidase activity in tissue samples or biological fluids. The compound's utility lies in its ability to serve as a probe for α-glucosidase enzyme activity.
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| Enzyme Assay |
p-Nitrophenyl alpha-D-glucopyranoside has been shown to be a substrate for the glucansucrases of various strains of Leuconostoc mesenteroides and Streptococcus mutans. The products from a digest of p-nitrophenyl alpha-D-glucopyranoside with L. mesenteroides B-512F dextransucrase were found to include dextran, a series of p-nitrophenyl isomaltodextrin glycosides, and p-nitrophenyl nigeroside. The kinetics of the reaction were non-Michaelis-Menten, possibly because p-nitrophenyl alpha-D-glucopyranoside has a dual role in the reaction as both a D-glucosyl donor and acceptor [2].
The in vitro enzyme assay for 4-Nitrophenyl aD-glucopyranoside involves incubating the compound with α-glucosidase enzyme preparations (e.g., tissue homogenates, cell lysates, or recombinant enzyme) in a suitable buffer system. The enzyme catalyzes the hydrolysis of the substrate to release 4-nitrophenol. The reaction is stopped by the addition of a basic solution (e.g., sodium carbonate), which develops the yellow color of the 4-nitrophenolate ion. The absorbance is measured at 400 nm, and the enzyme activity is calculated based on the rate of 4-nitrophenol formation. |
| Cell Assay |
Cellular assays for 4-Nitrophenyl aD-glucopyranoside typically use cell lines that express α-glucosidase, such as intestinal epithelial cells or hepatocytes. Cells are lysed, and the lysate is incubated with the substrate. The production of 4-nitrophenol is measured to quantify enzyme activity. Alternatively, live cells can be used to measure the hydrolysis of the substrate, which may be taken up by the cells. The compound's utility lies in its role as a substrate for α-glucosidase activity measurements.
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| Animal Protocol |
4-Nitrophenyl aD-glucopyranoside does not have specific in vivo animal study protocols as it is used as a substrate for in vitro enzyme assays. The compound may be used in ex vivo studies to measure α-glucosidase activity in tissue samples from animals treated with enzyme inducers or inhibitors.
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| ADME/Pharmacokinetics |
As a chromogenic substrate, 4-Nitrophenyl aD-glucopyranoside does not have conventional pharmacokinetic properties. The compound has a molecular weight of 301.25 g/mol and is typically stored under standard laboratory conditions. For research purposes, the compound is handled as a solid with standard safety precautions.
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| Toxicity/Toxicokinetics |
There is no specific toxicity data reported for 4-Nitrophenyl aD-glucopyranoside in the available literature. As a research chemical, the compound is intended for laboratory use only and should be handled with standard safety precautions. The compound is typically stored under standard laboratory conditions.
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| References | |
| Additional Infomation |
4-Nitrophenyl α-D-glucoside is an α-D-glucoside, a derivative of β-D-glucopyranose, in which the terminal hydroxyl hydrogen is replaced by 4-nitrophenyl. It is a chromogenic compound. It is a monosaccharide derivative, an α-D-glucoside, and a C-nitro compound. Its function is related to 4-nitrophenol. Since α-glucosidase is closely related to type 2 diabetes, studying its inhibitory effect is very important. Studies have found that morin has significant inhibitory activity against α-glucosidase, and the inhibition mode is reversible and mixed, with an IC50 value of (4.48 ± 0.04) μM. Fluorescence spectroscopy and circular dichroism analysis showed that the formation of the morin-α-glucosidase complex is mainly driven by hydrophobic interactions and hydrogen bonds, leading to a conformational change in α-glucosidase. Fluorescence phase diagrams showed that the conformational change process was a single-phase process without intermediates. Molecular docking results showed that morin mainly interacts with amino acid residues near the active site of α-glucosidase, which may move and cover the active pocket, thereby reducing substrate binding and inhibiting catalytic activity. In addition, morin was also found to inhibit the formation of advanced glycation end products (AGEs), which are associated with long-term complications of diabetes. [1]
4-Nitrophenyl aD-glucopyranoside (CAS#: 3767-28-0) is a chromogenic glycoside substrate commonly supplied as a crystalline powder. It features an α-D-glucopyranoside moiety linked to a 4-nitrophenyl group, serving as a sensitive indicator in enzymatic assays for α-glucosidase activity. The compound has a molecular formula of C12H15NO8 and a molecular weight of 301.25 g/mol. It acts as a chromogenic substrate for alpha-D-glucosidase and is also used in the detection of glucansucrases and for yeast alpha-D-glucosidase. |
| Molecular Formula |
C12H15NO8
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|---|---|
| Molecular Weight |
301.25
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| Exact Mass |
301.079
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| Elemental Analysis |
C, 47.84; H, 5.02; N, 4.65; O, 42.49
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| CAS # |
3767-28-0
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| PubChem CID |
92969
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| Appearance |
White to off-white solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
582.2±50.0 °C at 760 mmHg
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| Melting Point |
210-216ºC
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| Flash Point |
305.9±30.1 °C
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| Vapour Pressure |
0.0±1.7 mmHg at 25°C
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| Index of Refraction |
1.648
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| LogP |
-0.55
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
21
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| Complexity |
354
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| Defined Atom Stereocenter Count |
5
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| SMILES |
C1=CC(=CC=C1[N+](=O)[O-])O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
|
| InChi Key |
IFBHRQDFSNCLOZ-ZIQFBCGOSA-N
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| InChi Code |
InChI=1S/C12H15NO8/c14-5-8-9(15)10(16)11(17)12(21-8)20-7-3-1-6(2-4-7)13(18)19/h1-4,8-12,14-17H,5H2/t8-,9-,10+,11-,12+/m1/s1
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| Chemical Name |
(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxane-3,4,5-triol
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| Synonyms |
3767-28-0; 4-nitrophenyl-alpha-D-glucopyranoside; 4-Nitrophenyl alpha-D-glucopyranoside; 4-Nitrophenyl a-D-glucopyranoside; 4-Nitrophenyl alpha-glucoside; pNPalphaGlu; a-D-Glucopyranoside, 4-nitrophenyl; p-Nitrophenyl alpha-D-glucopyranoside;
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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) |
DMSO: 50 mg/mL (165.98 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.30 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 (8.30 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 (8.30 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 | 3.3195 mL | 16.5975 mL | 33.1950 mL | |
| 5 mM | 0.6639 mL | 3.3195 mL | 6.6390 mL | |
| 10 mM | 0.3320 mL | 1.6598 mL | 3.3195 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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