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15959-03-2 ,2-Aminophenyl b-D-glucuronide HCl, CAS:15959-03-2

15959-03-2 ,2-Aminophenyl b-D-glucuronide HCl,
CAS:15959-03-2
C12H15NO7·HCl / 321.71
MFCD00269899

2-Aminophenyl b-D-glucuronide HCl

邻氨基苯基-beta-D-葡萄糖醛酸苷盐酸盐,

2-Aminophenyl b-D-glucuronide is a cytosolic drug that is metabolized by the liver to mandelonitrile, which is then excreted in urine. 2-Aminophenyl b-D-glucuronide has been shown to inhibit the growth of fungi in vivo and has been shown to have a reversible binding affinity for fungal cell walls. This drug also inhibits the production of ergosterol, an important component of fungal cell membranes, which leads to cell death.

APGlu is a glucose derivative containing a uronic acid substituent attached to the anomeric carbon of the glucose residue. It belongs to the class of aryl-beta-D-glycosides with glucuronic acid. It is widely used as a chromogenic substrate for the detection of beta-glucuronidase, which is produced by bacteria that cause urinary tract infections, gonorrhea, and other diseases. APGlu is also used as an antiviral compound against hepatitis C virus.

Physical and Chemical Properties:

APGlu appears as a white crystalline powder that is soluble in water and alcohol, but insoluble in organic solvents. It has a melting point of 226-228 °C, and its absorption maximum is at 295 nm. APGlu is stable under normal conditions of storage and handling, but it may undergo hydrolysis in acidic conditions.

Synthesis and Characterization:

APGlu can be synthesized by the reaction of glucuronic acid or its derivatives with o-aminophenol in the presence of a weak base. The resulting APGlu can be characterized by various spectral techniques such as nuclear magnetic resonance (NMR), infrared spectroscopy, and mass spectrometry.

Analytical Methods:

APGlu can be analyzed by several analytical methods. High-performance liquid chromatography (HPLC) is the most commonly used method for the quantitative analysis of APGlu. HPLC coupled with tandem mass spectrometry (HPLC-MS/MS) is also used for the analysis of APGlu as a chromogenic substrate.

Biological Properties:

APGlu has been found to have anti-HIV and antiviral properties. Several studies have reported that APGlu inhibits the replication of HCV, HBV, and other viruses in vitro. APGlu has also been used as a diagnostic tool for the detection of bacterial infections.

Toxicity and Safety in Scientific Experiments:

Toxicity studies have shown that APGlu has low toxicity and is safe to use in scientific experiments. It does not cause any acute toxicity or harmful effects in animals even at high doses.

Applications in Scientific Experiments:

APGlu is widely used in microbiology and virology laboratories for the detection of beta-glucuronidase production by bacteria and in the development of new antiviral drugs against hepatitis C virus. APGlu is also used as a substrate in enzymatic assays and as a diagnostic tool in the detection of bacterial infections.

Current State of Research:

The current state of research on APGlu focuses on its antiviral properties against hepatitis C virus, the development of new diagnostic tools for bacterial infections, and the synthesis of new derivatives with improved biological properties.

Potential Implications in Various Fields of Research and Industry:

APGlu has potential implications in various fields of research and industry such as pharmaceuticals, diagnostics, and biotechnology. It can be used as a substrate in enzymatic assays, as a diagnostic tool for bacterial infections, and as an antiviral compound against hepatitis C virus. Its low toxicity and safety profile make it an attractive candidate for the development of new drugs and diagnostics.

Limitations and Future Directions:

Despite its potential applications, APGlu has several limitations, including low solubility in organic solvents, lack of stability in acidic conditions, and limited antiviral activity. Future directions for research include the synthesis of new derivatives with improved solubility, stability, antiviral activity, and diagnostic properties. APGlu also requires further investigation to determine its efficacy and safety in humans.

Some possible future directions for APGlu research include:

- Development of APGlu derivatives with improved antiviral activity against a broader range of viruses.

- Investigation of APGlu as a potential diagnostic tool for other bacterial infections.

- Development of APGlu-based biosensors for the rapid detection of beta-glucuronidase activity.

- Investigation of the mechanisms of action of APGlu as an antiviral compound.

- Clinical studies to evaluate the safety and efficacy of APGlu as a potential antiviral drug or diagnostic tool.

CAS Number15959-03-2
Product Nameo-Aminophenyl beta-D-glucopyranosiduronic acid
IUPAC Name(2S,3S,4S,5R,6S)-6-(2-aminophenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Molecular FormulaC12H15NO7
Molecular Weight285.25 g/mol
InChIInChI=1S/C12H15NO7/c13-5-3-1-2-4-6(5)19-12-9(16)7(14)8(15)10(20-12)11(17)18/h1-4,7-10,12,14-16H,13H2,(H,17,18)/t7-,8-,9+,10-,12+/m0/s1
InChI KeyZVFVTBSWJWONEI-GOVZDWNOSA-N
SMILESC1=CC=C(C(=C1)N)OC2C(C(C(C(O2)C(=O)O)O)O)O
Synonymso-Aminophenyl β-D-Glucopyranosiduronic Acid; 2-Aminophenol Glucopyranuronoside; 2-Aminophenol Glucuronide; NSC 89270;
Canonical SMILESC1=CC=C(C(=C1)N)OC2C(C(C(C(O2)C(=O)O)O)O)O
Isomeric SMILESC1=CC=C(C(=C1)N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C(=O)O)O)O)O
CAS No: 15959-03-2 MDL No: MFCD00269899 Chemical Formula: C12H15NO7·HCl Molecular Weight: 321.71


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