C12H17NO6 / 271.27
4-Aminophenyl a-D-mannopyranoside is a compound that has been shown to have anti-inflammatory properties. It is also used as a starting material in the synthesis of other drugs. Rats with chronic kidney disease were given 4-aminophenyl a-D-mannopyranoside daily for three weeks, and it was found that this compound prevented the development of kidney injury markers. This drug has also been shown to be effective against mouse strains with nervous system diseases. 4-Aminophenyl a-D-mannopyranoside binds to lysine residues on proteins and prevents the interactions between these residues and the amino acid glutathione, which is required for glut1 uptake in brain cells. This uptake is essential for cellular function, and therefore 4-aminophenyl a-D-mannopyranoside may be useful as chemotherapeutic treatment for brain cancer.
Definition and Background
4-Aminophenyl alpha-D-mannopyranoside (APM) is a type of carbohydrate derivative that is used in various fields of research and industry. APM belongs to the class of aminophenyl glycosides, which are molecules comprised of a phenyl ring attached to a sugar moiety. It is commonly used as a ligand for the detection and quantification of mannose binding proteins (MBPs) and other carbohydrate-binding proteins (CBPs).
APM was first synthesized in 1976 and has since become an essential tool in the study of glycobiology and related fields. Due to its unique chemical properties, APM is widely used in the development of new therapeutics, analytical assays, and diagnostic tools.
APM is an analog of D-mannose, a common sugar found in nature, and contains a phenyl ring attached to the C1 position of the mannose molecule. The phenyl ring can be modified to introduce different functional groups, such as amino and carboxyl groups, for various applications.
Synthesis and Characterization
The synthesis of APM involves the chemical modification of D-mannose through the reaction with 4-aminophenol in the presence of a reagent such as p-toluenesulfonic acid. The reaction yields APM as the primary product, along with some side products that can be removed through purification steps.
The structure of APM can be characterized using various techniques such as nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, and X-ray crystallography. These methods provide valuable information about the chemical properties of APM and enable researchers to optimize its use in various applications.
APM is commonly used as a ligand in the detection and quantification of MBPs and other carbohydrate-binding proteins. This application utilizes various analytical methods, such as surface plasmon resonance (SPR) and isothermal titration calorimetry (ITC), to measure the binding affinity and kinetics of the protein-ligand interaction.
Additionally, APM can be used as a substrate in enzymatic assays to measure the activity of enzymes that hydrolyze glycosidic linkages. This utilization of APM enables the development of new therapeutics that target specific enzymes involved in disease processes.
APM has been shown to exhibit biological activity such as antimicrobial and antitumor properties. It has also been shown to inhibit the replication of human papillomavirus (HPV) and other viral infections.
APM is a potent inhibitor of the lectin pathway of complement activation, a component of the immune system. It also exhibits renal protective effects through the inhibition of oxidative stress in vitro and in vivo.
Toxicity and Safety in Scientific Experiments
The toxicity and safety of APM in scientific experiments depend on its dose and route of administration. In vitro studies have demonstrated that APM is relatively non-toxic at concentrations typically used in scientific experiments.
However, some studies have reported adverse effects such as genotoxicity and cytotoxicity at higher concentrations. Further research is needed to determine the safety of APM in vivo and in humans.
Applications in Scientific Experiments
APM is widely used in various scientific experiments and applications, including:
1. Detection and quantification of MBPs and other CBPs.
2. Enzymatic assays to measure the activity of glycosidic enzymes.
3. Development of new therapeutics targeting specific glycosidic enzymes.
4. Inhibition of viral replication.
5. Inhibition of complement activation.
6. Renal protective effects.
Current State of Research
APM research is ongoing, and new applications and uses are continually being discovered. Current areas of research include the development of new diagnostic tools for infectious diseases, the role of MBPs in disease processes, and the development of glycosidic enzymes as drug targets.
Potential Implications in Various Fields of Research and Industry
APM has potential implications in various fields of research and industry, including:
1. Development of novel therapeutic agents.
2. Development of diagnostic tools for infectious diseases.
3. Development of glycosidic enzymes as drug targets.
4. Development of new materials for biomedical applications.
5. Food industry applications such as flavor enhancers and texture modifiers.
Limitations and Future Directions
Despite its many potential applications, APM has some limitations, which include:
1. Low solubility in water.
2. Limited stability under certain conditions.
3. Limited availability due to high cost and limited commercial sources.
Future directions for APM research include:
1. The development of more efficient synthesis methods and purification techniques.
2. The optimization of APM's properties for specific applications.
3. The development of new applications and uses of APM in various fields of research and industry.
4. The evaluation of the safety and toxicity of APM in humans.
5. The investigation of APM's potential in drug delivery and other biomedical applications.
|CAS No: 34213-86-0 Synonyms: p-Aminophenyl α-D-mannoside MDL No: MFCD00067366 Chemical Formula: C12H17NO6 Molecular Weight: 271.27|
Name: 4-Aminophenyl alpha-D-mannopyranoside
CAS: 34213-86-0 M.F.: C12H17NO6 M.W.: 271.27
White or off-white power
Soluble in water and
insoluble in ether
NMR and MS
IR and TLC
[a]20D [in CH3OH]
125o ~ 130o
Loss Weight On Dryness
Used as a carbohydrate ligand for preparing affinity adsorbents.
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