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  • 947175-17-9 , 6-Chloro-4-methylumbelliferyl b-D glucuronide,CMUG
947175-17-9 , 6-Chloro-4-methylumbelliferyl b-D glucuronide,CMUG

947175-17-9 , 6-Chloro-4-methylumbelliferyl b-D glucuronide,CMUG

Cas:947175-17-9 ,
6-Chloro-4-methylumbelliferyl b-D glucuronide,CMUG
C16H15ClO9 / 386.74
MFCD15146339

6-Chloro-4-methylumbelliferyl b-D glucuronide,CMUG

6-Chloro-4-methylumbelliferyl b-D glucuronide is a plant metabolite that has been found to inhibit the activity of an enzyme called factor receptor. It has also been shown to inhibit the synthesis of proteins and enzymes. 6-Chloro-4-methylumbelliferyl b-D glucuronide is soluble in lipophilic solvents such as chloroform, ethanol, and ether. This compound can be used as a substrate or inhibitor in vitro methods. 6-Chloro-4-methylumbelliferyl b-D glucuronide can be immobilized on particles to study enzyme substrates or factors that regulate growth.

6-Chloro-4-methylumbelliferyl beta-D-glucuronide, also known as CMUG, is a synthetic organic compound used as a fluorogenic substrate for glucuronidase enzymes. Glucuronidase enzymes are involved in the metabolism of a wide range of endogenous and exogenous compounds, including drugs, toxins, and xenobiotics. CMUG is a substrate that can be used to study these enzymes in vitro and in vivo, as it can be cleaved by glucuronidase enzymes to produce a fluorescent product, allowing for the detection and measurement of enzyme activity.

Physical and Chemical Properties:

CMUG has a molecular weight of 354.72 g/mol and a melting point of 220-222 °C. It is a white to light yellow crystalline powder that is soluble in water, ethanol, and methanol. The structure of CMUG consists of a coumarin fluorophore attached to a glucuronic acid moiety via an ether linkage.

Synthesis and Characterization:

CMUG can be synthesized by the reaction of 4-methylumbelliferone with glucuronic acid in the presence of a coupling reagent such as N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide (EDC) and a catalyst such as 4-dimethylaminopyridine (DMAP). The resulting product is then purified by chromatography and characterized by spectroscopic methods such as nuclear magnetic resonance (NMR) and mass spectrometry (MS).

Analytical Methods:

CMUG can be measured by various analytical methods, including fluorescence spectroscopy, high-performance liquid chromatography (HPLC), and electrophoresis. Fluorescence spectroscopy is the most common method used to measure CMUG, as it allows for sensitive detection of glucuronidase activity in biological samples.

Biological Properties:

CMUG has been shown to be a reliable substrate for the detection and measurement of glucuronidase activity in a wide range of biological samples, including urine, serum, and tissue homogenates. CMUG is stable in these samples and can be used to measure both endogenous and exogenous glucuronidase activity.

Toxicity and Safety in Scientific Experiments:

CMUG has been shown to be safe and non-toxic in scientific experiments when used at recommended concentrations. However, as with all chemicals, proper handling and disposal procedures should be followed to minimize the risk of exposure and harm to humans and the environment.

Applications in Scientific Experiments:

CMUG has a wide range of applications in scientific experiments, including the measurement of glucuronidase activity in drug metabolism and pharmacokinetics studies, the detection of bacterial and viral glucuronidase activity in clinical samples, and the evaluation of glucuronidase inhibitors for potential therapeutic use.

Current State of Research:

Research on CMUG has focused primarily on its use as a substrate for the measurement of glucuronidase activity in various biological systems. However, recent studies have also explored the use of CMUG in the development of new glucuronidase inhibitors for the treatment of various diseases, including cancer and infectious diseases.

Potential Implications in Various Fields of Research and Industry:

The use of CMUG in scientific research has potential implications in various fields, including drug discovery and development, clinical diagnostics, and environmental monitoring. In the drug development field, CMUG can be used to evaluate the pharmacokinetic and pharmacodynamic properties of drugs that are metabolized by glucuronidase enzymes. In clinical diagnostics, CMUG can be used to detect the presence and activity of glucuronidase enzymes in biological samples from patients with bacterial or viral infections. In environmental monitoring, CMUG can be used to detect the presence of glucuronidase-producing bacteria in water and soil samples, which can be used as indicators of environmental pollution.

Limitations and Future Directions:

The use of CMUG in scientific research is not without limitations. One limitation is the potential for interference from other compounds that may be present in biological samples, which can affect the accuracy of glucuronidase measurements. Future research could focus on developing new methods that can selectively measure glucuronidase activity in the presence of interfering compounds. Another limitation is the lack of information on the transport and metabolism of CMUG in vivo, which may affect the interpretation of glucuronidase measurements in certain biological systems. Future research could also focus on the development of new CMUG analogs that can be used to study glucuronidase in vivo with minimal interference.

Future Directions:

1. Development of new CMUG analogs with higher sensitivity and specificity for glucuronidase enzymes

2. Development of new methods for selective measurement of glucuronidase activity in complex biological samples

3. Investigation of the transport and metabolism of CMUG in vivo to improve interpretation of glucuronidase measurements

4. Development of new glucuronidase inhibitors for the treatment of various diseases, including cancer and infectious diseases

5. Evaluation of CMUG as a potential biomarker for the detection and monitoring of glucuronidase activity in various diseases

6. Investigation of the role of glucuronidase enzymes in drug resistance and toxicity.

CAS Number947175-17-9
Product Name6-Chloro-4-methylumbelliferyl beta-D-glucuronide
IUPAC Name(2S,3S,4S,5R,6S)-6-(6-chloro-4-methyl-2-oxochromen-7-yl)oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
Molecular FormulaC16H15ClO9
Molecular Weight386.7 g/mol
InChIInChI=1S/C16H15ClO9/c1-5-2-10(18)24-8-4-9(7(17)3-6(5)8)25-16-13(21)11(19)12(20)14(26-16)15(22)23/h2-4,11-14,16,19-21H,1H3,(H,22,23)/t11-,12-,13+,14-,16+/m0/s1
InChI KeyXDHZEATXDFGBFI-JHZZJYKESA-N
SMILESCC1=CC(=O)OC2=CC(=C(C=C12)Cl)OC3C(C(C(C(O3)C(=O)O)O)O)O
Canonical SMILESCC1=CC(=O)OC2=CC(=C(C=C12)Cl)OC3C(C(C(C(O3)C(=O)O)O)O)O
Isomeric SMILESCC1=CC(=O)OC2=CC(=C(C=C12)Cl)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)C(=O)O)O)O)O


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