4-Chlorophenyl b-D-glucopyranoside

4-氯苯基-beta-D-葡萄糖苷

4-Chlorophenyl-beta-D-glucopyranoside (CPBG) is a chemical compound belonging to the class of glucosides. It is widely used in scientific research as a reagent for chemical synthesis and in biochemical assays. Due to its unique chemical and biological properties, CPBG has attracted significant interest from researchers in various fields. In this review, we provide a comprehensive overview of CPBG, including its definition, background, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, and limitations and future directions.

Definition and Background

CPBG is a glucose derivative of 4-chlorophenyl alcohol. It has the chemical formula C12H15ClO6 and a molecular weight of 302.7 g/mol. CPBG is a white to off-white powder that is soluble in water and organic solvents. It is also known as 4-chloro-1-phenethyl-beta-D-glucopyranoside, 4-chloro-1-phenylethyl-beta-D-glucopyranoside, and p-chlorophenyl-beta-D-glucopyranoside.

Physical and Chemical Properties

CPBG is a crystalline solid with a melting point of 159-161 °C. It has a boiling point of 489.7 °C at 760 mmHg and a density of 1.44 g/cm3. CPBG is slightly soluble in ethanol and acetone but insoluble in methanol, chloroform, and ether. It has a moderate aqueous solubility of 277 mg/L at 25 °C and a pH of 7. CPBG is stable at room temperature and under dry conditions but can be decomposed under acidic or basic conditions.

Synthesis and Characterization

CPBG can be synthesized by the reaction of 4-chlorophenylethanol with D-glucose catalyzed by acetic anhydride. The reaction yields CPBG and acetic acid as byproduct. CPBG can be purified by recrystallization or chromatography techniques. The purity and identity of CPBG can be confirmed by various analytical methods, such as high-performance liquid chromatography (HPLC), gas chromatography-mass spectrometry (GC-MS), and nuclear magnetic resonance (NMR) spectroscopy.

Analytical Methods

CPBG can be detected and quantified using various analytical methods, such as HPLC, GC-MS, and NMR spectroscopy. HPLC is a widely used method that separates CPBG from other chemical compounds based on their chemical properties, such as solubility, polarity, and size. GC-MS is a sensitive method that analyzes the mass spectra of CPBG and identifies its molecular weight and structural features. NMR spectroscopy is a powerful method that provides information on the molecular structure and bonding of CPBG.

Biological Properties

CPBG exhibits potent biological activities, such as anti-inflammatory, antioxidant, antifungal, and antitumor properties. CPBG has been shown to inhibit the activity of various enzymes, such as lipase, serine protease, and xanthine oxidase. CPBG also has a chelating effect on metal ions, such as copper and iron, which may contribute to its antioxidant activity. CPBG has been found to inhibit the growth and proliferation of cancer cells, such as hepatocellular carcinoma and breast cancer cells, suggesting its potential as an anticancer agent.

Toxicity and Safety in Scientific Experiments

CPBG has been considered safe and non-toxic in scientific experiments. In vitro and in vivo studies have shown no significant toxicity or adverse effects of CPBG on human cells and animal models. However, caution should be taken when handling CPBG as it may cause irritation or sensitization to the skin, eyes, or respiratory system. Proper lab safety measures, such as wearing protective clothing and handling CPBG in a fume hood, should be followed to minimize the risk of exposure.

Applications in Scientific Experiments

CPBG has diverse applications in scientific experiments, such as chemical synthesis, biochemical assays, and drug discovery. CPBG can be used as a reagent for the synthesis of various chemical compounds, such as beta-glucosides, beta-lactams, and amino alcohols. CPBG can also be used as a substrate for various enzyme assays, such as glycosidases and glucosidases. CPBG has been used as a model compound for the study of enzyme kinetics and inhibition, such as the inhibition of alpha-glucosidase by CPBG analogs. CPBG has also been used as a lead compound for the development of new drugs, such as anti-inflammatory and antitumor agents.

Current State of Research

CPBG has been extensively studied in various fields of research, such as organic chemistry, biochemistry, and pharmacology. CPBG has been used as a reference compound for the study of carbohydrate chemistry and biochemistry. CPBG has also been studied for its potential as a therapeutic agent for various diseases, such as cancer, diabetes, and inflammation. Recent studies have focused on the development of new CPBG derivatives with improved biological activities and pharmacological properties.

Potential Implications in Various Fields of Research and Industry

CPBG has potential implications in various fields of research and industry, such as drug discovery, chemical synthesis, and biotechnology. CPBG and its derivatives may have applications as antitumor, anti-inflammatory, and antifungal agents. CPBG may also be used as a chiral building block for the synthesis of complex organic molecules, such as natural products and pharmaceuticals. CPBG may also have applications in biotechnology, such as the production of glycosylated proteins and enzymes.

Limitations and Future Directions

Despite its promising properties and applications, CPBG has some limitations and challenges that need to be addressed in future research. One limitation is the low solubility of CPBG in water, which may affect its bioavailability and pharmacokinetics. Another limitation is the lack of studies on the pharmacokinetics and pharmacodynamics of CPBG in vivo, which may limit its clinical application. Future research should focus on developing new CPBG derivatives with improved solubility, bioavailability, and pharmacological properties. Future research should also investigate the mechanisms and targets of CPBG's biological activities, such as its inhibition of enzyme activity and cancer cell growth.

Future Directions:

1. Design and synthesis of new CPBG derivatives with improved pharmacokinetics and pharmacodynamics

2. Investigation of the mechanism of CPBG's antitumor and anti-inflammatory activities

3. Development of new analytical methods for the detection and quantification of CPBG in complex biological samples

4. Investigation of the safety and toxicity of CPBG and its derivatives in animal models

5. Development of new applications of CPBG in biotechnology, such as the production of glycosylated proteins and enzymes

6. Investigation of the potential of CPBG as a lead compound for the development of new drugs for various diseases, such as cancer and diabetes

7. Investigation of the effect of CPBG on the gut microbiota and its potential implications in gut health and disease

8. Investigation of the synergistic effect of CPBG in combination with other drugs or compounds for the treatment of cancer and inflammatory diseases

9. Investigation of the molecular targets of CPBG's biological activity using proteomics and metabolomics approaches

10. Investigation of the effect of CPBG on gene expression and epigenetic regulation and its potential implications in gene therapy and regenerative medicine.