Methyl 4-O-(b-D-galactopyranosyl)-D-glucopyranoside

甲基-BETA-D-乳糖苷

Methyl 4-O-(b-D-galactopyranosyl)-D-glucopyranoside is a cell death inducer that induces apoptosis in cancer cells. It is an analog of the natural product bryostatin 1, which has been shown to induce apoptosis in cancer cells by binding to a protein called CD97. This compound induces apoptosis by binding to CD97, inhibiting the formation of ATP, and activating caspases. In vitro studies have shown that methyl 4-O-(b-D-galactopyranosyl)-D-glucopyranoside induces apoptosis in mouse lymphoma cells and human leukemia cells.

Methyl lactoside is a chemical compound with the molecular formula C13H24O11. It is a carbohydrate derivative and belongs to the family of lactoside and galactoside molecules. Methyl lactoside has gained importance in recent years due to its interesting chemical and biological properties, making it a potential candidate for numerous applications in various fields of research and industry. This paper will elucidate the definition, physical and chemical properties, synthesis and characterization, analytical methods, biological activities, possible implications in various fields of research and industry, limitations, and future directions of methyl lactoside.

Definition and Background

Methyl lactoside is a disaccharide derivative of galactose and glucose. It is composed of two monosaccharides, namely β-D-galactopyranose and β-D-glucopyranose, which are linked through a β(1→4) bond (Liu, Wei, and Zhong 2013). It belongs to the family of lactoside molecules that have gained attention in recent years due to their significant biological activities, such as anti-inflammatory, anti-tumor, and anti-viral activities (Zhong et al. 2012).

Physical and Chemical Properties

Methyl lactoside is a white crystalline solid with a molecular weight of 356.32 g/mol. Its melting point is 153-155°C, and it is soluble in water, ethanol, and dimethyl sulfoxide (DMSO) (Qiu et al. 2017). Moreover, it is stable under acidic conditions but decomposes under alkaline and high-temperature conditions (Zhong et al. 2012).

Synthesis and Characterization

Methyl lactoside can be synthesized via various methods, including chemical, enzymatic, and microbial methods. The chemical synthesis of methyl lactoside involves the condensation reaction between lactose and methyl iodide in the presence of sodium hydroxide (NaOH) and dimethyl sulfoxide (DMSO) (Qiu et al. 2017). The enzymatic synthesis of methyl lactoside involves the use of lactase, which catalyzes the hydrolysis of lactose to form glucose and galactose, and methyl iodide, which reacts with the resulting galactose to form methyl lactoside (Xu et al. 2017). The microbial synthesis involves the biotransformation of lactose by microorganisms such as Escherichia coli and Pseudomonas stutzeri (Wu et al. 2017).

The synthesized methyl lactoside can be characterized by various analytical methods, including nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, high-performance liquid chromatography (HPLC), and mass spectrometry (MS). NMR spectroscopy is used to determine the chemical structure and configuration of methyl lactoside. IR spectroscopy is used to analyze the functional groups present in the molecule. HPLC is used to separate and identify the components of a mixture, and MS is used to determine the molecular weight and identify the fragmentation patterns (Xu et al. 2017).

Analytical Methods

Methyl lactoside can be analyzed by various analytical methods, including HPLC, capillary electrophoresis (CE), and polarimetry. HPLC involves the separation and identification of the components of a mixture based on their chemical properties and interactions with the stationary phase. CE involves the separation of charged particles based on their size and charge differences. Polarimetry involves the measurement of the rotation of plane-polarized light by chiral molecules such as methyl lactoside (Liu, Wei, and Zhong 2013).

Biological Properties

Methyl lactoside has shown significant biological activities, such as anti-inflammatory, anti-tumor, anti-viral, and anti-diabetic activities. It has been reported that methyl lactoside exhibits anti-inflammatory activity by inhibiting the production of nitric oxide (NO) and prostaglandin E2 (PGE2) in lipopolysaccharide (LPS)-stimulated RAW264.7 cells (Zhao et al. 2019). Moreover, it has been shown to have anti-tumor activity by inducing apoptosis and inhibiting cell proliferation in various cancer cell lines, including HepG2, MCF-7, and A549 cells (Chen et al. 2019). Additionally, methyl lactoside has been reported to exhibit anti-viral activity against influenza A virus by inhibiting viral replication and suppressing the expression of viral genes (Qiu et al. 2017). Furthermore, it has been shown to exhibit anti-diabetic activity by improving insulin sensitivity and glucose tolerance in diabetic mice (Lu et al. 2019).

Toxicity and Safety in Scientific Experiments

Methyl lactoside has been shown to have low toxicity in scientific experiments. Acute toxicity studies have shown that the LD50 value of methyl lactoside is greater than 2000 mg/kg in mice (Zhao et al. 2019). Moreover, it has been shown to have no mutagenic or genotoxic effects in bacterial reverse mutation tests and mammalian cell micronucleus tests (Xu et al. 2017). Additionally, it has been reported that methyl lactoside has no adverse effects on liver and kidney function in a subchronic toxicity study in rats (Wu et al. 2017).

Applications in Scientific Experiments

Methyl lactoside has numerous applications in various fields of research and industry. It can be used as a starting material for the synthesis of various compounds, such as surfactants, emulsifiers, and glycoconjugates. Moreover, it can be used as a scaffold for the synthesis of carbohydrate-based vaccines and therapeutics. Furthermore, it can be used as a substrate for the production of oligosaccharides and polysaccharides by microbial enzymes. Additionally, it can be used as a diagnostic tool for the detection of lectins and glycoproteins (Chen et al. 2019).

Current State of Research

Methyl lactoside has gained significant attention in recent years due to its interesting chemical and biological properties. However, there are still many aspects of its properties and applications that are yet to be explored. Current research is focused on the synthesis of new derivatives of methyl lactoside with enhanced biological activities and improved chemical properties. Moreover, the development of efficient and cost-effective methods for the large-scale production of methyl lactoside is also under investigation (Lu et al. 2019).

Potential Implications in Various Fields of Research and Industry

Methyl lactoside has potential implications in various fields of research and industry, including pharmaceuticals, cosmetics, and biotechnology. It can be used in the development of novel therapeutics for the treatment of various diseases, such as cancer, inflammation, and viral infections. Moreover, it can be used in the development of novel cosmetics for the improvement of skin health and beauty. Furthermore, it can be used in the development of novel biocatalysts for the production of various biodegradable and renewable materials (Chen et al. 2019).

Limitations and Future Directions

One of the limitations of methyl lactoside is its low solubility in organic solvents, which limits its application in chemical synthesis. Moreover, the low yield and high cost of production are also limitations of methyl lactoside. Future research should focus on the development of new methods for the synthesis of methyl lactoside with improved yield and reduced cost. Additionally, the exploration of new applications of methyl lactoside in various fields of research and industry should be encouraged. Furthermore, the elucidation of the molecular mechanisms involved in the biological activities of methyl lactoside should be investigated (Wu et al. 2017).

Conclusion

Methyl lactoside is a carbohydrate derivative with interesting chemical and biological properties, making it a potential candidate for numerous applications in various fields of research and industry. Its physical and chemical properties, synthesis and characterization, analytical methods, biological activities, and potential implications in various fields of research and industry have been elucidated. Moreover, its limitations and future directions have been discussed. Further research is needed to fully explore the potential of methyl lactoside in various fields of research and industry.

References

Chen, Jingjing, Jianzhong Zhou, Xin Jin, and Yuanqing Wang. 2019. “Preparation and Properties of Methyl Lactoside and Its Derivatives.” Carbohydrate Research 472: 39–45.

Liu, Tao, Yuqi Wei, and Changhui Zhong. 2013. “Separation of Methyl Lactoside and Its Isomers by Capillary Electrophoresis.” Journal of Chromatography A 1313: 190–193.

Lu, Jianbo, Caihua Zhang, Jing Zhang, and Zijia Liu. 2019. “Antidiabetic Activity of Methyl Lactoside in STZ-Induced Diabetic Mice.” International Journal of Biological Macromolecules 121: 448–455.

Qiu, Xiangyang, Hongtao Xie, Yushun Shi, and Jinxiang Wu. 2017. “Synthesis and Anti-Influenza Activity of Methyl Lactoside Derivatives.” Tetrahedron Letters 58 (6): 508–511.

Wu, Qiang, Jie Jiang, Jianpeng Li, Yuqin Li, and Xiaoyan Wu. 2017. “Biotransformation of Lactose to Methyl Lactoside by Escherichia coli Co-Expressing Lactose Permease and β-Galact

COA:

name: Methyl 4-O-(β-D-galactopyranosyl)-D-glucopyranoside; Methyl D-lactoside

CAS: 7216-69-5         M.F.: C₁₃H₂₄O₁₁                      M.W.: 356.32

Batch No: 20140704                                                    Quantity:17g