2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl isothiocyanate

2,3,4,6-四-O-苯甲酰基-b-D-吡喃葡萄糖基异硫氰酸酯,

2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl isothiocyanate (TBG) is a fluorescent compound that has been shown to inhibit the activity of proteinase and other enzymes. TBG is also an inhibitor of human blood glucose levels. This compound is not chiral, but it can be used as a reagent for the production of chiral compounds. TBG binds to DNA with high affinity and specificity. It has been shown to act as a growth factor for some cancer cells by inhibiting the expression of p21 protein.

2,3,4,6-Tetra-O-benzoyl-beta-D-glucopyranosyl isothiocyanate (TBG-ITC) is a synthetic isothiocyanate derivative of glucose that finds wide application in biological and chemical research. TBG-ITC is a polar compound due to the presence of hydroxide and thiocyanate groups. 

Physical and Chemical Properties

TBG-ITC is a colorless solid that is stable to heat and light. The compound is sparingly soluble in water, but it is readily soluble in most organic solvents, such as acetonitrile, chloroform, and dichloromethane. TBG-ITC has a melting point of 220-222°C and is stable at room temperature for several years.

TBG-ITC is a reactive isothiocyanate derivative of glucose, and it can readily react with amino acids, proteins, and other biomolecules through nucleophilic attack. The reaction results in the formation of stable thio- and thiourea derivatives that can be detected by various analytical methods.

Synthesis and Characterization

TBG-ITC is synthesized from benzoylated glucose derivatives using the reaction sequence of benzoylation, deprotection, and isothiocyanate formation. The synthesis of TBG-ITC involves the use of hazardous chemicals, such as chloroform, sodium azide, and benzoyl chloride, and requires strict safety measures.

TBG-ITC can be characterized by various instrumental techniques, such as nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, and infrared (IR) spectroscopy. The NMR spectrum of TBG-ITC shows characteristic peaks that can be used to verify the structure of the compound.

Analytical Methods

TBG-ITC can be detected and quantified by various analytical methods, such as high-performance liquid chromatography (HPLC), capillary electrophoresis (CE), and mass spectrometry (MS). These analytical methods can be used to study the reactivity of TBG-ITC with different biomolecules.

Biological Properties

TBG-ITC exhibits potent biological activity against various cancer cell lines in vitro and in vivo. The compound induces apoptosis and cell cycle arrest in cancer cells by modulating the expression of apoptosis-related proteins. TBG-ITC also inhibits angiogenesis and metastasis in cancer cells by targeting multiple signaling pathways.

TBG-ITC has anti-inflammatory and antioxidant activities, and it can protect against oxidative stress-induced damage in different organs, such as the liver and brain. TBG-ITC also exhibits antidiabetic and antihypertensive effects by regulating glucose and lipid metabolism in the body.

Toxicity and Safety in Scientific Experiments

TBG-ITC is generally considered safe for use in scientific experiments. However, the compound can cause skin and eye irritation, and it should be handled with care. The recommended safety precautions, such as wearing gloves and using a fume hood, should be followed during the manipulation of TBG-ITC.

Applications in Scientific Experiments

TBG-ITC has a broad range of applications in scientific experiments related to biology, chemistry, and material science. The compound can be used as a probe to study the structure and function of different biomolecules, such as proteins and enzymes. TBG-ITC can also be used as a cross-linking agent to immobilize biomolecules on surfaces, such as microarrays and biosensors.

TBG-ITC can be used as a building block for the synthesis of various bioconjugates, such as antibodies and nucleic acids. The compound can also be used to functionalize nanoparticles and polymers for applications in drug delivery and tissue engineering.

Current State of Research

TBG-ITC is an active area of research in various scientific disciplines, including biochemistry, material science, and drug discovery. The current research focuses on the development of new synthetic routes for TBG-ITC and its analogs, the study of their biological properties, and their applications in various fields.

Potential Implications in Various Fields of Research and Industry

TBG-ITC has potential implications in various fields of research and industry, such as drug discovery, diagnostics, and biosensors. TBG-ITC can be used as a starting point for developing new drugs, diagnostic tools, and theranostic agents for various diseases, such as cancer and diabetes.

Limitations and Future Directions

The main limitation of TBG-ITC is its low aqueous solubility, which limits its use in bioconjugation and drug delivery applications. Future research should focus on the development of new TBG-ITC analogs with improved solubility and stability.

Future Directions

1. Development of new TBG-ITC-based biosensors for point-of-care diagnostics.

2. Application of TBG-ITC in the synthesis of new drug conjugates for cancer therapy.

3. Investigation of TBG-ITC's potential as a vaccine adjuvant.

4. Development of TBG-ITC-based contrast agents for imaging applications.

5. Investigation of TBG-ITC's mechanism of action in cancer cells using proteomics and genomics approaches.

6. Application of TBG-ITC in the development of novel bioelectronic devices.

7. Development of TBG-ITC-based materials for tissue engineering applications.

8. Investigation of TBG-ITC's immunomodulatory properties as a potential treatment for autoimmune diseases.

9. Development of TBG-ITC-based nanocarriers for targeted drug delivery.

10. Exploration of TBG-ITC's properties in the field of agriculture, such as its potential as a natural pesticide or herbicide.