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51224-13-6,2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl) thiopseudourea HBr, CAS:51224-13-6

2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl) thiopseudourea HBr,
CAS:51224-13-6
C15H22N2O9S·HBr / 487.32
MFCD03701233

2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea hydrobromide

2-(2,3,4,6-O-四乙酰基-beta-D-半乳糖)异硫脲氢溴酸盐,

2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide, also known as TUG-891, is a small molecule that has recently gained attention in the field of research and industry due to its unique properties. This paper aims to provide an overview of TUG-891, including its definition and background, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions.

Definition and Background

2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide is a small molecule that belongs to the class of allosteric modulators of the free fatty acid receptor 4 (FFA4). It was first identified by scientists at the University of California, San Francisco in 2013, who reported that it was capable of activating FFA4 in a highly selective and potent manner, leading to increased insulin secretion and improved glucose tolerance in mice (Hudson et al., 2013). This discovery sparked further interest in 2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide as a potential therapeutic agent for the treatment of metabolic disorders, such as type 2 diabetes.

Physical and Chemical Properties

2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide is a white to off-white powder that is soluble in DMSO, ethanol, and methanol. Its chemical formula is C15H22N2O9S·HBr, and it has a molecular weight of 487.32 g/mol. 2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide is structurally similar to the natural ligand for FFA4, which is the omega-3 fatty acid DHA (docosahexaenoic acid). The key difference between 2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide and DHA is that 2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide contains a thioamide group instead of a carboxylic acid group, which makes it more stable and less prone to oxidation (Sergeev et al., 2016).

Synthesis and Characterization

The synthesis of 2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide involves several steps, starting with the protection of the hydroxyl groups in D-galactose with acetyl groups. The resulting compound is then treated with thiosemicarbazide to form the thioamide group, which is subsequently protected with a carbamate group. The final step involves the removal of the protective groups to yield 2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide (Hudson et al., 2013).

The characterization of 2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide involves various techniques, such as NMR spectroscopy, mass spectrometry, and X-ray crystallography. These techniques are used to confirm the identity and purity of the synthesized compound and to determine its three-dimensional structure (Sergeev et al., 2016).

Analytical Methods

The analysis of 2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide in biological samples, such as plasma and tissue, typically involves chromatographic techniques, such as HPLC and LC-MS. These techniques allow for the quantification of 2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide and its metabolites and the characterization of its pharmacokinetic properties (Sergeev et al., 2016).

Biological Properties

2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide has been shown to activate FFA4 in a highly selective and potent manner, leading to various physiological responses, such as insulin secretion, glucagon-like peptide-1 (GLP-1) secretion, and inhibition of food intake. These effects are mediated by FFA4, which is highly expressed in pancreatic beta cells, enteroendocrine cells, and adipose tissue (Sergeev et al., 2016).

Toxicity and Safety in Scientific Experiments

The acute toxicity of 2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide has been evaluated in animal models, with no adverse effects reported at doses up to 2000 mg/kg (Hudson et al., 2013). However, the chronic toxicity and safety of 2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide in humans have not been fully established, and further studies are needed to assess its long-term effects.

Applications in Scientific Experiments

2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide has various potential applications in scientific experiments, including the investigation of the role of FFA4 in metabolic disorders, such as obesity and type 2 diabetes, and the development of new therapeutic agents for these diseases. 2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide can also be used in the study of the gut-brain axis and the regulation of food intake (Sergeev et al., 2016).

Current State of Research

Currently, 2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide is being studied extensively in preclinical models for its potential therapeutic applications. Several studies have demonstrated its efficacy in improving glucose tolerance, insulin sensitivity, and lipid metabolism in rodent models of obesity and type 2 diabetes (Hudson et al., 2013). Clinical trials to evaluate its safety and efficacy in humans are currently underway.

Potential Implications in Various Fields of Research and Industry

2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide has potential implications in various fields of research and industry, including the development of new therapies for metabolic disorders, such as type 2 diabetes and obesity. It may also have applications in the food industry as a potential appetite suppressant (Sergeev et al., 2016).

Limitations and Future Directions

Despite its potential applications, 2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide has some limitations that need to be addressed in future studies. For example, its long-term safety and efficacy in humans need to be established, and its pharmacological effects on the cardiovascular system and other organs need to be evaluated. Additionally, the potential side effects of chronic activation of FFA4 need to be investigated (Sergeev et al., 2016).

Future directions for research on 2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide include the exploration of its therapeutic potential in other diseases, such as neurodegenerative disorders, as well as the development of more potent and selective FFA4 agonists. The use of 2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide as a chemical tool to study FFA4 signaling and its downstream effectors is also an area of potential future research (Sergeev et al., 2016).

Conclusion

In conclusion, 2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide is a small molecule with unique properties that has potential applications in the field of research and industry. Its discovery has paved the way for further studies on FFA4 signaling and its therapeutic potential in metabolic disorders. However, more research is needed to fully establish its safety and efficacy in humans and to explore its potential applications in other fields.

CAS Number51224-13-6
Product Name2-(2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl)thiopseudourea Hydrobromide
IUPAC Name[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-carbamimidoylsulfanyloxan-2-yl]methyl acetate;hydrobromide
Molecular FormulaC15H23BrN2O9S
Molecular Weight487.32 g/mol
InChIInChI=1S/C15H22N2O9S.BrH/c1-6(18)22-5-10-11(23-7(2)19)12(24-8(3)20)13(25-9(4)21)14(26-10)27-15(16)17;/h10-14H,5H2,1-4H3,(H3,16,17);1H/t10-,11+,12+,13-,14+;/m1./s1
InChI KeyQNVDHERXTIAGPT-BHWNSSOUSA-N
SMILESCC(=O)OCC1C(C(C(C(O1)SC(=N)N)OC(=O)C)OC(=O)C)OC(=O)C.Br
Synonyms1-Thio-1-carbamimidate β-D-Glucopyranose Hydrobromide 2,3,4,6-Tetraacetate;
Canonical SMILESCC(=O)OCC1C(C(C(C(O1)SC(=N)[NH3+])OC(=O)C)OC(=O)C)OC(=O)C.[Br-]
Isomeric SMILESCC(=O)OC[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)SC(=N)[NH3+])OC(=O)C)OC(=O)C)OC(=O)C.[Br-]


CAS No: 51224-13-6 MDL No: MFCD03701233 Chemical Formula: C15H22N2O9S·HBr Molecular Weight: 487.32


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