4-Thiouridine
Catalog Number: BT-256842
CAS Number: 13957-31-8
Molecular Formula: C9H12N2O5S
Molecular Weight: 260.27 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction
Description
4-Thiouridine is a modified nucleoside that is commonly found in transfer RNA (tRNA) and ribosomal RNA (rRNA). It is formed by the substitution of a sulfur atom for the oxygen atom at the 4th position of the uridine molecule. This modification plays a crucial role in the structure and function of RNA molecules.
Properties
CAS Number
13957-31-8
Product Name
4-Thiouridine
IUPAC Name
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-sulfanylidenepyrimidin-2-one
Molecular Formula
C9H12N2O5S
Molecular Weight
260.27 g/mol
InChI
InChI=1S/C9H12N2O5S/c12-3-4-6(13)7(14)8(16-4)11-2-1-5(17)10-9(11)15/h1-2,4,6-8,12-14H,3H2,(H,10,15,17)/t4-,6-,7-,8-/m1/s1
InChI Key
ZLOIGESWDJYCTF-XVFCMESISA-N
SMILES
C1=CN(C(=O)NC1=S)C2C(C(C(O2)CO)O)O
Solubility
DMSO (Slightly), Methanol (Slightly)
Synonyms
4 Thiouridine
4-Thiouridine
Thiouridine
4-Thiouridine
Thiouridine
Canonical SMILES
C1=CN(C(=O)NC1=S)C2C(C(C(O2)CO)O)O
Isomeric SMILES
C1=CN(C(=O)NC1=S)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
Method of Synthesis or Extraction
There are several methods for the synthesis and extraction of 4-thiouridine. The most commonly used methods are chemical synthesis, enzymatic synthesis, and extraction from natural sources.
Chemical synthesis involves the reaction of uridine with sulfur-containing reagents such as Lawesson's reagent, thiourea, or sulfuric acid. The efficiency and yield of this method depend on the reaction conditions and the purity of the starting materials. However, this method has some environmental and safety considerations, as the reagents used are toxic and hazardous.
Enzymatic synthesis involves the use of enzymes such as thiolase or thioesterase to catalyze the formation of 4-thiouridine from uridine and a sulfur donor. This method has high efficiency and yield, and it is environmentally friendly and safe. However, it requires the use of expensive enzymes and specific reaction conditions.
Extraction from natural sources involves the isolation of 4-thiouridine from 4-Thiouridine or rRNA using various chromatographic techniques. This method has low efficiency and yield, and it requires large amounts of starting materials. However, it is a natural and sustainable method that does not involve any chemical reactions or hazardous reagents.
Chemical synthesis involves the reaction of uridine with sulfur-containing reagents such as Lawesson's reagent, thiourea, or sulfuric acid. The efficiency and yield of this method depend on the reaction conditions and the purity of the starting materials. However, this method has some environmental and safety considerations, as the reagents used are toxic and hazardous.
Enzymatic synthesis involves the use of enzymes such as thiolase or thioesterase to catalyze the formation of 4-thiouridine from uridine and a sulfur donor. This method has high efficiency and yield, and it is environmentally friendly and safe. However, it requires the use of expensive enzymes and specific reaction conditions.
Extraction from natural sources involves the isolation of 4-thiouridine from 4-Thiouridine or rRNA using various chromatographic techniques. This method has low efficiency and yield, and it requires large amounts of starting materials. However, it is a natural and sustainable method that does not involve any chemical reactions or hazardous reagents.
Chemical Structure and Biological Activity
The chemical structure of 4-thiouridine consists of a uridine molecule with a sulfur atom attached to the 4th position of the pyrimidine ring. This modification alters the hydrogen bonding and stacking interactions of the RNA molecule, leading to changes in its structure and function.
The biological activity of 4-thiouridine is mainly related to its role in RNA metabolism. It is involved in the recognition and binding of 4-Thiouridine to the ribosome during protein synthesis. It also plays a role in the regulation of gene expression and RNA splicing. Moreover, 4-thiouridine has been shown to have antioxidant and anti-inflammatory properties.
The biological activity of 4-thiouridine is mainly related to its role in RNA metabolism. It is involved in the recognition and binding of 4-Thiouridine to the ribosome during protein synthesis. It also plays a role in the regulation of gene expression and RNA splicing. Moreover, 4-thiouridine has been shown to have antioxidant and anti-inflammatory properties.
Biological Effects
The effects of 4-thiouridine on cell function and signal transduction depend on its concentration and the type of cells. At low concentrations, it enhances protein synthesis and cell proliferation. At high concentrations, it inhibits protein synthesis and induces cell death. Moreover, 4-thiouridine has been shown to modulate the activity of various signaling pathways, such as the MAPK and NF-κB pathways.
The potential therapeutic and toxic effects of 4-thiouridine are still under investigation. It has been suggested as a potential anticancer agent due to its ability to inhibit protein synthesis and induce cell death. However, it may also have toxic effects on normal cells and tissues.
The potential therapeutic and toxic effects of 4-thiouridine are still under investigation. It has been suggested as a potential anticancer agent due to its ability to inhibit protein synthesis and induce cell death. However, it may also have toxic effects on normal cells and tissues.
Applications
In medical research, 4-thiouridine has been used as a tool to study RNA structure and function. It has also been investigated as a potential therapeutic agent for cancer and other diseases. Clinical trials have shown promising results in the treatment of leukemia and lymphoma.
In environmental research, 4-thiouridine has been used as a biomarker for environmental pollution. It has been shown to accumulate in aquatic organisms exposed to pollutants such as heavy metals and pesticides. Moreover, it has been suggested as a potential tool for pollution management and sustainability.
In industrial research, 4-thiouridine has been used in the manufacturing of RNA-based products such as RNA vaccines and therapeutics. It has also been used to improve the quality and efficiency of RNA synthesis and purification processes. Health and safety considerations are important in the industrial use of 4-thiouridine, as it may have toxic effects on workers and the environment.
In environmental research, 4-thiouridine has been used as a biomarker for environmental pollution. It has been shown to accumulate in aquatic organisms exposed to pollutants such as heavy metals and pesticides. Moreover, it has been suggested as a potential tool for pollution management and sustainability.
In industrial research, 4-thiouridine has been used in the manufacturing of RNA-based products such as RNA vaccines and therapeutics. It has also been used to improve the quality and efficiency of RNA synthesis and purification processes. Health and safety considerations are important in the industrial use of 4-thiouridine, as it may have toxic effects on workers and the environment.
Future Perspectives and Challenges
The current limitations in the use and study of 4-thiouridine include the lack of understanding of its mechanism of action and its potential toxic effects. Possible solutions and improvements include the development of new synthesis and extraction methods, the use of advanced analytical techniques to study its biological activity, and the investigation of its potential therapeutic and toxic effects in preclinical and clinical studies.
Future trends and prospects in the application of 4-thiouridine in scientific research include the development of new RNA-based therapies and the use of 4-thiouridine as a tool for RNA engineering and synthetic biology. However, the challenges of safety and sustainability must be addressed to ensure the responsible use of this molecule in scientific research and industrial applications.
Conclusion:
In conclusion, 4-thiouridine is a modified nucleoside that plays a crucial role in RNA structure and function. It has potential applications in medical, environmental, and industrial research. However, its mechanism of action and potential toxic effects are still under investigation. The development of new synthesis and extraction methods, the use of advanced analytical techniques, and the investigation of its potential therapeutic and toxic effects are important for the responsible use of this molecule in scientific research and industrial applications.
Future trends and prospects in the application of 4-thiouridine in scientific research include the development of new RNA-based therapies and the use of 4-thiouridine as a tool for RNA engineering and synthetic biology. However, the challenges of safety and sustainability must be addressed to ensure the responsible use of this molecule in scientific research and industrial applications.
Conclusion:
In conclusion, 4-thiouridine is a modified nucleoside that plays a crucial role in RNA structure and function. It has potential applications in medical, environmental, and industrial research. However, its mechanism of action and potential toxic effects are still under investigation. The development of new synthesis and extraction methods, the use of advanced analytical techniques, and the investigation of its potential therapeutic and toxic effects are important for the responsible use of this molecule in scientific research and industrial applications.
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