5580-20-1

Basic information

• Product Name: 4-THIO-2'-DEOXYURIDINE
• Synonyms: Uridine, 2'-deoxy-4-thio-;1-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-thioxo-3,4-dihydropyrimidin-2(1H)-one
• CAS NO: 5580-20-1
• Molecular Formula: C₉H₁₂N₂O₄S
• Molecular Weight: 244.26
• Mol File: 5580-20-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 473°Cat760mmHg
• Flash Point: 239.9°C
• Appearance: /
• Density: 1.54g/cm³
• Storage Temp.: ?20°C
• CAS DataBase Reference: 4-THIO-2'-DEOXYURIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-THIO-2'-DEOXYURIDINE(5580-20-1)
• EPA Substance Registry System: 4-THIO-2'-DEOXYURIDINE(5580-20-1)

Safety Data

• Hazardous Substances Data: 5580-20-1(Hazardous Substances Data)

Usage

General Description

4-Thio-2'-deoxyuridine is a modified nucleoside analogue that has a thiol group attached to the 4-position of the pyrimidine ring. It is a potent radiosensitizer and cytotoxic agent, and has been studied for its potential use in cancer therapy. It works by incorporating into the DNA of rapidly dividing cells, leading to DNA damage and inhibition of DNA synthesis. This makes it particularly effective against cancer cells, which typically have high rates of replication. 4-Thio-2'-deoxyuridine has also been investigated for its potential antiviral properties, as it has been shown to inhibit the replication of certain viruses. Overall, this chemical has shown promise as a potential therapeutic agent for cancer and viral infections.

Upstream product

• 13030-62-1 3',5'-di-O-acetyl-2'-deoxyuridine 
• 1956-30-5 3',5'-O-diacetyl-5-iodo-2'-deoxyuridine 
• 1313407-40-7 5-iodo-4-thio-2'-deoxyuridine 
• 951-78-0 2'-deoxyuridine 

Downstream Products

• 139887-84-6 5'-O-dimethoxytrityl-4-S-pivaloyloxymethyl-2'-deoxy-4-thiouridine 
• 139887-90-4 5'-O-dimethoxytrityl-4-(S-pivaloyloxymethyl)-2'-deoxy-4-thiouridin-3'-yl hydrogenphosphonate 
• 1053267-72-3 C₄₈H₅₅N₄O₁₆PS 
• 1054624-48-4 C₄₈H₅₅N₄O₁₆PS 
• 150018-27-2 C₂₈H₂₆N₂O₄S 
• 1277164-90-5 C₂₉H₂₈N₂O₄S 

Relevant articles and documents

5-iodo-4-thio-2′-deoxyuridine as a sensitizer of X-ray induced cancer cell killing

Nucleosides, especially pyrimidines modified in the C5-position, can act as radiosensitizers via a mechanism that involves their enzymatic triphosphorylation, incorporation into DNA, and a subsequent dissociative electron attachment (DEA) process. In this paper, we report 5-iodo-4-thio-2′-deoxyuridine (ISdU) as a compound that can effectively lead to ionizing radiation (IR)-induced cellular death, which is proven by a clonogenic assay. The test revealed that the survival of cells, pre-treated with 10 or 100 μM solution of ISdU and exposed to 0.5 Gy of IR, was reduced from 78.4% (for non-treated culture) to 67.7% and to 59.8%, respectively. For a somewhat higher dose of 1 Gy, the surviving fraction was reduced from 68.2% to 54.9% and to 40.8% for incubation with 10 or 100 μM ISdU, respectively. The cytometric analysis of histone H2A.X phosphorylation showed that the radiosensitizing effect of ISdU was associated, at least in part, with the formation of double-strand breaks. Moreover, the cytotoxic test against the MCF-7 breast cancer cell line and human dermal fibroblasts (HDFa line) confirmed low cytotoxic activity of ISdU. Based on the results of steady state radiolysis of ISdU with a dose of 140 Gy and quantum chemical calculations explaining the origin of the MS detected radioproducts, the molecular mechanism of sensitization by ISdU was proposed. In conclusion, we found ISdU to be a potential radiosensitizer that could improve anticancer radiotherapy.