676556-11-9

Basic information

• Product Name: 5-BROMO-2'-DEOXY-4-THIOURIDINE
• Synonyms: 5-BROMO-2'-DEOXY-4-THIOURIDINE;5-BROMO-2''-DEOXY-4-THIOURIDINE 98.0%
• CAS NO: 676556-11-9
• Molecular Formula: C9H11BrN2O4S
• Molecular Weight: 323.16364
• Mol File: 676556-11-9.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-BROMO-2'-DEOXY-4-THIOURIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-2'-DEOXY-4-THIOURIDINE(676556-11-9)
• EPA Substance Registry System: 5-BROMO-2'-DEOXY-4-THIOURIDINE(676556-11-9)

Safety Data

• Hazardous Substances Data: 676556-11-9(Hazardous Substances Data)

Upstream product

• 59-14-3 5-bromo-2'-deoxyuridine 
• 34279-86-2 3',5'-O-bis-(trimethylsilyl)-5-bromo-2'-deoxyuridine 
• 6161-23-5 1-(3,5-di-O-acetyl-β-D-2-deoxyribofuranosyl)-5-bromouracil 

Relevant articles and documents

4-Thio-5-bromo-2′-deoxyuridine: Chemical synthesis and therapeutic potential of UVA-induced DNA damage

4-Thio-5-bromo-2′-deoxyuridine (3a) is prepared from 5-bromo-2′-deoxyuridine (BrdU) and its key properties are explored. The thionucleoside (3a) can react readily with monobromobimane and produces high fluorescence. 3a has UV maximum absorption at 340 nm and can be incorporated into cellular DNA. The cells containing 3a become sensitive to UVA light, offering therapeutic potential for UVA-induced cell killing.

Why does the type of halogen atom matter for the radiosensitizing properties of 5-halogen substituted 4-thio-20-deoxyuridines?

Radiosensitizing properties of substituted uridines are of great importance for radiotherapy. Very recently, we confirmed 5-iodo-4-thio-20-deoxyuridine (ISdU) as an efficient agent, increasing the extent of tumor cell killing with ionizing radiation. To our surprise, a similar derivative of 4-thio-2’-deoxyuridine, 5-bromo-4-thio-20-deoxyuridine (BrSdU), does not show radiosensitizing properties at all. In order to explain this remarkable difference, we carried out a radiolytic (stationary and pulse) and quantum chemical studies, which allowed the pathways to all radioproducts to be rationalized. In contrast to ISdU solutions, where radiolysis leads to 4-thio-2’-deoxyuridine and its dimer, no dissociative electron attachment (DEA) products were observed for BrSdU. This observation seems to explain the lack of radiosensitizing properties of BrSdU since the efficient formation of the uridine-5-yl radical, induced by electron attachment to the modified nucleoside, is suggested to be an indispensable attribute of radiosensitizing uridines. A larger activation barrier for DEA in BrSdU, as compared to ISdU, is probably responsible for the closure of DEA channel in the former system. Indeed, besides DEA, the XSdU anions may undergo competitive protonation, which makes the release of X? kinetically forbidden.