| Identification | More | [Name]
5-Bromo-2'-deoxycytidine | [CAS]
1022-79-3 | [Synonyms]
2'-DEOXY-5-BROMOCYTIDINE
5-BR-DC
5-BROMO-2'-DEOXYCYTIDINE
5-BROMO-2'-DEOXYCYTIDINE MONOHYDRATE
5-BROMODEOXYCYTIDINE
5-bromo-2’-deoxy-cytidin
5-Bromo-2'-deoxy-D-cytidine
5-BROMO-2''-DEOXYCYTIDINE(5-BRDC)
Bromodeoxycytidine
5-BROMO-2''-DEOXYCYTIDINE crystalline
5-BROMO-2''-DEOXYCYTIDINE, HPLC PURIFIED, 98% PURE WITH HPLC UV CHROMATOGRAM
4-Amino-5-bromo-1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
4-Amino-1-(2-deoxy-β-D-ribofuranosyl)-5-bromopyrimidin-2(1H)-one | [EINECS(EC#)]
213-824-2 | [Molecular Formula]
C9H12BrN3O4 | [MDL Number]
MFCD00047496 | [Molecular Weight]
306.11 | [MOL File]
1022-79-3.mol |
| Hazard Information | Back Directory | [Uses]
5-Bromo-2'-deoxycytidine (BrdC) is a brominated derivative of the deoxyribonucleoside 2’-deoxycytidine. It induces DNA cross-linking and the formation of DNA strand breaks when incorporated into a DNA fragment in place of cytosine and exposed to UVB damage. BrdC inhibits cytopathogenicity induced by herpes simplex virus 1 (HSV-1) and HSV-2 in infected primary rabbit kidney (PRK) cells (MICs = 0.2-0.3 μg/ml). It decreases the survival of U-1 melanoma cells and AG1522 non-cancerous cells and induces sensitization of both to radiation. BrdC also sensitizes tumors to radiation and reduces tumor volume in a mouse model of glioma using RT-2 cells infused with an adenovirus expressing HSV thymidine kinase (ADV-TK) after implantation. In vivo, BrdC is converted to 5-bromo-2'-deoxyuridine (BrdU) and has been used to label cardiac progenitor cells (CPCs) in a rat model of myocardial infarction.
| [Synthesis]
The general procedure for the synthesis of 4-amino-5-bromo-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-ones, using 4-amino-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one as a starting material was carried out in the following manner: under stirring conditions, 2 '-O-methyluridine (5, 0.103 g, 0.4 mmol) was dissolved in aqueous acetonitrile (H2O:CH3CN = 1:9, 5 mL). NaN3 (0.104 g, 1.6 mmol) was then added and SMBI (0.101 g, 0.44 mmol) was added at room temperature. The reaction mixture was stirred continuously and the progress of the reaction was monitored by thin layer chromatography (TLC). The reaction was completed after about 1.5 h. The reaction mixture was filtered, concentrated under reduced pressure and co-evaporated with acetonitrile (2 x 2 mL) to remove residual water. The crude product was purified by column chromatography using a solvent mixture of dichloromethane (DCM) and methanol (MeOH) (4%-6% MeOH in DCM, v/v) as eluent, resulting in purified bromonucleoside 6 (0.117 g, 93% yield) as a white solid. | [References]
[1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 5, p. 1007 - 1013
[2] Synthesis, 2009, # 23, p. 3957 - 3962
[3] European Journal of Organic Chemistry, 2010, # 24, p. 4713 - 4718
[4] Molecules, 2013, vol. 18, # 10, p. 12740 - 12750
[5] Journal of the American Chemical Society, 1959, vol. 81, p. 1756 |
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