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5-Bromo-2'-deoxycytidine

Product Name5-Bromo-2'-deoxycytidine
CAS1022-79-3
MFC9H12BrN3O4
MW306.11
EINECS213-824-2
MOL File1022-79-3.mol

Chemical Properties

Boiling point	510.8±60.0 °C(Predicted)
Density	2.12±0.1 g/cm3(Predicted)
RTECS	HA3705000
storage temp.	Store at 0°C
solubility	DMSO: Soluble Water: Soluble
form	Powder
pka	14.03±0.60(Predicted)
color	White to Pale Yellow
CAS DataBase Reference	1022-79-3(CAS DataBase Reference)

Safety Information

Hazard Codes	Xn
Risk Statements	40
Safety Statements	22-36
HS Code	29389090

Usage And Synthesis

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

951-77-9

1022-79-3

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
[6] THEODORE S. LAWRENCE M.D. PH.D. Mary A D Ph D. Selective radiosensitization and cytotoxicity of human melanoma cells using halogenated deoxycytidines and tetrahydrouridine[J]. International Journal of Radiation Oncology Biology Physics, 1989, 16 5: Pages 1243-1246. DOI: 10.1016/0360-3016(89)90291-5
[7] MAGDALENA ZDROWOWICZ . 5-Bromo-2′-deoxycytidine—a potential DNA photosensitizer1[J]. Organic & Biomolecular Chemistry, 2016, 14 39: Pages 9312-9321. DOI: 10.1039/c6ob01446a
[8] E DE CLERCQ. Antiviral, antimetabolic, and cytotoxic activities of 5-substituted 2’-deoxycytidines.[J]. Molecular Pharmacology, 1982, 21 1: 217-223.
[9] DAVID BRUST. Radiosensitization of rat glioma with bromodeoxycytidine and adenovirus expressing herpes simplex virus-thymidine kinase delivered by slow, rate-controlled positive pressure infusion[J]. Cancer gene therapy, 2000, 7 5: 778-788. DOI: 10.1038/sj.cgt.7700168
[10] LEONARDO BOCCHI. Growth factor-induced mobilization of cardiac progenitor cells reduces the risk of arrhythmias, in a rat model of chronic myocardial infarction.[J]. ACS Applied Bio Materials, 2011: e17750. DOI: 10.1371/journal.pone.0017750

5-Bromo-2'-deoxycytidine

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