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5-Bromo-2'-deoxycytidine

Product Name
5-Bromo-2'-deoxycytidine
CAS No.
1022-79-3
Chemical Name
5-Bromo-2'-deoxycytidine
Synonyms
5-BR-DC;Aids072378;5-Br-2'-dC;Aids-072378;5-Bromo-dcrd;Bromodeoxycytidine;5-BROMODEOXYCYTIDINE;5-Br-2'-deoxycytidine;2'-DEOXY-5-BROMOCYTIDINE;5-bromo-2’-deoxy-cytidin
CBNumber
CB8261438
Molecular Formula
C9H12BrN3O4
Formula Weight
306.11
MOL File
1022-79-3.mol
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5-Bromo-2'-deoxycytidine Property

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)
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Safety

Hazard Codes 
Xn
Risk Statements 
40
Safety Statements 
22-36
HS Code 
29389090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC
Product number
B678210
Product name
5-Bromo-2’-deoxycytidine
Packaging
100mg
Price
$75
Updated
2021/12/16
Biosynth Carbosynth
Product number
NB06450
Product name
5-Bromo-2'-deoxycytidine
Packaging
500mg
Price
$55
Updated
2021/12/16
Biosynth Carbosynth
Product number
NB06450
Product name
5-Bromo-2'-deoxycytidine
Packaging
1g
Price
$90
Updated
2021/12/16
AK Scientific
Product number
X0277
Product name
5-bromo-2'-deoxycytidine
Packaging
250mg
Price
$104
Updated
2021/12/16
Biosynth Carbosynth
Product number
NB06450
Product name
5-Bromo-2'-deoxycytidine
Packaging
2g
Price
$150
Updated
2021/12/16
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5-Bromo-2'-deoxycytidine Chemical Properties,Usage,Production

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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5-Bromo-2'-deoxycytidine Suppliers

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View Lastest Price from 5-Bromo-2'-deoxycytidine manufacturers

Shenzhen Nexcon Pharmatechs Ltd.
Product
5-Bromo-2'-deoxycytidine 1022-79-3
Price
US $0.00-0.00/G
Min. Order
1G
Purity
98%
Supply Ability
2000
Release date
2025-06-03
WUHAN FORTUNA CHEMICAL CO., LTD
Product
5-Bromo-2'-deoxycytidine 1022-79-3
Price
US $0.00-0.00/g
Min. Order
1g
Purity
98%min
Supply Ability
1000g
Release date
2021-09-07
Henan Aochuang Chemical Co.,Ltd.
Product
5-Bromo-2'-deoxycytidine 1022-79-3
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
1Ton
Release date
2022-09-26

1022-79-3, 5-Bromo-2'-deoxycytidineRelated Search:

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  • 5-Bromo-2'-deoxycytidine USP/EP/BP
  • 4-amino-5-bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
  • 5-Bromo-2'-deoxycytidine
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