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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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:

Zalcitabine Cytidine 5’-monophosphate Cytidine-5'-triphosphate disodium salt dihydrate Glycine 5-Azacytidine 6-Aminocaproic acid CHLOROPHOSPHONAZO III Cytarabine Tris(hydroxymethyl)nitromethane ALTRENOGEST Cytidine 2'-Deoxycytidine monohydrate Tris(hydroxymethyl)aminomethane Bromine Cytosine 2'-Deoxycytidine 5-BROMOCYTIDINE 5-BROMO-DC CEP

5-bromo-2’-deoxy-cytidin

2'-DEOXY-5-BROMOCYTIDINE

5-BR-DC

5-BROMO-2'-DEOXYCYTIDINE MONOHYDRATE

5-BROMODEOXYCYTIDINE

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

4-Amino-5-bromo-1-((2R,4S,5R)-4-hydroxy-5-(hydroxy-methyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)

5-Bromo-dcrd

Aids072378

Aids-072378

5-Bromo-2'-deoxycytidine ,98%

4-aMino-5-broMo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxyMethyl)oxolan-2-yl]-1,2-dihydropyriMidin-2-one

4-AMino-5-broMo-1-((2R,4S,5R)-4-hydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)pyriMidin-2(1H)-one

4-Amino-5-bromo-1-((2R,4S,5R)-4-hydroxy-5-(hydroxy-methyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-on

5-Br-2'-deoxycytidine

5-Br-2'-dC

Cytidine, 5-bromo-2'-deoxy-

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

5-Bromo-2''-deoxycytidine

5-BrdC (5-Bromo-2-Deoxycytidine)

5-bromo-2'-deoxycytidine

1022-79-3

C9H12BrN3O4

Nucleotides and Nucleic Acids