A derivative of 2’-deoxycytidine
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5-Bromo-2'-deoxycytidine

Item No. 40644

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-bromo-2’-deoxycytidine
CAS Number
1022-79-3
Synonyms
  • BrdC
  • BrdCyd
  • 5-Bromodeoxycytidine
  • NSC 61765
Molecular Formula
C9H12BrN3O4
Formula Weight
306.1
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleWater: Soluble
SMILES
O[C@@H]1[C@@H](CO)O[C@@H](N2C(N=C(N)C(Br)=C2)=O)C1
InChi Code
InChI=1S/C9H12BrN3O4/c10-4-2-13(9(16)12-8(4)11)7-1-5(15)6(3-14)17-7/h2,5-7,14-15H,1,3H2,(H2,11,12,16)/t5-,6+,7+/m0/s1
InChi Key
KISUPFXQEHWGAR-RRKCRQDMSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 mg

    $28

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    1 g

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    Product Description

    5-Bromo-2'-deoxycytidine (BrdC) is a brominated derivative of the deoxyribonucleoside 2’-deoxycytidine (Item No. 34708).1 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.2 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).3 It decreases survival of U-1 melanoma cells and AG1522 non-cancerous cells and induces sensitization of both to radiation.1 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.4 In vivo, BrdC is converted to 5-bromo-2'-deoxyuridine (BrdU; Item No. 15580) and has been used to label cardiac progenitor cells (CPCs) in a rat model of myocardial infarction.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lawrence, T.S., and Davis, M.A. Selective radiosensitization and cytotoxicity of human melanoma cells using halogenated deoxycytidines and tetrahydrouridine. Int. J. Radiat. Oncol. Biol. Phys. 16(5), 1243-1246 (1989).

    2. Zdrowowicz, M., Wityk, P., Michalska, B., et al. 5-Bromo-2'-deoxycytidine-a potential DNA photosensitizer. Org. Biomol. Chem. 14(39), 9312-9321 (2016).

    3. De Clercq, E., Balzarini, J., Descamps, J., et al. Antiviral, antimetabolic, and cytotoxic activities of 5-substituted 2'-deoxycytidines. Mol. Pharmacol. 21(1), 217-223 (1982).

    4. Brust, D., Feden, J., Farnsworth, J., et al. Radiosensitization of rat glioma with bromodeoxycytidine and adenovirus expressing herpes simplex virus-thymidine kinase delivered by slow, rate-controlled positive pressure infusion. Cancer Gene Ther. 7(5), 778-788 (2000).

    5. Bocchi, L., Savi, M., Graiani, G., et al. Growth factor-induced mobilization of cardiac progenitor cells reduces the risk of arrhythmias, in a rat model of chronic myocardial infarction. PLoS One 6(3), e17750 (2011).