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5-Bromo-2′-deoxycytidine (CAS 1022-79-3)

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Alternate Names:
5-Bromo-2′-deoxy-D-cytidine
CAS Number:
1022-79-3
Purity:
≥98%
Molecular Weight:
306.11
Molecular Formula:
C9H12BrN3O4
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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5-Bromo-2′-deoxycytidine is a synthetic nucleoside analogue. It bears a structural resemblance to cytidine and acts as an inhibitor of the enzyme DNA polymerase through intramolecular catalysis. As a result, the 5-bromo group undergoes deamination, impeding the ongoing synthesis of DNA.


5-Bromo-2′-deoxycytidine (CAS 1022-79-3) References

  1. 5-Bromo-2'-deoxycytidine (BCDR). II. Studies with murine neoplastic cells in culture and in vitro.  |  CRAMER, JW., et al. 1961. Biochem Pharmacol. 8: 331-5. PMID: 13881996
  2. 5-Bromo-2'-deoxycytidine (BCDR). I. Studies on metabolism in vitro and in mice.  |  PRUSOFF, WH., et al. 1961. Biochem Pharmacol. 8: 324-6. PMID: 14489045
  3. Sequence-dependent formation of intrastrand crosslink products from the UVB irradiation of duplex DNA containing a 5-bromo-2'-deoxyuridine or 5-bromo-2'-deoxycytidine.  |  Zeng, Y. and Wang, Y. 2006. Nucleic Acids Res. 34: 6521-9. PMID: 17130170
  4. Reaction of 2'-deoxycytidine with peroxynitrite in the presence of ammonium bromide.  |  Suzuki, T., et al. 2008. Bioorg Med Chem. 16: 5164-70. PMID: 18358730
  5. Mutational specificities of brominated DNA adducts catalyzed by human DNA polymerases.  |  Sassa, A., et al. 2011. J Mol Biol. 406: 679-86. PMID: 21241706
  6. Controlling DNA Fragmentation in MALDI-MS by Chemical Modification.  |  Tang, W., et al. 1997. Anal Chem. 69: 302-12. PMID: 21639184
  7. Effects of halides on reaction of nucleosides with ozone.  |  Suzuki, T., et al. 2012. Nucleosides Nucleotides Nucleic Acids. 31: 461-73. PMID: 22646086
  8. The radiosensitivity of 5- and 6-bromocytidine derivatives--electron induced DNA degradation.  |  Chomicz, L., et al. 2014. Phys Chem Chem Phys. 16: 19424-8. PMID: 25102433
  9. Reactivity pattern of bromonucleosides induced by 2-hydroxypropyl radicals: photochemical, radiation chemical, and computational studies.  |  Zdrowowicz, M., et al. 2015. J Phys Chem B. 119: 6545-54. PMID: 25971814
  10. Selective radiosensitization and cytotoxicity of human melanoma cells using halogenated deoxycytidines and tetrahydrouridine.  |  Lawrence, TS. and Davis, MA. 1989. Int J Radiat Oncol Biol Phys. 16: 1243-6. PMID: 2715074
  11. 5-Bromo-2'-deoxycytidine-a potential DNA photosensitizer.  |  Zdrowowicz, M., et al. 2016. Org Biomol Chem. 14: 9312-9321. PMID: 27714178
  12. Viral long terminal repeat substrate binding characteristics of the human immunodeficiency virus type 1 integrase.  |  Hazuda, DJ., et al. 1994. J Biol Chem. 269: 3999-4004. PMID: 8307956
  13. Mechanism of degradation of 2'-deoxycytidine by formamide: implications for chemical DNA sequencing procedures.  |  Saladino, R., et al. 1997. Bioorg Med Chem. 5: 2041-8. PMID: 9416421

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

5-Bromo-2′-deoxycytidine, 500 mg

sc-284555
500 mg
$204.00

5-Bromo-2′-deoxycytidine, 1 g

sc-284555A
1 g
$245.00

5-Bromo-2′-deoxycytidine, 2 g

sc-284555B
2 g
$306.00

5-Bromo-2′-deoxycytidine, 5 g

sc-284555C
5 g
$561.00

5-Bromo-2′-deoxycytidine, 10 g

sc-284555D
10 g
$1020.00