5-Bromo-2'-deoxycytidine - CAS 1022-79-3
Category:
Nucleosides
Product Name:
5-Bromo-2'-deoxycytidine
Catalog Number:
1022-79-3
CAS Number:
1022-79-3
Molecular Weight:
306.11
Molecular Formula:
C9H12BrN3O4
COA:
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MSDS:
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Structure\Application:
2'-Deoxy-Nucleosides
Chemical Structure
CAS 1022-79-3 5-Bromo-2'-deoxycytidine

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Reference Reading


1.The cyclobutane dimers of 2'-deoxyuridine, 2'-deoxycytidine, 5-methyl-2'-deoxycytidine and 5-bromo-2'-deoxyuridine.
Shetlar MD1, Chung J. Photochem Photobiol. 2012 Sep-Oct;88(5):1236-47. doi: 10.1111/j.1751-1097.2012.01169.x. Epub 2012 Jun 6.
Irradiation of DNA and RNA pyrimidine nucleosides with UV light in frozen aqueous solution or in solution with acetone often results in the formation of cyclobutane dimers (CBDs). Many of these photodimers have not been characterized. We present here the results of work designed to achieve the isolation, spectroscopic characterization and determination of the stereochemical nature of a number of little studied or previously unstudied CBDs of four 2'-deoxyribonuclesides. These nucleosides are 2'-deoxyuridine (dUrd), 2'-deoxycytidine (dCyd), 5-methyl-2'-deoxycytidine (5-MedCyd) and 5-bromo-2'-deoxyuridine (5-BrdUrd). In particular, we have isolated and characterized six dUrd CBDs, five dCyd CBDs, five 5-MedCyd CBDs and four 5-BrdUrd CBDs. Photoproducts were studied by UV spectroscopy, mass spectrometry, proton NMR spectroscopy and via chemical approaches. Also presented are results from less definitive studies of a number of (6-4) (or 5-4) photoadducts of these nucleosides.
2.Synthesis, molecular conformation and activity against herpes simplex virus of (E)-5-(2-bromovinyl)-2'-deoxycytidine analogs.
Zoghaib WM1, Mannala S, Gupta VS, Tourigny G. Nucleosides Nucleotides Nucleic Acids. 2012 Apr;31(4):364-76. doi: 10.1080/15257770.2012.661214.
Analogs of (E)-5-(2-bromovinyl)-2'-deoxycytidine (BrVdCyd) (1) by substitution at N(4) were synthesized to impart resistance against deamination. The anti-HSV-1 activity and solution conformation of these analogs were determined. N(4)-Acetyl-BrVdCyd (2) was a potent inhibitor of HSV-1 replication whereas N(4)-propanoyl-BrVdCyd (3) had good activity and N(4)-Butanoyl-BrVdCyd (4) had only low activity against HSV-1 replication. N(4)-Methyl-BrVdCyd (5) was devoid of activity against HSV-1.
3.Mutational specificities of brominated DNA adducts catalyzed by human DNA polymerases.
Sassa A1, Ohta T, Nohmi T, Honma M, Yasui M. J Mol Biol. 2011 Mar 11;406(5):679-86. doi: 10.1016/j.jmb.2011.01.005. Epub 2011 Jan 15.
Chronic inflammation is known to lead to an increased risk for the development of cancer. Under inflammatory condition, cellular DNA is damaged by hypobromous acid, which is generated by myeloperoxidase and eosinophil peroxidase. The reactive brominating species induced brominated DNA adducts such as 8-bromo-2'-deoxyguanosine (8-Br-dG), 8-bromo-2'-deoxyadenosine (8-Br-dA), and 5-bromo-2'-deoxycytidine (5-Br-dC). These DNA lesions may be implicated in carcinogenesis. In this study, we analyzed the miscoding properties of the brominated DNA adducts generated by human DNA polymerases (pols). Site-specifically modified oligodeoxynucleotides containing a single 8-Br-dG, 8-Br-dA, or 5-Br-dC were used as a template in primer extension reactions catalyzed by human pols α, κ, and η. When 8-Br-dG-modified template was used, pol α primarily incorporated dCMP, the correct base, opposite the lesion, along with a small amount of one-base deletion (4.8%).
4.Antiflammin-1 attenuates bleomycin-induced pulmonary fibrosis in mice.
Liu W1, Wan J, Han JZ, Li C, Feng DD, Yue SJ, Huang YH, Chen Y, Cheng QM, Li Y, Luo ZQ. Respir Res. 2013 Oct 8;14:101. doi: 10.1186/1465-9921-14-101.
BACKGROUND: Antiflammin-1 (AF-1), a derivative of uteroglobin (UG), is a synthetic nonapeptide with diverse biological functions. In the present study, we investigated whether AF-1 has a protective effect against bleomycin-induced pulmonary fibrosis.