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Issue 36, 2014
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The radiosensitivity of 5- and 6-bromocytidine derivatives – electron induced DNA degradation

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Abstract

Halogenated nucleotides belong to the group of radiosensitizers that sensitize solid tumors when incorporated into genomic DNA. Here, we consider the propensity of two isomeric bromocytidine derivatives, 3′,5′-diphosphates of 5-bromo-2′-deoxycytidine (5BrdCDP) and 6-bromo-2′-deoxycytidine (6BrdCDP), to be damaged by electrons – one of the most abundant products formed during radiotherapy. An intranucleotide degradation mechanism leading to phosphodiester bond breakage (a model of single strand breakage in labeled DNA) and a ketone derivative formation was found for 6BrdCDP, while for 5BrdCDP a similar mechanism is sterically hindered. 5BrdCDP is, therefore, suggested to undergo electron induced degradation involving hydrogen transfer from a neighboring nucleotide or environment.

Graphical abstract: The radiosensitivity of 5- and 6-bromocytidine derivatives – electron induced DNA degradation

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Publication details

The article was received on 16 Jul 2014, accepted on 25 Jul 2014 and first published on 28 Jul 2014


Article type: Paper
DOI: 10.1039/C4CP03139C
Citation: Phys. Chem. Chem. Phys., 2014,16, 19424-19428
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    The radiosensitivity of 5- and 6-bromocytidine derivatives – electron induced DNA degradation

    L. Chomicz, Ł. Golon and J. Rak, Phys. Chem. Chem. Phys., 2014, 16, 19424
    DOI: 10.1039/C4CP03139C

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