Reactivity pattern of bromonucleosides induced by 2-hydroxypropyl radicals: photochemical, radiation chemical, and computational studies

Magdalena Zdrowowicz , Lidia Chomicz , Justyna Miloch , Justyna Wiczk , Janusz Rak , Gabriel Kciuk , Krzysztof Bobrowski

Abstract

The bromonucleosides (BrdX’s) 5-bromo-2′-deoxyuridine (BrdU), 5-bromo-2′-deoxycytidine (BrdC), 8-bromo-2′-deoxyadenosine (BrdA), and 5-bromo-2′-deoxyguanosine (BrdG) may substitute for ordinary nucleosides in DNA. As indicated by electron-stimulated desorption experiments, such a modified biopolymer is greater than 2–3-fold more sensitive to damage induced by excess electrons. The other major product of water radiolysis, the •OH radical, may form a number of other radicals in chemical reactions with the complex content of the cell. Thus, the well-proved BrdU-labeled DNA radiosensitivity may be, at least in part, related to secondary organic radicals. Therefore, in the current study, the propensity of BrdX’s to damage induced by 2-hydroxypropyl radical (OHisop•)—a prototype radical species—was investigated. The HPLC and LC-MS analyses revealed the formation of two major products from the brominated pyrimidine nucleosides, a native nucleoside and an adduct of BrdX and OHisop• , and only an adduct of BrdX from the bromopurine nucleosides. Quantum chemical calculations ascribed this evident difference between purines and pyrimidines to the electron transfer from OHisop• to BrdX that is especially favorable in pyrimidines.
Author Magdalena Zdrowowicz (FCh / DPCh / LBS)
Magdalena Zdrowowicz,,
- Laboratory of Biological Sensitizers
, Lidia Chomicz (FCh / DPCh / LBS)
Lidia Chomicz,,
- Laboratory of Biological Sensitizers
, Justyna Miloch (FCh / DPCh / LBS)
Justyna Miloch,,
- Laboratory of Biological Sensitizers
, Justyna Wiczk (FCh / DPCh / LBS)
Justyna Wiczk ,,
- Laboratory of Biological Sensitizers
, Janusz Rak (FCh / DPCh / LBS)
Janusz Rak,,
- Laboratory of Biological Sensitizers
, Gabriel Kciuk
Gabriel Kciuk,,
-
, Krzysztof Bobrowski
Krzysztof Bobrowski,,
-
Journal seriesJournal of Physical Chemistry B, ISSN 1520-6106, (A 30 pkt)
Issue year2015
Vol119
No22
Pages6545-6554
Publication size in sheets0.5
ASJC Classification2505 Materials Chemistry; 2508 Surfaces, Coatings and Films; 1606 Physical and Theoretical Chemistry
DOIDOI:10.1021/acs.jpcb.5b01904
URL http://pubs.acs.org/doi/pdf/10.1021/acs.jpcb.5b01904
Languageen angielski
Score (nominal)30
Score sourcejournalList
ScoreMinisterial score = 30.0, 12-03-2020, ArticleFromJournal
Ministerial score (2013-2016) = 30.0, 12-03-2020, ArticleFromJournal
Publication indicators WoS Citations = 1; Scopus SNIP (Source Normalised Impact per Paper): 2015 = 1.058; WoS Impact Factor: 2015 = 3.187 (2) - 2015=3.265 (5)
Citation count*1 (2020-05-29)
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