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
AbstractThe 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.
|Journal series||Journal of Physical Chemistry B, ISSN 1520-6106, (A 30 pkt)|
|Publication size in sheets||0.5|
|ASJC Classification||; ;|
|Score|| = 30.0, 12-03-2020, ArticleFromJournal|
= 30.0, 12-03-2020, ArticleFromJournal
|Publication indicators||= 1; : 2015 = 1.058; : 2015 = 3.187 (2) - 2015=3.265 (5)|
|Citation count*||1 (2020-05-29)|
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.