Radiation Induced One-Electron Oxidation of 2-Thiouracil in Aqueous Solutions

Skotnicki, Konrad; Taras-Goslinska, Katarzyna; Janik, Ireneusz; Bobrowski, Krzysztof

doi:10.3390/molecules24234402

Radiation Induced One-Electron Oxidation of 2-Thiouracil in Aqueous Solutions

Journal Article · Sun Dec 01 23:00:00 EST 2019 · Molecules

DOI:https://doi.org/10.3390/molecules24234402· OSTI ID:1799648

Skotnicki, Konrad ^[1]; Taras-Goslinska, Katarzyna ^[2]; Janik, Ireneusz ^[3]; Bobrowski, Krzysztof ^[4]

Inst. of Nuclear Chemistry and Technology, 03-195 Warsaw (Poland). Centre of Radiation Research; OSTI
Adam Mickiewicz Univ., Poznan (Poland). Faculty of Chemistry
Univ. of Notre Dame, IN (United States). Notre Dame Radiation Lab.
Inst. of Nuclear Chemistry and Technology, 03-195 Warsaw (Poland). Centre of Radiation Research

Oxidative damage to 2-thiouracil (2-TU) by hydroxyl (•OH) and azide (N3) radicals produces various primary reactive intermediates. Their optical absorption spectra and kinetic characteristics were studied by pulse radiolysis with UV-vis spectrophotometric and conductivity detection and by time-dependent density functional theory (TD-DFT) method. The transient absorption spectra recorded in the reactions of •OH with 2-TU depend on the concentration of 2-TU, however, only slightly on pH. At low concentrations, they are characterized by a broad absorption band with a weakly pronounced maxima located at λ = 325, 340 and 385 nm, whereas for high concentrations, they are dominated by an absorption band with λmax ≈ 425 nm. Based on calculations using TD-DFT method, the transient absorption spectra at low concentration of 2-TU were assigned to the ∙OH-adducts to the double bond at C5 and C6 carbon atoms (3∙, 4∙) and 2c-3e bonded ∙OH adduct to sulfur atom (1…∙OH) and at high concentration of 2-TU also to the dimeric 2c-3e S-S-bonded radical in neutral form (2∙). The dimeric radical (2∙) is formed in the reaction of thiyl-type radical (6∙) with 2-TU and both radicals are in an equilibrium with Keq = 4.2 × 103 M-1. Similar equilibrium (with Keq = 4.3 × 103 M-1) was found for pH above the pKa of 2-TU which involves admittedly the same radical (6∙) but with the dimeric 2c-3e S-S bonded radical in anionic form (2∙-). In turn, ∙N3-induced oxidation of 2-TU occurs via radical cation with maximum spin location on the sulfur atom which subsequently undergoes deprotonation at N1 atom leading again to thiyl-type radical (6∙). This radical is a direct precursor of dimeric radical (2∙).

View Accepted Manuscript (DOE)

Research Organization:: Univ. of Notre Dame, IN (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: FC02-04ER15533

OSTI ID:: 1799648

Journal Information:: Molecules, Journal Name: Molecules Journal Issue: 23 Vol. 24; ISSN MOLEFW; ISSN 1420-3049

Publisher:: MDPICopyright Statement

Country of Publication:: United States

Language:: English

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