Stability of the parent anion of the potential radiosensitizer 8-bromoadenine formed by low-energy (<3 eV) electron attachment

Robin Schürmann , Katrin Tanzer , Iwona Dąbkowska , Stephan Denifl , Ilko Bald

Abstract

8-Bromoadenine (8BrA) is a potential DNA radiosensitizer for cancer radiation therapy due to its efficient interaction with low-energy electrons (LEEs). LEEs are a short-living species generated during the radiation damage of DNA by high-energy radiation as it is applied in cancer radiation therapy. Electron attachment to 8BrA in the gas phase results in a stable parent anion below 3 eV electron energy in addition to fragmentation products formed by resonant exocyclic bond cleavages. Density functional theory (DFT) calculations of the 8BrA– anion reveal an exotic bond between the bromine and the C8 atom with a bond length of 2.6 Å, where the majority of the charge is located on bromine and the spin is mainly located on the C8 atom. The detailed understanding of such long-lived anionic states of nucleobase analogues supports the rational development of new therapeutic agents, in which the enhancement of dissociative electron transfer to the DNA backbone is critical to induce DNA strand breaks in cancerous tissue.
Author Robin Schürmann
Robin Schürmann,,
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, Katrin Tanzer
Katrin Tanzer,,
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, Iwona Dąbkowska PChS
Iwona Dąbkowska,,
- Laboratory of Supramolecular Chemistry
, Stephan Denifl
Stephan Denifl,,
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, Ilko Bald
Ilko Bald,,
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Journal seriesJournal of Physical Chemistry B, ISSN 1520-6106
Issue year2017
Vol121
No23
Pages5730-5734
Publication size in sheets0.5
DOIDOI:10.1021/acs.jpcb.7b02130
URL https://pubs.acs.org/doi/pdf/10.1021/acs.jpcb.7b02130
Languageen angielski
Score (nominal)30
ScoreMinisterial score = 30.0, 26-02-2018, ArticleFromJournal
Ministerial score (2013-2016) = 30.0, 26-02-2018, ArticleFromJournal
Publication indicators WoS Impact Factor: 2016 = 3.177 (2) - 2016=3.177 (5)
Citation count*0
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