4.6 Article

Incorporation of a bromine atom into DNA-related molecules changes their electronic properties

Journal

PHYSICAL CHEMISTRY CHEMICAL PHYSICS
Volume 25, Issue 21, Pages 14836-14847

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d3cp01597a

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X-ray photoelectron spectroscopy (XPS) was used to study the mechanism of high radio-sensitisation in living cells with brominated genomic DNA. The bromine atom reduced the energy gap between the valence and conduction states, facilitating electron transfer and increasing the probability of reaction with low energy electrons. This leads to DNA damage and cytotoxic effects.
To understand the mechanism underlying the high radio-sensitisation of living cells possessing brominated genomic DNA, X-ray photoelectron spectroscopy (XPS) using synchrotron X-rays with energies of 2000 or 2500 eV was used to study brominated and nonbrominated nucleobases, nucleosides and nucleotides. The bromine atom significantly reduced the energy gap between the valence and conduction states, although the core level states were not greatly affected. This finding was supported by quantum chemical calculation for the nucleobases and nucleosides. Our findings strongly indicate that the energy gaps between the valence and conduction levels of the molecules are significantly reduced by bromination. Furthermore, the brominated molecules are more likely to produce inelastic scattering low energy electrons upon exposure to 2000 or 3000 eV X-rays. This modification of electronic properties around the brominated group may both facilitate electron transfer to the brominated site in DNA and increase the probability of reaction with low energy electrons. These processes can induce DNA damage, presumably resulting in debromination of the uracil moiety and a subsequent cytotoxic effect.

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