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1. Electron-Mediated Aminyl and Iminyl Radicals from C5 Azido-Modified Pyrimidine Nucleosides Augment Radiation Damage to Cancer Cells

Author

Wen, Zhiwei, Peng, Jufang, Tuttle, Paloma R., Ren, Yaou, Garcia, Carol, Debnath, Dipra, Rishi, Sunny, Hanson, Cameron, Ward, Samuel, Kumar, Anil, Liu, Yanfeng, Zhao, Weixi, Glazer, Peter M., Liu, Yuan, Sevilla, Michael D., Adhikary, Amitava, and Wnuk, Stanislaw F.

Abstract

Two classes of azido-modified pyrimidine nucleosides were synthesized as potential radiosensitizers; one class is 5-azidomethyl-2′-deoxyuridine (AmdU) and cytidine (AmdC), while the second class is 5-(1-azidovinyl)-2′-deoxyuridine (AvdU) and cytidine (AvdC). The addition of radiation-produced electrons to C5-azido nucleosides leads to the formation of π-aminyl radicals followed by facile conversion to σ-iminyl radicals either via a bimolecular reaction involving intermediate α-azidoalkyl radicals in AmdU/AmdC or by tautomerization in AvdU/AvdC. AmdU demonstrates effective radiosensitization in EMT6 tumor cells.

Published
2018
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