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电子介导的 C5 叠氮嘧啶核苷的氨甲酰基和亚氨自由基增强了癌细胞的辐射损伤。

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

机构信息

Department of Chemistry and Biochemistry , Florida International University , Miami , Florida 33199 , United States.

Department of Chemistry , Oakland University , Rochester , Michigan 48309 , United States.

出版信息

Org Lett. 2018 Dec 7;20(23):7400-7404. doi: 10.1021/acs.orglett.8b03035. Epub 2018 Nov 20.

DOI:10.1021/acs.orglett.8b03035
PMID:30457873
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6465127/
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.

摘要

两类叠氮修饰的嘧啶核苷被合成作为潜在的放射增敏剂；一类是 5-叠氮甲基-2'-脱氧尿苷（AmdU）和胞苷（AmdC），另一类是 5-（1-叠氮乙烯基）-2'-脱氧尿苷（AvdU）和胞苷（AvdC）。辐射产生的电子加到 C5-叠氮核苷上，导致形成π-氨基自由基，然后通过双分子反应容易转化为σ-亚氨基自由基，该反应涉及 AmdU/AmdC 中的中间α-叠氮烷基自由基，或通过 AvdU/AvdC 的互变异构化。AmdU 在 EMT6 肿瘤细胞中表现出有效的放射增敏作用。

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