期刊
NUCLEIC ACIDS RESEARCH
卷 47, 期 13, 页码 6578-6589出版社
OXFORD UNIV PRESS
DOI: 10.1093/nar/gkz512
关键词
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资金
- Japan Society for the Promotion of Science (JSPS)
- Research Program of 'Dynamic Alliance for Open Innovation Bridging Human, Environment and Materials'
- Sato Yo International Scholarship Foundation
- JSPS
- [JP15H05838]
Higher-ordered structure motifs of nucleic acids, such as the G-quadruplex (G-4), mismatched and bulge structures, are significant research targets because these structures are involved in genetic control and diseases. Selective alkylation of these higher-order structures is challenging due to the chemical instability of the alkylating agent and side-reactions with the single- or double-strand DNA and RNA. We now report the reactive OFF-ON type alkylating agents, vinyl-quinazolinone (VQ) precursors with a sulfoxide, thiophenyl or thiomethyl group for the OFF-ON control of the vinyl reactivity. The stable VQ precursors conjugated with aminoacridine, which bind to the G-4 DNA, selectively reacted with a T base on the G-4 DNA in contrast to the single- and double-strand DNA. Additionally, the VQ precursor reacted with the T or U base in the AP-site, G-4 RNA and T-T mismatch structures. These VQ precursors would be a new candidate for the T or U specific alkylation in the higher-ordered structures of nucleic acids.
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