通过双相内同步激活,利用取代的2-氨基-6-乙烯基嘌呤核苷的苯基硫化物衍生物与胞苷进行高效交联。

T Kawasaki, F Nagatsugi, M Maeda, S Sasaki
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引用次数: 3

摘要

我们之前已经描述过含有2-氨基-6-vinyulpurine核苷类似物(1)的苯基亚砜衍生物的寡核苷酸在双工中被激活,在靶位点选择性地形成与胞苷的交联。具有苯基亚砜结构(2)的新交联基序的特点是稳定的前体可以在双相中自动转化为活性物质。为了寻找更稳定的易被活化的前体,我们设计了一系列1的取代苯基硫化物类似物。结果表明,在苯基环上引入给电子基团可以改善交联反应。特别是,2-羧基苯基硫化物衍生物在没有化学氧化的情况下表现出与苯基亚砜衍生物一样有效的交联。
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Efficient cross-linking to cytidine using substituted phenylsulfide derivatives of 2-amino-6-vinylpurine nucleoside via synchronous activation within duplex.

We have previously described that oligonucleotides containing phenylsulfoxide derivative of 2-amino-6-vinyulpurine nucleoside analog (1) are activated within duplex to form cross-link toward cytidine selectively at the target site. The new cross-linking motif with phenylsulfoxide structure (2) is characteristic in that the stable precursor may be transformed automatically within duplex to a reactive species. To search for more stable precursor susceptible for activation, we designed a series of substituted phenylsulfide analogs of 1. It has been demonstrated that introduction of an electron-donating group on the phenyl ring improved the cross-linking reaction. Particularly, 2-carboxyphenyl sulfide derivative exhibited cross-linking as effectively as phenylsulfoxide derivative without chemical oxidation prior to cross-linking.

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