Design, Synthesis, and Characterization of Binaphthalene Precursors as Photoactivated DNA Interstrand Cross-Linkers.
Design, Synthesis, and Characterization of Binaphthalene Precursors as Photoactivated DNA Interstrand Cross-Linkers.
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作为光激活 DNA 链间交联剂的联萘前体的设计、合成和表征。
DOI：
10.1021/acs.joc.8b00642
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发表时间：
2018
期刊：
影响因子：
--
通讯作者：
Peng,Xiaohua
中科院分区：
文献类型：
--
作者：
Lin,Zechao;Fan,Heli;Zhang,Qi;Peng,Xiaohua
最近，通过光生碳阳离子的烷基化已被确定为双官能芳基化合物光诱导DNA链间交联（ICL）形成的新机制。然而，大多数化合物显示出低效率的DNA交联。在这里，我们开发了一系列新的1，1 ′-联萘类似物，它们在350 nm照射下通过产生的2-萘甲基阳离子有效地形成DNA ICL。DNA交联效率取决于萘部分的4位取代基以及离去基团。具有NO2、Ph、H、Br或OMe取代基的化合物导致比具有硼酸酯基团的化合物高2-4倍的DNA ICL产率。三甲基铵盐作为离去基团的化合物显示出比溴作为离去基团的化合物稍好的交联效率。这些化合物中的一些显示出比传统的烷基化剂，如氮芥类似物或醌甲基化物前体更好的交联效率。这些高效的光活化碳阳离子前体允许测定和表征的光生萘基阳离子和四个天然核苷之间形成的加合物，表明这些萘类似物的烷基化位点是dG，dA和dC。
Most recently, alkylation via photogenerated carbocations has been identified as a novel mechanism for photoinduced DNA interstrand cross-link (ICL) formation by bifunctional aryl compounds. However, most compounds showed a low efficiency for DNA cross-linking. Here, we have developed a series of new 1,1′-binaphthalene analogues that efficiently form DNA ICLs upon 350 nm irradiation via generated 2-naphthalenylmethyl cations. The DNA cross-linking efficiency depends on the substituents at position 4 of the naphthalene moiety as well as the leaving groups. Compounds with NO2, Ph, H, Br, or OMe substituents led to 2–4 times higher DNA ICL yields than those with a boronate ester group. Compounds with trimethylammonium salt as a leaving group showed slightly better cross-linking efficiency than those with bromo as a leaving group. Some of these compounds showed a better cross-linking efficiency than that of traditional alkylating agents, such as nitrogen mustard analogues or quinone methide precursors. These highly efficient photoactivated carbocation precursors allow determination and characterization of the adducts formed between the photogenerated naphthalenyl cations and four natural nucleosides, indicating that the alkylation sites for these naphthalene analogues are dG, dA, and dC.
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影响因子：
4.3
作者：
Cao, Sheng;Wang, Yibin;Peng, Xiaohua
通讯作者：
Peng, Xiaohua
对由修饰嘧啶形成的两个中间体的反应性进行解卷积。
影响因子：
5.2
作者：
Weng,Liwei;Horvat,SoniaM;Schiesser,CarlH;Greenberg,MarcM
通讯作者：
Greenberg,MarcM
影响因子：
16.6
作者：
Lin, Gengjie;Li, Lei
通讯作者：
Li, Lei
影响因子：
4.1
作者：
Han, Yanyan;Chen, Wenbing;Peng, Xiaohua
通讯作者：
Peng, Xiaohua
影响因子：
4.3
作者：
Chen, Wenbing;Han, Yanyan;Peng, Xiaohua
通讯作者：
Peng, Xiaohua