Remarkable stabilization of antiparallel DNA triplexes by strong stacking effects of consecutively modified nucleobases containing thiocarbonyl groups.

Remarkable stabilization of antiparallel DNA triplexes by strong stacking effects of consecutively modified nucleobases containing thiocarbonyl groups.
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通过连续修饰的含有硫代羰基的核碱基的强烈堆积效应,使反平行 DNA 三链体具有显着的稳定性。

DOI:
10.1016/j.bmcl.2012.11.079
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发表时间:
2013
期刊:
Bioorg Med Chem Lett.
影响因子:
--
通讯作者:
Sekine M.
Sekine M.
中科院分区:
--
文献类型:
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作者:
Yamada K;Hattori Y;Inde T;Kanamori T;Ohkubo A;Seio K;Sekine M.

文献摘要

相似文献

2'-脱氧-6-硫鸟苷(s6Gs)和4-硫代胸苷(s4Ts)在反平行三链体形成寡核苷酸(TFO)中的连续排列通过硫代羰基的强堆积效应大大稳定了所得的具有高碱基识别能力的反平行三链体。这一结果非常引人注目,因为反平行 TFO 的糖部分和核碱基的化学修饰通常会破坏三链体结构的稳定性。此外,与未修饰的TFO相比,发现含有s6G和s4T的TFO可以选择性地与互补的DNA双链体结合,但不能与不匹配的DNA双链体或单链RNA结合。
The consecutive arrangement of 2′-deoxy-6-thioguanosines (s6Gs) and 4-thiothymidines (s4Ts) in antiparallel triplex-forming oligonucleotides (TFOs) considerably stabilized the resulting antiparallel triplexes with high base recognition ability by the strong stacking effects of thiocarbonyl groups. This result was remarkable because chemical modifications of the sugar moieties and nucleobases of antiparallel TFOs generally destabilize triplex structures. Moreover, in comparison with unmodified TFOs, it was found that TFOs containing s6Gs and s4Ts could selectively bind to the complementary DNA duplex but not to mismatched DNA duplexes or single-stranded RNA.