PRODAN-conjugated DNA: synthesis and photochemical properties.
PRODAN-conjugated DNA: synthesis and photochemical properties.
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DOI：
10.1021/ja069156a
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发表时间：
2007-03
影响因子：
15
通讯作者：
Kazuki Tainaka;Kazuo Tanaka;S. Ikeda;Ken-ichiro Nishiza;Tomo Unzai;Yoshimasa Fujiwara;I. Saito;A. Okamoto
中科院分区：
文献类型：
--
作者：
Kazuki Tainaka;Kazuo Tanaka;S. Ikeda;Ken-ichiro Nishiza;Tomo Unzai;Yoshimasa Fujiwara;I. Saito;A. Okamoto
溶剂化显色荧光团 PRODAN 已被用作微环境敏感报告基因。基于 PRODAN 的化学性质，我们设计并合成了四种新型荧光核苷 PDNX（X = U、C、A 和 G），其中 PRODAN 荧光团连接在嘧啶 C5 或嘌呤 C8 处。荧光核苷根据溶剂的取向极化率敏感地改变斯托克斯位移值。掺入 DNA 中的 PDNX 还根据 DNA 结构改变了斯托克斯位移值。特别是，当 PDNX 对面的碱基可以与 PDNX 形成 Watson-Crick 碱基对时，含有 PDNX 的双链体的激发光谱会向更长的波长移动，并给出更小的斯托克斯位移值。含有 PDNX 的 DNA 的较低能量激发导致对 Watson-Crick 配对碱基具有选择性的强荧光发射。这种独特的光化学特征适用于基因单核苷酸多态性的有效分型。
A solvatochromic fluorophore, PRODAN, has been used as a microenvironment-sensitive reporter. Based on the chemistry of PRODAN, we designed and synthesized four novel fluorescent nucleosides, PDNX (X = U, C, A, and G), to which a PRODAN fluorophore was attached at pyrimidine C5 or purine C8. The fluorescent nucleosides sensitively varied the Stokes shift values depending on the orientational polarizability of the solvent. The PDNX incorporated into DNA also changed the Stokes shift values depending on the DNA structure. In particular, the excitation spectrum of the PDNX-containing duplex shifted to a longer wavelength and gave a smaller Stokes shift value when the base opposite PDNX could form a Watson-Crick base pair with PDNX. A lower energy excitation of PDNX-containing DNA resulted in a strong fluorescence emission selective to the Watson-Crick pairing base. This unique photochemical character was applicable to the efficient typing of single-nucleotide polymorphisms of genes.