具有四个二茂铁部分的萘二亚胺衍生物作为电化学DNA杂交指示剂的合成。

Synthesis of a naphthalene diimide derivative having four ferrocene moieties as an electrochemical DNA hybridization indicator.

作者信息

Sato Shinobu, Tsueda Masato, Watanabe Sadayoshi, Ohtsuka Keiichi, Takenaka Shigeori

机构信息

Department of Applied Chemistry, Kyushu Institute of Technology, Kitakyushu 804-8550, Japan.

出版信息

Nucleic Acids Symp Ser (Oxf). 2008(52):239-40. doi: 10.1093/nass/nrn121.

DOI:10.1093/nass/nrn121

PMID:18776342

Abstract

A new naphthalene diimide derivative carrying four ferrocene moieties, F(4)ND, was synthesized by the reaction of trimethylammoniummethylferrocene with the terminal amino moieties of two imide substituents of naphthalene diimide. Spectrophotometric binding studies of F(4)ND with calf thymus DNA showed its high affinity of 2 x 10(5) M(-1) in 10 mM MES buffer and 1 mM EDTA (pH 6.25) containing 0.10 M NaCl. The Osteryoung square wave voltammetry (SWV) of a DNA probe-immobilized electrode before and after hybridization with target DNA gave a larger peak current in an electrolyte containing F(4)ND than that containing FND carrying two ferrocene moieties. The current peak difference between mismatched and fully matched DNA was also greater with F(4)ND than that with FND.

摘要

通过三甲基铵甲基二茂铁与萘二亚胺两个酰亚胺取代基的末端氨基反应，合成了一种带有四个二茂铁基团的新型萘二亚胺衍生物F(4)ND。F(4)ND与小牛胸腺DNA的分光光度结合研究表明，在含有0.10 M NaCl的10 mM MES缓冲液和1 mM EDTA（pH 6.25）中，其亲和力高达2×10⁵ M⁻¹。与携带两个二茂铁基团的FND相比，固定有DNA探针的电极在与靶DNA杂交前后的奥斯特杨方波伏安法（SWV）显示，在含有F(4)ND的电解质中产生的峰值电流更大。F(4)ND导致的错配DNA与完全匹配DNA之间的电流峰值差异也大于FND。