化学学报 ›› 1993, Vol. 51 ›› Issue (3): 308-312. 上一篇    

研究论文

一种新的DNA探针-2-(N-二茂铁酰氨丙氧基)-6-氯-9-氨基吖啶的合成与性质

陈耀全   

  1. 中国科学院上海有机化学研究所;中国科学院生命有机化学国家重点实验室
  • 发布日期:1993-03-15

Synthesis and properties of 2-(N-ferrocenecarbonylaminopropoxy)-6-chloro-9-aminoacridine, a new DNA intercalatant containing iron atom

CHEN YAOQUAN   

  • Published:1993-03-15

本文合成了一种含二茂铁侧基的DNA荧光探针-2-(N-二茂铁酰氨丙氧基)-6-氯-9-氨基吖啶, 并对该化合物的紫外可见光谱, 荧光光谱, NMR谱以及它和小牛胸腺DNA的作用与二茂铁侧基的吖啶作了比较和讨论。

关键词: 紫外分光光度法, 脱氧核糖核酸, 吖啶 P, 核磁共振谱法, 荧光分光光度法, 二茂铁 P, 荧光探针

new iron containing acridine derivative was synthesized by acylation of 2-(3-aminopropoxy)-6-chloro-9-aminoacridine (II) with p-nitrophenyl ferrocenecarboxylate. This compound strongly interacts with DNA and might be suitable to be used for both fluorescent and electronic microscopy observations. In comparison with II and 9-aminoacridine, I displayed some interesting features due to the presence of ferrocenecarboxyl group. (1) Ferrocenecarboxyl group strongly diminished the UV absorption and fluorescence emission of I. The mol. extinction of I was about 1/5 of that of 9-aminoacridine, and the relative emission intensity of I was about 1/9 of that of II. (2) While the emission intensity of II gradually decreased with irradiation, that of I increased, the enhancement reached its max. at about 15 min irradiation, then decreased with irradiation (3) The NMR chem. shifts of the acridine ring protons of I moved upfield compared to those of 9-aminoacridine. (4) Compound I enhanced the Tm value of calf thymus DNA, but this enhancement was lower than that caused by 9-aminoacridine.

Key words: ULTRAVIOLET SPECTROPHOTOMETRY, DEOXYRIBONUCLEIC ACID, ACRIDINE P, NMR SPECTROMETRY, FLUOROSPECTROPHOTOMETRY, FERROCENE P, FLUORESCENCE PROBE

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