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通过铜辅助的前所未有的环化反应一锅法合成1,2-二氢[1,2,4]三嗪鎓盐:在DNA和蛋白质相互作用研究中的应用

One-Pot Synthesis of 1, 2-Dihydro [1,2,4] Triazinium Salt by Copper-Assisted Unprecedented Cyclization Reaction: Applications in DNA and Protein Interaction Studies.

作者信息

Maji Ankur, Yadav Aditya, Sharma Shubham, Saini Rajat, Singh Anshu, Mohanty Aurobinda, Nandi Chayan K, Ghosh Kaushik

机构信息

Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, Uttarakhand, 247667, India.

School of Basic Sciences, Indian Institute of Technology Mandi, Kamand Campus, VPO Kamand, Distt. Mandi Himachal Pradesh, 175075, India.

出版信息

Chempluschem. 2024 Dec;89(12):e202400219. doi: 10.1002/cplu.202400219. Epub 2024 Nov 21.

Abstract

Copper catalyzed intramolecular annulation of 2-((2-benzylidene-1-phenylhydrazineyl)methyl)pyridine derivatives was described. It was found that Cu(II) is reduced under the reaction condition to Cu(I). Synthesized 1,2-dihydro [1,2,4] triazinium salt showed fluorescence activity in the solid state. On treating with base, an instant increase in fluorescence was observed. A detailed physicochemical assessment underscored the robust DNA-binding capabilities of the [1,2,4]triazinium cationic species (C1-C3) via intercalative mechanisms. Notably, binding assays with BSA accentuated the heightened nucleic acid affinity of these cationic species.

摘要

描述了铜催化的2-((2-亚苄基-1-苯基肼基)甲基)吡啶衍生物的分子内环化反应。发现在反应条件下Cu(II)被还原为Cu(I)。合成的1,2-二氢[1,2,4]三嗪盐在固态下表现出荧光活性。用碱处理时,观察到荧光瞬间增强。详细的物理化学评估强调了[1,2,4]三嗪阳离子物种(C1-C3)通过插入机制具有强大的DNA结合能力。值得注意的是,与牛血清白蛋白的结合试验突出了这些阳离子物种对核酸的更高亲和力。

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