A convenient approach for generating dimeric nucleic acid dyes via click-chemistry

IF 2.5 4区 医学 Q3 CHEMISTRY, MEDICINAL Bioorganic & Medicinal Chemistry Letters Pub Date : 2024-10-30 DOI:10.1016/j.bmcl.2024.130013
Guorui Li , Guanghua Liu , Yawen Ruan , Chaoshui Liu , Xingnan Lian , Yangli Zheng
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Abstract

Fluorescent dyes are essential tools for visualizing DNA and RNA. Dimeric dyes like GelGreen have gained popularity as safer alternatives to ethidium bromide (EB) due to their reduced mutagenicity and genotoxicity. In this study, we present a straightforward method to synthesize novel acridine orange (AO)-based dimeric dyes using click chemistry. Starting from acridine orange, these dyes can be synthesized in just two steps. Compared to GelGreen, these new dyes incorporate additional triazole groups in their linkers. They exhibit a maximum absorption wavelength of approximately 472 nm, which shifts to around 503 nm upon binding with DNA, allowing excitation by blue light. These dyes show minimal fluorescence in aqueous solutions, indicating that they adopt a closed conformation where the fluorescence of acridine orange is quenched due to intramolecular aggregation. The presence of DNA significantly enhances their fluorescence at around 526 nm, suggesting that DNA binding induces an open conformation. This “light-up” property makes them highly sensitive DNA dyes with a strong signal-to-noise ratio. We successfully applied these novel dyes in agarose gel electrophoresis, where they demonstrated excellent performance.

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通过点击化学生成二聚核酸染料的便捷方法。
荧光染料是可视化 DNA 和 RNA 的重要工具。像 GelGreen 这样的二聚染料因其诱变性和基因毒性较低,作为溴化乙锭(EB)更安全的替代品而广受欢迎。在本研究中,我们提出了一种利用点击化学合成新型吖啶橙(AO)基二聚体染料的简单方法。从吖啶橙开始,这些染料只需两步即可合成。与 GelGreen 相比,这些新型染料在其连接体中加入了额外的三唑基团。它们的最大吸收波长约为 472 nm,与 DNA 结合后会转移到 503 nm 左右,从而可以被蓝光激发。这些染料在水溶液中的荧光最小,表明它们采用了封闭构象,由于分子内聚集,吖啶橙的荧光被淬灭。DNA 的存在会大大增强它们在 526 纳米波长处的荧光,这表明 DNA 结合会诱导它们形成开放构象。这种 "发光 "特性使它们成为高灵敏度、高信噪比的 DNA 染料。我们成功地将这些新型染料应用于琼脂糖凝胶电泳中,它们表现出了卓越的性能。
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来源期刊
CiteScore
5.70
自引率
3.70%
发文量
463
审稿时长
27 days
期刊介绍: Bioorganic & Medicinal Chemistry Letters presents preliminary experimental or theoretical research results of outstanding significance and timeliness on all aspects of science at the interface of chemistry and biology and on major advances in drug design and development. The journal publishes articles in the form of communications reporting experimental or theoretical results of special interest, and strives to provide maximum dissemination to a large, international audience.
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