Improved method for the preparation of nonyl acridine orange analogues and utilization in detection of cardiolipin,New Journal of Chemistry

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Improved method for the preparation of nonyl acridine orange analogues and utilization in detection of cardiolipin
New Journal of Chemistry ( IF 2.7 ) Pub Date : 2020-05-22 , DOI: 10.1039/d0nj02116d
Pavels Dimitrijevs _{1,

2,

2,

3,

4} , Ilona Domracheva _{1,

2,

3} , Pavel Arsenyan _{1,

2,

3}

Affiliation

This study was designed to develop a fast and convenient methodology for the preparation of 10-nonyl acridine orange (NAO) and its silyl analogues to improve their photo-physical properties for the detection and quantification of cardiolipin (CL). Optimized conditions allow the effective synthesis of NAO analogues with good yield and excellent purity. The introduction of a 3-(trimethylsilyl)propyl moiety improves the dye's solubility and stability in buffer solution and increases its emission intensity by ≈30%. The novel dye can be used for the selective quantification of CL in a liposomal inner mitochondrial membrane model with greater fluorescence intensity and linear slope compared to NAO. The novel silicon-containing NAO analogue has lower cytotoxicity, and is a convenient fluorescent dye for cell staining.

中文翻译：

壬基a啶橙类似物的制备及在心磷脂检测中的改进方法

本研究旨在开发一种快速便捷的方法来制备10-壬基a啶橙（NAO）及其甲硅烷基类似物，以改善其光物理特性，以检测和定量心磷脂（CL）。优化的条件可以高效合成NAO类似物，并具有良好的收率和优异的纯度。3-（三甲基甲硅烷基）丙基部分的引入提高了染料在缓冲溶液中的溶解度和稳定性，并使发光强度增加了约30％。与NAO相比，该新型染料可用于脂质体线粒体内膜模型中CL的选择性定量，其荧光强度和线性斜率更大。新型的含硅NAO类似物具有较低的细胞毒性，并且是用于细胞染色的方便的荧光染料。

更新日期：2020-05-22

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