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Improved method for the preparation of nonyl acridine orange analogues and utilization in detection of cardiolipin

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Abstract

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.

Graphical abstract: Improved method for the preparation of nonyl acridine orange analogues and utilization in detection of cardiolipin

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Supplementary files

Article information


Submitted
27 Apr 2020
Accepted
21 May 2020
First published
22 May 2020

New J. Chem., 2020, Advance Article
Article type
Paper

Improved method for the preparation of nonyl acridine orange analogues and utilization in detection of cardiolipin

P. Dimitrijevs, I. Domracheva and P. Arsenyan, New J. Chem., 2020, Advance Article , DOI: 10.1039/D0NJ02116D

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