Jump to main content
Jump to site search

Issue 28, 2019
Previous Article Next Article

Synthesis of azonia cyanine derivatives as NIR fluorescent probes for nucleic acid detection and cell imaging

Author affiliations

Abstract

Six azonia cyanine dyes (1a–f) based on the [1,2-a]pyrimidin-5-ium perchlorate unit were prepared to study their optical properties after interaction with nucleic acids and their potential applications in cell imaging. Dyes 1a–c consist of pyrimidin-5-ium perchlorates (4a–c) and a coumarin unit (5a) linked by conjugated double bonds, while 1d–f were endowed with different conjugated structures through the condensation between pyrimidin-5-ium perchlorates and 6-(diethylamino)-2,3-dihydro-1H-xanthene-4-carbaldehyde (5b). Due to these different structures, they demonstrate different properties. The optical properties of the dyes in five different solvents were measured; dyes 1a–c exhibited strong fluorescence in low polarity solvents (Φ up to 44.9% in dichloromethane) but much weaker fluorescence in high polarity solvents (Φ low to 1.5% in methanol), while dyes 1d–f showed no regular fluorescence properties in these solvents. Then, the optical responses of dyes 1a–f toward nucleic acid indicated that 1a–c are turn-on type near infrared (NIR) nucleic acid probes (maximum emission wavelength range: 678 nm to 698 nm) with large Stokes shifts (143 nm to 155 nm). Among these, the relative fluorescence quantum yield of 1a increased 25.2 times (from 0.4% to 10.1%) and the maximum fluorescence intensity was enhanced by 14.4 fold after interacting with RNA. Additionally, cell imaging experiments indicated that dyes 1a–c can be used to image the nucleolus in fixed HeLa cells.

Graphical abstract: Synthesis of azonia cyanine derivatives as NIR fluorescent probes for nucleic acid detection and cell imaging

Back to tab navigation

Supplementary files

Article information


Submitted
10 May 2019
Accepted
14 Jun 2019
First published
17 Jun 2019

Anal. Methods, 2019,11, 3523-3531
Article type
Paper

Synthesis of azonia cyanine derivatives as NIR fluorescent probes for nucleic acid detection and cell imaging

Y. Chen, X. Wei, R. Sun, Y. Xu and J. Ge, Anal. Methods, 2019, 11, 3523
DOI: 10.1039/C9AY00982E

Social activity

Search articles by author

Spotlight

Advertisements