Issue 28, 2019

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

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

Supplementary files

Article information

Article type
Paper
Submitted
10 5月 2019
Accepted
14 6月 2019
First published
17 6月 2019

Anal. Methods, 2019,11, 3523-3531

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements