A1 Journal article (refereed)
Development of functionalized SYBR green II related cyanine dyes for viral RNA detection (2020)

Saarnio, V. K., Salorinne, K., Ruokolainen, V. P., Nilsson, J. R., Tero, T.-R., Oikarinen, S., Wilhelmsson, L. M., Lahtinen, T. M., & Marjomäki, V. S. (2020). Development of functionalized SYBR green II related cyanine dyes for viral RNA detection. Dyes and Pigments, 177, Article 108282. https://doi.org/10.1016/j.dyepig.2020.108282

JYU authors or editors

Publication details

All authors or editors: Saarnio, Ville K.; Salorinne, Kirsi; Ruokolainen, Visa P.; Nilsson, Jesper R.; Tero, Tiia-Riikka; Oikarinen, Sami; Wilhelmsson, L. Marcus; Lahtinen, Tanja M.; Marjomäki, Varpu S.

Journal or series: Dyes and Pigments

ISSN: 0143-7208

eISSN: 1873-3743

Publication year: 2020

Volume: 177

Article number: 108282

Publisher: Elsevier

Publication country: United Kingdom

Publication language: English

DOI: https://doi.org/10.1016/j.dyepig.2020.108282

Publication open access: Not open

Publication channel open access:

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/73612


Fluorescent probes for sensing nucleic acids have found widespread use in the field of cell and molecular biology. However, probes combined with potential for post-synthetic conjugation, e.g. for intra-endosomal measurements of RNA, are unavailable. Herein we developed cyanine dyes that can be conjugated to viral capsid or other targets. First, we solved the crystal structure of SYBR Green II. The structural elucidation of this commonly used RNA probe provided the basis for synthesizing similar molecules with much desired function for post-synthetic conjugation. To address this need, cyanine dyes were prepared using an alternative synthesis protocol. All studied compounds showed considerable brightness upon binding to nucleic acids. However, regardless of the common chromophore on the dyes, the observed fluorescence emission intensities varied significantly, where methyl-substituted dye 1 gave values higher than SYBR Green II, whereas compounds 2–5 containing undecyl spacers had lower values. Studying the structure-activity relationship revealed the longer alkyl chains to induce slight perturbation in dye intercalation, as well as demanding larger binding area on the nucleic acid lattice, explaining these differences. To study the potential biological use of the dyes, the RNA genome of enterovirus echovirus 1 was studied in vitro with the probes. A novel method employing the low binding space requirement of 1 was developed to determine the single-to-double-stranded RNA ratio of a sample, whereas compound 4 was covalently bound to the viral capsid and used successfully to monitor the viral RNA release from within the capsid. The presented results open new possibilities for preparation and use of SYBR Green-based nucleic acid probes to further apply these compounds for increasingly demanding targeting in biological contexts.

Keywords: colouring agents; synthetic dyes; tracers (indicators); fluorescence; nucleic acids; RNA; viruses

Free keywords: cyanines; nucleic acids; fluorescent probes; RNA recognition; host-guest systems; viruses

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Ministry reporting: Yes

Reporting Year: 2020

JUFO rating: 1

Last updated on 2023-03-10 at 13:32