Targetable conformationally restricted cyanines enable photon-count-limited applications

Please always quote using this URN: urn:nbn:de:bvb:20-opus-256559
  • Cyanine dyes are exceptionally useful probes for a range of fluorescence-based applications, but their photon output can be limited by trans-to-cis photoisomerization. We recently demonstrated that appending a ring system to the pentamethine cyanine ring system improves the quantum yield and extends the fluorescence lifetime. Here, we report an optimized synthesis of persulfonated variants that enable efficient labeling of nucleic acids and proteins. We demonstrate that a bifunctional sulfonated tertiary amide significantly improves the opticalCyanine dyes are exceptionally useful probes for a range of fluorescence-based applications, but their photon output can be limited by trans-to-cis photoisomerization. We recently demonstrated that appending a ring system to the pentamethine cyanine ring system improves the quantum yield and extends the fluorescence lifetime. Here, we report an optimized synthesis of persulfonated variants that enable efficient labeling of nucleic acids and proteins. We demonstrate that a bifunctional sulfonated tertiary amide significantly improves the optical properties of the resulting bioconjugates. These new conformationally restricted cyanines are compared to the parent cyanine derivatives in a range of contexts. These include their use in the plasmonic hotspot of a DNA-nanoantenna, in single-molecule Förster-resonance energy transfer (FRET) applications, far-red fluorescence-lifetime imaging microscopy (FLIM), and single-molecule localization microscopy (SMLM). These efforts define contexts in which eliminating cyanine isomerization provides meaningful benefits to imaging performance.show moreshow less

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Metadaten
Author: Patrick Eiring, Ryan McLaughlin, Siddharth S. MatikondaORCiD, Zhongying Han, Lennart GrabenhorstORCiD, Dominic A. Helmerich, Mara Meub, Gerti Beliu, Michael Luciano, Venu Bandi, Niels Zijlstra, Zhen-Dan Shi, Sergey G. Tarasov, Rolf Swenson, Philip TinnefeldORCiD, Viktorija GlembockyteORCiD, Thorben Cordes, Markus Sauer, Martin J. SchnermannORCiD
URN:urn:nbn:de:bvb:20-opus-256559
Document Type:Journal article
Faculties:Fakultät für Biologie / Theodor-Boveri-Institut für Biowissenschaften
Language:English
Parent Title (English):Angewandte Chemie Internationale Edition
Year of Completion:2021
Volume:60
Issue:51
Pagenumber:26685–26693
Source:Angewandte Chemie Internationale Edition (2021) 60:51, 26685–26693. DOI: 10.1002/anie.202109749
DOI:https://doi.org/10.1002/anie.202109749
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 57 Biowissenschaften; Biologie / 570 Biowissenschaften; Biologie
Tag:DNA nanotechnology; biology; conformational restriction; cyanine dyes; fluorescent dyes; single-molecule fluorescence spectroscopy; super-resolution microscopy
Release Date:2022/02/25
EU-Project number / Contract (GA) number:638536
EU-Project number / Contract (GA) number:840741
OpenAIRE:OpenAIRE
Licence (German):License LogoCC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International