Polarity Sensitive Bioorthogonally Applicable Far-Red Emitting Labels for Postsynthetic Nucleic Acid Labeling by Copper-Catalyzed and Copper-Free Cycloaddition

Bioconjugate Chemistry
Ádám EördöghPéter Kele

Abstract

Two series of new, water-soluble, membrane-permeable, far-red/NIR emitting benzothiazolium-based fluorescent labels with large Stokes' shifts were synthesized that can be conjugated to alkyne-modified biomolecules through their azide moiety via azide-alkyne cycloaddition. We have used these azide bearing labels to make fluorescent DNA constructs using copper-catalyzed "click" reaction. All dyes showed good or remarkable fluorescence intensity enhancement upon conjugation to DNA. We also investigated the possibility to incorporate the benzocyclooctyne motif through rigid (ethnynyl) or flexible (ethyl) linkers into the DNA, thus enabling copper-free labeling schemes. We observed that there is a marked difference between the two linkers applied in terms of optical properties of the labeled oligonucleotides. We have also tested the in vivo labeling potential of these newly synthesized dyes on HeLa cells previously transfected with cyclooctynylated DNA. Confocal fluorescent images showed that the dyes are all able to cross the membrane and suitable for background-fluorescence free fluorescent tagging of nucleic acids. Moreover, we have observed different accumulation of the two dye series in the endosomal particles, or in the nuclei...Continue Reading

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Citations

May 10, 2017·Chembiochem : a European Journal of Chemical Biology·Krisana Peewasan, Hans-Achim Wagenknecht
Oct 12, 2018·Organic & Biomolecular Chemistry·Benjamin Lehmann, Hans-Achim Wagenknecht
Sep 19, 2019·Organic & Biomolecular Chemistry·Boonsong DitmangkloTirayut Vilaivan
Mar 25, 2016·Chemistry : a European Journal·Orsolya DemeterPéter Kele
Oct 22, 2020·Chemical Society Reviews·Nils KlöckerAndrea Rentmeister
Jul 2, 2021·Bioconjugate Chemistry·Aaditya Govindarajan, Vasuki Gnanasambandam
Jun 2, 2020·RSC Chemical Biology·Dorothée GanzHans-Achim Wagenknecht
Oct 12, 2021·Chemistry : a European Journal·Katja KrellHans-Achim Wagenknecht

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