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Synthesis of Wavelength-Shifting Fluorescent DNA and RNA with Two Photostable Cyanine-Styryl Dyes as the Base Surrogate Pair

Steinmeyer, Jeannine 1; Rönicke, Franziska 1; Schepers, Ute; Wagenknecht, Hans-Achim 1
1 Institut für Organische Chemie (IOC), Karlsruher Institut für Technologie (KIT)

Abstract:

Two nucleic acid building blocks were synthesized, consisting of two photostable green- and red-emitting cyanine–styryl dyes and (S)-3-amino-1,2-propanediol as a substitute for the ribofuranoside, and incorporated as base-pair surrogates by using automated phosphoramidte chemistry in the solid phase. The optical properties and, in particular, the energytransfer properties were screened in a range of DNA duplexes, in which the “counter bases” of the two dyes were varied and the distance between the two dyes was enlarged to up to three intervening adenosine–thymidine pairs. The DNA duplex with the best optical properties and the best red/green emission
ratio as the readout bore adenosine and thymidine opposite to the dyes, and the two dyes directly adjacent to each
other as the base surrogate pair. This structural arrangement can be transferred to RNA to obtain similarly fluorescent RNA probes. Representatively, the positively evaluated DNA duplex was applied to verify the fluorescence readout in living HeLa cells by using fluorescence confocal microscopy.


Volltext §
DOI: 10.5445/IR/1000071200
Originalveröffentlichung
DOI: 10.1002/open.201700059
Web of Science
Zitationen: 6
Dimensions
Zitationen: 7
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Institut für Toxikologie und Genetik (ITG)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2017
Sprache Englisch
Identifikator ISSN: 2191-1355, 2191-1363
urn:nbn:de:swb:90-712002
KITopen-ID: 1000071200
HGF-Programm 47.01.01 (POF III, LK 01) Biol.Netzwerke u.Synth.Regulat. ITG+ITC
Erschienen in ChemistryOpen
Verlag Wiley-VCH Verlag
Band 6
Heft 4
Seiten 514-518
Vorab online veröffentlicht am 07.06.2017
Nachgewiesen in Web of Science
Scopus
Dimensions
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