Development of red-shifted and fluorogenic nucleoside and oligonucleotide diarylethene photoswitches

• Verfasst von: Kolmar, Theresa [VerfasserIn]
• Verfasst von: Becker, Antonia [VerfasserIn]
• Verfasst von: Pfretzschner, Ronja A. [VerfasserIn]
• Verfasst von: Lelke, Alina [VerfasserIn]
• Verfasst von: Jäschke, Andres [VerfasserIn]
• Titel: Development of red-shifted and fluorogenic nucleoside and oligonucleotide diarylethene photoswitches
• Verf.angabe: Theresa Kolmar, Antonia Becker, Ronja A. Pfretzschner, Alina Lelke, and Andres Jäschke
• E-Jahr: 2021
• Jahr: October 19, 2021
• Umfang: 9 S.
• Fussnoten: Gesehen am 27.03.2023
• Titel Quelle: Enthalten in: Chemistry - a European journal
• Ort Quelle: Weinheim : Wiley-VCH, 1995
• Jahr Quelle: 2021
• Band/Heft Quelle: 27(2021), 69, Seite 17386-17394
• ISSN Quelle: 1521-3765
• DOI: doi:10.1002/chem.202103133
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: diarylethenes
• Sach-SW: fluorescence modulation
• Sach-SW: nucleic acids
• Sach-SW: photochromism
• Sach-SW: photoresponsive DNA
• K10plus-PPN: 1840130571
• K10plus-PPN:
  Universitätsbibliothek
• Lokale URL UB: Zum Volltext

Abstract

The reversible modulation of fluorescence signals by light is of high interest for applications in super-resolution microscopy, especially on the DNA level. In this article we describe the systematic variation of the core structure in nucleoside-based diarylethenes (DAEs), in order to generate intrinsically fluorescent photochromes. The introduction of aromatic bridging units resulted in a bathochromic shift of the visible absorption maximum of the closed-ring form, but caused reduced thermal stability and switching efficiency. The replacement of the thiophene aryl unit by thiazol improved the thermal stability, whereas the introduction of a benzothiophene unit led to inherent and modulatable turn-off fluorescence. This feature was further optimized by introducing a fluorescent indole nucleobase into the DAE core, resulting in an effective photoswitch with a fluorescence quantum yield of 0.0166 and a fluorescence turn-off factor of 3.2. The site-specific incorporation into an oligonucleotide resulted in fluorescence-switchable DNA with high cyclization quantum yields and switching efficiency, which may facilitate future applications.