Chemically- and photo-convertible dyes for fluorescence detection of biomolecules

by Elizaveta Savicheva
Doctoral thesis
Date of Examination:2023-12-20
Date of issue:2024-01-24
Advisor:Dr. Vladimir Belov
Referee:Prof. Dr. Lutz Ackermann
Referee:Prof. Dr. Stefan Hell
Persistent Address: http://dx.doi.org/10.53846/goediss-10303

 

 

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Abstract

English

Further progress in fluorescence microscopy and nanoscopy depends, among other factors, on the ease of detection, analysis, and selective imaging of bioconjugates prepared from fluorescent dyes with reactive groups and biomolecules. For that, new multifunctional fluorescent dyes which predictably change or acquire their emissive properties in the course of a chemical or photochemical transformation are highly demanded. These chemically- or photo-convertible dyes alter their spectral and emissive properties upon bioconjugation or photoactivation; they enable new imaging modalities and are highly favoured in fluorescence detection techniques. In this work, chemically and photoconvertible dyes were designed, prepared and studied. The dissertation consists of three chapters and experimental part. The first chapter deals with the synthesis of yellow-emitting negatively charged aminopyrenes for reductive amination and fluorescence detection of sugars. The second chapter is devoted to photoconvertible cyanines containing 4-amino-1-diazobutanone fragment attached to the polymethine chain via amino group. The new cyanines undergo irreversible photolysis upon irradiation with UV light. In this chapter, synthetic challenges and features of cyanine dyes are discussed. Chapter three presents a novel approach to the late-stage functionalisation of rhodamines and photoactivatable phenoxazines. An oxidative olefination method via C–H activation was used to introduce a linker with a carboxyl group for bioconjugation. The photolysis experiments involving functionalised phenoxazines are described. 
Keywords: fluorescent dyes; sugar analysis; cyanines; oxazines; rhodamines; C-H activation; photolysis
 
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