In vivo Markierung von Glykostrukturen mit Hilfe neuartiger, bioorthogonaler Azid-Alkin 1,3-dipolarer Cycloadditionen (English shop)

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Sugar compounds, also known as glycan structures, are present in almost all living systems. They cannot be genetically encoded and can only be modified post-translationally. With the aid of the intramolecularly catalysed bioorthogonal click reaction, glycans on the cell surface can be labelled in vivo. In order not to destroy the sugar structures on the cell surface, chemoselective fluorophores must be used that are not metabolised by the cell. For this purpose, both the strain-promoted azide–alkyne cycloaddition (SPAAC) and the Cu(I)-catalysed azide–alkyne cycloaddition (CuAAC) were employed and compared. For the CuAAC, a Cu(I) complex was used that had already been synthesised primarily as an emitter material in organic light-emitting diodes (OLEDs). Surprisingly, this luminescent, self-clicking Cu(I) complex showed no strong cytotoxic effects. Rather, it was distinguished by its high photobleaching stability, its high quantum yield and its short incubation time.