Evaluation of novel fluorescence probes for conjugation purposes using the traceless Staudinger Ligation. (February 2015)

• Record Type: Journal Article
• Authors: Wodtke, Robert; König, Jonas; Pigorsch, Arne; Köckerling, Martin; Mamat, Constantin
• Is Part Of: Dyes and pigments. Volume 113(2015)
• Page Start: 263
• Page End: 273
• Publication Date: 2015-02
• Subjects: Bioorthogonal -- Click -- Huisgen -- Labeling -- Coumarin -- Eph receptor; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2014.08.022
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: A robust and versatile method for the synthesis of selected azide, alkyne and phosphane functionalized coumarin derivatives from the corresponding 7-amino and 7-hydroxy analogs for an application in bioorthogonal conjugation and labeling reactions like the Staudinger Ligation or the Huisgen-click reaction is presented. Further, the convenient preparation of modified coumarins was performed and subsequent regio- and chemo-selective labeling reactions delivered the desired biologically active derivatives in high yields. These new compounds may thus constitute attractive scaffolds for designing novel fluorescence building blocks for various challenging biolabeling applications. Graphical abstract: Highlights: Simple preparation of capable azide and alkyne modified coumarins as fluorescence building blocks. Successful application of two bioorthogonal reactions for the mild introduction of coumarins into bioactive molecules. Utilization of the solid phase peptide synthesis for the fluorescence labeling of peptides of pharmacological interest.