Synthesis of N , N -Dialkylamino- nor -Dihydroxanthene-Hemicyanine Fused Near-Infrared Fluorophores and Their First Water-Soluble and/or Bioconjugatable Analogues

Abstract : The effective synthesis of extended conjugated N, N-dialkylamino-nor-dihydroxanthene-based fluorophores is described from diversely functionalized salicylic aldehydes. The access to these original fluorescent derivatives proceeded in two steps through a one-pot construction of the unusual nor-dihydroxanthene (nor-DHX) scaffold followed by a diversification step providing a wide variety of nor-DHXhemicyanine fused dyes emitting in the range of 730790 nm. The versatility of our approach has enabled a further extension to the late-stage introduction of negatively/posi-tively charged polar groups onto their terminal nitrogen heterocyclic subunit, thereby giving access to the first watersoluble and/or bioconjugatable members of this emerging class of NIR fluorophores. Our water-solubilizing method is easily implementable, and the nor-DHX-hemicyanine skeleton maintains satisfying fluorescence quantum yields (520%) under physiological conditions. Finally, the bioconjugation ability of fluorescent derivatives bearing a free carboxylic acid was demonstrated through the covalent labeling of a model protein, namely, bovine serum albumin.
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Chemistry - An Asian Journal, Wiley-VCH Verlag, 2017, 12 (8), pp.936 - 946. 〈http://onlinelibrary.wiley.com/doi/10.1002/asia.201700176/full〉. 〈10.1002/asia.201700176〉
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https://hal-univ-bourgogne.archives-ouvertes.fr/hal-01563171
Contributeur : Icmub - Université de Bourgogne <>
Soumis le : lundi 17 juillet 2017 - 13:19:14
Dernière modification le : vendredi 8 juin 2018 - 14:50:12

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Michelle Jui Hsien Ong, Sylvain Debieu, Mathieu Moreau, Anthony Romieu, Jean-Alexandre Richard. Synthesis of N , N -Dialkylamino- nor -Dihydroxanthene-Hemicyanine Fused Near-Infrared Fluorophores and Their First Water-Soluble and/or Bioconjugatable Analogues. Chemistry - An Asian Journal, Wiley-VCH Verlag, 2017, 12 (8), pp.936 - 946. 〈http://onlinelibrary.wiley.com/doi/10.1002/asia.201700176/full〉. 〈10.1002/asia.201700176〉. 〈hal-01563171〉

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