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Synthesis of N, N-Dialkylamino- nor-Dihydroxanthene-Hemicyanine Fused Near-Infrared Fluorophores and Their First Water-Soluble and/or Bioconjugatable Analogues.
- Source :
-
Chemistry - An Asian Journal . 4/18/2017, Vol. 12 Issue 8, p936-946. 11p. - Publication Year :
- 2017
-
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-DHX-hemicyanine fused dyes emitting in the range of 730-790 nm. The versatility of our approach has enabled a further extension to the late-stage introduction of negatively/positively charged polar groups onto their terminal nitrogen heterocyclic subunit, thereby giving access to the first water-soluble 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 (5-20 %) 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. [ABSTRACT FROM AUTHOR]
- Subjects :
- *FLUOROPHORES
*BIOCONJUGATES
*SALICYLIC acid
*ALDEHYDES
*HETEROCYCLIC chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 18614728
- Volume :
- 12
- Issue :
- 8
- Database :
- Academic Search Index
- Journal :
- Chemistry - An Asian Journal
- Publication Type :
- Academic Journal
- Accession number :
- 122576725
- Full Text :
- https://doi.org/10.1002/asia.201700176