Core remodeling leads to long wavelength fluoro-coumarins. Issue 28 (3rd July 2020)

• Record Type: Journal Article
• Authors: Matikonda, Siddharth S.; Ivanic, Joseph; Gomez, Miguel; Hammersley, Gabrielle; Schnermann, Martin J.
• Is Part Of: Chemical science. Volume 11:Issue 28(2020)
• Page Start: 7302
• Page End: 7307
• Publication Date: 2020-07-03
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0sc02566f
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Fluoro-Coumarins are a novel class of far-red and near-infrared solvent sensitive dyes of exceptionally low molecular weight. Abstract : Low molecular weight, uncharged far-red and NIR dyes would be enabling for a range of imaging applications. Rational redesign of the coumarin scaffold leads to Fluoro-Coumarins (FCs), the lowest molecular weight dyes with emission maxima beyond 700, 800, and 900 nm. FCs display large Stokes shifts and high environmental sensitivity, with a 40-fold increase in emission intensity in hydrophobic solvents. Untargeted variants exhibit selective lipid droplet and nuclear staining in live cells. Furthermore, sulfo-lipid derivatization enables active targeting to the plasma membrane. Overall, these studies report a promising platform for the development of biocompatible, context-responsive imaging agents.