Core remodeling leads to long wavelength fluoro-coumarins

Siddharth S. Matikonda; Joseph Ivanic; Miguel Gomez; Gabrielle Hammersley; Martin J. Schnermann

doi:10.1039/D0SC02566F

Core remodeling leads to long wavelength fluoro-coumarins†

Siddharth S. Matikonda,

^a Joseph Ivanic,

^b Miguel Gomez,

^a Gabrielle Hammersley

^a and Martin J. Schnermann

*^a

Author affiliations

* Corresponding authors

^a Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, National Institutes of Health, Frederick, Maryland 21702, USA
E-mail: martin.schnermann@nih.gov

^b Advanced Biomedical Computational Science, Frederick National Laboratory for Cancer Research, Frederick, Maryland 21702, USA

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.

This article is part of the themed collections: Most popular 2019-2020 analytical chemistry articles and 2020 Chemical Science HOT Article Collection

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Article information

DOI: https://doi.org/10.1039/D0SC02566F
Article type: Edge Article
Submitted: 06 May 2020
Accepted: 22 Jun 2020
First published: 03 Jul 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2020,11, 7302-7307

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Core remodeling leads to long wavelength fluoro-coumarins

S. S. Matikonda, J. Ivanic, M. Gomez, G. Hammersley and M. J. Schnermann, Chem. Sci., 2020, 11, 7302 DOI: 10.1039/D0SC02566F

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Chemical Science

Core remodeling leads to long wavelength fluoro-coumarins†

Abstract

Supplementary files

Article information

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Core remodeling leads to long wavelength fluoro-coumarins

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