Issue 51, 2017

Naphthalimide–coumarin conjugate: ratiometric fluorescent receptor for self-calibrating quantification of cyanide anions in cells

Abstract

Quantitative determination of toxic cyanide anions (CN) in biological samples is an important subject. We synthesized a naphthalimide–coumarin conjugate with a simple imine linker (1), which behaves as a fluorescent receptor for ratiometric quantification of CN. It exhibits green naphthalimide fluorescence at 533 nm, originating from the excited-state intramolecular charge transfer (ESICT) from coumarin to naphthalimide fluorophores. Selective CN addition to the imine linker affords an α-amino nitrile product. This suppresses ESICT and creates coumarin fluorescence at 444 nm and naphthalimide fluorescence at 533 nm originating from direct photoexcitation of the respective fluorophores. The emission intensity at 533 nm is maintained upon CN addition and can be used as an internal standard for analysis. This ratiometric response enables self-calibrating CN quantification based on the intensities of two emissions in solution and in cells. This facilitates rapid (within 3 min), selective, and sensitive ratiometric detection of very low levels of CN (>1.8 μM).

Graphical abstract: Naphthalimide–coumarin conjugate: ratiometric fluorescent receptor for self-calibrating quantification of cyanide anions in cells

Supplementary files

Article information

Article type
Paper
Submitted
13 May 2017
Accepted
16 Jun 2017
First published
23 Jun 2017
This article is Open Access
Creative Commons BY license

RSC Adv., 2017,7, 32304-32309

Naphthalimide–coumarin conjugate: ratiometric fluorescent receptor for self-calibrating quantification of cyanide anions in cells

Y. Shiraishi, N. Hayashi, M. Nakahata, S. Sakai and T. Hirai, RSC Adv., 2017, 7, 32304 DOI: 10.1039/C7RA05423H

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.

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