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Saito G, Velluto D, Resmini M. Synthesis of 1,8-naphthalimide-based probes with fluorescent switch triggered by flufenamic acid. R Soc Open Sci. 2018;5(6):172137doi: 10.1098/rsos.172137.
Saito, G., Velluto, D., & Resmini, M. (2018). Synthesis of 1,8-naphthalimide-based probes with fluorescent switch triggered by flufenamic acid. Royal Society open science, 5(6), 172137. https://doi.org/10.1098/rsos.172137
Saito, G, et al. "Synthesis of 1,8-naphthalimide-based probes with fluorescent switch triggered by flufenamic acid." Royal Society open science vol. 5,6 (2018): 172137. doi: https://doi.org/10.1098/rsos.172137
Saito G, Velluto D, Resmini M. Synthesis of 1,8-naphthalimide-based probes with fluorescent switch triggered by flufenamic acid. R Soc Open Sci. 2018 Jun 20;5(6):172137. doi: 10.1098/rsos.172137. eCollection 2018 Jun. PMID: 30110473; PMCID: PMC6030310.
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R Soc Open Sci. 2018 Jun 20;5(6):172137. doi: 10.1098/rsos.172137. eCollection 2018 Jun.

Synthesis of 1,8-naphthalimide-based probes with fluorescent switch triggered by flufenamic acid.

Royal Society open science

G Saito, D Velluto, M Resmini

Affiliations

  1. Department of Chemistry and Biochemistry, SBCS, Queen Mary University of London, E1 4NS London, UK.
  2. Diabetes Research Institute and Cell Transplant Center, University of Miami Leonard M. Miller School of Medicine, Miami, FL 33136, USA.

PMID: 30110473 PMCID: PMC6030310 DOI: 10.1098/rsos.172137

Abstract

In this work, we report the synthesis of novel fluorescent molecules, based on 1,8-naphthalimide thio- and amino-derivatives, designed to display an OFF-ON and ON-OFF photoelectron transfer fluorescence switch upon interaction with a proton-donor drug. We have functionalized the new probes to allow easy formation of a covalent link to polymer matrices, for future applications as drug delivery sensors. We have investigated the fluorescent switch of the new probes using flufenamic acid (FA, pKa 3.65), a water insoluble, non-steroidal anti-inflammatory drug, as a model drug and proton source. The rapid interaction of the new probes with FA resulted in fluorescence enhancement or decrease and a large Stokes shift, all of which allowed the detection of the drug in the nanomolar range. The new 1,8-naphthalimide fluorescent dyes reported in this work are interesting tools for the detection and quantification of acidic drugs and biomolecules.

Keywords: flufenamic acid; fluorescence; naphthalimide; pH switch

Conflict of interest statement

We declare we have no competing interests.

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