Fluorescent PET (Photoinduced Electron Transfer) sensors as potent analytical tools

This critical review focuses on the development of anion sensors, being either fluorescent and/or colorimetric, based on the use of the 1,8-naphthalimide structure; a highly versatile building unit that absorbs and emits at long wavelengths. The review commences with a short description of the most commonly used design principles employed in chemosensors, followed by a discussion on the photophysical properties of the 4-amino-1,8-naphthalimide structure which has been most commonly employed in both cation and anion sensing to date. This is followed by a review of the current state of the art in naphthalimide-based anion sensing, where systems using ureas, thioureas and amides as hydrogen-bonding receptors, as well as charged receptors have been used for anion sensing in both organic and aqueous solutions, or within various polymeric networks, such as hydrogels. The review concludes with some current and future perspectives including the use of the naphthalimides for sensing small biomolecules, such as amino acids, as well as probes for incorporation and binding to proteins; and for the recognition/sensing of polyanions such as DNA, and their potential use as novel therapeutic and diagnostic agents (95 references).

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“…[24][25][26] The binding site may be directly attached, or integrated, into the signalling moiety, such as shown in Fig. 1a.…”

Section: General Design Principles Employed In Colorimetric and Fluormentioning

confidence: 99%

Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1,8-naphthalimide-based chemosensors

et al. 2010

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“…Intensity-based probes are 'turn-on' fluorophores, and display a chelation-dependent increase in fluorescence intensity of up to 100-fold. Most of these probes are based on the modulation in the photon-induced electron transfer phenomenon (16)(17)(18) . Briefly, the probes are composed of a fluorophore, a spacer domain and an electron-rich metal chelate.…”

Section: Imaging Free Zn 2+ In Living Cellsmentioning

confidence: 99%

Intracellular zinc in insulin secretion and action: a determinant of diabetes risk?

et al. 2015

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Zinc is an important micronutrient, essential in the diet to avoid a variety of conditions associated with malnutrition such as diarrhoea and alopecia. Lowered circulating levels of zinc are also found in diabetes mellitus, a condition which affects one in twelve of the adult population and whose treatments consume approximately 10 % of healthcare budgets. Zn 2+ ions are essential for a huge range of cellular functions and, in the specialised pancreatic β-cell, for the storage of insulin within the secretory granule. Correspondingly, genetic variants in the SLC30A8 gene, which encodes the diabetes-associated granule-resident Zn 2+ transporter ZnT8, are associated with an altered risk of type 2 diabetes. Here, we focus on (i) recent advances in measuring free zinc concentrations dynamically in subcellular compartments, and (ii) studies dissecting the role of intracellular zinc in the control of glucose homeostasis in vitro and in vivo. We discuss the effects on insulin secretion and action of deleting or overexpressing Slc30a8 highly selectively in the pancreatic β-cell, and the role of zinc in insulin signalling. While modulated by genetic variability, healthy levels of dietary zinc, and hence normal cellular zinc homeostasis, are likely to play an important role in the proper release and action of insulin to maintain glucose homeostasis and lower diabetes risk.

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“…However, upon addition of metal ions, the receptor chelates the metal ions to form stable complexes, thereby deactivating the quenching by PET due to stabilization of the receptor's HOMO so that it lies below the energy level of the fluorophore's HOMO, and increasing the fluorescence intensity of the coumarin moiety. 15,16 Such transition metals as Fe 2+ , Ni 2+ , Cr 2+ , Cu 2+ , and Co 2+ are paramagnetic ions with an unfilled d shell, and are known to induce fluorescence quenching. Though Fe 2+ and Ni 2+ can take both high-spin and low-spin states, it is known that the fluorescence was quenched by the paramagnetic metal ions with a high-spin state.…”

Section: Metal Ion Selectivity Of Dpa-hc In An Aqueous Solventmentioning

confidence: 99%

Solvent Effect on the Fluorescence Response of Hydroxycoumarin Bearing a Dipicolylamine Binding Site to Metal Ions

et al. 2014

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The fluorescence behavior of a probe dpa-HC, which has a coumarin derivative that acts as a fluorophore and a dipicolylamine (DPA) unit that functions as a metal ion-recognition site, was investigated with various metal ions in aqueous and several non-aqueous solvents. In aqueous solution, the fluorescence of dpa-HC was enhanced by Zn 2+ and Cd 2+ , but was quenched by other metal ions. On the other hand, in an acetonitrile solution, only Mg 2+ enhanced the fluorescence, and the addition of a small amount of water quenched this fluorescence. This dramatic selectivity change is explained by stabilization of a metal-dpa-HC complex due to acetonitrile coordination and ON-OFF switching of the intramolecular photoinduced electron transfer (PET) from the nitrogen lone pair of DPA to the coumarin derivative. Scheme 1 Synthesis of 8-(2,2′-dipicolylaminomethyl)-7-hydroxycoumarin (dpa-HC). Keywords

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Fluorescent PET (Photoinduced Electron Transfer) sensors as potent analytical tools

Cited by 550 publications

References 96 publications

Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1,8-naphthalimide-based chemosensors

Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1,8-naphthalimide-based chemosensors

Intracellular zinc in insulin secretion and action: a determinant of diabetes risk?

Solvent Effect on the Fluorescence Response of Hydroxycoumarin Bearing a Dipicolylamine Binding Site to Metal Ions

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