“Alive” dyes as fluorescent sensors: fluorophore, mechanism, receptor and images in living cells
- 29 June 2010
- journal article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- Vol. 46 (35), 6418-6436
- https://doi.org/10.1039/c0cc00686f
Abstract
In this feature article, we report our recent progresses in fluorescent sensors of biological dyes from the viewpoint of supramolecular and bioorganic chemistry. For signalling fluorophores, we extended or created naphthalene-based ICT systems, e.g. amino-1,8-naphthalimides, amino-1,8-dicyanonaphthalenes and acenaphthopyrrol-9-carbonitriles. We also developed BODIPY derivatives with large Stokes shifts and high fluorescence quantum yields in polar solvents, and a rhodamine analogue working in strong competitive aqueous solution as well as its silaanthracene analogue with a bathochromic shift as large as 90 nm. For sensing mechanisms, we extended or developed the following methods to improve sensing: e.g. PET in a photogenerated electronic field, TICT promoted PET derived from aminoalkyl or piperazino aminonaphthalimides, and the translation/amplification effect of surfactant micelles or aggregation on fluorescent sensing. We also successfully designed deprotonation strengthened ICT, FRET-chemodosimeter sensing systems. For non-cyclic recognition receptors, naphthalimides with two or more side chains at their 4,5- or 3,4-positions, as a convenient and simple platform for ratiometric sensors, were created for the recognition of heavy and transition metallic cations; multi-armed polyamides with more side chains were innovated as a versatile platform for the sensing of metal ions with high affinity, selectivity and positive homotropic allosteric effects. We designed V-shape sensors of the bis(aminomethyl)pyridine receptor with two fluorophores to show high performance. Finally, the intracellular applications of the above sensors and dyes, e.g. imaging heavy and transition metal ions in cells, fluorescent marking of hypoxia of tumour cells, are also reviewed.Keywords
This publication has 90 references indexed in Scilit:
- Trace mercury (II) detection and separation in serum and water samples using a reusable bifunctional fluorescent sensorAnalytica Chimica Acta, 2009
- A pair of regio-isomeric compounds acting as molecular logic gates with different functionsJournal of Photochemistry and Photobiology A: Chemistry, 2009
- Effects of anionic surfactant SDS on the photophysical properties of two fluorescent molecular sensorsJournal of Photochemistry and Photobiology A: Chemistry, 2008
- Bulky 4-tritylphenylethynyl substituted boradiazaindacene: pure red emission, relatively large Stokes shift and inhibition of self-quenchingChemical Communications, 2008
- A new trend in rhodamine-based chemosensors: application of spirolactam ring-opening to sensing ionsChemical Society Reviews, 2008
- Novel Fluorescent Fluorine−Boron Complexes: Synthesis, Crystal Structure, Photoluminescence, and Electrochemistry PropertiesThe Journal of Organic Chemistry, 2008
- Metal Ion Induced FRET OFF−ON in Tren/Dansyl-Appended RhodamineOrganic Letters, 2007
- A pH-resistant Zn(ii) sensor derived from 4-aminonaphthalimide: design, synthesis and intracellular applicationsJournal of Materials Chemistry, 2005
- A Highly Selective and Sensitive Fluorescent Chemosensor for Hg2+ in Neutral Buffer Aqueous SolutionJournal of the American Chemical Society, 2004
- A fluorescent sensor for Cu2+ at the sub-ppm levelJournal of Photochemistry and Photobiology A: Chemistry, 1998