A Synthetically Simple, Click-Generated Cyclam-Based Zinc(II) Sensor

Tamanini, Emiliano; Katewa, Arna; Sedger, Lisa M.; Todd, Matthew H.; Watkinson, Michael

doi:10.1021/ic8017634

Cited by 162 publications

(92 citation statements)

References 54 publications

(30 reference statements)

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“…Here, the 4-amino moiety does not participate directly in ion binding and hence, the absorption spectrum was not significantly affected. Similarly, large enhancements were seen in the emission spectra of 5, developed by Watkinson et al, 43 upon binding to Zn(II). Recently, Watkinson et al, have extended their design to form naphthalimide dimers, using Cu(II) catalysed click chemistry.…”

Section: General Design Principles Employed In Colorimetric and Fluorsupporting

confidence: 53%

“…40 Many other examples of such pH dependent PET naphthalimide sensors have been developed to date, for use in solution or within, or on, solid supports. 18 In contrast, compound 3, possessing a crown ether receptor was developed for analysis of Na + in blood samples, 41 while 4 42 and 5 43 have been developed for detecting Zn(II). Structure 4 has also recently been used for imaging of bone structures using epifluorescence microscopy.…”

Section: General Design Principles Employed In Colorimetric and Fluormentioning

confidence: 99%

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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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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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Section: General Design Principles Employed In Colorimetric and Fluorsupporting

confidence: 53%

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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“…Compound 1 is a selective Zn II sensor, signalling metal coordination with a six-fold increase in fluorescence emission of the pendant naphthalimide. [8] The development of heterogeneous sol-gel sensors based on 1 has also been explored. [9] An alternative approach has involved compound 2, with the pendant biotin molecule acting as a binding site for avidin, and the loss of triazole coordination at the metal in the presence of avidin signalled by changes in the EPR spectrum.…”

Section: Introductionmentioning

confidence: 99%

A Click Fluorophore Sensor that Can Distinguish Cu^II and Hg^II via Selective Anion‐Induced Demetallation

Lau

Price

Todd

et al. 2011

Chemistry A European J

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A cyclam-based fluorescent sensor featuring a novel triazole pendant arm has been synthesised using click chemistry. The sensor is highly responsive to both Cu(II) and Hg(II) in neutral aqueous solution and displays excellent selectivity in the presence of various competing metal ions in 50-fold excess. The addition of specific anions such as I(-) and S(2)O(3)(2-) causes a complete revival of fluorescence only in the case of Hg(II), providing a simple and effective method for distinguishing solutions containing Cu(II), Hg(II) or a mixture of both ions, even in doped seawater samples. X-ray crystal structures of both the Hg(II) sensor complex and a model Cu(II) complex show that pendant triazole coordination occurs through the central nitrogen atom (N2), providing to the best of our knowledge the first reported examples of this unusual coordination mode in macrocycles. Fluorescence, mass spectrometry and (1)H NMR experiments reveal that the mechanism of anion-induced fluorescence revival involves either displacement of pendant coordination or complete removal of the Hg(II) from the macrocycle, depending on the anion.

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“…In recent decades, Zn 2+ chemical sensors based on luminescence have been developed and applied to Zn 2+ monitoring in various biological systems. 12,13 However, they suffer from drawbacks including complicated organic synthesis of the sensing platform on these sensors, harmful systems, insufficient selectivity and short excitation wavelength. 14 The application of functional nucleic acids has recently facilitated development of detection methods that do not require expensive instruments.…”

Section: Introductionmentioning

confidence: 99%

Label-free Detection of Zn2+ Based on G-quadruplex

et al. 2015

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Herein, we developed a sensing strategy for the label-free detection of Zn 2+ based on G-quadruplex. In the absence of Zn 2+ , there was a fluorescence enhancement of thioflavin T by interaction with human telomere sequence. On the addition of Zn 2+ , Zn 2+ induced a more compact G-quadruplex structure to release thioflavin T, resulting in a fluorescence decrease. This simple "mix-then-detect" method gave the detection limit of 0.91 μM with linear dynamic ranges from 0 to 10 μM. Because it does not require the use of expensive and unstable DNAzyme systems, or need synthesis and modification of nanomaterials, this label-free biosensor is simple, fast, cost-effective and applicable for real samples taken from lake water.

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A Synthetically Simple, Click-Generated Cyclam-Based Zinc(II) Sensor

Cited by 162 publications

References 54 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

A Click Fluorophore Sensor that Can Distinguish Cu^II and Hg^II via Selective Anion‐Induced Demetallation

Label-free Detection of Zn2+ Based on G-quadruplex

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A Synthetically Simple, Click-Generated Cyclam-Based Zinc(II) Sensor

Cited by 162 publications

References 54 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

A Click Fluorophore Sensor that Can Distinguish CuII and HgII via Selective Anion‐Induced Demetallation

Label-free Detection of Zn2+ Based on G-quadruplex

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Product

Resources

About

A Click Fluorophore Sensor that Can Distinguish Cu^II and Hg^II via Selective Anion‐Induced Demetallation