Calixarenes with dansyl groups as potential chemosensors

Ocak, Ümmühan; Ocak, Miraç; Bartsch, Richard A.

doi:10.1016/j.ica.2011.10.041

Cited by 32 publications

(23 citation statements)

References 61 publications

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“…Fluorescence of the 1-bound DNA strand is revealed only upon click conjugation, since unreacted dansyl azide is nonfluorescent. [16] Despite widespread use of the dansyl group in fluorescent labeling and detection methods, [17] to our knowledge, the ability of dansyl azide to become a "turn-on" fluorophore upon azide-alkyne cycloaddition has not been reported. This turn-on fluorescence capability of 1 with azide-containing fluorophores demonstrates its potential utility for cellular localization studies, as well as other imaging studies.…”

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confidence: 99%

An Alkyne‐Appended, Click‐Ready Pt^II Complex with an Unusual Arrangement in the Solid State

et al. 2014

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To better understand the range of cellular interactions of Pt(II) -based chemotherapeutics, robust and efficient methods to track and analyze Pt targets are needed. A powerful approach is to functionalize Pt(II) compounds with alkyne or azide moieties for post-treatment conjugation through the azide-alkyne cycloaddition (click) reaction. Herein, we report an alkyne-appended cis-diamine Pt(II) compound, cis-[Pt(2-(5-hexynyl)amido-1,3-propanediamine)Cl2] (1), the X-ray crystal structure of which exhibits a combination of unusual radially distributed CH/π(C≡C) interactions, Pt-Pt bonding, and NH:O/NH:Cl hydrogen bonds. In solution, 1 exhibits no Pt-alkyne interactions and binds readily to DNA. Subsequent click reactivity with nonfluorescent dansyl azide results in a 70-fold fluorescence increase. This result demonstrates the potential for this new class of alkyne-modified Pt compound for the comprehensive detection and isolation of Pt-bound biomolecules.

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An Alkyne‐Appended, Click‐Ready Pt^II Complex with an Unusual Arrangement in the Solid State

et al. 2014

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“…However, it is quite different in our case. This can be attributed to the dramatically reduced micro-environmental polarity of the dansyl fluorophore in the aggregated state, which may increase the radiative efficiency, and meanwhile the bulk steric effect caused by the calix [4]arene moiety prevented the compact stacking between the dansyl fluorophores. When the water fraction exceeds 60%, the fluorescence intensity is slightly quenched without a wavelength shift, indicating that precipitation of ligands from the solution started occurring.…”

Section: Resultsmentioning

confidence: 99%

“…5 (top). 32 In pure water, when the pH is lower than 4, more than 90% of aluminum exists as free [Al(H 2 O) 6 ] 3+ ; with the increase of pH but lower than 7, aluminum hydrolyzes to produce the precipitate Al(OH) 3 ; and when the pH is higher than 7, Al(OH) 3 is again transferred into Al(OH) 4 − . The pH effect on the spectral response of 3 to Al 3+ is quite similar to the curve of fraction distribution of Al(OH) 3 in water under different pH conditions, though with a narrower half-peak width.…”

Section: Resultsmentioning

confidence: 99%

“…25 Therefore the sulfonate group is considered an ideal choice in our present work to deal with water solubility and binding affinity with Al 3+ . For continuous work on the attempt at developing fluorescent chemosensors based on the framework of calix [4]arene, [26][27][28][29] we envisage to introduce the sulfonate groups into the calix [4]arene moiety bearing dansyl as the fluorophore and investigate the interaction between the sulfonate group and Al 3+ in a fluorometric manner.…”

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Aggregation-induced emission enhancement upon Al³⁺ complexation with a tetrasulfonated calix[4]bisazacrown fluorescent molecular sensor

2014

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Aggregation-induced emission and aggregation-induced emission enhancement have attracted much attention due to their great potential in real-world applications. Up to now most of the reports are based on the restriction of free rotation of the luminogens in the aggregates. In the present work, we found that the dansyl fluorophore with typical intramolecular charge transfer characteristic also exhibited aggregation-induced emission enhancement, which was based on the change of micro-environmental polarity of the fluorophore. In the light of the phenomenon, a new water-soluble ligand bearing a tetrasulfonated calix[4]arene was constructed for ratiometric detection of Al(3+) based on an aggregation-induced emission enhancement mechanism. It displayed a distinct selectivity to Al(3+) among the tested cations in lutidine buffer solution (pH 6-7) with a detection limit of 1.8 μM. A reversible response was also demonstrated by the addition of EDTA or F(-).

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“…It allows the nanoparticles to interact with substrates, for example, with biopolymers, with a high efficiency because of multiple simultaneous non‐covalent interactions. Nanosized structures formed by supramolecular self‐assembling and capable of interacting with biopolymers can be used as diagnostic systems, selective extractants, and drug delivery systems …”

Section: Introductionmentioning

confidence: 99%

Amphiphilic p‐tert‐butylthiacalix[4]arenes containing quaternary ammonium groups: from small molecules toward water‐soluble nanoscale associates

Andreyko

Padnya

Stoikov

2015

J of Physical Organic Chem

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The formation of supramolecular associates based on water‐soluble p‐tert‐butylthiacalix[4]arenes with amino acids has been studied. It was shown that amphiphilic p‐tert‐butylthiacalix[4]arenes preferably formed supramolecular associates with aromatic α‐amino acids (tyrosine and tryptophan). Increasing size of the substituents of p‐tert‐butylthiacalix[4]arenes led to increase molecular weight of supramolecular associates based on the macrocycles and “guest” molecules. The spatial structures of p‐tert‐butylthiacalix[4]arenes and their associates with phenylalanine were studied by two‐dimensional 1H‐1H nuclear Overhauser effect NMR spectroscopy. The ability of aggregates based on p‐tert‐butylthiacalix[4]arenes and amino acids to effectively interact with bovine serum albumin with the formation of 7‐ to 8‐nm nanoparticles was shown. Copyright © 2015 John Wiley & Sons, Ltd.

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Calixarenes with dansyl groups as potential chemosensors

Cited by 32 publications

References 61 publications

An Alkyne‐Appended, Click‐Ready Pt^II Complex with an Unusual Arrangement in the Solid State

An Alkyne‐Appended, Click‐Ready Pt^II Complex with an Unusual Arrangement in the Solid State

Aggregation-induced emission enhancement upon Al³⁺ complexation with a tetrasulfonated calix[4]bisazacrown fluorescent molecular sensor

Amphiphilic p‐tert‐butylthiacalix[4]arenes containing quaternary ammonium groups: from small molecules toward water‐soluble nanoscale associates

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Calixarenes with dansyl groups as potential chemosensors

Cited by 32 publications

References 61 publications

An Alkyne‐Appended, Click‐Ready PtII Complex with an Unusual Arrangement in the Solid State

An Alkyne‐Appended, Click‐Ready PtII Complex with an Unusual Arrangement in the Solid State

Aggregation-induced emission enhancement upon Al3+ complexation with a tetrasulfonated calix[4]bisazacrown fluorescent molecular sensor

Amphiphilic p‐tert‐butylthiacalix[4]arenes containing quaternary ammonium groups: from small molecules toward water‐soluble nanoscale associates

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An Alkyne‐Appended, Click‐Ready Pt^II Complex with an Unusual Arrangement in the Solid State

An Alkyne‐Appended, Click‐Ready Pt^II Complex with an Unusual Arrangement in the Solid State

Aggregation-induced emission enhancement upon Al³⁺ complexation with a tetrasulfonated calix[4]bisazacrown fluorescent molecular sensor