A sensitive colorimetric and fluorescent sensor based on imidazolium-functionalized squaraines for the detection of GTP and alkaline phosphatase in aqueous solution

Wu, Ningjie; Lan, Jingbo; Yan, Lipeng; You, Jingsong

doi:10.1039/c4cc00752b

Cited by 54 publications

(30 citation statements)

References 32 publications

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“…Because of these requirements, the recognition of a guanine base has achieved excellent specificity and interactions with the other nucleobases are nearly negligible. This selectivity is in contrast to the two recently reported GTP sensors for which the signal generated by ATP was about one‐third to one‐half of that produced by GTP ,…”

Section: Figurecontrasting

confidence: 91%

Exceptionally Selective and Tunable Sensing of Guanine Derivatives and Analogues by Structural Complementation in a G‐Quadruplex

Zheng

Hao

et al. 2016

Angew Chem Int Ed

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A guanine-vacancy-bearing G-quadruplex (GVBQ) interacts with guanine and derivatives by a structural complementation to form a more stable and intact G-quadruplex. Sensors using GVBQs are devised to detect guanine and other nucleobases, and their derivatives derived from structurally similar compounds. A strict requirement of Hoogsteen hydrogen bonds between the GVBQ and analyte in the structural complementation confers exceptional selectivity on the analyte. As such, subtle modifications on analytes affecting even a single hydrogen bond can preclude the recognition. In principle, the strategy may also be expanded to detect many planar cyclic compounds. Because nucleobases and derivatives/metabolites are involved in many physiological and pathological processes, this type of sensor may find applications in risk assessment of pathogenesis and therapeutics related to nucleic acid metabolism.

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Section: Figurecontrasting

confidence: 91%

Exceptionally Selective and Tunable Sensing of Guanine Derivatives and Analogues by Structural Complementation in a G‐Quadruplex

Zheng

Hao

et al. 2016

Angew Chem Int Ed

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“…Squaraine cyanine dyes, usually called squaraine dyes, are a family of compounds discovered in 1965 by Treibs and Jacob [13], whose suitable photochemical and photophysical properties give them the potential to be ideal for use in many biotechnological and biomedical applications, such as sensitizers for solar energy conversion [14,15], probes for metal ions and biomolecules detection [16][17][18][19][20], photodynamic therapy photosensitizers [7][8][9]21], among many others. The aforementioned dyes are known by their high molar extinction coefficient and also by their intense and narrow absorption bands in the visible and near-infrared regions due to the charge transfer system within the molecule.…”

Section: Introductionmentioning

confidence: 99%

Red and Near-Infrared Absorbing Dicyanomethylene Squaraine Cyanine Dyes: Photophysicochemical Properties and Anti-Tumor Photosensitizing Effects

et al. 2020

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Photodynamic therapy is a medical modality developed for the treatment of several diseases of oncological and non-oncological etiology that requires the presence of a photosensitizer, light and molecular oxygen, which combined will trigger physicochemical reactions responsible for reactive oxygen species production. Given the scarcity of photosensitizers that exhibit desirable characteristics for its potential application in this therapeutic strategy, the main aims of this work were the study of the photophysical and photochemical properties and the photobiological activity of several dicyanomethylene squaraine cyanine dyes. Thus, herein, the study of their aggregation character, photobleaching and singlet oxygen production ability, and the further application of the previously synthesized dyes in Caco-2 and HepG2 cancer cell lines, to evaluate their phototherapeutic effects, are described. Dicyanomethylene squaraine dyes exhibited moderate light-stability and, despite the low singlet oxygen quantum yields, were a core of dyes that exhibited relevant in vitro photodynamic activity, as there was an evident increase in the toxicity of some of the tested dyes exclusive to radiation treatments.

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“…Aggregation of the probe in aqueous solutionw as also observed by Youa nd coworkers. [17] They used squaramide-imidazolinium conjugate 16,w hich selectively forms aggregates in the presence of GTP. Interestingly,a mphiphilic dye 17 can also form self-assembled structuresb ut with am icelle-like structure,w hich can bind ATP on its outer surfacer esulting in fluorescence enhancement.…”

Section: Functional Dyes For Nucleotide Sensingmentioning

confidence: 99%

Molecular Receptors for Recognition and Sensing of Nucleotides

Agafontsev

Ravi

Shumilova

et al. 2018

Chemistry A European J

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Nucleotides are constituents of nucleic acids and they have a variety of functions in cellular metabolism. Synthetic receptors and sensors are required to reveal the role of nucleotides in living organisms and mechanisms of signal transduction events. In recent years, a large number of nucleotide‐selective synthetic receptors have been devised, which utilize different molecular designs and sensing mechanisms. This Minireview presents recent progress in the design of synthetic molecular receptors for selective recognition of nucleotides in aqueous solution. The binding properties of receptors and the origins of their selectivity for a particular nucleotide are discussed.

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A sensitive colorimetric and fluorescent sensor based on imidazolium-functionalized squaraines for the detection of GTP and alkaline phosphatase in aqueous solution

Abstract: Imidazolium-functionalized squaraine ImSQ8 is synthesized as a sensitive colorimetric and fluorescent chemosensor for GTP in aqueous solution. The detection limit of GTP reaches 5.4 ppb. Its applications in the live-cell imaging and enzyme activity assay have also been demonstrated.

Cited by 54 publications

References 32 publications

Exceptionally Selective and Tunable Sensing of Guanine Derivatives and Analogues by Structural Complementation in a G‐Quadruplex

Exceptionally Selective and Tunable Sensing of Guanine Derivatives and Analogues by Structural Complementation in a G‐Quadruplex

Red and Near-Infrared Absorbing Dicyanomethylene Squaraine Cyanine Dyes: Photophysicochemical Properties and Anti-Tumor Photosensitizing Effects

Molecular Receptors for Recognition and Sensing of Nucleotides

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