Sensitive water-soluble fluorescent chemosensor for chloride based on a bisquinolinium pyridine-dicarboxamide compound

Bazany‐Rodríguez, Iván J.; Martı́nez-Otero, Diego; Barroso-Flores, Joaquı́n; Yatsimirsky, Anatoly K.; Dorazco‐González, Alejandro

doi:10.1016/j.snb.2015.07.031

Cited by 36 publications

(24 citation statements)

References 60 publications

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“…Due to the strong chemical stability and inert chemical reaction of the chloride ion, there are only a few methods for the detection of the chloride ion based on chemiluminescence and fluorescence spectroscopy (Kim et al, 2017). For example, Han developed a fluorescent probe for the chloride ion using Ag-benzimidazole complexes (Kim et al, 2020), and Bazany-Rodríguez et al (2015) reported a watersoluble fluorescent probe for chloride based on a bisquinolinium pyridine-dicarboxamide compound. However, organic fluorescent probes have the disadvantages of poor stability and low fluorescence intensity, so it is necessary to develop chloride fluorescent probes based on nanomaterials.…”

Section: Introductionmentioning

confidence: 99%

One-Step Synthesis of Green Fluorescent Carbon Dots for Chloride Detecting and for Bioimaging

Yue

et al. 2021

Front. Chem.

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The chloride ion is an essential ion in organisms, which plays an important role in maintaining normal cell functions. It is involved in many cell activities, such as cell proliferation, cell excitability regulation, immune response, and volume regulation. Accurate detection of the chloride ion can balance its concentration in vivo, which is of great significance. In this study, we developed a green fluorescent carbon quantum dot to detect chloride concentration through the “off–on” mechanism. First, the fluorescence of carbon dots is quenched by the complex of sulfhydryl and silver ions on the surface of carbon dots. Then, the addition of chloride ions pulls away the silver ions and restores the fluorescence. The fluorescence recovery is linearly related to the concentration of chloride ions, and the limit of detection is 2.817 μM, which is much lower than those of other reported chloride probes. Besides, cell and zebrafish experiments confirmed the biosafety and biocompatibility of the carbon dots, which provided a possibility for further applications in bioimaging in vivo.

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Section: Introductionmentioning

confidence: 99%

One-Step Synthesis of Green Fluorescent Carbon Dots for Chloride Detecting and for Bioimaging

Yue

et al. 2021

Front. Chem.

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“…Furthermore, the absence of a pre-organization of the contact points decreases its iodide-selectivity and affinity. [92] Organic cationic fluorophores with a charge strongly delocalized such as N-quinoliniums, often have ion pairing association with voluminous anions such as iodide, as a result of the hydrophobic effect, with drastic changes in their fluorescent emission properties, which produces a high iodidesensitivity but low selectivity due to lack of a specific binding site.…”

Section: Discussionmentioning

confidence: 99%

Recent Advances in Luminescent Recognition and Chemosensing of Iodide in Water

Valdes‐García

Rosales‐Vázquez

Bazany‐Rodríguez

et al. 2020

Chemistry An Asian Journal

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This Minireview covers the latest developments of chemosensors based on transition-metal receptors and organic fluorophores with specific binding sites for the luminescent detection and recognition of iodide in aqueous media and real samples. In all selected examples within the last decade (made-post 2010), the iodide sensing and recognition is probed by monitoring real-time changes of the fluorescence or phosphorescence properties of the chemosensors. This review highlights effective strategies to iodide sensing from a structural approach where the iodide recognition/sensing process, through supramolecular interactions as coordination bonds, hydrogen bonds, halogen bonds and electrostatic interactions, is transduced into an optical change easily measurable. The selective iodide sensing is an active field of research with global interest due to the importance of iodide in biological, medicinal, industrial, environmental and chemical processes.

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“…Quinoline-based quaternary salts have attracted the attention of researchers in different areas of organic chemistry for their relevant applications such as DNA-intercalators (Mazzoli et al, 2011), fluorescent pH-sensors (Badugu et al, 2005a), fluorescent labels for antibiotics (Zeng et al, 2010), proteins (Hong et al, 2004), heparin (Sauceda et al, 2007), sacharides (Badugu et al, 2005b), fluorescent probes for fluoride and cyanide ions (Badugu et al, 2004) and nucleotides (Dorazco-Gonzá lez et al, 2014). These cationic organic compounds are probably the most used fluorescent sensors for chloride ions in aqueous media (Bazany-Rodríguez et al, 2015) and intracell samples (Baù et al, 2012). On the other hand, benzamide compounds are used as intermediaries for the synthesis of species with biological activity such as 1,4-benzodiazepinones, thiazoles and oxazoles (Majumdar & Ganai, 2011;Majumdar & Ghosh, 2013;Majumdar et al, 2012) and bicyclic Nheterocycles and nitrogen-rich medium-size heterocycles (Mondal et al, 2012;Zeni & Larock, 2006;Ohta et al, 2008;Majumdar et al, 2008;Raju et al, 2009;Evdokimov et al, 2011).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of 3-benzamido-1-(4-nitrobenzyl)quinolinium trifluoromethanesulfonate

et al. 2016

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In the title salt, each cation shows a moderate distortion between the planes of the amide groups and the quinolinium rings. The trifluoromethanesulfonate anions are linked to organic cations via N—H⋯O hydrogen-bonding interactions involving the NH amide groups. In the crystal, weak C—H⋯O hydrogen bonds and π-stacking interactions between the quinolinium and phenyl rings link the organic cations into chains.

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Sensitive water-soluble fluorescent chemosensor for chloride based on a bisquinolinium pyridine-dicarboxamide compound

Cited by 36 publications

References 60 publications

One-Step Synthesis of Green Fluorescent Carbon Dots for Chloride Detecting and for Bioimaging

One-Step Synthesis of Green Fluorescent Carbon Dots for Chloride Detecting and for Bioimaging

Recent Advances in Luminescent Recognition and Chemosensing of Iodide in Water

Crystal structure of 3-benzamido-1-(4-nitrobenzyl)quinolinium trifluoromethanesulfonate

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