A highly selective ‘turn-on’ fluorescent sensor for Zn2+ based on fluorescein conjugates

Chantalakana, Khwanchanok; Choengchan, Nathawut; Yingyuad, Peerada; Thongyoo, Panumart

doi:10.1016/j.tetlet.2016.01.106

Cited by 33 publications

(10 citation statements)

References 45 publications

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“…Growing interest in alternative chemical structures of azo dyes required for high‐tech applications (e.g., dye‐sensitized solar cells, anion sensors) has recently led chemists to focus on the synthesis of hybrid structures based on the functionalization of organic‐based fluorophores with one or several (di)aryl azo moieties. As partially illustrated in Figure , several fluorescent organic dyes belonging to different families, including BODIPYs, fluoresceins, 1,8‐napthalimides, porphyrins, perylenes, and pyrenes, have been converted into nonfluorescent azo dyes through either diazotization of their primary amino groups or covalent conjugation to a conventional bis(aryl) azo dye.…”

Section: Azo‐based Fluorogenic Probesmentioning

confidence: 99%

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Azo‐Based Fluorogenic Probes for Biosensing and Bioimaging: Recent Advances and Upcoming Challenges

Chevalier

Renard

Romieu

2017

Chemistry An Asian Journal

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The use of nonfluorescent azo dyes as dark quenchers in activatable optical bioprobes based on the Förster resonance energy transfer (FRET) mechanism and designed to target a wide range of enzymes has been established for over two decades. The key value of the azo moiety (-N=N-) to act as an efficient "ON-OFF" switch of fluorescence once introduced within the core structure of conventional organic-based fluorophores (mainly fluorescent aniline derivatives) has recently been exploited in the development of alternative reaction-based small-molecule probes based on the "profluorescence" concept. These unprecedented "azobenzene-caged" fluorophores are valuable tools for the detection of a wide range of reactive (bio)analytes. This review highlights the most recent and relevant advances made in the design and biosensing/bioimaging applications of azo-based fluorogenic probes. Emphasis is also placed on relevant achievements in the synthesis of bioconjugatable/biocompatible azo dyes used as starting building blocks in the rational and rapid construction of these fluorescent chemodosimeters. Finally, a brief glimpse of possible future biomedical applications (theranostics) of these "smart" azobenzene-based molecular systems is presented.

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Section: Azo‐based Fluorogenic Probesmentioning

confidence: 99%

“… Structures of nonfluorescent azo dyes derived from organic‐based fluorophores (BODIPY (a), fluorescein (b), 1,8‐naphthalimide (c), porphyrin (d), perylene, (e) and pyrene (f)) already reported in the literature.…”

Section: Azo‐based Fluorogenic Probesmentioning

confidence: 99%

Azo‐Based Fluorogenic Probes for Biosensing and Bioimaging: Recent Advances and Upcoming Challenges

Chevalier

Renard

Romieu

2017

Chemistry An Asian Journal

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“…On the other hand, the first generation of the PAMAM dendrimer was decorated with coumarin because of the large surface area of dendrimers for attachment of the donor molecules to increase sensitivity and applicability. , Figure shows the UV–vis spectroscopy diagrams for Fl, MCC-G1, MCC-Co, and fluorescein-doped MCC-Co (MCC-Co/Fl). There is no characteristic absorption peak in the spectrum of MCC-G1; however, absorption peaks at λ max = 280 and 310 nm were observed after functionalization of MCC-G1 with AMC, which confirms coupling of coumarin moieties on the surface of hybrid dendrimers. , On the other hand, the Fl spectrum shows a strong absorption band at 480 nm . After doping Fl in the MCC-Co aqueous dispersion, absorption bands of Fl and MCC-Co are observed.…”

Section: Resultsmentioning

confidence: 83%

Anti-Counterfeiting Inks Based on Förster Resonance Energy Transfer in Microcrystalline Cellulose-Grafted Poly(amidoamine) for Artificial Industries

Mardani

Roghani‐Mamaqani

Shahi

et al. 2023

ACS Appl. Polym. Mater.

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Counterfeiting and inverse engineering of different artificial industries have significantly increased, which is a challenge for the originality of the crafts that are known as the cultural products of different nations. To prevent counterfeiting in the art market, it is needed to mark the original crafts with anti-counterfeiting inks using high technologies for their easy authentication. In this study, poly(amidoamine) (PAMAM) dendrimer-modified microcrystalline cellulose decorated with coumarin moieties was prepared to design a biobased anti-counterfeiting ink for authentication of original artificial industries based on Förster resonance energy transfer (FRET). For this purpose, the first generation of the PAMAM dendrimer was divergently grown onto the microcrystalline cellulose (MCC) surface and subsequently decorated with coumarin moieties using a Michael addition reaction to obtain a fluorescent hybrid dendrimer. Physical incorporation of fluorescein into the aqueous hybrid dendrimer dispersion resulted in a chemosensor and also an anti-counterfeiting ink based on the FRET mechanism, where the coumarin-decorated hybrid dendrimer acts as a donor and fluorescein plays the role of an acceptor. This aqueous FRET probe based on bioresources was applicable for ion and pH sensing due to the presence of nitrogen atoms on the dendritic structure and also for preparation of anti-counterfeiting inks for use on cellulosic papers, security documents, and, most importantly, artificial industries. This work could help to reduce forgery in artificial industries, authentication of the original handicrafts from the fakes, and prevent from counterfeiting in the art market.

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“…Fluorescent chemosensors for Zn 2+ include various classes of compounds, viz., di-2-picolylamine-based, quinoline-based, bipyridine-based, acyclic and cyclic polyamine-based, iminodiacetic acid-based, triazole-based, and Schiff base-based sensors . In addition, anthracene-based, fluorescein-based, , oxazoline-based, 1,10-phenanthroline-based, coumarin-based, , benzimidazole-based, , rhodamine-based, BINOL-based, pyrazoline-based, pyrene-based, , and porphyrin and corrole analogue-based , compounds have also been reported as fluorescent chemosensors for Zn 2+ . Generally, photoinduced electron transfer (PET)- and intermolecular charge transfer (ICT)-based mechanisms for the fluorescence signaling for Zn 2+ sensors have been observed .…”

Section: Introductionmentioning

confidence: 99%

Design of a Highly Selective Benzimidazole-Based Derivative for Optical and Solid-State Detection of Zinc Ion

et al. 2022

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A novel series of benzimidazole-based molecules mimicking biological receptors, which exhibit selective coordination with zinc ions, were designed and synthesized. The photochromic behavior of these derivatives with various metal ions suggests a selective interaction of one of the receptors 2-(pyridin-2-yl)-4,7-di(thiophen-2-yl)-3H-benzo[d]imidazole (2c) with zinc ion. The lower limit of detection by photoluminescence quenching was determined to be 16 nM. The mechanism of selective complexation was elucidated by 1 H nuclear magnetic resonance titrations and dynamic light scattering analysis. The stoichiometry of the formation of the Zn(2c) 2 complex was evaluated by single-crystal X-ray diffraction and mass spectral techniques and calculated to be 2:1 (L:M). A change in the electronic energy levels on the sensor analyte interaction was observed by both ultraviolet photoelectron spectroscopy analysis and by density functional theory calculations, suggesting an electroactive semiconductor behavior. A symmetric Schottky structured sensor device was fabricated using the receptor 2c as the active sensing layer. A distinct change in current−voltage characteristics between the receptor and the complex suggests that the fabricated device could be used as a solid-state sensor for detecting zinc ion.

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A highly selective ‘turn-on’ fluorescent sensor for Zn2+ based on fluorescein conjugates

Cited by 33 publications

References 45 publications

Azo‐Based Fluorogenic Probes for Biosensing and Bioimaging: Recent Advances and Upcoming Challenges

Azo‐Based Fluorogenic Probes for Biosensing and Bioimaging: Recent Advances and Upcoming Challenges

Anti-Counterfeiting Inks Based on Förster Resonance Energy Transfer in Microcrystalline Cellulose-Grafted Poly(amidoamine) for Artificial Industries

Design of a Highly Selective Benzimidazole-Based Derivative for Optical and Solid-State Detection of Zinc Ion

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