Hydrazine-Selective Chromogenic and Fluorogenic Probe Based on Levulinated Coumarin

Choi, Myung Gil; Hwang, Ji-Young; Moon, Jung Ok; Sung, Jaeyoung; Chang, Suk‐Kyu

doi:10.1021/ol202136q

Cited by 166 publications

(46 citation statements)

References 32 publications

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“…Utilizing this type of approach, Chang et al . also developed a new levulinate coumarin derivative, 22 , for selective detection of hydrazine (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Recent Developments in Fluorometric and Colorimetric Chemodosimeters Targeted towards Hydrazine Sensing: Present Success and Future Possibilities

Manna¹,

Gangopadhyay

Maiti

et al. 2019

ChemistrySelect

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Recently, the design, synthesis and development of chemodosimeters for hydrazine with high selectivity and sensitivity has attracted tremendous attention due to its major contributions to human health and disease including applications in various platforms. In this review, we recapitulate different strategies for the design of reaction‐based colorimetric and fluorometric probes for the detection of hydrazine and their applications in hydrazine sensing in living systems. The sensing strategies for hydrazine have been divided into six categories: (a) cleavage of the acetoxy group; (b) the nucleophilic addition‐elimination on keto ester; (c) the nucleophilic substitution‐elimination to tandem cyclization on halo‐ester; (d) the nucleophilic addition reaction to phthalimide derivative to phthalhydrazide; (e) the chemical displacement of active methylene compound to hydrazone derivative and (f) Other different approaches. Additionally, a variety of techniques have been devised here for the detection of hydrazine over other comparable ions and neutral amines.

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“…Utilizing this type of approach, Chang et al . also developed a new levulinate coumarin derivative, 22 , for selective detection of hydrazine (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Recent Developments in Fluorometric and Colorimetric Chemodosimeters Targeted towards Hydrazine Sensing: Present Success and Future Possibilities

Manna¹,

Gangopadhyay

Maiti

et al. 2019

ChemistrySelect

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show abstract

“…However, to date, only a few papers are concerned with fluorescence methods for detection of N 2 H 4 . [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] Many recognizing moiety of fluorescence sensors for N 2 H 4 have been developed, mainly including acetyl, [23][24][25][26] 4-bromo butyrate, [27][28][29] levulinate, 30,31 phthalimide, [32][33][34] aldehyde, 35 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 …”

Section: Introductionmentioning

confidence: 99%

Naked-Eye and Near-Infrared Fluorescence Probe for Hydrazine and Its Applications in In Vitro and In Vivo Bioimaging

et al. 2015

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Hydrazine has been applied diffusely in most of the chemical industry; however, it is a hazardous environmental pollutant and highly toxic to organisms. Selective, rapid, and sensitive detection of hydrazine thus becomes absolutely necessary in both biological and environmental sciences. Accordingly, fluorescence probes for hydrazine have been paid great attention in recent years. Disclosed here is the near-infrared (NIR) fluorescence probe with a turn-on fluorescent probe CyJ based on the structure-emission property relationships of the NIR dyes containing an acetyl group as the recognizing moiety. This new probe not only can be readily prepared, but also shows excellent sensing properties. First and most important of all, CyJ is highly selective for N2H4 over various anions, cations, and other amino compounds and has a low limit of detection (LOD) of hydrazine (5.4 ppb as fluorescence sensor and 6.1 ppb as UV sensor). Besides, CyJ exhibited a dramatic increase in fluorescence at λmax = 706 nm in the presence of N2H4, and it offers a rapid, colorimetric and vapor sensing detection process for N2H4 in both aqueous solution and diluted human serum. Furthermore, CyJ has good cell-membrane permeability and low cytotoxicity. In addition, we have successfully applied the CyJ to visualize N2H4 in live mouse and, for the first time, in tissues such as the liver, lung, kidney, heart, and spleen.

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“…The resulting hydrazone can subsequently perform intramolecular attack on the ester carbonyl leading to cleavage of the ester function (Figure ). On the basis of this strategy, Chang and co‐workers first reported a fluorescent probe ( 65 ) for hydrazine by coupling levulinyl chloride with 3‐cyano‐7‐hydroxycoumarin (Figure ) . The treatment of probe 65 with hydrazine in a mixture of acetate buffer (pH 4.5, 10 mM) and DMSO (3:7, v / v ), lead to a dramatic fluorescence enhancement at 458 nm, which was attributed to the hydrazine‐mediated deprotection of the levulinate group and the subsequent release of fluorescent coumarin derivative.…”

Section: Probes Based On Levulinate Moietymentioning

confidence: 99%

Recent progress in the development of fluorescent probes for hydrazine

et al. 2018

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Hydrazine (N H ) is an important and commonly used chemical reagent for the preparation of textile dyes, pharmaceuticals, pesticides and so on. Despite its widespread industrial applications, hydrazine is highly toxic and exposure to this chemical can cause many symptoms and severe damage to the liver, kidneys, and central nervous system. As a consequence, many efforts have been devoted to the development of fluorescent probes for the selective sensing and/or imaging of N H . Although great efforts have been devoted in this area, the large number of important recent studies have not yet been systematically discussed in a review format so far. In this review, we have summarized the recently reported fluorescent N H probes, which are classified into several categories on the basis of the recognition moieties. Moreover, the sensing mechanism and probes designing strategy are also comprehensively discussed on aspects of the unique chemical characteristics of N H and the structures and spectral properties of fluorophores.

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Hydrazine-Selective Chromogenic and Fluorogenic Probe Based on Levulinated Coumarin

Cited by 166 publications

References 32 publications

Recent Developments in Fluorometric and Colorimetric Chemodosimeters Targeted towards Hydrazine Sensing: Present Success and Future Possibilities

Recent Developments in Fluorometric and Colorimetric Chemodosimeters Targeted towards Hydrazine Sensing: Present Success and Future Possibilities

Naked-Eye and Near-Infrared Fluorescence Probe for Hydrazine and Its Applications in In Vitro and In Vivo Bioimaging

Recent progress in the development of fluorescent probes for hydrazine

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