Dual signaling of hypochlorous acid by desulfurization of thiocoumarin

Moon, Jung Ok; Lee, Jung Woo; Choi, Myung Gil; Ahn, Sangdoo; Chang, Suk‐Kyu

doi:10.1016/j.tetlet.2012.09.110

Cited by 28 publications

(10 citation statements)

References 36 publications

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“…Considering the unique properties of coumarin and the specific reaction between HOCl and the chalcogenide [72,186,187], Li et al synthesized the selenoxide elimination reaction based fluorescent probes, CM1 and CM2 (Fig. 10), for HOCl detection [188].…”

Section: <Fig 8 Is Here>mentioning

confidence: 99%

Bioanalytical methods for hypochlorous acid detection: Recent advances and challenges

Zhang

Song

Yuan

2018

TrAC Trends in Analytical Chemistry

217

115

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Hypochlorous acid (HOCl), a well-known universal disinfectant in clinical practice, plays important roles in immune systems of animal and human bodies. For understanding the roles of HOCl in living systems, a number of approaches, including chemiluminescence, colorimetric, electrochemical and chromatographic methods have been explored. For the detection of HOCl in live organisms, cuttingedge techniques, such as fluorescence/phosphorescence molecular probes, responsive nanoprobes, Raman and activatable photoacoustic sensors, have also been developed recently. In this review, the recent advances in the development of bioanalytical methods for detection of HOCl in environmental and biological specimens were summarized. More specifically, traditional techniques for assay of HOCl in bulk solution were initially discussed, and then fluorescence molecular probes, phosphorescence probes, responsive nanoprobes and other methods for HOCl detection were reviewed, which gives an overview of the developments and applications in bioanalytical methods for HOCl detection.

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Section: <Fig 8 Is Here>mentioning

confidence: 99%

Bioanalytical methods for hypochlorous acid detection: Recent advances and challenges

Zhang

Song

Yuan

2018

TrAC Trends in Analytical Chemistry

217

115

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“…In the presence of oxidant, thiocoumarin is readily transformed to coumarin. 28,29 There is a distinct difference in the photophysical properties of coumarin and thiocoumarin. 30,31 34 Coumarin and thiocoumarin have absorption in different wavelength regions.…”

Section: Introductionmentioning

confidence: 99%

“…Chang and his group, have studied conversion of different thiocoumarins to coumarins in the presence of various oxidising agents like hypochlorous acid (HOCl), m-chloroperoxy benzoic acid (m-CPBA), or trichloroisocyanuric acid. 28,29,32 They have demonstrated that during the conversion of the thioketone group to ketone group, the fluorescence signal was increased substantially. Also, they have shown that fluorescence signalling was less affected in the presence of common interfering cations and anions.…”

Section: Introductionmentioning

confidence: 99%

Colorimetric and fluorescence signalling of thioesculetin in presence of oxidising agent

2018

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Thioesculetin (TE) is a sulfur analogue of esculetin. The UV-Vis absorption maximum of TE at 470 nm shifted to 357 nm in the presence of oxidising agent such as m-chloroperoxy benzoic acid (m-CPBA). With gradual increase in the m-CPBA concentration, the absorption band at 470 nm decreases while the band at 357 nm increases. The same system shows gradual increase in the fluorescence signal at 463 nm in the presence of m-CPBA. The fluorescence signal was unaffected in the presence of common anions and metal cations. The mechanism for optical signalling was due to the conversion of weakly fluorescent TE to fluorescent esculetin through desulfurization reaction. 13 C-NMR shows strong evidence in support of the chemical conversion of TE to esculetin. TE may find applications to probe the redox environment in various chemical and biochemical processes.

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“…These indicator mechanisms include p -methoxyphenol oxidation to p -benzoquinones, 18–23 oxime oxidation to aldehydes, 24–29 the chlorination of thioesters and amides, 30–40 p -aminophenol analog oxidation, 4,41–44 thioether to sulfonate and selenide to selenoxide transformations, 5,45–59 the cleavage of carbon-carbon double bonds, 2,60–62 and oxidative processes in metal complexes. 7,63–67 This review classifies probes for HOCl based on the seven different detection mechanisms.…”

Section: Introductionmentioning

confidence: 99%

Recent progress in chromogenic and fluorogenic chemosensors for hypochlorous acid

Yue

Huo

Yin

et al. 2016

Analyst

168

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Due to the biological and industrial importance of hypochlorous acid, the development of optical probes for HOCl has been an active research area. Hypochlorous acid and hypochlorite can oxidize electron-rich analytes with accompanying changes in molecular sensor spectroscopic profiles. Probes for such processes may monitor HOCl levels in the environment or in an organism and via bio-labeling or bioimaging techniques. This review summarizes recent developments in the area of chromogenic and fluorogenic chemosensors for HOCl.

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Dual signaling of hypochlorous acid by desulfurization of thiocoumarin

Cited by 28 publications

References 36 publications

Bioanalytical methods for hypochlorous acid detection: Recent advances and challenges

Bioanalytical methods for hypochlorous acid detection: Recent advances and challenges

Colorimetric and fluorescence signalling of thioesculetin in presence of oxidising agent

Recent progress in chromogenic and fluorogenic chemosensors for hypochlorous acid

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