A Hydroxytricyanopyrrole-Based Fluorescent Probe for Sensitive and Selective Detection of Hypochlorous Acid

Zeng, Chunhua; Chen, Zhengjun; Yang, Mingyan; Lv, Jiajia; Li, Hongyu; Gao, Jie; Yuan, Zeli

doi:10.3390/molecules27217237

Cited by 7 publications

(4 citation statements)

References 77 publications

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“…The main scavengers of HOCl are thiols and thioethers, of which reaction rate constants with HOCl range from 10 7 to 10 8 M −1 s −1 . The HOCl reaction rate constants for amines cover several orders of magnitude (10 1 –10 6 M −1 s −1 ) [ 59 , 62 , 63 , 64 , 65 ]. To investigate whether the NBD-S-TM probe can efficiently scavenge HOCl, we determined the second-order reaction rate constant of this reaction ( Figure 13 ).…”

Section: Resultsmentioning

confidence: 99%

A New and Fast-Response Fluorescent Probe for Monitoring Hypochlorous Acid Derived from Myeloperoxidase

2023

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Hypochlorous acid (HOCl) has been implicated in numerous pathologies associated with an inflammatory component, but its selective and sensitive detection in biological settings remains a challenge. In this report, imaging of HOCl was realized with a thiomorpholine-based probe as derivative of nitrobenzothiadiazole (NBD-S-TM). The fluorescence is based on photoinduced electron transfer by using nitrobenzothiadiazole core as a donor and thiomorpholine substituent as an acceptor. NBD-S-TM showed high sensitivity and a fast response to HOCl k = (2.6 ± 0.2) × 107 M−1s−1 with a 1:1 stoichiometry. The detection limit for HOCl was determined to be 60 nM. Furthermore, the desirable features of NBD-S-TM for the detection of HOCl in aqueous solutions, such as its reliability at physiological pH, rapid fluorescence response, and biocompatibility, enabled its application in the detection of HOCl in myeloperoxidase enzymatic system. Moreover, NBD-S-TM exhibited excellent selectivity and sensitivity for HOCl over other biologically relevant species, such as hydrogen peroxide and peroxynitrite. The fluorescent S-oxidized product (NBD-S-TSO) is only formed in the presence of HOCl. Probing with NBD-S-TM may be helpful to further the development of high throughput screening assays to monitor the activity of myeloperoxidase.

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Section: Resultsmentioning

confidence: 99%

A New and Fast-Response Fluorescent Probe for Monitoring Hypochlorous Acid Derived from Myeloperoxidase

2023

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“…Compounds 116 and 117 with directly functionalized first and fifth positions of the pyrrole ring exhibit negative photochromism along with maximum absorption wavelength at 434 nm and 431 nm in ethanol solution. Furthermore, HTCP derivatives can also be applied for fluorescent donor–acceptor chromophores [ 124 , 125 , 126 ], fluorescent probes [ 127 ], and so on.…”

Section: Negatively Photochromic Compoundsmentioning

confidence: 99%

From Visible to Near–Infrared Light–Triggered Photochromism: Negative Photochromism

Li,

Mou,

Yamada

et al. 2023

Molecules

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Photochromic compounds, whose key molecular properties can be effectively modulated by light irradiation, have attracted significant attention for their potential applications in various research fields. The restriction of photoisomerization coloration induced by ultraviolet light limits their applications in the biomedical field and some other fields. Negative photochromism, wherein a relatively stable colored isomer transforms to a colorless metastable isomer under low–energy light irradiation, offers advantages in applications within materials science and life science. This review provides a summary of negatively photochromic compounds based on different molecular skeletons. Their corresponding design strategies and photochromic properties are presented to provide practical guidelines for future investigations. Negatively photochromic compounds can effectively expand the range of photochromic switches for future applications, offering unique properties such as responsiveness to visible to near–infrared light.

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“…As an ICT (Intramolecular Charge Transfer)-based fluorescent dye, 4 -hydroxybiphenyl-4-carbonitrile (dye 2) has many desirable features, which are attributed to its great pushpull electronic system, such as emission in the cyan spectral region and good photostabilities [33]. In addition, the N, N-dimethylthiocarbamate group has been widely used as a specific response site for ClO − [34][35][36][37]. Based on the above excellent photophysical properties, in this work, we design a new cyan fluorescence probe 1, which was composed of the ICT-based fluorophore, 4 -hydroxybiphenyl-4-carbonitrile and N, Ndimethylthiocarbamate group for the selectivity detection of ClO − .…”

Section: Introductionmentioning

confidence: 99%

A Simple ICT-Based Fluorescent Probe for HOCl and Bioimaging Applications

Zheng

Bing

et al. 2023

Biosensors

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Over the past few decades, drug-induced liver damage (DILI) has become a serious public health problem due to drug abuse. Among multifarious reactive oxygen species, mounting evidence attests that ClO− has been used as a potential biomarker in DILI. In this work, a new “turn-on” fluorescent probe 1 was designed and synthesized by modifying 4′-hydroxybiphenyl-4-carbonitrile (dye 2) with N, N-dimethylthiocarbamate as a response site for detecting ClO−. Probe 1 displayed a low detection limit (72 nM), fast response time (30 s), wide pH operating range (6–8), great tissue penetration, large Stokes shift (125 nm) and 291-fold fluorescence enhancement at 475 nm in the mapping of ClO−. Probe 1 could trace amounts of exogenous and endogenous ClO− with high sensitivity in MCF-7 cells and HeLa cells. Expectantly, the fluoxetine-induced liver injury model is successfully established, and probe 1 has been used for detecting the fluctuation of ClO− levels in the mouse model of fluoxetine-induced liver injury. All in all, probe 1 with its high specificity, good biological compatibility and liver tissue penetration ability is expected to assist with the early diagnosis of DILI and the clinical screening of various new drugs. We expect that probe 1 could be efficiently used as a powerful molecular tool to predict clinical DILI and explore molecular mechanisms between molecules and disease.

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A Hydroxytricyanopyrrole-Based Fluorescent Probe for Sensitive and Selective Detection of Hypochlorous Acid

Cited by 7 publications

References 77 publications

A New and Fast-Response Fluorescent Probe for Monitoring Hypochlorous Acid Derived from Myeloperoxidase

A New and Fast-Response Fluorescent Probe for Monitoring Hypochlorous Acid Derived from Myeloperoxidase

From Visible to Near–Infrared Light–Triggered Photochromism: Negative Photochromism

A Simple ICT-Based Fluorescent Probe for HOCl and Bioimaging Applications

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