A novel quinoline-BODIPY fluorescent probe for fast sensing biothiols via hydrogen bonds assisted-deprotonation mechanism and its application in cells and zebrafish imaging

Wang, Lingfeng; Qian, Ying

doi:10.1016/j.jphotochem.2018.12.013

Cited by 33 publications

(8 citation statements)

References 47 publications

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“…[57] The DNBS masked hydroxy auxochrome in the phenyl group was also frequently linked to BODIPY dyes at the meso position to developv arious fluorescent probesf or sulfhydryl amino acid by regulation of the PET process (22-25,F igure 6). [58][59][60] Probe 22 had the meso phenol 2,4-dinitrobenzenesulfonate scaffold and provided green emission in responset o biothiols. [58] In contrast, the same capping strategy on extended conjugatedB ODIPY dyes afforded farred (656 nm) responsive probe 23.…”

Section: Probesf or Sulfhydryl Amino Acidmentioning

confidence: 99%

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BODIPY‐Based Fluorescent Probes for Biothiols

Zhang

Wang

et al. 2020

Chemistry A European J

191

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Fluorescent probes for biothiols have aroused increasing interest owing to their potential to enable better understanding of the diverse physiological and pathological processes related to the biothiol species. BODIPY fluorophores exhibit excellent optical properties, which can be readily tailored by introducing diverse functional units at various positions of the BODIPY core. In the present review, the development of fluorescent probes based on BODIPYs for the detection of biothiols are systematically summarized, with emphasis on the preferable detection of individual biothiols, as well as simultaneous discrimination among cysteine (Cys), homocysteine (Hcy), reduced glutathione (GSH). In addition, organelle‐targeting probes for biothiols are also highlighted. The general design principles, various recognition mechanisms, and biological applications are elaboratively discussed, which could provide a useful reference to researchers worldwide interested in this area.

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Section: Probesf or Sulfhydryl Amino Acidmentioning

confidence: 99%

“…Qian et al introduced DNBS-protected 8-hydroxyquinoline moiety linked throught he 2-postion of the quinoline moiety to the meso position of BODIPY to give fluorescent probe 25 for the detection of biothiols ( Figure 6). [60] The probe wass uccessfully used for imaging of biothiols in HepG2 cellsa nd zebrafish.…”

Section: Probesf or Sulfhydryl Amino Acidmentioning

confidence: 99%

BODIPY‐Based Fluorescent Probes for Biothiols

Zhang

Wang

et al. 2020

Chemistry A European J

191

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“…Up to now, there are several analytical methods for detecting Cys including capillary electrophoresis, mass spectrometry, electrochemical analysis, colorimetric assay, high-performance liquid chromatography, and so on. − However, these detection methods are complex for sample pretreatment and long time-consuming and have serious background interference. By comparison, a fluorescent probe has been considered as a promising tool because of its simple implementation, rapid response, low cost, and nondestructive analysis. − In recent years, a great number of fluorescent probes for Cys detection have been developed based on diverse fluorescent scaffolds including coumarin, fluorescein, naphthalimide, pyrene, flavonol, BODIPY dye, and imidazo [1,5-α]pyridine. − However, in spite of prominent photophysical properties, these fluorescent scaffolds are often limited by short emission wavelength and small Stokes shift, which restrict their detection performances in biological systems because of the interference from self-absorption and background auto-fluorescence. Moreover, a certain portion of these reported fluorescent probes are unqualified for discriminating Cys from glutathione (GSH) and homocysteine (HCy) as a result of their extremely similar structures and activities .…”

Section: Introductionmentioning

confidence: 99%

Novel Bis-Camphor-Derived Colorimetric and Fluorescent Probe for Rapid and Visual Detection of Cysteine and Its Versatile Applications in Food Analysis and Biological Imaging

Wang

Zhang

Liang

et al. 2022

J. Agric. Food Chem.

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A new colorimetric and fluorescent turn-on probe named 2,4-bis(camphor-3-methylene)phenylacrylate (BCP−Cys) was designed for highly sensitive and specific monitoring of cysteine (Cys). The probe BCP−Cys was strategically constructed by employing a new bis-camphor-derived scaffold (BCP-OH) as the fluorophore and an acrylate group as the recognition site and fluorescence quencher. The acrylate group of BCP−Cys could be exclusively cleaved by Cys and release the fluorophore BCP-OH, thereby causing a significantly enhanced red fluorescence and a naked-eye colorimetric change from colorless to yellow. The probe BCP−Cys exhibited promising sensing performances for Cys including large Stokes shift (184 nm), fast response time (<1 min), wide linear range (0−100 nM), and low detection limit (0.0728 μM). Moreover, the probe BCP−Cys could be utilized as a powerful tool for real-time determination of Cys levels within different food samples, such as onion, cabbage, broccoli, garlic, cauliflower, and bamboo sprout. In addition, this probe was also capable of imaging endogenous and exogenous Cys in living cells.

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“…37,38 Fluorescein in 0.1 M sodium hydroxide solution ( ϕ r = 0.95) was selected as the reference 40 for testing the fluorescence quantum yield. 41 The detailed methods of these two experiments were described in the ESI †…”

Section: Methodsmentioning

confidence: 99%