A dual-analytes responsive fluorescent probe for discriminative detection of ClO− and N2H4 in living cells

Zhu, Beitong; Wu, Xiaoli; Rodrigues, João; Hu, Xiang‐Guo; Sheng, Ruilong; Bao, Guirong

doi:10.1016/j.saa.2020.118953

Cited by 19 publications

(4 citation statements)

References 34 publications

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“…According to a reported method, compound 2 was prepared from compound 1 . [ 31,32 ] Compound 1 (0.67 g, 1.8 mM), anhydrous CH 3 OH (35 ml) and diethyl malonate (0.32 g, 2 mM) were added to a 100‐ml round‐bottomed flask. Then, piperidine (50 μl) and glacial CH 3 COOH (25 μl) were added, stirred for 30 min and then refluxed for 16 h. The final product was purified by silica gel chromatography using CH 2 Cl 2 :ethyl acetate (30:1, v/v) as the eluent.…”

Section: Methodsmentioning

confidence: 99%

A highly sensitive ratiometric fluorescent probe based on fluorescein coumarin for detecting hydrazine in actual water and biological samples

Luo

Zhou

et al. 2023

Luminescence

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Hydrazine (N 2 H 4 ) is a highly toxic and harmful chemical reagent. Fluorescent probes are simple and efficient tools for sensitive monitoring of N 2 H 4 enrichment in the environment, humans, animals, and plants. In this work, a ratiometric fluorescent probe (FP-1) containing coumarin was used for hydrazine detection. The proposed FP-1 probe had a linear detection range of 0-250 μM and a limit of detection (LOD) of 0.059 μM (1.89 ppb). A large red Stokes shift was observed in fluorescence and UV-vis absorption spectra due to the hydrolysis of ester bonds between FP-1 and hydrazine. The hydrazine detection mechanism of FP-1 was also investigated using density functional theory (DFT) calculations. Finally, FP-1 could sensitively and selectively monitor hydrazine in actual water samples and BEAS-2B cells. Therefore, it has great application potential in environmental monitoring and disease diagnosis.

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Section: Methodsmentioning

confidence: 99%

A highly sensitive ratiometric fluorescent probe based on fluorescein coumarin for detecting hydrazine in actual water and biological samples

Luo

Zhou

et al. 2023

Luminescence

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“…Fluorescence-based methods, meanwhile, have been broadly applied to verify different analytes, including metal ions, anions, and biomolecules, because of their simple operation, high sensitivity, good selectivity, non-invasiveness, and good biocompatibility [15,16]. Several selective N 2 H 4 fluorescent probes (FPs) with various recognition mechanisms [17,18], including selective deprotection [19][20][21][22]; reaction with diketones to form rings [23,24]; reactions with aromatic aldehydes, dicyanovinyl, or monocyanovinyl to form hydrazones [25][26][27][28][29]; cleavage of carbon-carbon double bonds Molecules 2023, 28, 7629 2 of 13 to form hydrazones [30,31]; and hydrazine-induced ring-opening reactions [32,33] have been reported. However, many of these probes still possess disadvantages, such as their complex synthesis, narrow pH range, low sensitivity, and small detection range, which have limited their application.…”

Section: Introductionmentioning

confidence: 99%

“…(FPs) with various recognition mechanisms [17,18], including selective deprotection [19][20][21][22]; reaction with diketones to form rings [23,24]; reactions with aromatic aldehydes, dicyanovinyl, or monocyanovinyl to form hydrazones [25][26][27][28][29]; cleavage of carbon-carbon double bonds to form hydrazones [30,31]; and hydrazine-induced ring-opening reactions [32,33] have been reported. However, many of these probes still possess disadvantages, such as their complex synthesis, narrow pH range, low sensitivity, and small detection range, which have limited their application.…”

Section: Introductionmentioning

confidence: 99%

A Ratiometric Fluorescent Probe for N2H4 Having a Large Detection Range Based upon Coumarin with Multiple Applications

Sheng,

Sun,

Zhang

et al. 2023

Molecules

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Although hydrazine (N2H4) is a versatile chemical used in many applications, it is toxic, and its leakage may pose a threat to both human health and environments. Consequently, the monitoring of N2H4 is significant. This study reports a one-step synthesis for coumarin-based ratiometric fluorescent probe (FP) CHAC, with acetyl as the recognition group. Selected deprotection of the acetyl group via N2H4 released the coumarin fluorophore, which recovered the intramolecular charge transfer process, which caused a prominent fluorescent, ratiometric response. CHAC demonstrated the advantages of high selectivity, a strong capacity for anti-interference, a low limit of detection (LOD) (0.16 μM), a large linear detection range (0–500 μM), and a wide effective pH interval (6–12) in N2H4 detection. Furthermore, the probe enabled quantitative N2H4 verifications in environmental water specimens in addition to qualitative detection of N2H4 in various soils and of gaseous N2H4. Finally, the probe ratiometrically monitored N2H4 in living cells having low cytotoxicity.

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“…One kind simultaneously introduces S=O and C=C bonds to the molecule of the fluorescence probe because N 2 H 4 can induce C=C double bond cleavage and ClO − can induced sulfur oxidation respectively. According to this, Li's team synthesized a carbazole derivative probe for detecting N 2 H 4 and ClO − in 2020 [41]. Hu's team designed a fluorescent sensor with two action sites for the separate detection of N 2 H 4 and ClO − in 2021 [42].…”

Section: Introductionmentioning

confidence: 99%

Point-of-Care and Dual-Response Detection of Hydrazine/Hypochlorite-Based on a Smart Hydrogel Sensor and Applications in Information Security and Bioimaging

Zhang

et al. 2023

Molecules

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A novel dual-response fluorescence probe (XBT-CN) was developed by using a fluorescence priming strategy for quantitative monitoring and visualization of hydrazine (N2H4) and hypochlorite (ClO−). With the addition of N2H4/ClO−, the cleavage reaction of C=C bond initiated by N2H4/ClO− was transformed into corresponding hydrazone and aldehyde derivatives, inducing the probe XBT-CN appeared a fluorescence “off-on” response, which was verified by DFT calculation. HRMS spectra were also conducted to confirm the sensitive mechanism of XBT-CN to N2H4 and ClO−. The probe XBT-CN had an obvious fluorescence response to N2H4 and ClO−, which caused a significant color change in unprotected eyes. In addition, the detection limits of XBT-CN for N2H4 and ClO− were 27 nM and 34 nM, respectively. Interference tests showed that other competitive analytes could hardly interfere with the detection of N2H4 and ClO− in a complex environment. In order to realize the point-of-care detection of N2H4 and ClO−, an XBT-CN@hydrogel test kit combined with a portable smartphone was developed. Furthermore, the portable test kit has been applied to the detection of N2H4 and ClO− in a real-world environment and food samples, and a series of good results have been achieved. Attractively, we demonstrated that XBT-CN@hydrogel was successfully applied as an encryption ink in the field of information security. Finally, the probe can also be used to monitor and distinguish N2H4 and ClO− in living cells, exhibiting excellent biocompatibility and low cytotoxicity.

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A dual-analytes responsive fluorescent probe for discriminative detection of ClO− and N2H4 in living cells

Cited by 19 publications

References 34 publications

A highly sensitive ratiometric fluorescent probe based on fluorescein coumarin for detecting hydrazine in actual water and biological samples

A highly sensitive ratiometric fluorescent probe based on fluorescein coumarin for detecting hydrazine in actual water and biological samples

A Ratiometric Fluorescent Probe for N2H4 Having a Large Detection Range Based upon Coumarin with Multiple Applications

Point-of-Care and Dual-Response Detection of Hydrazine/Hypochlorite-Based on a Smart Hydrogel Sensor and Applications in Information Security and Bioimaging

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