Water-soluble Hantzsch ester as switch-on fluorescent probe for efficiently detecting nitric oxide

Wang, Huili; Liu, Fu-Tao; Ding, Aixiang; Ma, Sufang; Liu, Lin; Lu, Zhong‐Lin

doi:10.1016/j.saa.2016.06.014

Cited by 25 publications

(5 citation statements)

References 46 publications

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“…[10] Till now, a variety of fluorescent probes involving synthetic organic molecules, polymers, metal complexes, or nanoparticles have been reported for the detection of NO. [11][12][13][14][15] Most of the organic molecule-based probes have O-diamine or aromatic primary amine as a functionality coupled to a fluorophore. [10,[16][17][18] These probes show fluorescence signals towards NO either by deamination of monoamine moiety or the formation of triazoles from diamine moiety.…”

Section: Introductionmentioning

confidence: 99%

“…Among these techniques, the fluorescence‐based detection technique so far outweighs the other techniques as it satisfies almost all the requirements such as biocompatibility, non‐toxicity, specificity, fast, direct, and non‐invasive detection [10] . Till now, a variety of fluorescent probes involving synthetic organic molecules, polymers, metal complexes, or nanoparticles have been reported for the detection of NO [11–15] . Most of the organic molecule‐based probes have O ‐diamine or aromatic primary amine as a functionality coupled to a fluorophore [10,16–18] .…”

Section: Introductionmentioning

confidence: 99%

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Aggregation‐Induced Quenching of Carbon Dots for Detection of Nitric oxide

et al. 2022

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This study reports the synthesis of three types of carbon dots (CDs) prepared using citric acid as a carbon source and three different biomolecules (L‐serine, L‐threonine, and adenine) individually as an amine source. The obtained nanomaterials were characterized by powder XRD, TEM, FTIR, 13C NMR, distortionless enhancement by polarization transfer using a 135‐degree decoupler pulse (DEPT 135), dynamic light scattering (DLS), and Small‐Angle X‐ray Scattering (SAXS) techniques. After ensuring the formation of desired structures, prepared CDs were used for exploring the detection capabilities of different reactive nitrogen species and reactive oxygen species. Following the screening of their detection capabilities specifically for nitric oxide, different sensing parameters viz the limit of detection, quenching constant, and interferences were evaluated. Among the synthesized CDs, the lowest detection limit of 0.1 μM was determined for the serine‐derived dots while 0.12 and 0.19 μM was obtained for adenine and threonine‐derived dots, respectively. Eventually, a possible sensing mechanism for the detection of NO by the prepared nanomaterials is proposed.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Aggregation‐Induced Quenching of Carbon Dots for Detection of Nitric oxide

et al. 2022

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“…Such transformation causes significant growth of fluorescence quantum yield by blocking the photoinduced electron transfer [ 7 , 8 ]. To this day, a wide range of NO probes utilizing the abovementioned principle have been reported with BODIPY [ 9 ], coumarin [ 10 , 11 ], fluorescein [ 12 ], rhodamine [ 13 , 14 ], and other fluorophores. Several commercially available substances, such as DAN, DAR, or DAF ( Figure 1 ), have found wide applications for the detection and imaging of NO in living cells [ 15 ].…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of New Acridone-Based Nitric Oxide Fluorescent Probe

et al. 2021

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Nitric oxide (NO) is an important signaling molecule involved in a wide range of physiological and pathological processes. Fluorescent imaging is a useful tool for monitoring NO concentration, which could be essential in various biological and biochemical studies. Here, we report the design of a novel small-molecule fluorescent probe based on 9(10H)acridone moiety for nitric oxide sensing. 7,8-Diamino-4-carboxy-10-methyl-9(10H)acridone reacts with NO in aqueous media in the presence of O2, yielding a corresponding triazole derivative with fivefold increased fluorescence intensity. The probe was shown to be capable of nitric oxide sensing in living Jurkat cells.

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“…Among many detection methods reported, fluorescence imaging occupies a very advantageous position in the detection of biological species due to its superiority of convenient use, noninvasive detection, real-time visualization, and low cost. , So far, a number of fluorescent probes have been developed for the detection of NO. , These probes are basically constructed by linking a fluorophore at a certain optical window to a recognition moiety, which specifically reacts with NO under physiological conditions. The reported reactions include o -phenylenediamine (OPD) cyclization, − dihydropyridine (DHP) oxidation, − metal coordination, − etc. − However, the inherent defects of these reactions with NO have greatly limited the biological applications of these probes. For example, fluorescent probes based on OPD and DHP can be oxidized by biologically active species like ascorbic acid (AA), dehydroascorbic acid (DHA), and methylglyoxal (MGO) and produce false positive signals .…”

mentioning

confidence: 99%

Development of a Facile Lysosome-Targeting Nitric Oxide Fluorescent Probe Based on a Novel Reaction Mechanism

et al. 2023

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As a ubiquitous signal molecule in biosystems, nitric oxide (NO) plays an important role in many physiological and pathological processes. Therefore, it is of great significance to detect NO in organisms for the study of related diseases. Currently, a variety of NO fluorescent probes have been developed based on several types of reaction mechanisms. However, due to the inherent disadvantages of these reactions, like potential interference by biologically related species, there is a great need to develop NO probes based on the new reactions. Herein, we report our discovery of the unprecedented reaction between a widely used fluorophore of 4-(dicyanomethylene)-2-methyl-6-(p-(dimethylamino)styryl)-4H-pyran (DCM) and NO under mild conditions with fluorescence changes. By the analysis of the structure of the product, we proved that DCM undergoes a particular nitration process and proposed a mechanism for fluorescence changes due to the interruption of the intramolecular charge transfer (ICT) process of DCM by the nitrated product of DCM-NO 2 . Based on the understanding of this specific reaction, we then easily constructed our lysosomal-localized NO fluorescent probe LysoNO-DCM by linking DCM and a morpholine group, a lysosomal-targeting functional group. LysoNO-DCM exhibits excellent selectivity, sensitivity, pH stability, and outstanding lysosome localization ability with Pearson’s colocalization coefficient of up to 0.92 and is successfully applied to the imaging of exogenous and endogenous NO in cells and zebrafish. Our studies expand design methods for NO fluorescence probes based on the novel reaction mechanism and will benefit the studies of this signaling molecule.

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Water-soluble Hantzsch ester as switch-on fluorescent probe for efficiently detecting nitric oxide

Cited by 25 publications

References 46 publications

Aggregation‐Induced Quenching of Carbon Dots for Detection of Nitric oxide

Aggregation‐Induced Quenching of Carbon Dots for Detection of Nitric oxide

Design and Synthesis of New Acridone-Based Nitric Oxide Fluorescent Probe

Development of a Facile Lysosome-Targeting Nitric Oxide Fluorescent Probe Based on a Novel Reaction Mechanism

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