A near-infrared turn on fluorescent probe for cysteine based on organic nanoparticles

Wang, Lingyun; Zhuo, Shaochun; Tang, Hao; Cao, Derong

doi:10.1016/j.snb.2018.09.038

Cited by 17 publications

(3 citation statements)

References 54 publications

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“…A21 detects Cys as a NIR turn-on sensor at 654 nM at a LOD of 53.1 nM. 97 Xing's group also designed FON A22 with sugar moieties to improve solubility and ratiometric detection. FON A22 undergoes two consecutive Michael reactions with Cys.…”

Section: Sensing Of Biomoleculesmentioning

confidence: 99%

Recent advances in aggregation-induced emission (AIE)-based chemosensors for the detection of organic small molecules

Chua,

Hui,

Chin

et al. 2023

Mater. Chem. Front.

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Section: Sensing Of Biomoleculesmentioning

confidence: 99%

Recent advances in aggregation-induced emission (AIE)-based chemosensors for the detection of organic small molecules

Chua,

Hui,

Chin

et al. 2023

Mater. Chem. Front.

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“…Using diketopyrrolopyrrole (DPP) as the backbone, our group has conducted a lot of investigations on fluorescent materials. − DPP, on the other hand, is an ACQ molecule; therefore, it must be modified to have AIE qualities. Organic two-photon materials, − fluorescent probes, − humidity sensors, , and many other sectors have benefited from the development of DPP derivatives with AIE capabilities. These AIE molecules were mainly designed to take advantage of traditional AIEgens such as triphenylamine, tetraphenylene, and anthrone in a restriction of intramolecular rotation mechanism.…”

Section: Introductionmentioning

confidence: 99%

Exactly Opposite Luminescence Behaviors of Aggregated Diketopyrrolopyrrole Derivatives Depending on Different Molecular Conformations

Wang

2022

J. Phys. Chem. C

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A new diketopyrrolopyrrole (DPP) derivative, DPPA-4-Caz, with a distorted molecular conformation has been synthesized, exhibiting aggregation-induced emission (AIE) and mechanofluorochromic (MFC) properties, with a solid-state fluorescence quantum yield of 0.286 and a 37 nm redshift in emission upon grinding. This compound can exhibit either AIE or aggregation-caused quenching effect, and these totally contradictory phenomena are attributed to its two polymorphic forms correspondingly. When the molecule bending is S-type, a loose intermolecular packing pattern is formed in the aggregation state, where the aromatic rings’ rotation is constrained, leading to luminescence. When bending is Z-type, the molecules are parallel-stacked and quench upon aggregation. Five other compounds with similar structures were also synthesized in order to investigate the effects of substituents and alkyl chain length on the properties of AIE and MFC. The results show that the electronic effect of the substituent plays a major role in the production of AIE, while the alkyl chain length has a greater effect on MFC properties.

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“…Despite significant advances, a great number of these fluorescent probes exhibited absorption and emission in the ultraviolet or visible‐light range, which may be strongly interfered by biological autofluorescence [13–18] . On the other hand, near‐infrared region (650–900 nm) fluorescent probes emissive have been developed for biothiols in favour of the advantages of minimal damage, less light scattering, deep tissue penetration, and low background interference [28–48] …”

Section: Introductionmentioning

confidence: 99%

Detecting Cysteine in Bioimaging with a Near‐Infrared Probe Based on a Novel Fluorescence Quenching Mechanism

Tao

Zhang

et al. 2020

ChemBioChem

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Near-infrared (NIR) fluorescent probes are very significant for detecting cysteine in biological systems. Herein, we report a highly selective and sensitive NIR turn-on fluorescent probe (BDP-NIR) based on BODIPY with large Stokes shift (105 nm) for detecting Cys. We clarified the sensing mechanism based on the different thiol-induced S N Ar substitution/rearrangement reaction of the probe with cysteine and homocysteine/ glutathione, which leads to the corresponding amino-and thiol-BODIPY dyes with distinct photophysical properties. Moreover , a novel mechanism of fluorescence quenching was demonstrated by density functional theory calculation. The reason for the fluorescence quenching of the probe might be intersystem crossing (from singlet to triplet excited state). Moreover, BDP-NIR had a high linear dynamic range of 0-500 μM, which was promising for detecting cysteine quantificationally. Significantly, BDP-NIR was capable of sensing endogenous cysteine in living cells and in vivo.

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A near-infrared turn on fluorescent probe for cysteine based on organic nanoparticles

Cited by 17 publications

References 54 publications

Recent advances in aggregation-induced emission (AIE)-based chemosensors for the detection of organic small molecules

Recent advances in aggregation-induced emission (AIE)-based chemosensors for the detection of organic small molecules

Exactly Opposite Luminescence Behaviors of Aggregated Diketopyrrolopyrrole Derivatives Depending on Different Molecular Conformations

Detecting Cysteine in Bioimaging with a Near‐Infrared Probe Based on a Novel Fluorescence Quenching Mechanism

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