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1.
J Am Chem Soc ; 142(14): 6777-6785, 2020 04 08.
Artigo em Inglês | MEDLINE | ID: mdl-32182060

RESUMO

Photoinduced electron transfer (PET) is one of the most important mechanisms for developing fluorescent probes and biosensors. Quantitative prediction of the quantum yields of these probes and sensors is crucial to accelerate the rational development of novel PET-based functional materials. Herein, we developed a general descriptor (ΔE) for predicting the quantum yield of PET probes, with a threshold value of ∼0.6 eV. When ΔE < ∼0.6 eV, the quantum yield is low (mostly <2%) due to the substantial activation of PET in polar environments; when ΔE > ∼0.6 eV, the quantum yield is high because of the inhibition of PET. This simple yet effective descriptor is applicable to a wide range of fluorophores, such as BODIPY, fluorescein, rhodamine, and Si-rhodamine. This ΔE descriptor enables us not only to establish new applications for existing PET probes but also to quantitatively design novel PET-based fluorophores for wash-free bioimaging and AIEgen development.

2.
Anal Chem ; 91(2): 1472-1478, 2019 01 15.
Artigo em Inglês | MEDLINE | ID: mdl-30482012

RESUMO

Although some progress has been made in distinguishing the detection of biothiols, NIR biothiol fluorescent probes for simultaneously distinguishing detection of Cys, Hcy, and GSH in vivo have not been reported. The design of these probes involves the introduction of NIR fluorophores and multiple binding sites; thus, the integrated design of probes remains a challenge. Although Cys, Hcy, and GSH have common functional groups, a sulfydryl group and an amino group, due to their differences in spatial structure, they may react with multiple binding site probes to produce different reaction products in different bonding mechanisms, resulting in different colors and fluorescent signal changes of the system. Therefore, multiple binding site fluorescent probes can realize their discrimination detection. For an NIR fluorescent probe, it is easier to realize in vivo imaging to promote the research of biothiols in clinical diagnosis. In our work, not only were multiple binding sites constructed in the compound but also NIR fluorophores were introduced. This enables the probe to not only efficiently distinguish detection of Cys/Hcy and GSH but also achieve fluorescence imaging in vivo. We believe this result is a milestone in the discrimination detection of biothiols.


Assuntos
Colorimetria/métodos , Cisteína/metabolismo , Corantes Fluorescentes/química , Glutationa/metabolismo , Homocisteína/metabolismo , Raios Infravermelhos , Imagem Óptica , Animais , Sítios de Ligação , Cisteína/química , Glutationa/química , Células Hep G2 , Homocisteína/química , Humanos , Limite de Detecção , Camundongos
3.
Angew Chem Int Ed Engl ; 56(43): 13188-13198, 2017 10 16.
Artigo em Inglês | MEDLINE | ID: mdl-28703457

RESUMO

Biothiols such as cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) play crucial roles in maintaining redox homeostasis in biological systems. This Minireview summarizes the most significant current challenges in the field of thiol-reactive probes for biomedical research and diagnostics, emphasizing the needs and opportunities that have been under-investigated by chemists in the selective probe and sensor field. Progress on multiple binding site probes to distinguish Cys, Hcy, and GSH is highlighted as a creative new direction in the field that can enable simultaneous, accurate ratiometric monitoring. New probe design strategies and researcher priorities can better help address current challenges, including the monitoring of disease states such as autism and chronic diseases involving oxidative stress that are characterized by divergent levels of GSH, Cys, and Hcy.

4.
Spectrochim Acta A Mol Biomol Spectrosc ; 223: 117350, 2019 Dec 05.
Artigo em Inglês | MEDLINE | ID: mdl-31306961

RESUMO

The intracellular pH has a significant effect on several essential biological processes such as material transfer, enzymatic action, cell apoptosis et al. Thus, it is necessary to monitor pH fluctuation in living cells. Here, we designed a near-infrared ratiometric fluorescence probe for pH detection. The spectroscopic responses of probe to pH variations were investigated in CH3OH/PBS (v/v, 1:1) mixed solution at different pH values. The experimental results showed that the probe is sensitive to acidity, and the pKa of probe is calculated to be 4.85. When the pH was decreased from 9.0 to 1.0, the color of probe solution change from purple to yellow was found by naked eye. Moreover, the probe can be a practical tool for assessing cellular pH by cell imaging.


Assuntos
Benzopiranos/química , Corantes Fluorescentes/química , Indóis/química , Nitrocompostos/química , Espectroscopia de Luz Próxima ao Infravermelho , Células A549 , Sobrevivência Celular , Corantes Fluorescentes/síntese química , Humanos , Concentração de Íons de Hidrogênio , Espectroscopia de Prótons por Ressonância Magnética , Solventes , Espectrometria de Fluorescência , Espectrofotometria Ultravioleta , Fatores de Tempo
5.
Artigo em Inglês | MEDLINE | ID: mdl-27214272

RESUMO

In this work, two high selective and sensitive fluorescent probes for ClO(-), 7-Hydroxycoumarin and 4-Hydroxycoumarin were designed. The reaction mechanism that we speculated was the oxidized ring opening reaction and hydrolysis. The detection could be realized in quasi-aqueous phase and the detection limits of probe [7] and probe [4] for ClO(-) were found to be 56.8nM and 70.5nM. Furthermore, the probes can be used to cell imagings.


Assuntos
4-Hidroxicumarinas/química , Corantes Fluorescentes/química , Ácido Hipocloroso/análise , Umbeliferonas/química , Células Hep G2 , Humanos , Hidrólise , Limite de Detecção , Microscopia de Fluorescência/métodos , Imagem Óptica/métodos , Oxirredução , Espectrometria de Fluorescência/métodos , Espectrofotometria Ultravioleta/métodos
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