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•Production and functions of Cys in biological systems were introduced.•Recent development of bioanalytical probes for Cys detection was reviewed.•Sensing mechanisms in designing of ...Cys-specific probes were highlighted.•Performance of probes in the discrimination and detection of Cys were discussed.•Challenges and research perspectives for the development of bioanalytical probes for Cys detection were outlined.
Cysteine (Cys), one of three endogenous biothiols, is involved in a variety of biological processes, such as protein and peptide biosynthesis, enzyme active sites and cofactors, and redox balance regulations. An imbalance in the measured levels of Cys, against normative levels of Cys, is implicated in a series of human diseases, so that Cys has been recognized as one of the most important biomarkers in early diagnosis and treatment as well as the monitoring of the stage of diseases. Rapid and accurate quantification of Cys within complex biological systems enables in the advance of future personalized diagnostics and therapies. In the past few years, many Cys-responsive luminescence probes have been developed for the quantitative detection of Cys; studies where the full prepared probe is validifed by investigations in vitro and in vivo. In this review, advances in the development of Cys-responsive luminescence probes, including molecular probes and nanoprobes, are included and discussed in sections corresponding to their response mechanisms. The structure of molecular probes are included; performances of various bioanalytical probes in Cys detection are compared in aspects of excitation/emission wavelengths, detection limits and dynamic ranges, as well as experimental conditions for practical applications. Current challenges and future research directions for designing and preparing new Cys-selective probes are proposed.
•Ln2O2S:Tb3+ and Ln2O2S:Eu3+ were prepared by a thermolysis method and modified by polyethylenimine.•La2O2S: Tb3+ and La2O2S: Eu3+ were used to construct fluorescence resonance energy transfer ...systems with Au nanoparticles respectively.•Determination of cysteine with high selectivity and sensitivity.
Biothiols are biologically important targets because their transport and metabolism are closely related to the activities of many proteins and biological enzymes. In this paper, a kind of biological probe based on the fluorescence resonance energy transfer between lanthanide oxysulfide and gold nanoparticles was developed for the detection of cysteine. Ln2O2S:Tb3+ and Ln2O2S:Eu3+ nanoparticles were prepared by a thermolysis method. The as-prepared fluorescent nanoparticles were modified by polyethylenimine ligand exchange to increase their hydrophilicity. Then, Au nanoparticles were added to form fluorescence resonance energy transfer systems in which Au NPs and La2O2S:Ln3+ act as the acceptor and donor, respectively. Among the Ln2O2S:Tb3+ and Ln2O2S:Eu3+ systems, the cysteine content and fluorescence intensity showed good proportional proportionality, with detection limits of 6.75 nM and 14.09 nM in the range of 50∼1500 nM, respectively. The results of anti-interference experiments showed that this biological probe is highly selective for cysteine detection.
In this paper, a kind of biological probe based on the fluorescence resonance energy transfer between lanthanide oxysulfide and gold nanoparticles was developed for the detection of cysteine. Ln2O2S:Tb3+ and Ln2O2S:Eu3+ nanoparticles were prepared by a thermolysis method. The as-prepared fluorescent nanoparticles were modified by polyethylenimine ligand exchange to increase their hydrophilicity. Then, Au nanoparticles were added to form fluorescence resonance energy transfer systems in which Au NPs and La2O2S:Ln3+ act as the acceptor and donor, respectively. Among the Ln2O2S:Tb3+ and Ln2O2S:Eu3+ systems, the cysteine content and fluorescence intensity showed good proportional proportionality, with detection limits of 6.75 nM and 14.09 nM in the range of 50∼1500 nM, respectively. The results of anti-interference experiments showed that this biological probe is highly selective for cysteine detection.
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•A novel near-infrared fluorescent probe (2-OH-TCF-NBD) for the detection and discrimination of Cys/Hcy, GSH/H2S was developed.•The detection limits of the probe for Cys, Hcy, GSH and ...H2S were determined to be 0.029, 0.020, 0.29, and 0.20 μM, respectively.•The possible response mechanism was also proposed and validated by HPLC analysis of the reaction process.
A novel dual-emission responsive near-infrared fluorescent probe (2-OH-TCF-NBD) for the detection and discrimination of Cys/Hcy, GSH/H2S was developed on the basis of the conjugation of a tricyanofuran-based fluorophore (2-OH-TCF) and 4-chloro-7-nitrobenzofurazan (NBD-Cl). When the probe was added to the Cys/Hcy solution, it resulted in significant fluorescence enhancement at both 527 and 630 nm, while GSH/H2S induced major fluorescence emission only at 630 nm. The detection limits for Cys, Hcy, GSH, and H2S were determined to be 0.029, 0.020, 0.29, and 0.20 μM, respectively. Furthermore, the probe demonstrated some merits including easy preparation, rapid response time, and good anti-interference ability. The possible response mechanism was also proposed and validated by HPLC analysis of the reaction process. Therefore, the probe can be a potential tool for discriminating the detection of Cys/Hcy and GSH/H2S under physiological conditions.
Biothiols, a vital branch of reactive sulfur species (RSS) family, are indispensable in human physiology. However, the exact functional roles of each biothiol involved in complicated physiological ...activities are still not fully clarified. A critical barrier is a lack of robust molecular tools which can simultaneously visualize different biothiols with distinct emission signals. Herein, the first lysosome-targetable fluorescent probe, Lyso-RC, which could respond to Cys/Hcy, GSH, and H
S with different sets of signal patterns was developed. Lyso-RC responds to Cys/Hcy, GSH, and H
S with the fluorescence signal patterns of blue-red, green-red, and red, respectively. Significantly, Lyso-RC is capable of discriminating lysosomal Cys/Hcy, GSH, and H
S in HeLa cells.
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.
Probing biothiols: Cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) play crucial roles in human health. There are very few molecular probes and abiotic sensors that can simultaneously discriminate among biothiols. Recent progress on probes featuring multiple binding sites to distinguish Cys, Hcy, and GSH is summarized, and a variety of unmet critical needs and opportunities for chemists in the thiol probe field are discussed.
Biothiols derivatives including cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) play critical roles in maintaining physiological and pathological processes. Developing optical probes for ...biothiols has attracted great attention owing to their excellent properties like high sensitivity, fast response times and invasive on-time imaging. However, discrimination of Cys, Hcy, and GSH present great challengings due to the similar structures and reactivities of these thiols. This review focuses on the design of fluorescent and colorimetric probes for biothiol detection. Herein, we classify the fluorescent probes for detection biothiols based on various fluorophores like BODIPY, rhodamine, tetraphenylethylene, coumarin, naphthalimide and polymethine. The sensing mechanisms such as Michael addition, cyclization with aldehydes, conjugate addition-cyclization with acrylates, native chemical ligation, cleavage of sulfonamide and sulfonate esters were also included in this review. We hope that much more biothiols fluorescent probes could be explored through the inspiration of this review.
•Summarize the recent biothiols probes based on various fluorophores like BODIPY, rhodamine and coumarin et al.•Summarize the detection mechanisms of biothiols probes.•Analyze the designing strategies of near-infrared biothiols probes.•Provide the application examples in living cells, organism, and mouse.
Simultaneous detection of two or more biothiols by using fluorescent methods is in particular importance for biological research and disease diagnosis. Because (1) the variation of one biothiol level ...under specific cellular metabolism may lead to the change of another biothiol, and (2) several diseases such as Alzheimer's disease associate with joint action from two or more biothiols. In this paper, we provide an overview of the fluorescent probes with multiple channels that have been applied to simultaneous detection of biothiols. The present review highlights the basic characteristics of probes with multi-channel in the respect of design principle, photophysical process, sensing mechanism, sensing performance, and bioapplications. This review aims to offer a comprehensive summary for researchers to inspire new probe design, and also push forward the advancement of simultaneous detection of biothiols based on multi-channel probes.
•The fluorescent probes with multiple channels for simultaneous detection of biothiols are reviewed.•The necessity of simultaneous detection of biothiols is introduced.•The design mechanism of fluorescent probes with multiple channels has been discussed and categorized.•The overall sensing performances and bioapplications of probes are summarized.
A long-wavelength fluorescent probe NR-CY was developed for simultaneous identification of cysteine/glutathione and sulphide by combining the derivative of Nile red with 7-nitrobenzofurazan. The ...response of NR-CY to thiols is regulated by intramolecular charge transfer and photoinduced electron transfer mechanisms. For sulphide at 560 nm, cysteine at 475 nm and glutathione at 425 nm, different absorbance increases can be observed. NR-CY can detect cysteine at fluorescence emission 543 nm and distinguish sulphide from other analytes by kinetic experiments at 636 nm. The probe showed a rapid response to these thiols (cysteine was 90 s and sulphide was 30 s). In addition, NR-CY has been successfully applied to live MCF-7 cell imaging.
A long-wavelength fluorescent probe NR-CY was developed for simultaneous identification of cysteine/glutathione and sulphide by combining the derivative of Nile red with 7-nitrobenzofurazan. The response of NR-CY to thiols is regulated by intramolecular charge transfer and photoinduced electron transfer mechanisms. For sulphide at 560 nm, cysteine at 475 nm and glutathione at 425 nm, different absorbance increases can be observed. NR-CY can detect cysteine at fluorescence emission 543 nm and distinguish sulphide from other analytes by kinetic experiments at 636 nm. The probe showed a rapid response to these thiols (cysteine was 90 s and sulphide was 30 s). In addition, NR-CY has been successfully applied to live MCF-7 cell imaging. Display omitted
•A new long-wavelength-emitting fluorescent turn-on probe NR-CY for simultaneous determination of biothiols was developed.•This probe is easily prepared from readily available inexpensive reagents.•Probe shows rapid response (90 s for Cys, 30 s for H2S) to these thiols.•The first PET and ICT-based fluorescent probe is suitable for biological imaging applications.
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.
Biothiol probes: The development of BODIPY‐based fluorescent probes for the detection of biothiols, preferable detection of individual biothiols, as well as simultaneous discrimination among Cys, Hcy, and reduced glutathione (GSH) is systematically summarized.
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