选择性检测谷胱甘肽的荧光探针

本文设计合成了一种基于BODIPY衍生物选择性检测谷胱甘肽的比率式荧光探针1。荧光探针1中BODIPY的3位连有苯乙炔基团,5位连有咪唑盐离去基团,利用其与谷胱甘肽和半胱氨酸反应机理的不同实现了对谷胱甘肽的选择性检测。紫外可见吸收光谱和荧光光谱实验结果表明探针分子1与谷胱甘肽反应后的光谱发生明显红移,可以实现对谷胱甘肽的比率式检测。探针分子1对谷胱甘肽有极高的选择性,不受其它氨基酸尤其是半胱氨酸的干扰。荧光滴定实验表明探针分子1可实现对谷胱甘肽的定量检测,检测限为3.3×10-8 mol/L。探针分子成功地应用于活体细胞中检测谷胱甘肽。     

Single-fluorophore-based fluorescent probes enable dual-channel detection of Ag and Hg with high selectivity and sensitivity

A new type of fluorescent probe capable of detecting Ag⁺ and Hg²⁺ in two independent channels was developed in the present work. Specifically, in CH₃CN–MOPS mixed solvents with CH₃CN/MOPS ratio (v/v) of 15/85, this type of probe fluoresced weakly, and the addition of Ag⁺ remarkably induced fluorescence enhancement of the probe. In CH₃CN–MOPS mixed solvents with the percentage of CH₃CN increased up to 65%, the probe was highly fluorescent and addition of Hg²⁺ dramatically induced the fluorescence quenching. Thus, using such single-fluorophore-based probe and tuning the polarity of the mixed solvent, Ag⁺, and Hg²⁺ can be detected in independent channels with high selectivity and sensitivity. As a result, the mutual interference usually encountered in most cases of Ag⁺ and Hg²⁺ sensing owing to the similar fluorescence response that these two ions induced, can be effectively circumvented by using the probes developed herein.     

基于新型不对称BODIPY的GSH荧光探针

本文通过在BODIPY母体中引入丙二腈,设计合成了一个新型不对称BODIPY荧光染料CN-B-Cl。由于丙二腈强吸电作用,荧光染料CN-B-Cl具有优异的化学活性,能够与含巯基的化合物在buffer体系中迅速发生芳香亲核取代反应;与GSH反应生成硫取代BODIPY,而与Cys/Hcy反应生成氮取代BODIPY。根据不同取代基BODIPY化合物发光性能的不同,该荧光探针可选择性区分GSH与Cys/Hcy。     

A ratiometric near-infrared naphthalimide-based fluorescent probe with high sensitivity for detecting Fe2+ in vivo

Iron is one of the essential trace elements in the human body. It plays an important role in human biology and pathology. Deregulation of iron levels in cells is associated with disease development. In this work, we synthesized a novel near-infrared intramolecular charge transfer (ICT) based ratiometric fluorescent probe to detect Fe²⁺, by using naphthalimide and indole moieties as building blocks. Our work showed that the radiometric probe has excellent selectivity, sensitivity and rapid response. Moreover, we could successfully perform real-time monitoring of Fe²⁺ in HeLa cells and C. elegans.     

A ratiometric fluorescent probe for alkaline phosphatase with high sensitivity

Alkaline phosphatase(ALP)is one of essential biomarkers in mammalian tissue.Here we report a ratiometric probe for ALP,which is rationally designed and synthesized by employing ESIPT fluorophore N-(3-(benzo[d]thiazol-2-yl)-4-hydroxyphenyl)benzamide(BTHPB).The enzymatic dephosphorylation converts the probe to BTHPB,which exhibits a large spectral red-shift(120 nm),allowing extremely high sensitivity of ALP sensing at 0.004 mU/mL.The probe also shows excellent biocompatibility and has been applied for monitoring the endogenic ALP in living cells.     

A boronate-based ratiometric fluorescent probe for fast selective detection of peroxynitrite

Given that peroxynitrite (ONOO^?) is profoundly associated with health and diseases, a new fluorescent probe ABT was designed and synthesized for detection of ONOO^?. ABT manifested not only ratiometric fluorescence signals simultaneously in response to concentrations of ONOO^? (within 10?s), but high selectivity and sensitivity towards ONOO^? over other physiological relevant species (detection limit?=?26.3?nM). Moreover, ABT worked in a broad pH range with biological relevance. Thus, ABT could be used to quantitative detection of ONOO^? concentration and has the potential to efficiently monitor ONOO^? in living organisms.     

Small molecule fluorescent probes of protein vicinal dithiols

The vicinal dithiol motif is widely present in proteins, and is critical for proteins' structures and functions.In recent years, a variety of fluorescent probes with high specificity and outstanding optical properties for sensing protein vicinal dithiols have been developed. In this review, we summarized the fluorescent probes of protein vicinal dithiols in literature. These probes are classified into four types based on their acceptor sites, i.e., biarsenical probes, monoarsenical probes, dimaleimide probes and diacrylate probes.Through analyzing the properties of different probes, we expect that this review would help readers further understand the structural factors of these probes and provide the design strategy for novel fluorescent probes with improved properties.     

Small molecule fluorescent probes of protein vicinal dithiols

Small molecule fluorescent probes that recognize and label protein vicinal dithiols have been summarized according to their different acceptor sites. This review will provide the purposeful design strategy of novel probes for detecting vicinal dithiols.     

A ratiometric merocyanine-based fluorescent probe for detecting hydrazine in living cells and zebra fish

We developed a merocyanine-based fluorescent probe,NEPB,for tracing hydrazine(N_2 H_4) in a ratiometric manner with large Stokes shifts and long emission wavelength.The fluorescence color of probe NEPB changed from green to yellow upon addition of hydrazine.Probe NEPB displayed high selectivity and sensitivity to hydrazine in solution,and could ratiometrically monitor N_2 H_4 in living cells and zebrafish with low cytotoxicity.     

A colorimetric,ratiometric and water-soluble fluorescent probe for simultaneously sensing glutathione and cysteine/homocysteine

A chlorinated coumarin-aldehyde was developed as a colorimetric and ratiometric fluorescent probe for distinguishing glutathione (GSH), cystenine (Cys) and homocysteine (Hcy). The GSH-induced substitution-cyclization and Cys/Hcy-induced substitution-rearrangement cascades lead to the corresponding thiol-coumarin-iminium cation and amino-coumarin-aldehyde with distinct photophysical properties. The probe can be used to simultaneously detect GSH and Cys/Hcy by visual determination based on distinct different colors – red and pale-yellow in PBS buffer solution by two reaction sites. From the linear relationship of fluorescence intensity and biothiols concentrations, it was determined that the limits of detection for GSH, Hcy and Cys are 0.08, 0.09 and 0.18 μM, respectively. Furthermore, the probe was successfully used in living cell imaging with low cell toxicity.     

Reversible fluorescent probes for chemical and biological redox process

In this review, we discuss the recent progress of reversible fl uorescent probes for chemical and biological redox process according to different active centers.     

A chloroacetate based ratiometric fluorescent probe for cysteine detection in biosystems

The specific detection of cysteine (Cys) over homocysteine (Hcy), glutathione (GSH) and other amino acids is of great significance for studying its biological functions as well as for the diagnosis of related diseases. Chloroacetyl group was often used as a reaction site for cysteine fluorescent probes for its sensitivity and selectivity. However, high background fluorescence and low stability are common problems encountered by such probes. Here, four chloroacetyl group based fluorescent probes (C1, C2, C3, and H4) was synthesized for a comparative study. We found that the inefficient quenching ability of chloroacetyl group turned into an advantage when connected with a ratiometric fluorophore. With the modification of chloroacetyl group, probe H4 displayed excellent ratiometric property and great selectivity for Cys, the stability was also improved. Additionally, the probe was successfully applied for quantitative detection of Cys in fetal bovine serum and real-time imaging in living HeLa cells with low toxicity.     

Mitochondria-targeted ratiometric fluorescent probes for micropolarity and microviscosity and their applications

Two fluorescent "off-on" probes YYH1 and YYH2 were used for bioimaging mitochondrial polarity and viscosity.     

A ratiometric fluorescent probe for the detection of hypochlorous acid in living cells and zebra fish with along wavelength emission

A ratiometric fluorescence probe, NClO, for the rapid and selective detection of HClO had been designed and synthesized based on a 1,8-naphthalimide derivative. Probe NClO displayed a red emission(λ_(max)= 615 nm). In the presence of HClO, the solution of probe NClO gave off a strong green fluorescence(λ_(em), _(max)= 520 nm) with a rapid response(within seconds). This probe had been applied to image HClO in living cells and zebra fish.     

氨肽酶N荧光探针的研究进展

氨肽酶N(aminopeptidase N,APN)是一种外肽酶,广泛存在于哺乳动物体内,可从蛋白质多肽链的N末端水解中性或碱性氨基酸,在人体中具有多种重要的生理功能。APN可作为癌症诊断的标志物,尿液中APN也可作为肾小球肾炎的早期生物标志物。本文综述了APN荧光探针的研究进展,主要包括亲和力型APN荧光探针和反应型APN荧光探针,并对它们的优缺点进行了比较;最后对APN荧光探针的发展前景进行了展望。     

A ratiometric near-infrared naphthalimide-based fluorescent probe with high sensitivity for detecting Fe2+ in vivo

Iron is one of the essential trace elements in the human body. It plays an important role in human biology and pathology. Deregulation of iron levels in cells is associated with disease development. In this work, we synthesized a novel near-infrared intramolecular charge transfer (ICT) based ratiometric fluorescent probe to detect Fe²⁺, by using naphthalimide and indole moieties as building blocks. Our work showed that the radiometric probe has excellent selectivity, sensitivity and rapid response. Moreover, we could successfully perform real-time monitoring of Fe²⁺ in HeLa cells and C. elegans.     

A mitochondria-targeted fluorescent probe for ratiometric detection of hypochlorite in living cells

A new fl uorescent probe 1 was designed for mitochondrial localization and ratiometric detection of hypochlorite in living cells. It is noteworthy that a high Pearson’s co-localization coeffi cient (Rr) we have obtained was calculated to be 0.97.     

Development of a BODIPY-based ratiometric fluorescent probe for hypochlorous acid and its application in living cells

A BODIPY-based ratiometric fluorescent probe for HOCl has been designed based on the transduction of thioether to sulfoxide function. This probe features a marked absorption and emission blue-shift upon the HOCl-promoted rapid transduction, enabling the highly selective and ratiometric detection. In addition, the probe works excellently within a wide pH range of 4–10, addressing the existing pH dependency issue. Living cells studies demonstrate that the probe is cell membrane permeable and can be employed successfully to image endogenous HOCl generation in macrophage cells.     

Small-molecule fluorescent probes for the detection of carbon dioxide

This review summarizes the design principles, recognition mechanisms, properties and functions of various kinds of small-molecule fluorescent probes for the detection of carbon dioxide     

Rational design of a bifunctional fluorescent probe for distinguishing Hcy/Cys from GSH with ideal properties

By pairing two fluoropho res according to their optical prope rties such as absorption spectral overlap and absorptivity,fluorescent quantum yield and emission spectral separation,a bifunctional fluorescent probe,TQBF-NBD,was rationally designed and synthesized to discriminatively sense Hcy/Cys and GSH with good selectivity and sensitivity.It is noted that this probe could work under a single-wave length excitation and displayed a mega-large Stokes shift.TQBF-NBD reacted with Hcy/Cys to give a mixed green-red fluorescence and displayed a red fluorescence upon the treatment with GSH.Distinguishable imaging of intracellular Hcy/Cys from GSH with the help of TQBF-NBD was realized in living cells and zebrafish.