Fluorescein applications as fluorescent probes for the detection of analytes

https://doi.org/10.1016/j.trac.2017.08.013Get rights and content

Highlights

  • Methods for synthesis of “OFF–ON” fluorescein fluorescent probes.

  • Sensing mechanisms and sensor design using fluorescein.

  • Sensing applications and properties to various analytes.

Abstract

Fluorescein derivatives are important fluorescent probes which can be used for detection and optical imaging. Fluorescein derivatives are usually constructed by introducing aldehyde groups or esterified onto fluorescein xanthene ring and benzene moiety. Typically, the research direction of connecting amino groups with fluorescein monoaldehyde is in hot. Because of their high activity, these derivatives can be complexed with the analytes to produce changes of colors and the increase or decrease of fluorescence intensity. This article reviewed fluorescein probes in the past two years according to classification of different analytes including metal ions, anions, small molecules and biological macromolecules. The synthesis methods, optical properties, possible mechanisms and applications of fluorescein probes are summarized. This article provides a reference for the screening of fluorescein probes with high sensitivity and biological detection and can propel their further applications in sensing and detection of analytes.

Graphical abstract

Fluorescein is an important class of fluorescent probes. This article reviewed fluorescein fluorescent probes in the past two years according to classification of different analytes including metal ions, anions, small molecules and biological macromolecules. The synthesis method, optical properties, possible mechanisms and applications of “OFF–ON” fluorescein fluorescent probes were summarized in here.

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Introduction

Fluorescein is widely employed as a platform for various fluorescent probes and fluorescent labels because of their high-intensity emission peaks, high molar absorption coefficients and quantum yields in aqueous media [1]. Since Bayer first synthesized fluorescein in 1871, it has received much attention and has shown great promise in a variety of applications, especially in the field of smart sensors and bioimaging [2].

Over the last decade, amazing progress has been made in the use of fluorescent probes for the development of probes due to their unique photoluminescence properties [3]. Compared with traditional techniques including titrimetry, chromatography, electrochemistry, chemiluminescence and flow injection analysis, these probes open up a new avenue for fast-responding, highly sensitive, non-sample destructing and on-site analysis of specific targets [4]. A great variety of fluorophores including organic molecules, metal nanoclusters, semiconductor quantum dots (QDS), etc. with improved properties are increasingly available. A benefit of synthetic organic molecules is the ability to employ chemical approaches to control the properties and direct the position of the fluorophore. Applying organic synthesis enables efficient tailoring of the structure to obtain fluorescent probes for specific sensitive experiments. Accordingly, the development of preparative strategy toward functional fluorescein structure is highly desired.

Fluorescein has been frequently utilized as the fluorescent core due to its characteristic spirolactam structure, which can ‘close–open’ with an ‘turn-on’ fluorescence response in specific environments or as a result of specific events, and made it an excellent dye for the design of probes. Recently, functional fluorescence probes based on the fluorescein structure have attracted growing interest [5]. Functional fluorescence probes based on the fluorescein structure are available for modification by organic synthesis at two moieties: the xanthene ring and the benzoic acid moiety (hereafter called the benzene moiety). Its unique characteristic in every moiety is worth summarizing.

Herein, the past two-years' advances of fluorescein probes about the synthesis methods, optical properties, possible mechanisms and applications of fluorescein probes are summarized [6], [7]. Common fluorescein probes mechanisms include the ‘off–on’ structure, fluorescence resonance energy transfer (FRET), photo induced electron transfer (PET) and chelation enhanced fluorescence (CHEF) [8], [9]. This article reviewed fluorescein probes according to classifications of different analytes, including metal ions, anions, small molecules and biological macromolecules. It could facilitate the researchers to design and develop proper fluorescent probes in future work.

Section snippets

Fluorescein probes design mechanisms

Functional fluorescence probes based on the fluorescein structure are available for modification by organic synthesis at two parts: the xanthene ring and the benzene moiety. The two moieties are orthogonal to each other. Its unique characteristic in every moiety is worth summarizing. Rational design strategies based on the five positions of the two parts have allowed us to rapidly develop a wide range of fluorescein probes (Fig. 1).

The rational design of a chromogenic/ratiometric fluorescein

Fluorescein probes detection of metal ions

Probes for metal ions based on the fluorescein structure are modified by the five positions. When the probes combined with metal ions, it can lead to the changes of colors and the increase or decrease of fluorescence intensity. Based on this, the purpose of detection can be achieved [10]. In aqueous solution and living cell, the fluorescein probes can be used to detect such as copper ions, zinc ions, mercury ions, gold ions, silver ions, palladium ions, iron ions, magnesium ions, cadmium ions

Conclusion

This article reviewed fluorescein probes in the past two years according to classification of different analytes including metal ions, anions, small molecules and biological macromolecules. Functional fluorescence probes based on the fluorescein structure are available for modification by organic synthesis at five positions: the xanthene ring 2, 3, 5 sites and the benzene moiety 1, 4 sites. Schiff base fluorescein probes are achieved through fluorescein derivatives based on Schiff base reaction

Acknowledgments

The work described in this manuscript was supported by the National Natural Science Foundation of China (Nos. 21374078, 51678409) and Tianjin Research Program of Application Foundation and Advanced Technology (Nos. 15JCYBJC18100, 15ZCZDSF00880).

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