Yuming Yang,†,§ Qiang Zhao,‡,§ Wei Feng,† and Fuyou Li*,† †Department of Chemistry and State Key Laboratory of Molecular Engineering of Polymers and Institutes of Biomedical Sciences, Fudan University, Shanghai 200433, P. R. China ‡Key Laboratory for Organic Electronics and Information Displays (KLOEID) and Institute of Advanced Materials (IAM), Nanjing University of Posts and Telecommunications, Nanjing 210046, P. R. China.

Luminescent chemodosimeters for bioimaging.

The long wavelength (far-red to NIR) analyte-responsive fluorescent probes are advantageous for in vivo bioimaging because of minimum photo-damage to biological samples, deep tissue penetration, and minimum interference from background auto-fluorescence by biomolecules in the living systems. Thus, great interest in the development of new long wavelength analyte-responsive fluorescent probes has emerged in recent years. This review highlights the advances in the development of far-red to NIR fluorescent probes since 2000, and the probes are classified according to their organic dye platforms into various categories, including cyanines, rhodamine analogues, BODIPYs, squaraines, and other types (240 references).

Far-red to near infrared analyte-responsive fluorescent probes based on organic fluorophore platforms for fluorescence imaging

The dynamic chemical diversity of elements, ions and molecules that form the basis of life offers both a challenge and an opportunity for study. Small-molecule fluorescent probes can make use of selective, bioorthogonal chemistries to report on specific analytes in cells and in more complex biological specimens. These probes offer powerful reagents to interrogate the physiology and pathology of reactive chemical species in their native environments with minimal perturbation to living systems. This Review presents a survey of tools and tactics for using such probes to detect biologically important chemical analytes. We highlight design criteria for effective chemical tools for use in biological applications as well as gaps for future exploration.

Reaction-based small-molecule fluorescent probes for chemoselective bioimaging

Design strategies for water-soluble small molecular chromogenic and fluorogenic probes.

Quantitative determination of specific analytes is essential for a variety of applications ranging from life sciences to environmental monitoring. Optical sensing allows non-invasive measurements within biological milieus, parallel monitoring of multiple samples, and less invasive imaging. Among the optical sensing methods currently being explored, ratiometric fluorescence sensing has received particular attention as a technique with the potential to provide precise and quantitative analyses. Among its advantages are high sensitivity and inherent reliability, which reflect the self-calibration provided by monitoring two (or more) emissions. A wide variety of ratiometric sensing probes using small fluorescent molecules have been developed for sensing, imaging, and biomedical applications. In this research highlight, we provide an overview of the design principles underlying small fluorescent probes that have been applied to the ratiometric detection of various analytes, including cations, anions, and biomolecules in solution and in biological samples. This highlight is designed to be illustrative, not comprehensive.

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Small molecule-based ratiometric fluorescence probes for cations, anions, and biomolecules

This tutorial review presents some recent developments in the construction and applications of cassettes based on resonance energy transfer between fluorescent dyes in the visible and infrared region. We focused on the contributions of different connections between the energy donor and acceptor according to the “through-space” and “through-bond” methods, and emphasised their applications in ratiometric sensing for the detection of ions and small molecules.

Energy transfer cassettes based on organic fluorophores: construction and applications in ratiometric sensing

Mild chemical processes of various analytes and detection methods involving revolutionary strategies in the fields of analytical chemistry, biology and environmental sciences have been extensively developed. This critical review focuses on representative examples of mild chemical processes that can be used in fluorescent chemodosimeters for ion sensing (anions and cations). A systematisation according to the type of reaction mechanism is established. Numerous examples including extensions combined with catalytic and material sciences applicable in fluorescence imaging and water treatment are also discussed (151 references).

Fluorescent chemodosimeters using “mild” chemical events for the detection of small anions and cations in biological and environmental media

An ICT-based ratiometric probe for hydrazine and its application in live cells.

A fluorescent ratiometric chemodosimeter for Cu2+ based on TBET and its application in living cells.

A novel molecule T1 with efficient intramolecular charge transfer was designed as a fluorescent chemodosimeter for cysteine (Cys) and homocysteine (Hcy). Upon addition of Cys/Hcy, T1 exhibited greatly enhanced fluorescence intensity as well as a large absorption peak shift (70 nm), and can be used for bioimaging of Cys/Hcy in living cells and detection in human plasma by visual color change. The detection mechanism was proved by 1H NMR, mass spectrometry analysis and Gaussian calculations.

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Mingming Hu

Papers

Energy transfer cassettes based on organic fluorophores: construction and applications in ratiometric sensing

Fluorescent chemodosimeters using “mild” chemical events for the detection of small anions and cations in biological and environmental media

An ICT-based ratiometric probe for hydrazine and its application in live cells.

A fluorescent ratiometric chemodosimeter for Cu2+ based on TBET and its application in living cells.

Fluorescent chemodosimeter for Cys/Hcy with a large absorption shift and imaging in living cells.