Front Cover: Modification of Carbon Fibre Surfaces by Sulfur-Fluoride Exchange Click Chemistry (ChemPhysChem 23/2018)

The lack of simple, efficient [18F]fluorination processes and new target-specific organofluorine probes remains the major challenge of fluorine-18-based positron emission tomography (PET). We report here a fast isotopic exchange method for the radiosynthesis of aryl [18F]fluorosulfate based PET agents enabled by the emerging sulfur fluoride exchange (SuFEx) click chemistry. The method has been applied to the fully-automated 18F-radiolabeling of twenty-five structurally diverse aryl fluorosulfates with excellent radiochemical yield (83–100%) and high molar activity (up to 281 GBq µmol–1) at room temperature in 30 seconds. The purification of radiotracers requires no time-consuming high-performance liquid chromatography (HPLC), but rather a simple cartridge filtration. The utility of aryl [18F]fluorosulfate is demonstrated by the in vivo tumor imaging by targeting poly(ADP-ribose) polymerase 1 (PARP1).

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Front Cover: Induction of Planar Chirality Using Asymmetric Click Chemistry by a Novel Desymmetrisation of 1,3-Bisalkynyl Ferrocenes (Eur. J. Org. Chem. 43/2019)

European Journal of Organic Chemistry ◽

10.1002/ejoc.201901631 ◽

2019 ◽

Vol 2019 (43) ◽

pp. 7186-7186

Author(s):

Adam J. Wright ◽

David L. Hughes ◽

Phillip C. Bulman Page ◽

G. Richard Stephenson

Keyword(s):

Click Chemistry ◽

Front Cover ◽

Planar Chirality

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[18F]SuFEx Click Chemistry Enabled Ultrafast Late-stage Radiosynthesis

10.26434/chemrxiv.10314647.v2 ◽

2020 ◽

Author(s):

Qinheng Zheng ◽

Hongtao Xu ◽

Hua Wang ◽

Wen-Ge Han Du ◽

Nan Wang ◽

...

Keyword(s):

Click Chemistry ◽

High Performance ◽

Isotopic Exchange ◽

Tumor Imaging ◽

Radiochemical Yield ◽

Exchange Method ◽

Molar Activity ◽

Positron Emission ◽

Sulfur Fluoride

The lack of simple, efficient [18F]fluorination processes and new target-specific organofluorine probes remains the major challenge of fluorine-18-based positron emission tomography (PET). We report here a fast isotopic exchange method for the radiosynthesis of aryl [18F]fluorosulfate based PET agents enabled by the emerging sulfur fluoride exchange (SuFEx) click chemistry. The method has been applied to the fully-automated 18F-radiolabeling of twenty-five structurally diverse aryl fluorosulfates with excellent radiochemical yield (83–100%) and high molar activity (up to 281 GBq µmol–1) at room temperature in 30 seconds. The purification of radiotracers requires no time-consuming high-performance liquid chromatography (HPLC), but rather a simple cartridge filtration. The utility of aryl [18F]fluorosulfate is demonstrated by the in vivo tumor imaging by targeting poly(ADP-ribose) polymerase 1 (PARP1).

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[18F]SuFEx Click Chemistry Enabled Ultrafast Late-stage Radiosynthesis

10.26434/chemrxiv.10314647 ◽

2020 ◽

Cited By ~ 1

Author(s):

Qinheng Zheng ◽

Hongtao Xu ◽

Hua Wang ◽

Wen-Ge Han Du ◽

Nan Wang ◽

...

Keyword(s):

Click Chemistry ◽

High Performance ◽

Isotopic Exchange ◽

Tumor Imaging ◽

Radiochemical Yield ◽

Exchange Method ◽

Molar Activity ◽

Positron Emission ◽

Sulfur Fluoride

The lack of simple, efficient [18F]fluorination processes and new target-specific organofluorine probes remains the major challenge of fluorine-18-based positron emission tomography (PET). We report here a fast isotopic exchange method for the radiosynthesis of aryl [18F]fluorosulfate based PET agents enabled by the emerging sulfur fluoride exchange (SuFEx) click chemistry. The method has been applied to the fully-automated 18F-radiolabeling of twenty-five structurally diverse aryl fluorosulfates with excellent radiochemical yield (83–100%) and high molar activity (up to 281 GBq µmol–1) at room temperature in 30 seconds. The purification of radiotracers requires no time-consuming high-performance liquid chromatography (HPLC), but rather a simple cartridge filtration. The utility of aryl [18F]fluorosulfate is demonstrated by the in vivo tumor imaging by targeting poly(ADP-ribose) polymerase 1 (PARP1).

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Tailoring the fibre-to-matrix interface using click chemistry on carbon fibre surfaces

Journal of Materials Chemistry A ◽

10.1039/c7ta00922d ◽

2017 ◽

Vol 5 (22) ◽

pp. 11204-11213 ◽

Cited By ~ 27

Author(s):

Linden Servinis ◽

Kathleen M. Beggs ◽

Thomas R. Gengenbach ◽

Egan H. Doeven ◽

Paul S. Francis ◽

...

Keyword(s):

Surface Chemistry ◽

Carbon Fibre ◽

Click Chemistry ◽

Chemical Reduction ◽

Surface Characteristic ◽

Diazonium Salts ◽

Effective Strategy ◽

Matrix Interface ◽

Carbon Fibres

A convenient and effective strategy to control the surface chemistry of carbon fibres is presented, comprising electro-chemical reduction of aryl diazonium salts onto the surface, followed by ‘click chemistry’ to tether the desired surface characteristic of choice.

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SuFEx-enabled, agnostic discovery of covalent inhibitors of human neutrophil elastase

Proceedings of the National Academy of Sciences ◽

10.1073/pnas.1909972116 ◽

2019 ◽

Vol 116 (38) ◽

pp. 18808-18814 ◽

Cited By ~ 24

Author(s):

Qinheng Zheng ◽

Jordan L. Woehl ◽

Seiya Kitamura ◽

Diogo Santos-Martins ◽

Christopher J. Smedley ◽

...

Keyword(s):

Click Chemistry ◽

Serine Protease ◽

Neutrophil Elastase ◽

Human Neutrophil ◽

Cathepsin G ◽

Human Neutrophil Elastase ◽

Biological Assays ◽

Covalent Inhibitors ◽

Sulfur Fluoride ◽

New Generation

Sulfur fluoride exchange (SuFEx) has emerged as the new generation of click chemistry. We report here a SuFEx-enabled, agnostic approach for the discovery and optimization of covalent inhibitors of human neutrophil elastase (hNE). Evaluation of our ever-growing collection of SuFExable compounds toward various biological assays unexpectedly revealed a selective and covalent hNE inhibitor: benzene-1,2-disulfonyl fluoride. Synthetic derivatization of the initial hit led to a more potent agent, 2-(fluorosulfonyl)phenyl fluorosulfate with IC50 0.24 μM and greater than 833-fold selectivity over the homologous neutrophil serine protease, cathepsin G. The optimized, yet simple benzenoid probe only modified active hNE and not its denatured form.

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5 Sulfur Fluoride Exchange (SuFEx)

10.1055/sos-sd-235-00230 ◽

2022 ◽

Author(s):

M.-C. Giel ◽

C. J. Smedley ◽

J. E. Moses

Keyword(s):

Click Chemistry ◽

Oxidation State ◽

High Oxidation State ◽

Sulfuryl Fluoride ◽

Metal Free ◽

Sulfur Fluoride ◽

New Generation ◽

Sulfonyl Fluoride ◽

Absolute Reliability ◽

Generation Technology

AbstractSulfur Fluoride Exchange (SuFEx) click chemistry is a new generation technology for creating stable molecular connections with absolute reliability under metal-free conditions. SuFEx builds upon the fundamental principles of click chemistry by exploiting a unique blend of stability and latent reactivity of high oxidation state sulfur fluoride [e.g., S(VI)] functionalities to forge stable covalent linkages at connective SuFEx hubs. In this review, we focus mainly on the SuFEx hubs, sulfuryl fluoride (SO2F2), thionyl tetrafluoride (SOF4), ethenesulfonyl fluoride (ESF), 1-bromoethene-1-sulfonyl fluoride (BESF) and, 2-substituted alkyne-1-sulfonyl fluorides (SASFs). We describe each connector’s unique reactivity and their application to SuFEx click chemistry.

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