Multiphoton Activation of Photo-Strain-Promoted Azide Alkyne Cycloaddition “Click” Reagents Enables in Situ Labeling with Submicrometer Resolution

2017/09/19 by Christopher D. McNitt, Hazel Cheng, Susanne Ullrich +2 · 78 citations
Biochemistry, Genetics and Molecular Biology · Chemistry · Materials Science · #Alkyne #Azide #Chemical Synthesis and Analysis #Chemistry #Click Chemistry and Applications #Click chemistry #Combinatorial chemistry #Cycloaddition #Derivatization #Excitation #Femtosecond #High-performance liquid chromatography #In situ #Irradiation #Laser #Optics #Organic chemistry #Photochemistry #Photochromic and Fluorescence Chemistry #Physical chemistry #Reagent #Two-photon excitation microscopy

paper · doi:10.1021/jacs.7b08472

published in Journal of the American Chemical Society 139(40), 14029-14032 (American Chemical Society)

openalex publication_date 2017/09/19 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/01

Abstract

Irradiation of cyclopropenone-masked dibenzocyclooctynes with near-infrared pulses from a femtosecond laser triggers photodecarbonylation via nonresonant two- or three-photon excitation. Multiphoton-generated cyclooctynes undergo a SPAAC reaction with organic azides, yielding the expected triazoles. Multiphoton-triggered SPAAC (MP-SPAAC) enables high resolution 3-D photoclick derivatization of hydrogels and tissues.

Citations

• Selective Labeling of Living Cells by a Photo-Triggered Click Reaction
• Temporal Labeling of Nascent RNA Using Photoclick Chemistry in Live Cells

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