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    Sydnone Reporters for Highly Fluorogenic Copper-Free Click Ligations
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    † Institut Européen de Chimie et Biologie, Université de Bordeaux, 2 rue Robert Escarpit, 33607 Pessac, France
    ‡ Institut de Neurosciences Cognitives et Intégratives d’Aquitaine, CNRS UMR5287, Bordeaux, France
    § Basic Science Department, Loma Linda University, Loma Linda, California 92350, United States
    *E-mail: [email protected]
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2018, 83, 4, 2058–2066
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    https://doi.org/10.1021/acs.joc.7b03004
    Published February 1, 2018
    Copyright © 2018 American Chemical Society
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    Abstract

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    Bioorthogonal fluorescent turn-on reactions are attractive for the sensitive real-time detection of a variety of phenomena including bioconjugation, chemical reactivity, and material assembly. Herein we describe the use of 3,4-disubstituted sydnones, a singular class of mesoionic dipoles, for highly fluorescent turn-on copper-free click cycloadditions with the fluorogenic dibenzocyclooctyne Fl-DIBO. Coherent with time-dependent density functional theory calculations, the pyrazole cycloadducts were found to be highly fluorescent with compelling photophysical properties including excellent fluorescence enhancement (up to 240-fold), high quantum yields (over 45%), and large Stokes shift (over 100 nm). Furthermore, the good stability and reactivity of 4-chlorosydnones with Fl-DIBO allowed us to employ them as chemical reporters for the challenging detection of modified-proteins in complex cellular extracts, with exquisite specificity in no-wash conditions. This novel fluorogenic system significantly expands our chemical biology toolbox and should be beneficial in countless applications.

    Copyright © 2018 American Chemical Society

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.joc.7b03004.

    • 1H and 13C NMR spectra of all synthesized compounds, absorbance and emission spectra of pyrazoles 6a–c, 6e–h, and 6j–n, kinetics plots, 1H NMR data for the stability study of sydnone 4e, and TD-DFT calculations (PDF)

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    This article is cited by 40 publications.

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    12. Zoeisha S. Chinoy, Frédéric Friscourt. Expanding the Strain‐Promoted 1,3‐Dipolar Cycloaddition Arsenal for a More Selective Bioorthogonal Labeling in Living Cells. Israel Journal of Chemistry 2023, 63 (1-2) https://doi.org/10.1002/ijch.202200055
    13. Mingjun Xiao, Yi‐Kang Zhang, Ranran Li, Shengtao Li, Di Wang, Peng An. Photoactivatable Fluorogenic Azide‐Alkyne Click Reaction: A Dual‐Activation Fluorescent Probe. Chemistry – An Asian Journal 2022, 17 (17) https://doi.org/10.1002/asia.202200634
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    29. Il’ya A. Cherepanov, Sergey K. Moiseev. Recent developments in the chemistry of sydnones and sydnone imines. 2020, 49-164. https://doi.org/10.1016/bs.aihch.2019.11.003
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    33. Xiaocui Zhang, Xueting Wu, Shichao Jiang, Jingshuo Gao, Zhuojun Yao, Jiajie Deng, Linmeng Zhang, Zhipeng Yu. Photo-accelerated “click” reaction between diarylsydnones and ring-strained alkynes for bioorthogonal ligation. Chemical Communications 2019, 55 (50) , 7187-7190. https://doi.org/10.1039/C9CC02882J
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    39. Juan García de la Concepción, Martín Ávalos, Pedro Cintas, José Luis Jiménez. Computational Screening of New Orthogonal Metal‐Free Dipolar Cycloadditions of Mesomeric Betaines. Chemistry – A European Journal 2018, 24 (29) , 7507-7512. https://doi.org/10.1002/chem.201800869
    40. Huimin Tao, Fang Liu, Ruxin Zeng, Zhuzhou Shao, Lufeng Zou, Yang Cao, Jennifer M. Murphy, K. N. Houk, Yong Liang. Origins of halogen effects in bioorthogonal sydnone cycloadditions. Chemical Communications 2018, 54 (40) , 5082-5085. https://doi.org/10.1039/C8CC02128G
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2018, 83, 4, 2058–2066
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.7b03004
    Published February 1, 2018
    Copyright © 2018 American Chemical Society
    Request reuse permissions

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