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BODIPY–Tetrazine Derivatives as Superbright Bioorthogonal Turn-on Probes

Authors

  • Dr. Jonathan C. T. Carlson,

    1. Center for Systems Biology, Massachusetts General Hospital, 185 Cambridge Street, Boston, MA 02114 (USA)
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    • These authors contributed equally to this work.

  • Dr. Labros G. Meimetis,

    1. Center for Systems Biology, Massachusetts General Hospital, 185 Cambridge Street, Boston, MA 02114 (USA)
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    • These authors contributed equally to this work.

  • Dr. Scott A. Hilderbrand,

    1. Center for Systems Biology, Massachusetts General Hospital, 185 Cambridge Street, Boston, MA 02114 (USA)
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  • Prof. Ralph Weissleder

    Corresponding author
    1. Center for Systems Biology, Massachusetts General Hospital, 185 Cambridge Street, Boston, MA 02114 (USA)
    2. Harvard Medical School, 200 Longwood Avenue, Boston, MA 02115 (USA)
    • Center for Systems Biology, Massachusetts General Hospital, 185 Cambridge Street, Boston, MA 02114 (USA)

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  • Part of this work was supported by NHI RO1EB010011 and 2P50A086355. J.C. was supported by a DFCI-MGH Hematology Oncology Fellowship. We thank Prof. Ralph Mazitschek for many insightful discussions, Dr. Katy Yang for cell culture assistance, Dr. Sarit Agasti for the gift of reagents, Alex Zaltsman for microscopy assistance, and Dr. Eszter Boros for her assistance with NMR spectroscopy. BODIPY=boron dipyrromethene.

Abstract

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The fastest and the brightest: A new design that intimately connects tetrazine to a BODIPY fluorophore enables exceptionally efficient energy transfer and quenching. Upon reaction of the tetrazine, the brightness of the fluorophore increases more than a thousand-fold, which is a fluorogenic activation up to two orders of magnitude greater than previously described.

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