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Caged Molecular Glues as Photoactivatable Tags for Nuclear Translocation of Guests in Living Cells

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Department of Chemistry and Biotechnology, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan
Riken Center for Emergent Matter Science, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan
Cite this: J. Am. Chem. Soc. 2018, 140, 7, 2687–2692
Publication Date (Web):January 30, 2018
https://doi.org/10.1021/jacs.7b13614
Copyright © 2018 American Chemical Society

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    Abstract

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    We developed dendritic caged molecular glues (CagedGlue-R) as tags for nucleus-targeted drug delivery, whose multiple guanidinium ion (Gu+) pendants are protected by an anionic photocleavable unit (butyrate-substituted nitroveratryloxycarbonyl; BANVOC). Negatively charged CagedGlue-R hardly binds to anionic biomolecules because of their electrostatic repulsion. However, upon exposure of CagedGlue-R to UV light or near-infrared (NIR) light, the BANVOC groups of CagedGlue-R are rapidly detached to yield an uncaged molecular glue (UncagedGlue-R) that carries multiple Gu+ pendants. Because Gu+ forms a salt bridge with PO4, UncagedGlue-R tightly adheres to anionic biomolecules such as DNA and phospholipids in cell membranes by a multivalent salt-bridge formation. When tagged with CagedGlue-R, guests can be taken up into living cells via endocytosis and hide in endosomes. However, when the CagedGlue-R tag is photochemically uncaged to form UncagedGlue-R, the guests escape from the endosome and migrate into the cytoplasm followed by the cell nucleus. We demonstrated that quantum dots (QDs) tagged with CagedGlue-R can be delivered efficiently to cell nuclei eventually by irradiation with light.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.7b13614.

    • Synthesis of CagedGlue-NBD, Glue-NBD, and CagedGlue-DBCO; 1H NMR, 13C NMR, and MALDI-TOF-MS spectral data; cytotoxicity profiles; and related experimental procedures (PDF)

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