Vinyl Ether/Tetrazine Pair for the Traceless Release of Alcohols in Cells

  1. Jiménez-Moreno, E. 2
  2. Guo, Z. 2
  3. Oliveira, B.L. 2
  4. Albuquerque, I.S. 4
  5. Kitowski, A. 4
  6. Guerreiro, A. 4
  7. Boutureira, O. 2
  8. Rodrigues, T. 4
  9. Jiménez-Osés, G. 13
  10. Bernardes, G.J.L. 24
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  2. 2 University of Cambridge
    info

    University of Cambridge

    Cambridge, Reino Unido

    ROR https://ror.org/013meh722

  3. 3 Universidad de Zaragoza
    info

    Universidad de Zaragoza

    Zaragoza, España

    ROR https://ror.org/012a91z28

  4. 4 Universidade de Lisboa
    info

    Universidade de Lisboa

    Lisboa, Portugal

    ROR https://ror.org/01c27hj86

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Revista:
Angewandte Chemie International

ISSN: 1433-7851

Año de publicación: 2017

Volumen: 56

Número: 1

Páginas: 243-247

Tipo: Artículo

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DOI: 10.1002/ANIE.201609607 SCOPUS: 2-s2.0-85006386992 WoS: WOS:000394861200034 GOOGLE SCHOLAR

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Resumen

The cleavage of a protecting group from a protein or drug under bioorthogonal conditions enables accurate spatiotemporal control over protein or drug activity. Disclosed herein is that vinyl ethers serve as protecting groups for alcohol-containing molecules and as reagents for bioorthogonal bond-cleavage reactions. A vinyl ether moiety was installed in a range of molecules, including amino acids, a monosaccharide, a fluorophore, and an analogue of the cytotoxic drug duocarmycin. Tetrazine-mediated decaging proceeded under biocompatible conditions with good yields and reasonable kinetics. Importantly, the nontoxic, vinyl ether duocarmycin double prodrug was successfully decaged in live cells to reinstate cytotoxicity. This bioorthogonal reaction presents broad applicability and may be suitable for in vivo applications. © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.