Cell-Penetrating Peptides Containing Fluorescent d-Cysteines

  1. Navo, C.D. 2
  2. Asín, A. 2
  3. Gómez-Orte, E. 1
  4. Gutiérrez-Jiménez, M.I. 2
  5. Compañón, I. 2
  6. Ezcurra, B. 1
  7. Avenoza, A. 2
  8. Busto, J.H. 2
  9. Corzana, F. 2
  10. Zurbano, M.M. 2
  11. Jiménez-Osés, G. 2
  12. Cabello, J. 1
  13. Peregrina, J.M. 2
  1. 1 Centro de Investigación Biomédica de La Rioja
    info

    Centro de Investigación Biomédica de La Rioja

    Logroño, España

    ROR https://ror.org/03vfjzd38

  2. 2 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Revista:
Chemistry - A European Journal

ISSN: 0947-6539

Año de publicación: 2018

Volumen: 24

Número: 31

Páginas: 7991-8000

Tipo: Artículo

DOI: 10.1002/CHEM.201800603 SCOPUS: 2-s2.0-85046547377 GOOGLE SCHOLAR

Otras publicaciones en: Chemistry - A European Journal

Repositorio institucional: lockAcceso abierto Editor

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Resumen

A series of fluorescent d-cysteines (Cys) has been synthesized and their optical properties were studied. The key synthetic step is the highly diastereoselective 1,4-conjugate addition of aryl thiols to a chiral bicyclic dehydroalanine recently developed by our group. This reaction is fast at room temperature and proceeds with total chemo- and stereoselectivity. The Michael adducts were easily transformed into the corresponding amino acids to study their optical properties and, in some selected cases, into the corresponding N-Fmoc-d-cysteine derivatives to be used in solid-phase peptide synthesis (SPPS). To further demonstrate the utility of these non-natural Cys-derived fluorescent amino acids, the coumaryl and dansyl derivatives were incorporated into cell-penetrating peptide sequences through standard SPPS and their optical properties were studied in different cell lines. The internalization of these fluorescent peptides was monitored by fluorescence microscopy. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim