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Chem Sci. 2019 Dec 18;11(5):1368-1374. doi: 10.1039/c9sc05558d.

Fluorogenic Trp(redBODIPY) cyclopeptide targeting keratin 1 for imaging of aggressive carcinomas.

Chemical science

Ramon Subiros-Funosas, Vivian Cheuk Lam Ho, Nicole D Barth, Lorena Mendive-Tapia, Morena Pappalardo, Xavier Barril, Ruoyu Ma, Cheng-Bin Zhang, Bin-Zhi Qian, Miquel Sintes, Ouldouz Ghashghaei, Rodolfo Lavilla, Marc Vendrell

Affiliations

  1. Centre for Inflammation Research, University of Edinburgh 47 Little France Crescent EH16 4TJ Edinburgh UK [email protected].
  2. Laboratory of Physical Chemistry, Facultat de Farmàcia, Universitat de Barcelona and Institut de Biomedicina de la Universitat de Barcelona (IBUB) Av. Joan XXIII s/n 08028 Barcelona Spain.
  3. MRC Centre for Reproductive Health, University of Edinburgh 47 Little France Crescent EH16 4TJ Edinburgh UK.
  4. Laboratory of Medicinal Chemistry, Faculty of Pharmacy, University of Barcelona and Institut de Biomedicina de la Universitat de Barcelona (IBUB) Avda Joan XXIII 27-30 Barcelona 08028 Spain [email protected].

PMID: 34123261 PMCID: PMC8148049 DOI: 10.1039/c9sc05558d

Abstract

Keratin 1 (KRT1) is overexpressed in squamous carcinomas and associated with aggressive pathologies in breast cancer. Herein we report the design and preparation of the first Trp-based red fluorogenic amino acid, which is synthetically accessible in a few steps and displays excellent photophysical properties, and its application in a minimally-disruptive labelling strategy to prepare a new fluorogenic cyclopeptide for imaging of KRT1+ cells in whole intact tumour tissues.

This journal is © The Royal Society of Chemistry.

Conflict of interest statement

The authors declare no conflicts of interest.

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