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

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 p...

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Published in:Chemical science (Cambridge) Vol. 11; no. 5; pp. 1368 - 1374
Main Authors: Subiros-Funosas, Ramon, Ho, Vivian Cheuk Lam, Barth, Nicole D, Mendive-Tapia, Lorena, Pappalardo, Morena, Barril, Xavier, Ma, Ruoyu, Zhang, Cheng-Bin, Qian, Bin-Zhi, Sintes, Miquel, Ghashghaei, Ouldouz, Lavilla, Rodolfo, Vendrell, Marc
Format: Journal Article
Language:English
Published: CAMBRIDGE Royal Soc Chemistry 2020
Royal Society of Chemistry
The Royal Society of Chemistry
Subjects:
Chemistry
Chemistry, Multidisciplinary
Keratin
Organic chemistry
Physical Sciences
Science & Technology
BREAST-CANCER
TRYPTOPHAN
AMINO-ACID
FLUORESCENT-PROBE
PEPTIDE
RAY CRYSTAL-STRUCTURE
ISSN:2041-6520, 2041-6539
Online Access:Get full text
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Summary: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. Trp(redBODIPY) is the first red-emitting Trp-based amino acid for the preparation of fluorogenic peptides with retention of target binding affinity.
Bibliography:Electronic supplementary information (ESI) available: Full synthetic procedures and chemical characterization, additional spectroscopic and biological data. See DOI
10.1039/c9sc05558d
Marie Curie Actions (MSCA)
European Research Council (ERC)
UKRI
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ISSN:2041-6520
2041-6539
DOI:10.1039/c9sc05558d