Cell-Penetrating Peptides Containing Fluorescent d-Cysteines
| Autor: | Marta I. Gutiérrez-Jiménez, Jesús H. Busto, Claudio D. Navo, Jesús M. Peregrina, Ismael Compañón, Gonzalo Jiménez-Osés, Francisco Corzana, Eva Gómez-Orte, Alberto Avenoza, Alicia Asín, Juan Cabello, Begoña Ezcurra, María M. Zurbano |
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| Rok vydání: | 2018 |
| Předmět: |
Cell Survival
Peptide Cell-Penetrating Peptides 010402 general chemistry 01 natural sciences Catalysis chemistry.chemical_compound Dehydroalanine Fluorescence microscope Peptide synthesis Humans Cysteine Solid-Phase Synthesis Techniques Fluorescent Dyes chemistry.chemical_classification Bicyclic molecule 010405 organic chemistry Organic Chemistry Optical Imaging General Chemistry Combinatorial chemistry Fluorescence 0104 chemical sciences Amino acid Spectrometry Fluorescence chemistry Michael reaction HeLa Cells |
| Zdroj: | Chemistry (Weinheim an der Bergstrasse, Germany). 24(31) |
| ISSN: | 1521-3765 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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