Bioconjugatable azo-based dark-quencher dyes: synthesis and application to protease-activatable far-red fluorescent probes. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2013

Bioconjugatable azo-based dark-quencher dyes: synthesis and application to protease-activatable far-red fluorescent probes.

Résumé

We describe the efficient synthesis and one-step derivatization of novel, nonfluorescent azo dyes based on the Black Hole Quencher-3 (BHQ-3) scaffold. These dyes were equipped with various reactive and/or bioconjugatable groups (azido, α-iodoacetyl, ketone, terminal alkyne, vicinal diol). The azido derivative was found to be highly reactive in the context of copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions and allowed easy synthetic access to the first water-soluble (sulfonated derivative) and aldehyde-modified BHQ-3 dyes, the direct preparation of which failed by means of conventional azo-coupling reactions. The aldehyde- and α-iodoacetyl-containing fluorescence quenchers were readily conjugated to aminooxy- and cysteine-containing peptides by the formation of a stable oxime or thioether linkage, respectively. Further fluorescent labeling of the resultant peptide conjugates with red- or far-red-emitting rhodamine or cyanine dyes through sequential and/or one-pot bioconjugations, led to novel Förster resonance energy transfer (FRET) based probes suitable for the in vivo detection and imaging of urokinase plasminogen activator, a key protease in cancer invasion and metastasis.

Domaines

Chimie organique

Dates et versions

hal-00996530 , version 1 (26-05-2014)

Identifiants

Citer

Arnaud Chevalier, Cédrik Massif, Pierre-Yves Renard, Anthony Romieu. Bioconjugatable azo-based dark-quencher dyes: synthesis and application to protease-activatable far-red fluorescent probes.. Chemistry - A European Journal, 2013, 19 (5), pp.1686-1699. ⟨10.1002/chem.201203427⟩. ⟨hal-00996530⟩
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