Targeted Luminescent Europium Peptide Conjugates: Comparative Analysis Using Maleimide and para-Nitropyridyl Linkages for Organelle Staining

Matthieu Starck, Jack D. Fradgley, Stefania Di Vita, Jackie Mosely, Robert Pal, David Parker

Research output: Contribution to journalArticlepeer-review

Abstract

The syntheses and photophysical behavior of nine strongly luminescent nonadentate Eu(III) complexes are reported. Each complex is based on N-functionalized 1,4,7-triazacyclononane, and linkage to other groups or targeting vectors can occur either via amide bond formation to a coordinated pyridine p-aminopropyl group or via a nucleophilic substitution reaction involving thiol attack on a metal coordinated p-nitropyridyl moiety. Evidence is presented in favor of the latter conjugation strategy, as parallel work with maleimide conjugates was complicated or compromised by the propensity to undergo post-conjugation thiol exchange or succinimide ring hydrolysis reactions. Confocal microscopy and spectral imaging studies revealed that the peptide conjugate of AcCFFKDEL was found to localize selectively in the endoplasmic reticulum of mouse fibroblast cells, whereas the related maleimide conjugate was only observed in cellular lysosomes.
Original languageEnglish
Pages (from-to)229-240
JournalBioconjugate Chemistry
Volume31
Issue number2
DOIs
Publication statusPublished - 21 Nov 2019

Bibliographical note

Funding Information:
We thank the Royal Society (RP), the EPSRC (MS, grant/EP 025013/1), and Cisbio Bioassays (JDF) for support.

Publisher Copyright:
Copyright © 2019 American Chemical Society.

Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.

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