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

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

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


Authors

Matthieu Starck

Jack D. Fradgley

Stefania Di Vita

Jackie Mosely



Abstract

The syntheses and photophysical behaviour of nine, strongly luminescent nonadentate Eu(III) complexes are reported. Each complex is based on N-functionalised 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 favour of the latter conjugation strategy, as parallel work with maleimide conjugates was complicated or compromised by the propensity to undergo postconjugation thiol exchange or succinimide ring hydrolysis reactions. Confocal microscopy and spectral imaging studies revealed that the peptide conjugate of AcCFFKDEL was found to localise selectively in the endoplasmic reticulum of mouse fibroblast cells, whereas the related maleimide conjugate was only observed in cellular lysosomes

Citation

Starck, M., Fradgley, J. D., Di Vita, S., Mosely, J., Pal, R., & Parker, D. (2020). Targeted Luminescent Europium Peptide Conjugates: Comparative Analysis Using Maleimide and para-Nitropyridyl Linkages for Organelle Staining. Bioconjugate Chemistry, 31(2), 229-240. https://doi.org/10.1021/acs.bioconjchem.9b00735

Journal Article Type Article
Online Publication Date Nov 21, 2019
Publication Date Nov 21, 2020
Deposit Date Nov 25, 2019
Publicly Available Date Nov 21, 2020
Journal Bioconjugate Chemistry
Print ISSN 1043-1802
Electronic ISSN 1520-4812
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 31
Issue 2
Pages 229-240
DOI https://doi.org/10.1021/acs.bioconjchem.9b00735

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Copyright Statement
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Bioconjugate Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.bioconjchem.9b00735





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