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

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
• Public URL: https://durham-repository.worktribe.com/output/1282664