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

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...

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Bibliographic Details
Published in:Bioconjugate chemistry 2020-02, Vol.31 (2), p.229-240
Main Authors: Starck, Matthieu, Fradgley, Jack D, Di Vita, Stefania, Mosely, Jackie A, Pal, Robert, Parker, David
Format: Article
Language:English
Subjects:
Animals
Comparative analysis
Confocal microscopy
Conjugates
Conjugation
Coordination Complexes - analysis
Endoplasmic reticulum
Endoplasmic Reticulum - ultrastructure
Europium
Europium - analysis
Fibroblasts - ultrastructure
Luminescent Agents - analysis
Lysosomes
Maleimides - analysis
Mice
Microscopy, Confocal
NIH 3T3 Cells
Optical Imaging
Organelles
Peptides
Peptides - analysis
Pyridines
Substitution reactions
Succinimide
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Summary: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.
ISSN:1043-1802
1520-4812
DOI:10.1021/acs.bioconjchem.9b00735