Rational design of a water-soluble, lipid-compatible fluorescent probe for Cu() with sub-part-per-trillion sensitivity

Fluorescence probes represent an attractive solution for the detection of the biologically important Cu( i ) cation; however, achieving a bright, high-contrast response has been a challenging goal. Concluding from previous studies on pyrazoline-based fluorescent Cu( i ) probes, the maximum attainabl...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2016-01, Vol.7 (2), p.1468-1473
Main Authors: Morgan, M. T, McCallum, A. M, Fahrni, C. J
Format: Article
Language:English
Subjects:
Agglomeration
Aggregates
Chemical compounds
Design optimization
Fluorescence
Ligands
Lipids
Optimization
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Summary:Fluorescence probes represent an attractive solution for the detection of the biologically important Cu( i ) cation; however, achieving a bright, high-contrast response has been a challenging goal. Concluding from previous studies on pyrazoline-based fluorescent Cu( i ) probes, the maximum attainable fluorescence contrast and quantum yield were limited due to several non-radiative deactivation mechanisms, including ternary complex formation, excited state protonation, and colloidal aggregation in aqueous solution. Through knowledge-driven optimization of the ligand and fluorophore architectures, we overcame these limitations in the design of CTAP-3, a Cu( i )-selective fluorescent probe offering a 180-fold fluorescence enhancement, 41% quantum yield, and a limit of detection in the sub-part-per-trillion concentration range. In contrast to lipophilic Cu( i )-probes, CTAP-3 does not aggregate and interacts only weakly with lipid bilayers, thus maintaining a high contrast ratio even in the presence of liposomes. Knowledge-driven optimization of the ligand and fluorophore architectures yielded an ultrasensitive Cu( i )-selective fluorescent probe featuring a 180-fold fluorescence contrast and 41% quantum yield.
ISSN:2041-6520
2041-6539
DOI:10.1039/c5sc03643g