Synthetic Macrocyclic Peptidomimetics as Tunable pH Probes for the Fluorescence Imaging of Acidic Organelles in Live Cells

Acid test: Macrocyclic compounds that comprise a 9,10‐anthracene subunit linked by a C2‐symmetric peptidomimetic chain (see formula) are useful as fluorescent probes in a pH range of biomedical interest. Changes in the size of the macrocycle (n=3,4,6,8) produce a shift in the pKa values. Experiments...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2005-10, Vol.44 (40), p.6504-6508
Main Authors: Galindo, Francisco, Burguete, M. Isabel, Vigara, Laura, Luis, Santiago V., Kabir, Nurul, Gavrilovic, Jelena, Russell, David A.
Format: Article
Language:English
Subjects:
Animals
Anthracenes - chemistry
biosensors
Cell Line
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
Fluorescent Dyes - pharmacokinetics
fluorescent probes
Hydrogen-Ion Concentration
macrocycles
Macrocyclic Compounds - chemical synthesis
Macrocyclic Compounds - chemistry
Macrocyclic Compounds - pharmacokinetics
Macrophages - metabolism
Macrophages - ultrastructure
Mice
Molecular Mimicry
Molecular Structure
Organelles - metabolism
Organelles - ultrastructure
Peptides - chemistry
peptidomimetics
protonation
Spectrometry, Fluorescence
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Summary:Acid test: Macrocyclic compounds that comprise a 9,10‐anthracene subunit linked by a C2‐symmetric peptidomimetic chain (see formula) are useful as fluorescent probes in a pH range of biomedical interest. Changes in the size of the macrocycle (n=3,4,6,8) produce a shift in the pKa values. Experiments with live mouse macrophage cells show the selective localization of the probe in the acidic organelles (see differential interference contrast image).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200501920