Issue 30, 2012

Amphiphilic dynamic NDI and PDI probes: imaging microdomains in giant unilamellar vesicles

Abstract

Dynamic amphiphiles provide access to transmembrane ion transport, differential sensing and cellular uptake. In this report, we introduce dynamic amphiphiles with fluorescent tails. Core-substituted naphthalenediimides (cNDIs) and perylenediimides (cPDIs) are tested. Whereas the latter suffer from poor partitioning, dynamic cNDI amphiphiles are found to be purifiable by RP-HPLC, to partition selectively into liquid-disordered (Ld) microdomains of mixed lipid bilayers and to activate DNA as transporters. Importantly, fluorescence properties, partitioning and activity can be modulated by changes in the structure of mixed amphiphiles. These results confirm the potential of dynamic fluorescent amphiphiles to selectively label extra- and intracellular membrane domains and visualize biological function.

Graphical abstract: Amphiphilic dynamic NDI and PDI probes: imaging microdomains in giant unilamellar vesicles

Supplementary files

Article information

Article type
Paper
Submitted
16 jan 2012
Accepted
28 feb 2012
First published
13 apr 2012

Org. Biomol. Chem., 2012,10, 6087-6093

Amphiphilic dynamic NDI and PDI probes: imaging microdomains in giant unilamellar vesicles

D. A. Doval, A. Fin, M. Takahashi-Umebayashi, H. Riezman, A. Roux, N. Sakai and S. Matile, Org. Biomol. Chem., 2012, 10, 6087 DOI: 10.1039/C2OB25119A

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