title: 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.
authors.affiliation: School of Chemistry and Biochemistry, University of Geneva, Geneva, Switzerland.
authors.forename: David Alonso
authors.initials: DA
authors.lastname: Doval
authors.forename: Andrea
authors.initials: A
authors.lastname: Fin
authors.forename: Miwa
authors.initials: M
authors.lastname: Takahashi-Umebayashi
authors.forename: Howard
authors.initials: H
authors.lastname: Riezman
authors.forename: Aurelien
authors.initials: A
authors.lastname: Roux
authors.forename: Naomi
authors.initials: N
authors.lastname: Sakai
authors.forename: Stefan
authors.initials: S
authors.lastname: Matile
mesh_terms: D005456:Fluorescent Dyes / Q000737:chemistry / Q000378:metabolism; D057927:Hydrophobic and Hydrophilic Interactions; D007094:Imides / Q000737:chemistry* / Q000378:metabolism*; D021962:Membrane Microdomains / Q000378:metabolism*; D057054:Molecular Imaging; D009281:Naphthalenes / Q000737:chemistry* / Q000378:metabolism*; D010569:Perylene / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D053835:Unilamellar Liposomes / Q000737:chemistry / Q000378:metabolism*
chemical_list: D005456:Fluorescent Dyes; D007094:Imides; D009281:Naphthalenes; D053835:Unilamellar Liposomes; C521332:perylenediimide; C542131:naphthalenediimide; D010569:Perylene