Premium
Dynamic Octopus Amphiphiles as Powerful Activators of DNA Transporters: Differential Fragrance Sensing and Beyond
Author(s) -
Montenegro Javier,
Bonvin Pauline,
Takeuchi Toshihide,
Matile Stefan
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001352
Subject(s) - amphiphile , counterion , chemistry , vesicle , octopus (software) , cationic polymerization , alkyl , combinatorial chemistry , enantiomer , transporter , biophysics , membrane , organic chemistry , biochemistry , biology , computational chemistry , ion , copolymer , polymer , gene
We report the design, synthesis and evaluation of dynamic “octopus” amphiphiles with emphasis on their efficiency as activators in synthetic membrane‐based sensing systems. Previously, we found that the in situ treatment of charged hydrazides with hydrophobic aldehydes or ketones gives amphiphilic counterion activators of polyion transporters in lipid bilayers, and that their efficiency increases with the number of their hydrophobic tails. Herein, we expand this series to amphiphiles with one cationic head (guanidinium or ammonium) and four exchangeable hydrophobic tails. These results, with the highest number of tails reported to date, confirm that dynamic octopus amphiphiles provide access to maximal activity and selectivity. Odorants, such as muscone, carvone, or anisaldehyde are used to outline their usefulness in differential sensing systems that operate based on counterion‐activated DNA transporters in fluorogenic vesicles. The enhanced ability of octopus amphiphiles to enable the discrimination of enantiomers as well as that of otherwise intractable ortho , meta , and para isomers and short cyclo‐/alkyl tails is demonstrated. These findings identify dynamic octopus amphiphiles as being promising for application to differential sensing, “fragrant” cellular uptake, and slow release.