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Issue 8, 2011
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Comprehensive screening of octopus amphiphiles as DNA activators in lipid bilayers: implications on transport, sensing and cellular uptake

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Abstract

Dynamic octopus amphiphiles contain one charged “head,” here a guanidinium cation, together several hydrophobic “tails” (or “tentacles”) that can be attached and exchanged in situ by reversible hydrazone formation. Quite surprisingly, their ability to activate DNA as transporters in lipid bilayer membranes was found to increase with the number of tails (up to four) as well as with their length (up to eight carbons). Both encouraged and puzzled by these results, we decided that a comprehensive screening of octopus amphiphiles with regard to number (from one to six) and length (from three to eighteen carbons) of their tails would be appropriate at this point. For this purpose, we here report the synthesis of cationic hexahydrazide peptide dendrons together with that of aldehydes with long, saturated, unsaturated and branched hydrophobic tails. Comprehensive screening of the completed collection of tails and heads reveals that the ability of octopus amphiphiles to activate DNA transporters shifts with increasing number of tails to decreasing length of the tails. Moreover, cis-alkenyl and branched alkyl tails are more active than their linear analogs, branched aromatic tails are best. These overall very meaningful trends for octopus amphiphiles will be of importance for sensing applications and fragrant cellular uptake.

Graphical abstract: Comprehensive screening of octopus amphiphiles as DNA activators in lipid bilayers: implications on transport, sensing and cellular uptake

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Supplementary files

Article information


Submitted
28 Oct 2010
Accepted
12 Jan 2011
First published
04 Mar 2011

Org. Biomol. Chem., 2011,9, 2641-2647
Article type
Paper

Comprehensive screening of octopus amphiphiles as DNA activators in lipid bilayers: implications on transport, sensing and cellular uptake

J. Montenegro, A. Fin and S. Matile, Org. Biomol. Chem., 2011, 9, 2641
DOI: 10.1039/C0OB00948B

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