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

Content Provider	Royal Society of Chemistry (RSC)
Author	Montenegro, Javier Fin, Andrea Matile, Stefan
Copyright Year	2011
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.
Starting Page	2641
Ending Page	2647
Page Count	7
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	9
Issue Number	8
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/c0ob00948b
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Alkyl Guanidine DNA Lipid bilayer Ion Hydrophobe Hydrazone Peptide
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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