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Issue 3, 2014
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Double-degradable responsive self-assembled multivalent arrays – temporary nanoscale recognition between dendrons and DNA

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Abstract

This article reports self-assembling dendrons which bind DNA in a multivalent manner. The molecular design directly impacts on self-assembly which subsequently controls the way these multivalent nanostructures bind DNA – this can be simulated by multiscale modelling. Incorporation of an S–S linkage between the multivalent hydrophilic dendron and the hydrophobic units responsible for self-assembly allows these structures to undergo triggered reductive cleavage, with dithiothreitol (DTT) inducing controlled breakdown, enabling the release of bound DNA. As such, the high-affinity self-assembled multivalent binding is temporary. Furthermore, because the multivalent dendrons are constructed from esters, a second slow degradation step causes further breakdown of these structures. This two-step double-degradation mechanism converts a large self-assembling unit with high affinity for DNA into small units with no measurable binding affinity – demonstrating the advantage of self-assembled multivalency (SAMul) in achieving highly responsive nanoscale binding of biological targets.

Graphical abstract: Double-degradable responsive self-assembled multivalent arrays – temporary nanoscale recognition between dendrons and DNA

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Article information


Submitted
07 Nov 2013
Accepted
13 Nov 2013
First published
22 Nov 2013

Org. Biomol. Chem., 2014,12, 446-455
Article type
Paper

Double-degradable responsive self-assembled multivalent arrays – temporary nanoscale recognition between dendrons and DNA

A. Barnard, P. Posocco, M. Fermeglia, A. Tschiche, M. Calderon, S. Pricl and D. K. Smith, Org. Biomol. Chem., 2014, 12, 446
DOI: 10.1039/C3OB42202J

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