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Issue 7, 2011
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Peptide-based lipid mimetics with tunable core properties viathiol–alkyne chemistry

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Abstract

Thiolalkyne chemistry is utilized to produce peptide-based A2B star polymers. This topography resembles a phospholipid where the polypeptide B block represents a functional, polar head group and the A blocks represent lipophilic units. We utilize a convergent, modular approach to produce lipid mimetics through conjugation of poly(L-glutamic acid) with three different lipophilic moieties (octadecane, cholesterol and polyhedral oligomeric silsesquioxane). All samples are shown to self-assemble in aqueous solution into pH-responsive vesicles. The self-assembly and pH-responsiveness were characterized using circular dichroism spectroscopy and light scattering. Detailed light scattering experiments determined that the aggregation number of the vesicles remains nearly constant as a function of pH, suggesting that the pH-responsiveness is a result of both the helix–coil transition as well as a change in chain packing at the vesicle interface.

Graphical abstract: Peptide-based lipid mimetics with tunable core properties viathiol–alkyne chemistry

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Publication details

The article was received on 05 Jan 2011, accepted on 15 Feb 2011 and first published on 08 Mar 2011


Article type: Paper
DOI: 10.1039/C1PY00003A
Polym. Chem., 2011,2, 1536-1541

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    Peptide-based lipid mimetics with tunable core properties viathiol–alkyne chemistry

    J. G. Ray, J. T. Ly and D. A. Savin, Polym. Chem., 2011, 2, 1536
    DOI: 10.1039/C1PY00003A

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