Synthesis of amphiphilic naturally-derived oligosaccharide-block-wax oligomers and their self-assembly

Julia D. Cushen, Kadhiravan Shanmuganathan, Dustin W. Janes, C. Grant Willson, Christopher J. Ellison

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Self-assembly characteristics of amphiphilic macromolecules into micelles, nanoparticles and vesicles has been of fundamental interest for many applications including designed nanoscale therapeutic delivery systems and enzymatic reactors. In this work, a class of amphiphilic block oligomers was synthesized from naturally occurring oligosaccharides and aliphatic alcohol precursors, which are all currently prominent in the pharmaceutical, food, and supplement industries. These block oligomer materials were synthesized by functionalization of the precursor materials followed by subsequent coupling by azide-alkyne cycloaddition and their bulk self-assembly was investigated after solvent vapor annealing. Self-assembly of the amphiphilic materials into liposomes in aqueous solution was also investigated after preparing solutions using a nanoprecipitation method. Encapsulation of hydrophobic components was demonstrated and verified using dynamic light scattering, transmission electron microscopy, and fluorescence spectroscopy experiments. (Chemical Equation Presented).

Original languageEnglish (US)
Pages (from-to)839-844
Number of pages6
JournalACS Macro Letters
Volume3
Issue number9
DOIs
StatePublished - Sep 16 2014
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2014 American Chemical Society.

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