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Article
Aromatically Functionalized Cyclic Tricholate Macrocycles: Aggregation, Transmembrane Pore Formation, Flexibility, and Cooperativity
Journal of Organic Chemistry
  • Lakmini Sandachaya Widanapathirana, Iowa State University
  • Yan Zhao, Iowa State University
Document Type
Article
Disciplines
Publication Version
Published Version
Publication Date
4-1-2012
DOI
10.1021/jo3004056
Abstract
The aggregation of macrocyclic oligocholates with introverted hydrophilic groups and aromatic side chains was studied by fluorescence spectroscopy and liposome leakage assays. Comparison between the solution and the membrane phase afforded insight into the solvophobically driven aggregation. The macrocycles stacked over one another in lipid membranes to form transmembrane nanopores, driven by a strong tendency of the water molecules in the interior of the amphiphilic macrocycles to aggregate in a nonpolar environment. The aromatic side chains provided spectroscopic signatures for stacking, as well as additional driving force for the aggregation. Smaller, more rigid macrocycles stacked better than larger, more flexible ones because the cholate building blocks in the latter could rotate outward and diminish the conformation needed for the water-templated hydrophobic stacking. The acceptor–acceptor interactions among naphthalenediimide (NDI) groups were more effective than the pyrene–NDI donor–acceptor interactions in promoting the transmembrane pore formation of the oligocholate macrocycles.
Comments

Reprinted (adapted) with permission from Journal of Organic Chemistry 77 (2012): 4679, doi:10.1021/jo3004056. Copyright 2012 American Chemical Society.

Copyright Owner
American Chemical Society
Language
en
File Format
application/pdf
Citation Information
Lakmini Sandachaya Widanapathirana and Yan Zhao. "Aromatically Functionalized Cyclic Tricholate Macrocycles: Aggregation, Transmembrane Pore Formation, Flexibility, and Cooperativity" Journal of Organic Chemistry Vol. 77 Iss. 10 (2012) p. 4679 - 4687
Available at: http://works.bepress.com/yan_zhao/5/