Jump to main content
Jump to site search

Issue 42, 2016
Previous Article Next Article

Cyclodextrin-based facial amphiphiles: assessing the impact of the hydrophilic–lipophilic balance in the self-assembly, DNA complexation and gene delivery capabilities

Author affiliations

Abstract

Exhaustive structure–efficacy relationship studies on nonviral gene delivery systems are often hampered by the ill-defined or polydisperse nature of the formulations. Facial amphiphiles based on rigid cage-type molecular scaffolds offer unique possibilities towards these studies. Taking advantage of regioselective functionalization schemes, we have synthesized a library of cationic cyclodextrin (CD) derivatives combining a range of hydrophilic and lipophilic domains. We have scrutinized how the hydrophilic–lipophilic balance (HLB) around the CD scaffold determines their self-assembly capabilities and the DNA binding and release abilities of the corresponding CD : DNA nanocomplexes (CDplexes). These features have been ultimately correlated with their capabilities to deliver a reporter luciferase-encoding pDNA into COS-7 cells. The ensemble of results demonstrates that fine tuning of the HLB is critical to induce compaction of DNA by the CD-based facial amphiphiles into transfection-productive CDplexes.

Graphical abstract: Cyclodextrin-based facial amphiphiles: assessing the impact of the hydrophilic–lipophilic balance in the self-assembly, DNA complexation and gene delivery capabilities

Back to tab navigation

Supplementary files

Publication details

The article was received on 26 Aug 2016, accepted on 22 Sep 2016 and first published on 26 Sep 2016


Article type: Paper
DOI: 10.1039/C6OB01882C
Citation: Org. Biomol. Chem., 2016,14, 10037-10049
  •   Request permissions

    Cyclodextrin-based facial amphiphiles: assessing the impact of the hydrophilic–lipophilic balance in the self-assembly, DNA complexation and gene delivery capabilities

    I. Pflueger, C. Charrat, C. O. Mellet, J. M. García Fernández, C. Di Giorgio and J. M. Benito, Org. Biomol. Chem., 2016, 14, 10037
    DOI: 10.1039/C6OB01882C

Search articles by author

Spotlight

Advertisements