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

AuthorsPflueger, Iris; Charrat, Coralie; Ortiz-Mellet, Carmen; García-Fernández, José Manuel; Di Giorgio, Christophe; Benito, Juan M.
Issue Date2016
PublisherRoyal Society of Chemistry (UK)
CitationOrganic and Biomolecular Chemistry 14: 10037- 10049 (2016)
AbstractExhaustive 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.
Identifiersdoi: 10.1039/c6ob01882c
issn: 1477-0520
Appears in Collections:(IIQ) Artículos
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