Cyclic Disulfide Liposomes for Membrane Functionalization and Cellular Delivery.

Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 9513783 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1521-3765 (Electronic) Linking ISSN: 09476539 NLM ISO Abbreviation: Chemistry Subsets: MEDLINE

Original Publication: Weinheim, Germany : Wiley-VCH

Drug Delivery Systems*/methods ; Liposomes*/metabolism; Disulfides ; Lipids ; Sulfhydryl Compounds

Liposomes are effective therapeutic delivery nanocarriers due to their ability to encapsulate and enhance the pharmacokinetic properties of a wide range of therapeutics. Two primary areas in which improvement is needed for liposomal drug delivery is to enhance the ability to infiltrate cells and to facilitate derivatization of the liposome surface. Herein, we report a liposome platform incorporating a cyclic disulfide lipid (CDL) for the dual purpose of enhancing cell entry and functionalizing the liposome membrane through thiol-disulfide exchange. In order to accomplish this, CDL-1 and CDL-2, composed of lipoic acid (LA) or asparagusic acid (AA) appended to a lipid scaffold, were designed and synthesized. A fluorescence-based microplate immobilization assay was implemented to show that these compounds enable convenient membrane decoration through reaction with thiol-functionalized small molecules. Additionally, fluorescence microscopy experiments indicated dramatic enhancements in cellular delivery when CDLs were incorporated within liposomes. These results demonstrate that multifunctional CDLs serve as an exciting liposome system for surface decoration and enhanced cellular delivery.
(© 2022 Wiley-VCH GmbH.)

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DMR-1807689 Directorate for Mathematical and Physical Sciences

Keywords: cellular delivery; cyclic disulfides; fluorescence microscopy; lipids; liposomes

0 (Disulfides)
0 (Lipids)
0 (Liposomes)
0 (Sulfhydryl Compounds)

Date Created: 20220614 Date Completed: 20220816 Latest Revision: 20220816

20240105

10.1002/chem.202201164

35699671