Triggered Liposomal Release through a Synthetic Phosphatidylcholine Analogue Bearing a Photocleavable Moiety Embedded within thesn-2 Acyl Chain

Autor:	Shahrina Alam, Andrew M. Bayer, Michael D. Best, Samuel I. Mattern-Schain
Rok vydání:	2014
Předmět:	Phosphatidylethanolamine Liposome Chemical Phenomena Stereochemistry Phosphatidylethanolamines Organic Chemistry Nile red General Chemistry Lipids Controlled release Catalysis Polyethylene Glycols Kinetics chemistry.chemical_compound Cholesterol Drug Delivery Systems Membrane chemistry Phosphatidylcholine Liposomes Drug delivery Phosphatidylcholines Biophysics Moiety
Zdroj:	Chemistry - A European Journal. 20:3350-3357
ISSN:	0947-6539
DOI:	10.1002/chem.201304094
Popis:	Liposomes represent promising carriers for drug delivery applications. To maximize this potential, there has been significant interest in developing liposomal systems encapsulating molecular cargo that are highly stable until their contents are released remotely in a controlled manner. Herein, we describe the design, synthesis, and analysis of a photocleavable analogue of the ubiquitous lipid phosphoatidylcholine (PC) for the development of highly stable and controllable photodisruptable membranes. Our strategy was to develop a lipid that closely mimics the structure of PC to optimize favorable properties including biocompatibility and stability of subsequent liposomes when mixed with lipids possessing a broad range of physicochemical properties. Thus, NB-PC was designed, which contains a photocleavable 2-nitrobenzyl group embedded within the acyl chain at the sn-2 position. Following the synthesis of NB-PC, liposome disruption efficacy was evaluated through photolysis studies involving the detection of nile red release. Studies performed using a range of liposomes with different percentages of NB-PC, PC, phosphatidylethanolamine (PE), cholesterol, and polyethylene glycol-PE (PEG-PE) demonstrated minimal background release in controls, release efficacies that correlate directly with the amount of NB-PC incorporation, and that release is only minimally impacted by the inclusion of the lipids PE and cholesterol that possess disparate properties. These results demonstrate that the NB-PC system is a highly stable, flexible, and tunable system for photoinitiated release from liposomal systems.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::6295c1cefdb4047aa309597555716697 https://doi.org/10.1002/chem.201304094 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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