Issue 23, 2009

Target-selective vesicle fusion system with pH-selectivity and responsiveness

Abstract

The present paper reports on induction of target-selective liposomal vesicle fusion triggered by molecular recognition on a vesicle surface. Phosphatidylinositol (PI) having a sugar-like cyclic cys-diol structure was selected as a recognition target. Since diol sugars are abundant on cell surfaces, vesicle fusion systems based on the recognition of diol functionalities can be relevant for liposome-based drug delivery. Here, we design and synthesize a novel phenylboronic acid derivative with a tertiary amine group adjacent to the boron atom as a pilot molecule toward PI at a physiological condition. The pilot vesicle, or EggPC liposome containing this phenylboronic acid derivative causes selective membrane fusion toward a target liposomal vesicle containing sugar-like cyclic cys-diol structure at a physiological condition. From lipid mixing and inner-leaflet mixing assays, we demonstrate that the fusion event activated by inter-vesicular complex formation occurs rapidly. Furthermore, we also construct the target selective fusion system working only at the endosomal pH by the use of weakly acidic lipid, 1,2-dipalmitoyl-sn-glycero-3-succinate (DPGS) containing the pilot vesicle. The lipid mixing and inner-leaflet mixing assays make it clear that the vesicle fusion proceeds over pH range 5.0–5.5, whose range is upper than the pKa of the boronic acid moiety on cys-diol complexation and lower than the pKa of the carboxyl group of DPGS.

Graphical abstract: Target-selective vesicle fusion system with pH-selectivity and responsiveness

Supplementary files

Article information

Article type
Paper
Submitted
13 May 2009
Accepted
17 Aug 2009
First published
14 Sep 2009

Soft Matter, 2009,5, 4719-4725

Target-selective vesicle fusion system with pH-selectivity and responsiveness

A. Kashiwada, M. Tsuboi, T. Mizuno, T. Nagasaki and K. Matsuda, Soft Matter, 2009, 5, 4719 DOI: 10.1039/B909503A

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