Abstract
A series of externally and internally sensitized photolabile amphiphiles having their hydrophilic headgroups and hydrophobic tails tethered via the dithiane-based photocleavable “latch” is prepared. These lipids are tested in various formulations with naturally occurring phospholipids and/or cholesterol to prepare light-sensitive liposomes. Irradiation of such liposomes in phosphate-buffered saline solution (medium-pressure mercury lamp, Pyrex filter, λ > 300 nm) increases the bilayer permeability and accelerates the release of entrapped small organic molecules by up to an order of magnitude. A novel assay, based on 1H or 19F pulsed field gradient NMR measurements of diffusion coefficients, is developed to monitor the lifetimes of dark leakage and light-induced unloading of the probe molecules.
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