Photolabile lipids based on dithiane-carbonyl adducts: toward light-sensitive liposomes

ORGN 539

Andrei G. Kutateladze and Zaiguo Li. Department of Chemistry and Biochemistry, University of Denver, 2190 E. Iliff Ave., F.W. Olin Hall, rm.202, Denver, CO 80208-2436
A series of externally and internally sensitized photolabile amphiphiles having their hydrophilic head groups 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 PBS buffer (medium pressure mercury lamp, Pyrex filter, l > 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 PFG NMR measurements of diffusion coefficients, is developed to monitor the lifetimes of dark leakage and light-induced unloading of the probe molecules.
 

Bioorganic, Molecular Recognition, Asymmetric Reactions and Syntheses
11:00 AM-1:00 PM, Wednesday, September 10, 2003 Javits Convention Center -- Hall 1B/1C, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, September 8, 2003 Javits Convention Center -- North Pavillion, Sci-Mix

Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003