Syntheses of Polymerizable Triacyl-type Phosphocholines and Their Polymerized Vesicles

Abstract

Symmetrical phospholipids having three polymerizable acyl groups, ο-[2, 2, 2-tris(2, 4 alkadienoyloxymethypethyl)ethyl]phosphocholines [2a-e] and their saturated models [1a-e] were synthesized (Scheme 1 and 2), and these were dispersed in water by sonication. Formation of (polymerized) vesicles were confirmed by DSC, electron microscopy, submicron partic le analyzer and GPC (Figs.1, 3 and 4, Tables 4 and 5). When the carbon number of the acyl chain was longer than 14, large unilamellar vesicles with diameter of 80-100 nm were formed (Table 5). Polymerized vesicles of [2a-e] were more stable than those of diacyl-type DODPC against detergent attack (Fig.5). They were stable even upon freeze-thaw treatment and against phospholipase D attack (Tables 6 and 7).