Lysolecithin analogues: azido- and aminolysolecithin mimics derived from 2,2-bis(dihydroxymethyl)propionic acid.

Lysolecithins have attracted much interest due to some of their physicochem ical and biological properties. These molecules are composed of three parts , a lipophilic tail (fatty acid), a central module (glycerol) and a lipopho bic head (phosphatidylcholine). We describe here the synthesis, following a modular strategy, of lysolecithin analogues starting from 2-azidomethyl-2- methyl-3-hydroxypropionic acid as a glycerol mimic. The reduction of the az ido group leads to amines with good yields for both hydrogenated and fluori nated compounds. The study of the surface properties of aqueous solutions o f these analogues gives evidence for a behaviour similar to that of natural lysolecithins, but they present also some analogies with ionic surfactants . Concerning the impact on cell cultures, our products inhibit cellular gro wth for a concentration above 5 x 10(-4) mol L-1. Cellular death occurs ess entially by necrosis; this phenomenon can be interpreted by a penetration o f the compounds into the membrane, disrupting it by forming mixed micelles (lysolecithin analogues-membrane phospholipids).