Arsonolipids,pseudo arsonolipids,arsinolipids and arsonoliposomes: Preparations,biophysical,biochemical and biological aspects

Abstract

This article describes the preparation of the unnatural arsonolipids 7–9, pseudo arsonolipids 10 and 11, and arsinolipids 12–14 (Fig. 3). Their preparation was motivated by the unique properties of the arsenic compared to phosphorus atom of the –AsO₃H₂ and >AsO₂H groups. It was anticipated that these lipids will show interesting physical, chemical, biochemical and biological properties. Two key points in their preparation have been identified and studied: the preparation of the precursor hydroxy-containing arsonic and arsinic acids and their subsequent acylation to the corresponding arsono- and arsinolipids. The most intensively studied were the arsonolipids 7 which showed quite interesting physical properties forming in water super structures and interacted with carbonic anhydrase and phospholipase A₂. They formed arsonoliposomes either in the absence or in the presence of cholesterol and a phospholipid. The latter arsonoliposomes alone, i.e. in the absence of a trapped drug, revealed quite promising selective toxicity against protozoal parasites, various cancer cells in vitro and prostate cancer in vivo.