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

Article type: Research Article

Authors: Ioannou, Panayiotis V.^{; *}

Affiliations: Department of Chemistry, University of Patras, Patras, Greece

Correspondence: [*] Corresponding author: Panayiotis V. Ioannou, Department of Chemistry, University of Patras, 26504 Patras, Greece. Fax: +30 2610 997 118; E-mail: [email protected].

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.

Keywords: Arsenic, arsonolipids, pseudo arsonolipids, arsinolipids, preparations, properties

DOI: 10.3233/MGC-180255

Journal: Main Group Chemistry, vol. 17, no. 2, pp. 111-132, 2018