The reaction of L-cysteine, L-cysteine hydrochloride and glutathione with arsonolipids (2,3-diacyloxypropylarsonic acids) and their arsenoso derivatives

Article type: Research Article

Authors: Ioannou, Panayiotis V.^{; *} | Vachliotis, Dimitris G.

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 997118; E-mail: [email protected].

Abstract: From the arsonolipids (2,3-diacyloxypropylarsonic acids, 1) the stearoyl and palmitoyl are not reduced by ascorbic acid/iodine in methanol while the myristoyl and lauroyl arsonolipids are reduced to the arsenoso compounds 3. The reaction of arsenoso compounds 3 and of arsonolipids 1 with L-cysteine (cysSH), L-cysteine hydrochloride (cysSH·HCl) and glutathione (GSH) under various conditions was studied. Lipo-dithioarsonites [R-As(SR′)2] 4 have been isolated with GSH with both lipids 1 and 3. The product 4 was obtained only from 3 and cysSH. The salt cysSH·HCl reacted with 3 in methanol but gave it back on attempts at isolation of 4, while in DMSO unknown products were obtained. The arsonolipids 1 can be components of biological membranes and all lipo-dithioarsonites 4 prepared were insoluble in water and once formed must remain anchored in a membrane, thus altering its properties.

Keywords: Arsonolipids, arsenoso compounds, L-cysteine, L-cysteine hydrochloride, glutathione

DOI: 10.3233/MGC-190794

Journal: Main Group Chemistry, vol. 18, no. 4, pp. 445-457, 2019