A new class of sulfoxide surfactants derived from Tris. Synthesis and preliminary assessments of their properties

A new class of non-ionic amphiphilic molecules suitable for biological purposes, especially extraction of membrane proteins, is reported. Such surfactants were prepared in two steps : addition of alkyl or fluoroalkyl mercaptan on Tris(hydroxymethyl)acrylamidomethane (THAM) derivatives, followed by the oxydation of sulfide group in sulfoxide moiety in order to provide water solubility to the molecule. The detergent efficiency of these new surfactants were assayed on rat liver cells. Ionic or free radical addition of alkyl or fluoroalkyl mercaptan (RSH) on Tris(hydroxymethyl)acrylamidomethane, then oxydation of sulfide in sulfoxide moiety lead to new non ionic surfactants which could be used for protein solubilization.