Solid-phase synthesis of fluorescent sphingolipids.

Abstract

Sphingomyelinases (SMases) hydrolyze sphingomyelin, a component of cell membranes, into ceramide and phosphorylcholine. Ceramide is a suspected lipid mediator of apoptosis in several cell types. Presently, there are only a handful of assays for SMase activity, many of which require using radioactive substrates. With the goal of developing a simple fluorescence-based Smase assay, fluorescent analogs of sphingomyelin and ceramide were prepd. DPH propionic acid and 1-pyrenehexanoic acid were coupled to polystyrene-tetrafluorophenol resins, then the activated resins were treated with appropriate amines. Preliminary enzyme studies show that the DPH-sphingomyelin acts as a substrate for Bacillus cereus SMase. [on SciFinder(R)]