In situ synthesis of fluorescent membrane lipids (ceramides) using click chemistry

Abstract

Ceramide analogues containing azide groups either in the polar head or in the hydrocarbon chains are nonfluorescent. When incorporated into phospholipid bilayers, they can react in situ with a non-fluorescent 1,8-naphthalimide using click chemistry giving rise to fluorescent ceramide derivatives emitting at ̃440 nm. When incorporated into giant unilamellar vesicles, two-photon excitation at 760 nm allows visualization of the ceramide-containing bilayers. This kind of method may be of general applicability in the study of model and cell membranes. © Springer-Verlag 2012.