Synthesis, physicochemical and photophysical characterization of 4-(1-Pyrenyl)-Butyl-α-d-mannopyranoside

Glycolipids are biomolecules composed of a lipid chain (lipophilic) and a monosaccharide or oligosaccharide as hydrophilic group. Their chemical structure and biological role make them undoubtedly good candidates for a large and continuously growing number of biotechnological applications. Mannose is a carbohydrate present on membrane glycolipids of a wide number of pathogenic microorganisms (bacteria, fungi, protozoa, and viruses) and specifically recognized by several lectins. We synthesized a mannose derivative linked through a short methylene chain to a pyrene moiety which behaves as a surfactant, able to aggregate, and retains the photophysical properties of pyrene: showing comparable absorption and emission spectra, having lower fuorescence quantum yield and the ability to form excimer, and finally the ability to produce O₂(¹Δ_g) with high quantum yields. Thus, this novel molecule would open future applications for detection (fuorescence) or inactivation (singlet oxygen) of bacterial pathogens, viruses, tumor cells, or particular cells.