Chameleonic amphiphile: The unique multiple self-assembly properties of a natural glycolipid in excess of water

Chameleons are stunning reptiles which change colour according to the surrounding environment. In astrophysics, chameleons are particles whose mass varies in the surrounding matter. Here, we show the chameleonic self-assembly behavior of a low molecular weight (LMW) amphiphile, a broad class of molecules widely studied for several decades. Their ability to self-assemble in water make them both fascinating and useful compounds for a number of applications. Under thermodynamic conditions, their thermotropic and lyotropic phase behavior is generally predicted in relation to their molecular shape, as seen for classical head-tail molecules like surfactants or phospholipids. However, many exceptions do exist, either when amphiphiles have unconventional shapes, e.g., bolaform or gemini, or when they contain functional groups which undergo specific interactions such as H-bonding or π-π stacking. In excess water, surfactants form micelles, phospholipids form vesicles or lamellar phases, and functional amphiphiles often form micelles or fibers. Here, we show the multiphase behavior, much richer and more unpredictable than what it is known for most amphiphiles, of a biobased glycolipid produced by the yeast S. bombicola ΔugtB1. In excess water and within a narrow pH range around neutrality, this compound assembles into micelles, uni- and multilamellar vesicles, lamellae and fibers, simply as a function of changing pH, temperature and counterions. This rich phase behavior is not only interesting in itself, it also generates a number of diverse biocompatible and biodegradable soft self-assembled materials like hydrogels, complex coacervates and drug carriers.