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Bicelles are generally formed by phospholipid-based systems and are useful for various applications, such as nanocarriers or membrane protein crystallization. The same disc-like assemblies, nonionic surfactant bicelles (NSBs), can also be formed using nonionic amphiphiles, but this has not been reported extensively. We report a novel NSB system that employs the double-tailed nonionic amphiphile, polyglyceryl dialkyl ether (C12CmGn), which has two alkyl chains and a polyglyceryl group. A symmetric-tail molecule, C12C12G13.8, formed vesicles, whereas an asymmetric-tail molecule, C12C14G15.5, formed NSBs through a simple one-step process using ultrasonication. The 1 wt% aqueous solution of C12C14G15.5 was in a two-phase equilibrium of a lamellar phase and a water phase. Transparent dispersion was obtained through ultrasonication treatment. The size distribution in the dispersion was obtained by dynamic light scattering (DLS), resulting in a narrow distribution of around 20 nm in diameter. A negatively-stained transmission electron microscopy (TEM) image showed oblong and spherical shapes, which are typically observed in bicelle-forming systems. A small angle neutron scattering (SANS) measurement well proved bicelle formation by fitting a core–shell bicelle form factor model. The disc thickness and diameter were in agreement with the values obtained by DLS and TEM, respectively. A larger shell thickness at the rim part than at the flat disc part suggested that NSB aggregates have inhomogeneous molecular distribution. Similar to phospholipid systems, the bicelle-forming C12C14G15.5 system produced a defective lamellar phase formation at high surfactant concentrations, whereas a general lamellar phase was formed in the vesicle-forming C12C12G13.8 system. [ABSTRACT FROM AUTHOR]

Abstract: A novel and highly convenient process is described for the asymmetric synthesis of polyhydroxylated pyrrolizidine alkaloids, (+)-alexine [(1R,2R,3R,7S,7aS)-3-hydroxymethyl-1,2,7-trihydroxypyrrolizidine] and (−)-7-epi-alexine [(1R,2R,3R,7R,7aS)-3-hydroxymethyl-1,2,7-trihydroxypyrrolizidine], as the potent glycosidase inhibitors by featuring the efficient and stereodefined elaboration of the functionalized pyrrolidine derivatives, which were, in turn, prepared via stereoselective manipulation of the homochiral allyl alcohol precursors derived from l-xylose. [Copyright &y& Elsevier]

Vesicles with synthetic nonionic surfactants are called niosomes or NSVs, and these have been the focus of attention as an alternative to phospholipid liposomes as drug carriers. Especially it is demanded to discover novel niosomal systems with polyol-type nonionic surfactants from the viewpoint of environmental aspects. In this paper, a novel series of double-tailed nonionic surfactants, polyglyceryl dialkyl ethers, (C12)2Gn (n = 2.3, 5.4, 9.4, and 13.8), was synthesized, and its aqueous phase behavior and niosome formation were studied. Because of its double-tailed molecular structure, a lamellar liquid crystalline phase was dominant in the binary phase diagrams for different polyglyceryl chain lengths. The single lamellar liquid crystalline phase region was expanded as the polymerization degree in the hydrophilic moiety increased. Small-angle X-ray scattering spectra revealed the lamellar structure for the (C12)2G2.3 was extremely loose. Molecular packing in the lamellar phase was analyzed except for the (C12)2G2.3 system by using a geometrical model of the lamellar phase. The effective cross-sectional area per molecule at the interface increased extensively as dilution for the (C12)2G13.8 system but remained almost unchanged for the (C12)2G5.4 system. From the molecular parameters, water-holding ability in the lamellar phase was evaluated, and the results indicated strong hydration ability of the long polyglyceryl chain. In a dilute region, micron-sized giant niosomes and small niosomes of about 100 nm were formulated by vortex mixing and ultrasonication, respectively. The multilamellar structure of the small niosomes was confirmed by transmission electron microscopy. Cholesterol addition in the present surfactant lamellar phase induced the phase transition to the liquid ordered phase, which is the same phenomenon in a phospholipid-cholesterol mixture. The stability of niosomes with/without cholesterol was monitored by the niosome size change. In both cases, the niosomes were stable for at least 100 days.