Enhanced assembly stability for amine-based cationic glycolipid.

Glycolipids incorporating positive charges, mediated by an imidazolium cation, have shown potential for effective formulation of vesicular drug carriers, reflecting repulsive electrostatic forces, promoting the formation of nanosized assemblies and preventing unwanted Oswald ripening (Goh et al. (2019), ACS Omega 4, 17,039). Our continuous development of an assembly-based drug delivery system prompted us to investigate a pH-sensitive analogue, leading to the synthesis of a 6-amino-Guerbet glycoside.

Biomimetic Targeted Theranostic Nanoparticles for Breast Cancer Treatment.

The development of biomimetic drug delivery systems for biomedical applications has attracted significant research attention. As the use of cell membrane as a surface coating has shown to be a promising platform for several disease treatments. Cell-membrane-coated nanoparticles exhibit enhanced immunocompatibility and prolonged circulation time.

Sugar based cationic magnetic core-shell silica nanoparticles for nucleic acid extraction.

Nucleic acid (NA) extraction is an essential step in molecular testing for a wide range of applications. Conventional extraction protocols usually suffer from time consuming removal of non-nucleic acid impurities. In this study, a new magnetic nanoparticle (MNP) is presented to simplify the NA extraction.

Ionic magnetic core-shell nanoparticles for DNA extraction.

Magnetic nanoparticles with specific surface features are interesting materials for biomedical applications. The combination of molecular interactions on small particles with macroscopic cohesion forces offers unique opportunities. This work reports the synthesis of magnetic core-shell nanoparticles with alkylimidazolium coated surface for effective DNA extraction.

Imidazolium-Linked Azido-Functionalized Guerbet Glycosides: Multifunctional Surfactants for Biofunctionalization of Vesicles.

Aiming for glycolipid-based vesicles for targeted drug delivery, cationic Guerbet glycosides with spacered click functionality were designed and synthesized. The cationic charge promoted the distribution of the glycolipids during the formulation, thereby leading to homogeneously small vesicles. The positive surface charge of the vesicles stabilizes them against unwanted fusion and promotes interactions of the drug carriers with typical negative charge-dominated target cells.

Functionalized glycolipids for potential bioconjugation of vesicles.

Two azide-terminated oligoethylene oxide spacered glycolipids have been synthesized, and their assembly behavior has been studied in comparison to the corresponding base surfactants. The results suggest potential of the Guerbet lactoside-based compound for targeted drug delivery, while a coiling of the ethylene oxide linker disfavors the application of the glucoside.

Renewable resources-based approach to biantennary glycolipids.

A new synthesis approach towards biantennary lipids of Guerbet glycoside type was developed based on oleic acid as sustainable resource. Functionalization of the double bond provided access to primary alcohols with α-branched C-skeleton. Formulation studies with corresponding lactosides indicated formation of vesicles with high assembly stability.

Secondary bonding in di-methyl-bis-(morpholine-4-carbodi-thio-ato-κ,')tin(IV): crystal structure and Hirshfeld surface analysis.

The title compound, [Sn(CH)(CHNOS)], has the Sn atom bound by two methyl groups which lie over the weaker Sn-S bonds formed by two asymmetrically chelating di-thio-carbamate ligands so that the coordination geometry is skew-trapezoidal bipyramidal. The most prominent feature of the mol-ecular packing are secondary Sn⋯S inter-actions [Sn⋯S = 3.5654 (7) Å] that lead to centrosymmetric dimers.

-Di-chlorido-bis-(dimethyl sulfoxide-κ)bis-(4-fluoro-benzyl-κ)tin(IV): crystal structure and Hirshfeld surface analysis.

The Sn atom in the title diorganotin compound, [Sn(CHF)Cl(CHOS)], is located on a centre of inversion, resulting in the CClO donor set having an all- disposition of like atoms. The coordination geometry approximates an octa-hedron. The crystal features C-H⋯F, C-H⋯Cl and C-H⋯π inter-actions, giving rise to a three-dimensional network.

['-(4-Dec-yloxy-2-oxido-benzyl-idene)-3-hy-droxy-2-naphtho-hydrazidato-κ,,']di-methyl-tin(IV): crystal structure and Hirshfeld surface analysis.

The title diorganotin compound, [Sn(CH)(CHNO)], features a distorted SnCNO coordination geometry almost inter-mediate between ideal trigonal-bipyramidal and square-pyramidal. The dianionic Schiff base ligand coordinates in a tridentate fashion two alkoxide O and hydrazinyl N atoms; an intra-molecular hy-droxy-O-H⋯N(hydrazin-yl) hydrogen bond is noted. The alk-oxy chain has an all- conformation, and to the first approximation, the mol-ecule has local mirror symmetry relating the two Sn-bound methyl groups.

Alkyl-imidazolium glycosides: non-ionic-cationic hybrid surfactants from renewable resources.

A series of surfactants combining carbohydrate and imidazolium head groups were prepared and investigated on their assembly behavior. The presence of the imidazolium group dominated the interactions of the surfactants, leading to high CMCs and large molecular surface areas, reflected in curved rather than lamellar surfactant assemblies. The carbohydrate, on the other hand, stabilized molecular assemblies slightly and reduced the surface tension of surfactant solutions considerably.

Functional glycolipid-crown-ethers by click chemistry.

A series of glycolipid crown ether analogs was prepared by bis-propargylation of lauryl glycoside followed by subsequent click-coupling with ethylene glycol-based diazides. The triazole-linked macrocycles were obtained in remarkable high yields. While the surfactant assembly was affected by presence of sodium ions, suggesting the formation of complexes, no ion-selectivity was observed for the macrocylic ligands.

New Y-shaped surfactants from renewable resources.

A series of sugar-based surfactants, involving a single hydrophobic chain (C12) and two side-by-side arranged head groups, was prepared form simple glucose precursors. All surfactants were highly water soluble and exhibited exclusively micellar assemblies. This behavior makes them interesting candidates for oil in water emulsifiers.

4-Formyl-phenyl 2,3,4,6-tetra-O-acetyl-β-d-galactopyran-oside.

The galactose ring in the title compound, C(21)H(24)O(11), has a chair conformation with the substituted benzene ring occupying an equatorial position. The crystal packing features C-H⋯O inter-actions that lead to the formation of supra-molecular layers in the ab plane.

4-Formyl-phenyl 2,3,4,6-tetra-O-acetyl-β-d-glucopyran-oside.

The pyran-oside ring in the title compound, C(21)H(24)O(11), has a chair conformation with the substituted benzene ring occupying an equatorial position. The crystal packing is dominated by C-H⋯O inter-actions that lead to the formation of supra-molecular layers in the ab plane.