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. Herein, human red blood cell (RBC) membrane-cloaked nanoparticles with enhanced targeting functionality were designed as a targeted nanotheranostic against cancer. Naturally, derived human RBC membrane modified with targeting ligands coated onto polymeric nanoparticle cores containing both chemotherapy and imaging agent. Using epithelial cell adhesion molecule (EpCAM)-positive MCF-7 breast cancer cells as a disease model, the nature-inspired targeted theranostic human red blood cell membrane-coated polymeric nanoparticles (TT-RBC-NPs) platform was capable of not only specifically binding to targeted cancer cells, effectively delivering doxorubicin (DOX), but also visualizing the targeted cancer cells. The TT-RBC-NPs achieved an extended-release profile, with the majority of the drug release occurring within 5 days. The TT-RBC-NPs enabled enhanced cytotoxic efficacy against EpCAM positive MCF-7 breast cancer over the non-targeted NPs. Additionally, fluorescence images of the targeted cancer cells incubated with the TT-RBC-NPs visually indicated the increased cellular uptake of TT-RBC-NPs inside the breast cancer cells. Taken together, this TT-RBC-NP platform sets the foundation for the next-generation stealth theranostic platforms for systemic cargo delivery for treatment and diagnostic of cancer.

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. A core-shell design, comprising of a ferromagnetic core coated with mesoporous silica, forms the basis of the functional nanoparticle. Chemical functionalization of the silica coating includes a multistep synthesis, in which an activated nanoparticle is coupled with a triethylene glycol spaced glycosyl imidazole. The molecular design aims for charge interactions between the imidazolium-based positive nanoparticle surface and nucleic acids, with specific hydrogen bonding between the surface bonded carbohydrate and nucleic acid targets to ensure nucleic acid selectivity and avoid protein contamination. Two different carbohydrates, differing in molecular size, were selected to compare the efficiency in terms of NA extraction. A triethylene glycol spacer provides sufficient flexibility to remove particle surface constraints for the interaction. The Brunauer-Emmett-Teller (BET) analysis shows a significantly larger surface area for the disaccharide-based particles NpFeSiImMalt (∼181 m2 g-1) compared to the monosaccharide analogue NpFeSiImGlc (∼116 m2 g-1) at small particles sizes (range ∼ 15 nm) and sufficient magnetization (29 emu g-1) for easy isolation by an external magnetic field. The particles enabled a high DNA particle loading ratio of 30-45 wt% (MNP/DNA ratio), reflecting an efficient extraction process. A high desorption rate (7 min) with more than 86% of unchanged DNA loading was recorded, indicating low damage to the target extract.

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 C19-skeleton. Formulation studies with corresponding lactosides indicated formation of vesicles with high assembly stability. A relatively narrow bimodal size distribution of the latter, which turns into a narrow unimodal distribution of small vesicles upon addition of an ionic cosurfactant, suggests potential for a vesicular drug delivery system.

Secondary bonding in di-methyl-bis-(morpholine-4-carbodi-thio-ato-κ2S,S')tin(IV): crystal structure and Hirshfeld surface analysis.

The title compound, [Sn(CH3)2(C5H8NOS2)2], has the SnIV 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. These are connected into a three-dimensional architecture via methyl-ene-C-H⋯S and methyl-C-H⋯O(morpholino) inter-actions. The Sn⋯S inter-actions are clearly evident in the Hirshfeld surface analysis of the title compound along with a number of other inter-molecular contacts.

trans-Di-chlorido-bis-(dimethyl sulfoxide-κO)bis-(4-fluoro-benzyl-κC1)tin(IV): crystal structure and Hirshfeld surface analysis.

The SnIV atom in the title diorganotin compound, [Sn(C7H6F)2Cl2(C2H6OS)2], is located on a centre of inversion, resulting in the C2Cl2O2 donor set having an all-trans 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. The respective influences of the Cl⋯H/H⋯Cl and F⋯H/H⋯F contacts to the mol-ecular packing are clearly evident from the analysis of the Hirshfeld surface.

[N'-(4-Dec-yloxy-2-oxido-benzyl-idene)-3-hy-droxy-2-naphtho-hydrazidato-κ3N,O,O']di-methyl-tin(IV): crystal structure and Hirshfeld surface analysis.

The title diorganotin compound, [Sn(CH3)2(C28H32N2O4)], features a distorted SnC2NO2 coordination geometry almost inter-mediate between ideal trigonal-bipyramidal and square-pyramidal. The dianionic Schiff base ligand coordinates in a tridentate fashion via 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-trans conformation, and to the first approximation, the mol-ecule has local mirror symmetry relating the two Sn-bound methyl groups. Supra-molecular layers sustained by imine-C-H⋯O(hy-droxy), π-π [between dec-yloxy-substituted benzene rings with an inter-centroid separation of 3.7724 (13) Å], C-H⋯π(arene) and C-H⋯π(chelate ring) inter-actions are formed in the crystal; layers stack along the c axis with no directional inter-actions between them. The presence of C-H⋯π(chelate ring) inter-actions in the crystal is clearly evident from an analysis of the calculated Hirshfeld surface.

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. A comparative emulsion study discourages the use of pure alkyl imidazolium glycosides owing to reduced assembly stabilities compared with APGs. However, the surfactants are believed to have potential as component in carbohydrate based surfactant mixtures.

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-ß-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.

4-Formyl-phenyl 2,3,4,6-tetra-O-acetyl-ß-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.