Mimicking Complex Biological Membranes and Their Programmable Glycan Ligands with Dendrimersomes and Glycodendrimersomes

Abstract

Synthetic vesicles have been assembled and coassembled from phospholipids, their modified versions, and other single amphiphiles into liposomes, and from block copolymers into polymersomes. Their time-consuming synthesis and preparation as stable, monodisperse, and biocompatible liposomes and polymersomes called for the elaboration of new synthetic methodologies. Amphiphilic Janus dendrimers (JDs) and glycodendrimers (JGDs) represent the most recent self-assembling amphiphiles capable of forming monodisperse, stable, and multifunctional unilamellar and multilamellar onion-like vesicles denoted dendrimersomes (DSs) and glycodendrimersomes (GDSs), dendrimercubosomes (DCs), glycodendrimercubosomes (GDCs), and other complex architectures. Amphiphilic JDs consist of hydrophobic dendrons connected to hydrophilic dendrons and can be thought of as monodisperse oligomers of a single amphiphile. They can be functionalized with a variety of molecules such as dyes, and, in the case of JGDs, with carbohydrates. Their iterative modular synthesis provides efficient access to sequence control at the molecular level, resulting in topologies with specific epitope sequence and density. DSs, GDSs, and other architectures from JDs and JGDs serve as powerful tools for mimicking biological membranes and for biomedical applications such as targeted drug and gene delivery and theranostics. This Review covers all aspects of the synthesis of JDs and JGDs and their biological activity and applications after assembly in aqueous media.

Janus dendrimersomes coassembled from fluorinated, hydrogenated, and hybrid Janus dendrimers as models for cell fusion and fission

“…Their simple preparation by injection of THF, ethanol, and other organic solutions of JDs into aqueous media results in monodisperse assemblies of predictable size with bilayer thicknesses of 4.5-6 nm, which are similar to those of biological membranes (11,12). DSs together with their sugar (glycan)-presenting counterparts glycodendrimersomes (13) combine the biological compatibility of liposomes with the robustness of polymersomes, providing improved synthetic vesicles for mimicking biological membranes including by hybrid coassembly with bacterial membranes (14) and for biomedical applications (15).…”

Merging Macromolecular and Supramolecular Chemistry into Bioinspired Synthesis of Complex Systems

“…Stability, polydispersity and dimensions together with bilayer thickness and method of their preparation are the major obstacles to be overcomed in order to make progress in this field. Recently self‐assembling amphiphilic Janus dendrimers and Janus glycodendrimers have been discovered to self‐assemble by simple injection from an organic solvent such as ethanol into water or buffer into monodisperse vesicles with predictable dimensions named dendrimersomes and glycodendrimersomes exhibiting similar bilayer thickness with that of natural cell membranes –. They can be co‐assembled with bacterial and mammalian cell membranes and their engineered surface can generate rafts that are accessible for structural analysis by diffraction and diffraction‐like methods –…”

Functionalized Truxene Scaffold: A Promising Advanced Organic Material for Digital Era

“…From the last few decades, much interests were awakened towards π‐conjugated arylamines because of their usage in hole‐transporting materials (HTMs), and high performing perovskite‐based solar cells (PSCs). The perovskite which acts as a light absorber and HTM is used for the extraction of photogenerated holes and their transport to the electrode . The spirobifluorene derivative 72 is expensive, low hole conductive and is difficult to synthesize.…”