Boron‐Containing Lipids and Liposomes: New Conjugates of Cholesterol with Polyhedral Boron Hydrides

Abstract

A series of boron‐containing lipids were prepared by reactions of cyclic oxonium derivatives of polyhedron boranes and metallacarboranes (closo‐dodecaborate anion, cobalt and iron bis(dicarbollides)) with amine and carboxylic acids which are derived from cholesterol. Stable liposomal formulations, on the basis of synthesized boron‐containing lipids, hydrogenated soybean l‐α‐phosphatidylcholine and (HSPC) 1,2‐distearoyl‐sn‐glycero‐3‐phosphoethanolamine‐N‐[methoxy(polyethylene glycol)‐2000] (DSPE‐PEG) as excipients, were prepared and then characterized by dynamic light scattering (DLS) that revealed the formation of particles to be smaller than 200 nm in diameter. The resulting liposomal formulations showed moderate to excellent loading and entrapment efficiency, thus justifying the design of the compounds to fit in the lipid bilayer and ensuring ease of in vivo use for future application. The liposomal formulations based on cobalt and iron bis(dicarbollide)‐based lipids were found to be nontoxic against both human breast normal epithelial cells MCF‐10A and human breast cancer cells MCF‐7.