Carborane-containing amino acids and peptides: Synthesis, properties and applications

Derivatives of dicarba-closo-dodecaboranes and dicarba-nido-undecaboranes (carboranes) are of increasing interest for modern medicinal chemistry and materials science. The combination of carborane residues and amino acid fragments in one structure can serve as a basis for obtaining promising medicinal agents (primarily, for boron neutron capture therapy), as well as for design the materials with unique properties. For the first time, this review summarizes and analyzes information on the methods of preparation and possible applications of compounds combining in their structure amino acid and peptide residues and carborane clusters, their biological and physicochemical properties. Special attention is paid to the preparation of enantiopure conjugates, the chirality of which is due to both the presence of an asymmetric carbon atom in amino acid fragments and the planar chirality of the carborane cluster. We believe that this review provides comprehensive information about carborane-containing amino acids and peptides and will give a new impetus to the in-depth fundamental research in this field. (C) 2021 Elsevier B.V. All rights reserved.

Automated summary

This review highlights the increasing interest in derivatives of dicarba-closo-dodecaboranes and dicarba-nido-undecaboranes (carboranes) for modern medicinal chemistry and materials science. It discusses the combination of carborane residues and amino acid fragments to obtain promising medicinal agents and unique materials, as well as the preparation and applications of compounds combining amino acid and peptide residues with carborane clusters. Special attention is given to the preparation of enantiopure conjugates and the chirality origins in these compounds, aiming to stimulate further fundamental research in this field.