Anomeric sugar boronic acid analogues as potential agents for boron neutron capture therapy

Abstract

After the development of accelerators as neutron source, the access to new suitable agents for boron neutron capture therapy (BNCT) became a major need. Among many others, sugar boronic acids have recently attracted attention as boron carriers. Herein we report the synthesis and preliminary biological studies of two new sugar analogues containing a boronic acid at the anomeric position. The analogues were obtained by hydroboration of proper open-chain terminal alkenes that, after quenching with water, spontaneously afforded cyclic boronic acids with hemiacetal-like structures.

A Short and Convenient Synthesis of closo‐Dodecaborate Sugar Conjugates

“…These include boron‐containing porphyrins, polyamines, amino acids, nucleosides, peptides, sugars, monoclonal antibodies, liposomes, nanoparticles, boron cluster compounds and co‐polymers . Recently, boronic acid derivatives of monosaccharides have been proposed . Simple sugars represent an interesting tool in delivering boron to malignant cells, exploiting the concept of the Warburg effect.…”

Virtual Screening and Biochemical Testing of Borocycles as Immunoproteasome Inhibitors

“…These include vaborbactam, a β-lactamase inhibitor, tavaborole, a leucyl-tRNA synthetase inhibitor, and crisaborole, a phosphodiesterase-4 inhibitor. Several other borocycles acting as β-lactamase inhibitors were identified [16][17][18][19], and Imperio et al reported cyclic boronic acid sugar analogues which could function as potential agents in boron neutron capture therapy [20]. Nevertheless, to the best of our knowledge, no cyclic boronates were investigated as iCP inhibitors until the present work.…”

Sweet Boron: Boron-Containing Sugar Derivatives as Potential Agents for Boron Neutron Capture Therapy

“…A further report on boronic acid analogs of monosaccharides describes the synthesis of the hexose analogs 30 and 34 [37] (Scheme 5) bearing the boron atom at the anomeric position. As already reported for other sugar boronic acids, compound 30 gave a slow elimination reaction to the alkenol 31, while 34 was shown to be very stable.…”

“…The stability of 27e can be attributed to the rigidity of the structure, which could hamper the β-elimination reaction, which probably requires a periplanar conformation. To summarize, it appears from literature data that β-hydroxyboronic A further report on boronic acid analogs of monosaccharides describes the synthesis of the hexose analogs 30 and 34 [37] (Scheme 5) bearing the boron atom at the anomeric position. As already reported for other sugar boronic acids, compound 30 gave a slow elimination reaction to the alkenol 31, while 34 was shown to be very stable.…”