Targeting extracellular glycans: tuning multimeric boronic acids for pathogen-selective killing of Mycobacterium tuberculosis

Abstract

Innovative chemotherapeutic agents that are active against Mycobacterium tuberculosis (Mtb) are urgently required to control the tuberculosis (TB) epidemic.

A boronic acid-functionalized phthalocyanine with an aggregation-enhanced photodynamic effect for combating antibiotic-resistant bacteria

“… 18 , 19 In addition, recent studies have suggested that boronic acid groups are very useful for bacterial targeting because of their ability to form a pair of covalent bonds with glycans on the surface of bacteria. 20 – 22 Therefore, the 3-{ N -(4-boronobenzyl)- N , N -dimethylammonium}phenoxy-substituted zinc( ii ) phthalocyanine PcN4-BA ( Fig. 1a ) was herein designed to be a new PS for antimicrobial PDT.…”

A Pragmatic Guide to Enrichment Strategies for Mass Spectrometry–Based Glycoproteomics

“…This presents a disadvantage for enriching many low-abundance glycopeptides that may be outcompeted during the enrichment process. Recently, several reports have shown that boronic acid–glycan interactions can be enhanced through screening of boronic acid compounds or through increasing avidity via dendrimeric boronic acid–functionalized materials ( 345 , 346 , 349 , 350 , 351 ).…”

Recent developments in the medicinal chemistry of single boron atom-containing compounds

“…Guy et al. 32 designed multimeric boronic acids to selectively target structurally unique Mtb cell envelope glycans, in order to overcome the Mtb cell envelope barrier ( Fig. 20 ).…”

“…The boronic acid pharmacophore is an established glycan-binding functional group that forms reversible complexes with diol groups commonly found in sugar molecules and glycoproteins 28 , 29 , 30 , 31 . Exploiting this behavior, multimeric boronic acids have been designed to target pathogens’ extracellular glycans, both to overcome inherent cell envelope barriers and to prevent the development of drug resistance 32 . Boronic acid-containing prodrugs of hydroxylated drug molecules have also been developed to reduce first-pass metabolism and thus to increase bioavailability 33 , 34 , 35 .…”