Heterocyclic boronic acids display sialic acid selective binding in a hypoxic tumor relevant acidic environment.

ABSTRACT: Boronic acids are well known for their ability to reversibly interact with the diol groups found in sugars and glycoproteins. However, they are generally indiscriminate in their binding. Herein we describe the discovery of a group of heterocyclic boronic acids demonstrating unusually high affinity and selectivity for sialic acids (SAs or N-acetylneuraminic acid), which are sugar residues that are intimately linked with tumor growth and cancer progression. Remarkably, these interactions strengthen under the weakly acidic pH conditions associated with a hypoxic tumoral microenvironment. In vitro competitive binding assays uncovered a significantly higher ability of 5-boronopicolinic acid, one of the derivatives identified in this work as a strong SA-binder, to interact with cel

SUBMITTER: Matsumoto A 

PROVIDER: S-EPMC5627601 | biostudies-literature | 2017 Sep

REPOSITORIES: biostudies-literature