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Structural and biological overview of Boron-containing amino acids in the medicinal chemistry field.

Antonio A. Garcia,Alexey Rayevski,Erik Andrade-Jorge,J. Trujillo-Ferrara

Published 2019 in Current Medicinal Chemistry

ABSTRACT

Amino acids are the basic structural units of proteins as well as the precursors of many compounds with biological activity. The addition of boron reportedly induces changes in the chemical-biological profile of amino acids. METHODS We compiled information on the biological effect of some compounds and discuss the structure-activity relationship of the addition of boron. The specific focus presently is on borinic derivatives of α-amino acids, the specific changes in biological activity caused by the addition of a boron-containing moiety, and the identification of some attractive compounds for testing as potential new drugs. RESULTS Borinic derivatives of α-amino acids have been widely synthesized and tested as potential new therapeutic tools. The B-N (1.65 A°) or B-C (1.61 A°) or B-O (1.50 A°) bond is often key for the stability at different pHs and temperatures and activity of these compounds. The chemical features of synthesized derivatives, such as the specific moieties and the logP, polarizability and position of the boron atom are clearly linked to their pharmacodynamic and pharmacokinetic profiles. Some mechanisms of action have been suggested or demonstrated, while those responsible for other effects remain unknown. CONCLUSION The increasing number of synthetic borinic derivatives of α-amino acids as well as the recently reported crystal structures are providing new insights into the stability of these compounds at different pHs and temperatures, their interactions on drug targets, and the ring formation of five-membered heterocycles. Further research is required to clarify the ways to achieve specific synthesis, the mechanisms involved in the observed biological effect, and the toxicological profile of this type of boron-containing compounds (BCCs).

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