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Molecules 2016, 21(9), 1185; doi:10.3390/molecules21091185

Boronic Acid Group: A Cumbersome False Negative Case in the Process of Drug Design

1
Department of Pharmaceutical Chemistry, School of Pharmacy, Aristotle University of Thessaloniki, University Campus, 54124 Thessaloniki, Greece
2
Laboratory of Applied Quantum Chemistry, School of Chemistry, Aristotle University of Thessaloniki, University Campus, 54124 Thessaloniki, Greece
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 18 July 2016 / Revised: 23 August 2016 / Accepted: 2 September 2016 / Published: 7 September 2016
(This article belongs to the Special Issue Drug Design and Discovery: Principles and Applications)
View Full-Text   |   Download PDF [3443 KB, uploaded 7 September 2016]   |  

Abstract

Herein we present, an exhaustive docking analysis considering the case of autotaxin (ATX). HA155, a small molecule inhibitor of ATX, is co-crystallized. In order to further extract conclusions on the nature of the bond formed between the ligands and the amino acid residues of the active site, density functional theory (DFT) calculations were undertaken. However, docking does not provide reproducible results when screening boronic acid derivatives and their binding orientations to protein drug targets. Based on natural bond orbital (NBO) calculations, the formed bond between Ser/Thr residues is characterized more accurately as a polar covalent bond instead of a simple nonpolar covalent one. The presented results are acceptable and could be used in screening as an active negative filter for boron compounds. The hydroxyl groups of amino acids are bonded with the inhibitor’s boron atom, converting its hybridization to sp3. View Full-Text
Keywords: virtual screening; autotaxin; boronic acid; organoboron; drug design; warhead virtual screening; autotaxin; boronic acid; organoboron; drug design; warhead
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Katsamakas, S.; Papadopoulos, A.G.; Hadjipavlou-Litina, D. Boronic Acid Group: A Cumbersome False Negative Case in the Process of Drug Design. Molecules 2016, 21, 1185.

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