Structure-based design of novel boronic acid-based inhibitors of autotaxin.

Structure-based design of novel boronic acid-based inhibitors of autotaxin.
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DOI:
10.1021/jm200310q
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发表时间:
2011-07-14
影响因子:
7.3
通讯作者:
Ovaa H
Ovaa H
中科院分区:
医学1区
文献类型:
--
作者:
Albers HM;Hendrickx LJ;van Tol RJ;Hausmann J;Perrakis A;Ovaa H

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Autotaxin (ATX) is a secreted phosphodiesterase that hydrolyzes the abundant phospholipid lysophosphatidylcholine (LPC) to produce lysophosphatidic acid (LPA). The ATX-LPA signaling axis has been implicated in inflammation, fibrosis, and tumor progression, rendering ATX an attractive drug target. We recently described a boronic acid-based inhibitor of ATX, named HA155 (1). Here, we report the design of new inhibitors based on the crystal structure of ATX in complex with inhibitor 1. Furthermore, we describe the syntheses and activities of these new inhibitors, whose potencies can be explained by structural data. To understand the difference in activity between two different isomers with nanomolar potencies, we performed molecular docking experiments. Intriguingly, molecular docking suggested a remarkable binding pose for one of the isomers, which differs from the original binding pose of inhibitor 1 for ATX, opening further options for inhibitor design.
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