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Bioorg Med Chem. 2013 Mar 15;21(6):1511-5. doi: 10.1016/j.bmc.2012.08.057. Epub 2012 Sep 7.

Salicylaldoxime derivatives as new leads for the development of carbonic anhydrase inhibitors.

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Dipartimento di Scienze Farmaceutiche, Università degli Studi di Pisa, Via Bonanno 6, 56126 Pisa, Italy.


New compounds containing a novel zinc binding group (salicylaldoxime system) were identified as effective inhibitors of carbonic anhydrases (CAs). This structural motif seems to bind the catalytic zinc ion of CAs, revealing itself as a new valid alternative to the sulfonamide group. Computational procedures were used to investigate the binding mode of this class of compounds, within the active site of CAII. This study suggests that the salicylaldoxime moiety binds the zinc ion through the oxime oxygen atom that also forms an H-bond with T199. The results herein obtained will allow the development of new CA-inhibitors bearing the salicylaldoxime moiety.

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