Carborane-Containing Hydroxyamidine Scaffolds as Novel Inhibitors of Indoleamine 2,3-Dioxygenase 1 (IDO1)

Christopher J D Austin, Michael Moir, Jan Kahlert, Jason R. Smith, Joanne F. Jamie, Michael Kassiou, Louis M. Rendina*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Two new carborane-containing hydroxyamidines were prepared as potential inhibitors of the indoleamine 2,3-dioxygenase 1 (IDO1) enzyme. One compound (3) displayed low micromolar (1.90 μM) inhibition of IDO1, with the related compound (4) displaying >5-fold lower inhibitory activity, i.e. subtle differences in structure between the two carborane compounds led to dramatic changes in inhibitor binding. In silico docking experiments unravel a possible molecular mechanism that is consistent with the observed difference in IDO1 binding for 3 and 4 and also for the phenyl bioisosteres 1 and 2.

Original languageEnglish
Pages (from-to)1866-1870
Number of pages5
JournalAustralian Journal of Chemistry
Volume68
Issue number12
DOIs
Publication statusPublished - 2015

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