Poster Presentation RACI Biomolecular Division Conference 2013

The Design of Inhibitors of the Kynurenine Aminotransferases: the Enabling Tools. (#90)

Guanchen Sun 1 , Naveed A Nadvi 1 , Ann H Kwan 2 , Mark D Gorrell 3 , William B Church 1
  1. Faculty of Pharmacy, The University of Sydney, Sydney, NSW, Australia
  2. School of Molecular Bioscience, The University of Sydney, Sydney, NSW, Australia
  3. Centenary Institute, Sydney, NSW, Australia

Abnormal levels of kynurenic acid (KA) has been thought to accompany several neuropsychiatric diseases. This is consistent with the role of KA as an antagonist acting at the glutamate-binding site of the N-methyl D-aspartic acid receptor. Overproduction of this metabolite by kynurenine aminotransferases (hKATs), could contribute to pathophysiology of psychosis, making the kynurenine pathway a valuable target for the treatment of such disease. Novel inhibitors will be valuable, and on this basis we have been pursuing the design of inhibitors.

Both hKAT-I and hKAT-2 catalyse the production of kynurenic acid from kynurenine. We have prepared recombinant hKAT-I and reported a series of phenyl hydrazone compounds and seven candidates were found to inhibit hKAT-I representing the best reported inhibitors1. To assist our study, we have now embarked upon the heterologous expression of hKAT-2 from which we will be able to pursue the design of selective inhibitors.  These proteins are required in a fully functional state and in quantities suitable to allow us to advance our structure-base drug design program, and our strategies have required combinations of codon optimisation, E. coli and insect cell (Sf9) expression systems, as well as optimised purification strategies sometimes including his-tagging. Most recently we have successfully expressed hKAT-2 in Rosetta E.coli cells using an optimized hKAT-2 codon sequence. Purification has proceeded with a his-tagged hKAT-2 using immobilized nickel affinity chromatography and a concentration step, and the recombinant hKAT-2 was shown to be active in our activity assay. The hKAT-2 expression and purification will be further optimized for its supply in inhibitor design, including crystallographic studies.

  1. Fady N. Akladios, Naveed A. Nadvi, Joohong Park, Jane R. Hanrahan, Vimal Kapoor, Mark D. Gorrell, W. Bret Church (2012). Design and synthesis of novel inhibitors of human kynurenine aminotransferase-I, Bioorganic and Medicinal Chemistry Letters, 22, 1579-1581