Discovery and optimization of aspartate aminotransferase 1 inhibitors to target redox balance in pancreatic ductal adenocarcinoma

Bioorg Med Chem Lett. 2018 Sep 1;28(16):2675-2678. doi: 10.1016/j.bmcl.2018.04.061. Epub 2018 Apr 27.

Abstract

Pancreatic ductal adenocarcinoma (PDAC) is a lethal malignancy that is extremely refractory to the therapeutic approaches that have been evaluated to date. Recently, it has been demonstrated that PDAC tumors are dependent upon a metabolic pathway involving aspartate aminotransferase 1, also known as glutamate-oxaloacetate transaminase 1 (GOT1), for the maintenance of redox homeostasis and sustained proliferation. As such, small molecule inhibitors targeting this metabolic pathway may provide a novel therapeutic approach for the treatment of this devastating disease. To this end, from a high throughput screen of ∼800,000 molecules, 4-(1H-indol-4-yl)-N-phenylpiperazine-1-carboxamide was identified as an inhibitor of GOT1. Mouse pharmacokinetic studies revealed that potency, rather than inherent metabolic instability, would limit immediate cell- and rodent xenograft-based experiments aimed at validating this potential cancer metabolism-related target. Medicinal chemistry-based optimization resulted in the identification of multiple derivatives with >10-fold improvements in potency, as well as the identification of a tryptamine-based series of GOT1 inhibitors.

Keywords: Aspartate aminotransferase-1; Cancer metabolism; Glutamic-oxaloacetic transaminase-1; Inhibitor; Pancreatic ductal adenocarcinoma.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Aspartate Aminotransferase, Cytoplasmic
  • Aspartate Aminotransferases / antagonists & inhibitors*
  • Carcinoma, Pancreatic Ductal / drug therapy
  • Drug Discovery
  • Drug Stability
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacokinetics
  • Enzyme Inhibitors / therapeutic use*
  • Female
  • Indoles / chemical synthesis
  • Indoles / chemistry
  • Indoles / pharmacokinetics
  • Indoles / therapeutic use*
  • Mice
  • Phenylurea Compounds / chemical synthesis
  • Phenylurea Compounds / chemistry
  • Phenylurea Compounds / pharmacokinetics
  • Phenylurea Compounds / therapeutic use*
  • Piperazines / chemical synthesis
  • Piperazines / chemistry
  • Piperazines / pharmacokinetics
  • Piperazines / therapeutic use*
  • Structure-Activity Relationship
  • Transaminases / antagonists & inhibitors*

Substances

  • Enzyme Inhibitors
  • Indoles
  • Phenylurea Compounds
  • Piperazines
  • Aspartate Aminotransferase, Cytoplasmic
  • Got1 protein, mouse
  • Transaminases
  • Aspartate Aminotransferases