2-Aminomethylene-5-sulfonylthiazole Inhibitors of Lysyl Oxidase (LOX) and LOXL2 Show Significant Efficacy in Delaying Tumor Growth

J Med Chem. 2020 Mar 12;63(5):2308-2324. doi: 10.1021/acs.jmedchem.9b01112. Epub 2019 Sep 4.

Abstract

The lysyl oxidase (LOX) family of extracellular proteins plays a vital role in catalyzing the formation of cross-links in fibrillar elastin and collagens leading to extracellular matrix (ECM) stabilization. These enzymes have also been implicated in tumor progression and metastatic disease and have thus become an attractive therapeutic target for many types of invasive cancers. Following our recently published work on the discovery of aminomethylenethiophenes (AMTs) as potent, orally bioavailable LOX/LOXL2 inhibitors, we report herein the discovery of a series of dual LOX/LOXL2 inhibitors, as well as a subseries of LOXL2-selective inhibitors, bearing an aminomethylenethiazole (AMTz) scaffold. Incorporation of a thiazole core leads to improved potency toward LOXL2 inhibition via an irreversible binding mode of inhibition. SAR studies have enabled the discovery of a predictive 3DQSAR model. Lead AMTz inhibitors exhibit improved pharmacokinetic properties and excellent antitumor efficacy, with significantly reduced tumor growth in a spontaneous breast cancer genetically engineered mouse model.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amination
  • Amino Acid Oxidoreductases / antagonists & inhibitors*
  • Amino Acid Oxidoreductases / metabolism
  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacokinetics
  • Antineoplastic Agents / pharmacology*
  • Antineoplastic Agents / therapeutic use
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacokinetics
  • Enzyme Inhibitors / pharmacology*
  • Enzyme Inhibitors / therapeutic use
  • Female
  • Humans
  • Mice
  • Mice, Inbred BALB C
  • Models, Molecular
  • Neoplasms / drug therapy*
  • Neoplasms / enzymology
  • Neoplasms / metabolism
  • Neoplasms / pathology
  • Protein-Lysine 6-Oxidase / antagonists & inhibitors*
  • Protein-Lysine 6-Oxidase / metabolism
  • Rats
  • Sulfinic Acids / chemistry
  • Sulfinic Acids / pharmacokinetics
  • Sulfinic Acids / pharmacology
  • Sulfinic Acids / therapeutic use
  • Thiazoles / chemistry
  • Thiazoles / pharmacokinetics
  • Thiazoles / pharmacology*
  • Thiazoles / therapeutic use

Substances

  • Antineoplastic Agents
  • Enzyme Inhibitors
  • Sulfinic Acids
  • Thiazoles
  • Amino Acid Oxidoreductases
  • LOXL2 protein, human
  • Protein-Lysine 6-Oxidase