Cathepsin B inhibitors: Further exploration of the nitroxoline core

Bioorg Med Chem Lett. 2018 Apr 15;28(7):1239-1247. doi: 10.1016/j.bmcl.2018.02.042. Epub 2018 Feb 23.

Abstract

Human cathepsin B is a cysteine protease with many house-keeping functions, such as intracellular proteolysis within lysosomes. Its increased activity and expression have been strongly associated with many pathological processes, including cancers. We present here the design and synthesis of novel derivatives of nitroxoline as inhibitors of cathepsin B. These were prepared either by omitting the pyridine part, or by modifying positions 2, 7, and 8 of nitroxoline. All compounds were evaluated for their ability to inhibit endopeptidase and exopeptidase activities of cathepsin B. For the most promising inhibitors, the ability to reduce extracellular and intracellular collagen IV degradation was determined, followed by their evaluation in cell-based in vitro models of tumor invasion. The presented data show that we have further defined the structural requirements for cathepsin B inhibition by nitroxoline derivatives and provided additional knowledge that could lead to non-peptidic compounds with usefulness against tumor progression.

Keywords: Human cathepsin B; Nitroxoline derivatives; Structure-activity relationships; Tumor invasion.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cathepsin B / antagonists & inhibitors*
  • Cathepsin B / metabolism
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Cysteine Proteinase Inhibitors / chemical synthesis
  • Cysteine Proteinase Inhibitors / chemistry
  • Cysteine Proteinase Inhibitors / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Structure
  • Nitroquinolines / chemical synthesis
  • Nitroquinolines / chemistry
  • Nitroquinolines / pharmacology*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Cysteine Proteinase Inhibitors
  • Nitroquinolines
  • nitroxoline
  • CTSB protein, human
  • Cathepsin B