Arylamino bisphosphonates: potent and selective inhibitors of the tumor-associated carbonic anhydrase XII

Bioorg Med Chem Lett. 2014 Apr 15;24(8):1941-3. doi: 10.1016/j.bmcl.2014.03.001. Epub 2014 Mar 12.

Abstract

A set of matrix metalloproteinases (MMPs) inhibitors, containing a bisphosphonate moiety (BP), has been evaluated for the inhibitory activity of carbonic anhydrases (CAs, EC 4.2.1.1). Human (h) isoforms hCA I, II, IX, XII and XIV were included in the study due to their involvement in crucial physiologic and pathologic processes. Some of these molecules selectively inhibited CA XII in the nanomolar range, showing an attractive dual mechanism (anti-MMP and anti-CA) of action as potential antitumor agents. The BP inhibitors investigated in this study are also excellent leads for obtaining even more effective compounds able to selectively target membrane-bound CA XII and having the potential to be used as tools for understanding physiologic processes regulated by this isoform.

Keywords: Antitumor agent; Bisphosphonate; Carbonic anhydrase; Isoform-selective inhibitor; Matrix metalloproteinase inhibitor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetazolamide / chemistry
  • Acetazolamide / pharmacology
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Carbonic Anhydrase Inhibitors / chemical synthesis*
  • Carbonic Anhydrase Inhibitors / chemistry
  • Carbonic Anhydrase Inhibitors / pharmacology*
  • Carbonic Anhydrases / chemistry*
  • Diphosphonates / chemical synthesis*
  • Diphosphonates / chemistry
  • Diphosphonates / pharmacology*
  • Drug Delivery Systems
  • Enzyme Activation / drug effects
  • Humans
  • Imidazoles / chemistry
  • Imidazoles / pharmacology
  • Inhibitory Concentration 50
  • Molecular Structure
  • Protein Isoforms / chemistry
  • Structure-Activity Relationship
  • Zoledronic Acid

Substances

  • Antineoplastic Agents
  • Carbonic Anhydrase Inhibitors
  • Diphosphonates
  • Imidazoles
  • Protein Isoforms
  • Zoledronic Acid
  • Carbonic Anhydrases
  • carbonic anhydrase XII
  • Acetazolamide