Manganese-mefenamic acid complexes exhibit high lipoxygenase inhibitory activity

Dalton Trans. 2014 Jul 28;43(28):10930-9. doi: 10.1039/c4dt01111b.

Abstract

The coordination of non-steroidal anti-inflammatory drugs (NSAIDs) to metal ions could improve the pharmaceutical efficacy of NSAIDs due to the unique characteristics of metal complexes. However, the structures of many metal-NSAID complexes are not well characterized; the functional mechanism and pharmaceutical effect of these complexes thus are not fully understood. In this work, three manganese-mefenamic acid (Mn-mef) complexes were synthesized and structurally characterized, and their pharmaceutical effect was investigated. We found that the three Mn-mef complexes exhibit higher lipoxygenase (LOX-1) inhibitory activity (IC50 values are 16.79, 38.63 and 28.06 μM, respectively) than the parent ligand mefenamic acid (78.67 μM). More importantly, the high inhibitory activity of the Mn-mef complexes is closely related to their spatial arrangements, which determine their interaction with LOX-1. Computer docking of the Mn-mef complexes with the LOX-1 confirms the experimental results: smaller Mn-mef complexes tend to bind competitively to LOX-1 at the substrate binding site, which is also analogous to the binding of the ligand mefenamic acid, while the bulky metal complexes inhibit the enzyme activity un-competitively. In addition, the Mn-mef complexes exhibit higher anti-oxidant activity than the ligand mefenamic acid. The higher anti-oxidant activity of the Mn-mef complexes apparently originated from the manganese centre of the complexes. We thus conclude that Mn-mef complexes enhance the anti-inflammatory activity of mefenamic acid by increasing their activity via changing their interaction mode with the enzymes, and/or by improving their anti-oxidant ability using metal ions. This work provides experimental evidence that with the unique spatial arrangements, metal-NSAID complexes could interact with the target enzymes more specifically and efficiently, which is superior to their parent NSAID ligand.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents, Non-Steroidal / chemistry*
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Coordination Complexes / chemistry*
  • Coordination Complexes / pharmacology
  • Lipoxygenase Inhibitors / chemistry*
  • Lipoxygenase Inhibitors / pharmacology
  • Manganese / chemistry*
  • Mass Spectrometry
  • Mefenamic Acid / chemistry*
  • Mefenamic Acid / pharmacology
  • Molecular Docking Simulation
  • Molecular Structure
  • Protein Binding
  • Scavenger Receptors, Class E / chemistry*
  • Spectroscopy, Fourier Transform Infrared
  • X-Ray Diffraction

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Coordination Complexes
  • Lipoxygenase Inhibitors
  • OLR1 protein, human
  • Scavenger Receptors, Class E
  • Mefenamic Acid
  • Manganese