Novel binuclear μ-oxo diruthenium complexes combined with ibuprofen and ketoprofen: Interaction with relevant target biomolecules and anti-allergic potential

J Inorg Biochem. 2015 Dec:153:178-185. doi: 10.1016/j.jinorgbio.2015.08.004. Epub 2015 Aug 8.

Abstract

This work presents the synthesis and characterization of two novel binuclear ruthenium compounds of general formula [Ru2O(carb)2(py)6](PF6)2, where py=pyridine and carb are the non-steroidal anti-inflammatory drugs ibuprofen (1) and ketoprofen (2). Both complexes were characterized by ESI-MS/MS spectrometry. The fragmentation patterns, which confirm the proposed structures, are presented. Besides that, compounds 1 and 2 present the charge transfer transitions within 325-330nm; and the intra-core transitions around 585nm, which is the typical spectra profile for [Ru2O] analogues. This suggests the carboxylate bridge has little influence in their electronic structure. The effects of the diruthenium complexes on Ig-E mediated mast cell activation were evaluated by measuring the enzyme β-hexosaminidase released by mast cells stimulated by antigen. The inhibitory potential of the ketoprofen complex against mast cell stimulation suggests its promising application as a therapeutic agent for treating or preventing IgE-mediated allergic diseases. In addition, in vitro metabolism assays had shown that the ibuprofen complex is metabolized by the cytochrome P450 enzymes.

Keywords: Antiallergic potential; Binuclear ruthenium compounds; Cytochrome P450 enzymes; Ibuprofen; IgE-mediated allergic diseases; Ketoprofen.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Allergic Agents / chemical synthesis
  • Anti-Allergic Agents / chemistry
  • Anti-Allergic Agents / pharmacology*
  • Cell Degranulation / drug effects
  • Cell Line, Tumor
  • Coordination Complexes / chemical synthesis
  • Coordination Complexes / chemistry
  • Coordination Complexes / pharmacology*
  • Cytochrome P-450 Enzyme System / metabolism
  • Ibuprofen / chemical synthesis
  • Ibuprofen / chemistry
  • Ibuprofen / pharmacology*
  • Immunoglobulin E / immunology
  • Ketoprofen / chemical synthesis
  • Ketoprofen / chemistry
  • Ketoprofen / pharmacology*
  • Male
  • Mast Cells / drug effects
  • Mast Cells / immunology
  • Mast Cells / metabolism
  • Microsomes, Liver / metabolism
  • Rats
  • Rats, Wistar
  • Ruthenium / chemistry*
  • Spectrometry, Mass, Electrospray Ionization
  • beta-N-Acetylhexosaminidases / antagonists & inhibitors

Substances

  • Anti-Allergic Agents
  • Coordination Complexes
  • Immunoglobulin E
  • Ruthenium
  • Cytochrome P-450 Enzyme System
  • Ketoprofen
  • beta-N-Acetylhexosaminidases
  • Ibuprofen