New ibuprofen derivatives as H2S and NO donors as safer anti-inflammatory agents

Future Med Chem. 2019 Dec;11(23):3029-3045. doi: 10.4155/fmc-2018-0467. Epub 2019 Nov 4.

Abstract

Aim: Nonsteroidal anti-inflammatory drugs are expansively used worldwide. However, their prolonged administration is associated with serious side effects, especially gastrointestinal ulceration. Materials & methods: New ibuprofen derivatives hybridized with H2S- or NO-donating moieties were synthesized and evaluated for their anti-inflammatory activity and ulcerogenic effect. COX-1/COX-2 isozymes selectivity test for the most promising derivatives was performed. Molecular docking studies were performed. Results: Most of the compounds showed promising anti-inflammatory activity comparable to that of ibuprofen (% edema inhibition = 76.6 and ulcer index = 21.26) with much better gastrointestinal tract tolerance (ulcer indices ranging from 0 to 14.67), especially compound 2 -H2S donor- (% edema inhibition = 75.5 and ulcer index = 11.75) and compound 16 -NO donor- (% edema inhibition = 65.4 and ulcer index = 8.66).

Keywords: COX enzyme; H2S donors; ibuprofen; safer anti-inflammatory agents; ulcer index.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Anti-Inflammatory Agents, Non-Steroidal / toxicity
  • Cyclooxygenase 1 / metabolism
  • Cyclooxygenase 2 / metabolism
  • Edema / drug therapy
  • Hydrogen Sulfide / chemistry*
  • Ibuprofen / analogs & derivatives*
  • Molecular Docking Simulation
  • Molecular Structure
  • Nitric Oxide Donors / chemistry*
  • Protein Binding
  • Rats
  • Stomach Ulcer / chemically induced
  • Structure-Activity Relationship

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Nitric Oxide Donors
  • Cyclooxygenase 1
  • Cyclooxygenase 2
  • Ibuprofen
  • Hydrogen Sulfide