title: Molecular orbital theory applied to the study of nonsteroidal anti-inflammatory drug efficiency.
abstract: Using a simple quantum mechanical method, we calculated the energy of the highest-occupied molecular orbital (E(HOMO)) of three groups of anti-inflammatory compounds, and we have found correlations between E(HOMO) of these molecules and experimental data previously reported on (1) inhibition of sheep-vesicular-gland prostaglandin cyclooxygenase by phenolic compounds, (2) inhibition of prostaglandin cyclooxygenase in mouse macrophages by salicylates, benzoates and phenols, and (3) peroxyl-radical scavenging and radioprotection of a bacterial virus by NSAID drugs, including metiazinic acid, sulindac, D-penicillamine, piroxicam, indomethacin, benoxaprofen, and aspirin. Our correlations using a systematic evaluation of the HOMO energies can be of predictive value in the search for new anti-inflammatory drugs as well as for new radioprotectors.
authors.affiliation: Laboratoire de Chimie Organique Physique, Université des Sciences et Technologies de Lille, CNRS UA 351, Villeneuve d'Ascq, France.
authors.forename: V
authors.initials: V
authors.lastname: Zoete
authors.forename: F
authors.initials: F
authors.lastname: Bailly
authors.forename: F
authors.initials: F
authors.lastname: Maglia
authors.forename: M
authors.initials: M
authors.lastname: Rougée
authors.forename: R V
authors.initials: RV
authors.lastname: Bensasson
mesh_terms: D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry* / Q000494:pharmacology*; D001435:Bacteriophages / Q000187:drug effects / Q000528:radiation effects; D016861:Cyclooxygenase Inhibitors / Q000737:chemistry / Q000494:pharmacology; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology; D066298:In Vitro Techniques; D008264:Macrophages / Q000187:drug effects / Q000201:enzymology; D051379:Mice; D008956:Models, Chemical; D011789:Quantum Theory; D012756:Sheep; D013329:Structure-Activity Relationship; D013816:Thermodynamics
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D016861:Cyclooxygenase Inhibitors; D016166:Free Radical Scavengers