title: Theoretical assessment of norfloxacin redox and photochemistry.
abstract: Norfloxacin, 1-ethyl-6-fluoro-1,4-dihydo-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid, NOR, is an antibiotic drug from the fluoroquinoline family. The different protonation states of this drug formed throughout the pH range is studied by means of density functional theory (DFT) and the spectra of the NOR species computed using time-dependent DFT. Details about their photochemistry are obtained from investigating the highest occupied and lowest unoccupied molecular orbitals. The predominant species under physiological pH, the zwitterion, is the most photoliable one, capable of producing singlet oxygen or/and superoxide radical anions from its triplet state. In addition, the main photodegradation step, defluorination, occurs more easily from this species compared with the other forms. The defluorination from the excited triplet state requires passing a barrier of 16.3 kcal/mol in the case of the zwitterion. The neutral and cationic forms display higher transition barriers, whereas the reaction path of defluorination is completely endothermic for the anionic species. The theoretical results obtained herein are in line with previous experimental data.
authors.affiliation: Orebro Life Science Center, School of Science and Technology, Orebro University, 701 82 Orebro, Sweden.
authors.forename: Klefah A K
authors.initials: KA
authors.lastname: Musa
authors.forename: Leif A
authors.initials: LA
authors.lastname: Eriksson
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000528:radiation effects*; D006863:Hydrogen-Ion Concentration; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D009643:Norfloxacin / Q000737:chemistry* / Q000528:radiation effects*; D010084:Oxidation-Reduction; D055668:Photochemical Processes; D010777:Photochemistry; D011522:Protons; D013816:Thermodynamics
chemical_list: D000900:Anti-Bacterial Agents; D011522:Protons; D009643:Norfloxacin