title: Efficient approach to acyloxymethyl esters of nalidixic acid and in vitro evaluation as intra-ocular prodrugs.
abstract: Various alkylcarbonyloxymethyl esters of nalidixic acid ranging from 3 to 15 carbon units in the pro-moiety have been prepared and assessed as potential prodrugs. Their chromatographic retention factors k', silicone oil solubilities and in vitro conversion to nalidixic acid by a commercial esterase were determined together with their in vitro antimicrobial activity and cytotoxicity. The preliminary results suggest that silicone oil may have potential for the intra-ocular delivery of antibacterial compounds. Moreover, the in vitro release rate can be controlled by the lipophilicity of the prodrug.
authors.affiliation: Groupe de RMN Biomédicale, Laboratoire de Synthèse et Physicochimie de Molécules d'Intérêt Biologique, UMR CNRS 5068, Université Paul Sabatier, 118 route de Narbonne, 31062 Toulouse cedex 9, France.
authors.forename: Joëlle
authors.initials: J
authors.lastname: Azéma
authors.forename: Brigitte
authors.initials: B
authors.lastname: Guidetti
authors.forename: Myriam
authors.initials: M
authors.lastname: Malet-Martino
authors.forename: Robert
authors.initials: R
authors.lastname: Martino
authors.forename: Christine
authors.initials: C
authors.lastname: Roques
mesh_terms: D000900:Anti-Bacterial Agents / Q000008:administration & dosage / Q000737:chemistry* / Q000494:pharmacology*; D004333:Drug Administration Routes; D004952:Esters / Q000737:chemistry*; D005123:Eye; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D009268:Nalidixic Acid / Q000008:administration & dosage / Q000737:chemistry* / Q000494:pharmacology*; D011355:Prodrugs; D012827:Silicone Oils / Q000737:chemistry; D012995:Solubility
chemical_list: D000900:Anti-Bacterial Agents; D004952:Esters; D011355:Prodrugs; D012827:Silicone Oils; D009268:Nalidixic Acid