title: Sensing of enantiomeric excess in chiral carboxylic acids.
abstract: Cinchona alkaloids (quinine, quinidine, cinchonine, cinchonidine) alkylated at N(1) with chloromethyl anthracene can serve as fluorescent sensors for chiral carboxylic acids. These cinchona ammonium salts are shown to bind chiral carboxylic acids while displaying an increase in fluorescence intensity that can be utilized in determination of enantiomeric excess (ee). Sensor arrays composed of four cinchona ammonium salts are used for quantitative analysis of ee in several non-steroidal anti-inflammatory drugs (NSAIDs), such as enantiomers of ibuprofen, ketoprofen, and naproxen.
authors.affiliation: Department of Chemistry and Center for Photochemical Sciences, Bowling Green State University, Bowling Green, Ohio 43403, USA. pavel@bgsu.edu.
authors.forename: Ali
authors.initials: A
authors.lastname: Akdeniz
authors.forename: Lorenzo
authors.initials: L
authors.lastname: Mosca
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Minami
authors.forename: Pavel
authors.initials: P
authors.lastname: Anzenbacher
mesh_terms: D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000032:analysis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000032:analysis* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000032:analysis / Q000737:chemistry; D007052:Ibuprofen / Q000032:analysis* / Q000737:chemistry; D007660:Ketoprofen / Q000032:analysis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009288:Naproxen / Q000032:analysis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D002264:Carboxylic Acids; D005456:Fluorescent Dyes; D009288:Naproxen; D007660:Ketoprofen; D007052:Ibuprofen