title: Assessment of the chromatographic lipophilicity of eight cephalosporins on different stationary phases.
abstract: The retention behaviors were investigated for a series of eight cephalosporins in thin-layer chromatography (TLC) using stationary phases of RP-2, RP-8, RP-18, NH2, DIOL, and CN chemically bonded silica gel. Additionally, various binary mobile phases (water/methanol and water/acetone) were used in different volume proportions. The retention behavior of the analyzed molecules was defined by RM0constant. In addition, reversed phase high performance liquid chromatography (RP-HPLC) was performed in lipophilicity studies by using immobilized artificial membrane (IAM) stationary phase. Obtained chromatographic data (RM0and logk'IAM) were correlated with the lipophilicity, expressed as values of the log calculated (logPcalc) and experimental (logPexp(shake-flask)) partition coefficient. Principal component analysis (PCA) was applied in order to obtain an overview of similarity or dissimilarity among the analyzed compounds. Hierarchical cluster analysis (HCA) was performed to compare the separation characteristics of the applied stationary phases. This study was undertaken to identify the best chromatographic system and chromatographic data processing method to enable the prediction of logP values. A comprehensive chromatographic investigation into the retention of the analyzed cephalosporins revealed a similar behavior on RP-18, RP-8 and CN stationary phases. The weak correlations obtained between experimental and certain computed lipophilicity indices revealed that RM0and PC1/RM are relevant lipophilicity parameters and the RP-8, CN and RP-18 plates are appropriate stationary phases for lipophilicity investigation, whereas computational approaches still cannot fully replace experimentation.
authors.affiliation: Department of Inorganic and Analytical Chemistry, Faculty of Pharmacy, Jagiellonian University Medical College, 9 Medyczna St, 30-688 Krakow, Poland. Electronic address: mtylka@cm-uj.krakow.pl.
authors.forename: Monika
authors.initials: M
authors.lastname: Dąbrowska
authors.affiliation: Department of Inorganic and Analytical Chemistry, Faculty of Pharmacy, Jagiellonian University Medical College, 9 Medyczna St, 30-688 Krakow, Poland.
authors.forename: Małgorzata
authors.initials: M
authors.lastname: Starek
authors.affiliation: Department of Medicinal Chemistry, Medical University of Lublin, 4 Jaczewskiego St, 20-090 Lublin, Poland.
authors.forename: Łukasz
authors.initials: Ł
authors.lastname: Komsta
authors.affiliation: Department of Organic Chemistry, Faculty of Pharmacy, Jagiellonian University Medical College, 9 Medyczna St, 30-688 Krakow, Poland.
authors.forename: Przemysław
authors.initials: P
authors.lastname: Szafrański
authors.affiliation: Department of Organic Chemistry, Faculty of Pharmacy, Jagiellonian University Medical College, 9 Medyczna St, 30-688 Krakow, Poland.
authors.forename: Anna
authors.initials: A
authors.lastname: Stasiewicz-Urban
authors.affiliation: Department of Inorganic and Analytical Chemistry, Faculty of Pharmacy, Jagiellonian University Medical College, 9 Medyczna St, 30-688 Krakow, Poland.
authors.forename: Włodzimierz
authors.initials: W
authors.lastname: Opoka
mesh_terms: D002511:Cephalosporins / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D056148:Chromatography, Reverse-Phase / Q000379:methods; D002855:Chromatography, Thin Layer / Q000379:methods; D057927:Hydrophobic and Hydrophilic Interactions; D000432:Methanol / Q000737:chemistry; D025341:Principal Component Analysis; D014867:Water / Q000737:chemistry
chemical_list: D002511:Cephalosporins; D014867:Water; D000432:Methanol
keywords: Cephalosporins; Chromatography; HCA; Lipophilicity; PCA