title: Theoretical Models and QSRR in Retention Modeling of Eight Aminopyridines.
abstract: In this article, retention modeling of eight aminopyridines (synthesized and characterized at the Faculty of Pharmacy) in reversed-phase high performance liquid chromatography (RP-HPLC) was performed. No data related to their retention in the RP-HPLC system were found. Knowing that, it was recognized as very important to describe their retention behavior. The influences of pH of the mobile phase and the organic modifier content on the retention factors were investigated. Two theoretical models for the dependence of retention factor of organic modifier content were tested. Then, the most reliable and accurate prediction of log k was created, testing multiple linear regression model-quantitative structure-retention relationships (MLR-QSRR) and support vector regression machine-quantitative structure-retention relationships (SVM-QSRR). Initially, 400 descriptors were calculated, but four of them (POM, log D, M-SZX/RZX and m-RPCG) were included in the models. SVM-QSRR performed significantly better than the MLR model. Apart from aminopyridines, four structurally similar substances (indapamide, gliclazide, sulfamethoxazole and furosemide) were followed in the same chromatographic system. They were used as external validation set for the QSRR model (it performed well within its applicability domain, which was defined using a bounding box approach). After having described retention of eight aminopyridines with both theoretical and QSRR models, further investigations in this field can be conducted.
authors.affiliation: Department of Drug Analysis, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, Belgrade 11000, Serbia.
authors.forename: Anja
authors.initials: A
authors.lastname: Tumpa
authors.affiliation: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, Belgrade 11000, Serbia.
authors.forename: Marko
authors.initials: M
authors.lastname: Kalinić
authors.affiliation: Department of Organic Chemistry, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, Belgrade 11000, Serbia.
authors.forename: Predrag
authors.initials: P
authors.lastname: Jovanović
authors.affiliation: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, Belgrade 11000, Serbia.
authors.forename: Slavica
authors.initials: S
authors.lastname: Erić
authors.affiliation: Department of Drug Analysis, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, Belgrade 11000, Serbia.
authors.forename: Tijana
authors.initials: T
authors.lastname: Rakić
authors.affiliation: Department of Drug Analysis, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, Belgrade 11000, Serbia jancic.stojanovic@pharmacy.bg.ac.rs.
authors.forename: Biljana
authors.initials: B
authors.lastname: Jančić-Stojanović
authors.affiliation: Department of Physical Chemistry and Instrumental Methods, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, Belgrade 11000, Serbia.
authors.forename: Mirjana
authors.initials: M
authors.lastname: Medenica
mesh_terms: D000097:Acetonitriles; D000631:Aminopyridines / Q000138:chemical synthesis / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid / Q000379:methods* / Q000706:statistics & numerical data; D056148:Chromatography, Reverse-Phase / Q000379:methods* / Q000706:statistics & numerical data; D006863:Hydrogen-Ion Concentration; D015233:Models, Statistical; D012996:Solutions; D012997:Solvents; D014867:Water
chemical_list: D000097:Acetonitriles; D000631:Aminopyridines; D012996:Solutions; D012997:Solvents; D014867:Water; C032159:acetonitrile