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Chromatographic Determination of Thermodynamic Acid Dissociation Constants of Tetracycline Antibiotics and Their Epimers. 2019

İlkay Konçe, and Ebru Çubuk Demiralay, and Hülya Yılmaz Ortak
Department of Chemistry, Faculty of Science and Literature, Süleyman Demirel University, 32260 Isparta, Turkey.

The presented study describes the development of reversed-phase liquid chromatography method using a core-shell particle column with a pentafluorophenyl stationary phase for the dissociation constant (pKa) determination of the tetracycline group antibiotics (tetracycline, oxytetracycline, chlortetracycline) and their epimers (4-epitetracycline, 4-epioxytetracycline, 4-epichlortetracycline). The pH values were measured in the acetonitrile (ACN)-water binary mixtures, used as mobile phases, instead of in water and take into account the effect of the activity coefficients. Thermodynamic acid dissociation constant (pKa1) values of studied antibiotics and their epimers were calculated using retention factor (k) at different mobile phase pH values in studied binary mixtures with ACN percentages of 20, 25, 30 and 35% (v/v). Experimental data were analyzed by using an Origin 7.0 program to fit experimental data to the nonlinear expression derived. From calculated pKa1 values, the aqueous pKa values of studied compounds were calculated by different approaches and these values were compared.

UI MeSH Term Description Entries
D007536 Isomerism The phenomenon whereby certain chemical compounds have structures that are different although the compounds possess the same elemental composition. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Isomerisms
D007700 Kinetics The rate dynamics in chemical or physical systems.
D006863 Hydrogen-Ion Concentration The normality of a solution with respect to HYDROGEN ions; H+. It is related to acidity measurements in most cases by pH pH,Concentration, Hydrogen-Ion,Concentrations, Hydrogen-Ion,Hydrogen Ion Concentration,Hydrogen-Ion Concentrations
D000143 Acids Chemical compounds which yield hydrogen ions or protons when dissolved in water, whose hydrogen can be replaced by metals or basic radicals, or which react with bases to form salts and water (neutralization). An extension of the term includes substances dissolved in media other than water. (Grant & Hackh's Chemical Dictionary, 5th ed) Acid
D000900 Anti-Bacterial Agents Substances that inhibit the growth or reproduction of BACTERIA. Anti-Bacterial Agent,Anti-Bacterial Compound,Anti-Mycobacterial Agent,Antibacterial Agent,Antibiotics,Antimycobacterial Agent,Bacteriocidal Agent,Bacteriocide,Anti-Bacterial Compounds,Anti-Mycobacterial Agents,Antibacterial Agents,Antibiotic,Antimycobacterial Agents,Bacteriocidal Agents,Bacteriocides,Agent, Anti-Bacterial,Agent, Anti-Mycobacterial,Agent, Antibacterial,Agent, Antimycobacterial,Agent, Bacteriocidal,Agents, Anti-Bacterial,Agents, Anti-Mycobacterial,Agents, Antibacterial,Agents, Antimycobacterial,Agents, Bacteriocidal,Anti Bacterial Agent,Anti Bacterial Agents,Anti Bacterial Compound,Anti Bacterial Compounds,Anti Mycobacterial Agent,Anti Mycobacterial Agents,Compound, Anti-Bacterial,Compounds, Anti-Bacterial
D013754 Tetracyclines Closely congeneric derivatives of the polycyclic naphthacenecarboxamide. (Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed, p1117)
D013816 Thermodynamics A rigorously mathematical analysis of energy relationships (heat, work, temperature, and equilibrium). It describes systems whose states are determined by thermal parameters, such as temperature, in addition to mechanical and electromagnetic parameters. (From Hawley's Condensed Chemical Dictionary, 12th ed) Thermodynamic
D056148 Chromatography, Reverse-Phase A chromatography technique in which the stationary phase is composed of a non-polar substance with a polar mobile phase, in contrast to normal-phase chromatography in which the stationary phase is a polar substance with a non-polar mobile phase. Chromatography, Reversed-Phase Liquid,Reversed-Phase Chromatography,Reversed-Phase Liquid Chromatography,Reverse-Phase Chromatography,Reverse-Phase Liquid Chromatography,Chromatography, Reverse Phase,Chromatography, Reversed-Phase,Reverse Phase Chromatography,Reversed Phase Chromatography

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