Experimental and theoretical studies on the molecular properties of ciprofloxacin, norfloxacin, pefloxacin, sparfloxacin, and gatifloxacin in determining bioavailability
| Autor: | Ewa Kłosińska-Szmurło, Alexander P. Mazurek, F. A. Pluciński, Joanna Biernacka, Monika Grudzień, Katarzyna Betlejewska-Kielak |
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| Rok vydání: | 2014 |
| Předmět: |
Models
Molecular Octanols Molecular model Static Electricity Molecular Conformation Biophysics Biological Availability Molecular modeling Buffers Lipophilic properties Gatifloxacin Partition coefficient Phosphates Ciprofloxacin Computational chemistry Molecule Solubility Molecular Biology Original Paper Chromatography Chemistry Hydrogen bond Intermolecular force Solvation Cell Biology Hydrogen-Ion Concentration Pefloxacin Atomic and Molecular Physics and Optics Bioavailability Gastrointestinal Absorption Solvents Thermodynamics Fluoroquinolones Norfloxacin |
| Zdroj: | Journal of Biological Physics |
| ISSN: | 1573-0689 0092-0606 |
| Popis: | The aim of this investigation is to identify, by in silico and in vitro methods, the molecular determinants, e.g., solubility in an aqueous medium and lipophilic properties, which have an effect on the bioavailability of five selected fluoroquinolones. These properties were estimated by analysis of the electrostatic potential pattern and values of free energy of solvation as well as the partition coefficients of the studied compounds. The study is based on theoretical quantum-chemical methods and a simple experimental shake-flask technique with two immiscible phases, n-octanol and phosphate buffer. The solvation free energy values of compounds in both environments appeared to be negative. The wide range of electrostatic potential from negative to positive demonstrates the presence of dipole–dipole intermolecular interactions, while the high electron density at various sites indicates the possibility of hydrogen bond formation with solvent molecules. High partition coefficient values, obtained by summing the atomic contributions, did not take various correction factors into account and therefore were not accurate. Theoretical partition coefficient values based on more accurate algorithms, which included these correction factors (fragmental methods), yielded more accurate values. Theoretical methods are useful tools for predicting the bioavailability of fluoroquinolones. |
| Databáze: | OpenAIRE |
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