Journal ArticleDOI
Calculation of Abraham descriptors from experimental data from seven HPLC systems; evaluation of five different methods of calculation
Andreas M. Zissimos,Michael H. Abraham,Chau M. Du,Klára Valkó,Chris Bevan,Derek P. Reynolds,John Wood,Kin Yip Tam +7 more
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TLDR
In this article, Abraham descriptors dipolarity/polarizability S, hydrogen bond acidity A, and hydrogen bond basicity B were obtained for seven high performance liquid chromatographic (HPLC) systems, generated in the reverse phase mode with fast gradient elution.Abstract:
Solvation equations have been obtained for seven high performance liquid chromatographic (HPLC) systems, generated in the reverse phase (RP) mode with fast gradient elution. A training set of 40 compounds was used for each system. The seven equations were then used to calculate Abraham descriptors for a completely separate 40-compound test set. In this way the three descriptors dipolarity/polarizability S, hydrogen bond acidity A, and hydrogen bond basicity B were obtained. Five different procedures were used to calculate the descriptors, (i) Microsoft ‘Solver’, (ii) a program that uses a set of three simultaneous equations, and which we denote as ‘TripleX’, (iii) a program similar to Solver that we denote as ‘Descfit’, (iv) a series of regression equations developed from compounds with known descriptors and (v) a series of modified regression equations. We show that RP-HPLC data for a given compound in seven systems can be used to calculate the three Abraham descriptors reliably. We compare descriptors, and errors in the method, with those obtained from water–solvent partition systems.read more
Citations
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Journal ArticleDOI
Determination of sets of solute descriptors from chromatographic measurements
TL;DR: It is concluded that for processes that entail transfer of a solute from one phase to another, only a small number of solute descriptors is needed to provide a reasonably accurate analysis of the process.
Journal ArticleDOI
The chemical interpretation and practice of linear solvation energy relationships in chromatography
Mark F. Vitha,Peter W. Carr +1 more
TL;DR: This review focuses on the use of linear solvation energy relationships (LSERs) to understand the types and relative strength of the chemical interactions that control retention and selectivity in the various modes of chromatography ranging from gas chromatography to reversed phase and micellar electrokinetic capillary chromatography.
Journal ArticleDOI
Polyparameter linear free energy relationships for estimating the equilibrium partition of organic compounds between water and the natural organic matter in soils and sediments.
TL;DR: The development of a new pp-LFER for organic chemical partitioning with soil/sediment organic matter (SOM) using a data set of 356 carefully selected experimental values of log Koc for 75 chemicals, including apolar, monopolar, and bipolar compounds is presented.
Journal ArticleDOI
Applications of polyparameter linear free energy relationships in environmental chemistry.
TL;DR: The state of the art of the PP-LFER approaches in environmental chemical applications is reviewed, the solute descriptors and system parameters reported in the literature and the availability of their database are summarized, and their calibration and prediction methods are overviewed.
Journal ArticleDOI
Determination of solute descriptors by chromatographic methods.
TL;DR: A large database of experimental retention factors and partition coefficients is constructed after first applying selection tools to remove unreliable experimental values and an optimized collection of varied compounds with descriptor values suitable for calibrating chromatographic systems is presented.
References
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Journal ArticleDOI
Scales of solute hydrogen-bonding: their construction and application to physicochemical and biochemical processes
Journal ArticleDOI
Hydrogen bonding. 32. An analysis of water-octanol and water-alkane partitioning and the Δlog p parameter of seiler
TL;DR: A general linear solvation energy equation has been used to analyze published partition coefficients in the systems water-octanol, water-hexadecane), water-alkane, and water-cyclohexane and shows that solute hydrogen-bond basicity, dipolarity/polarizability and size are significant factors that influence the delta log P parameter.
Journal ArticleDOI
Property-based design: optimization of drug absorption and pharmacokinetics.
Journal ArticleDOI
Evaluation of human intestinal absorption data and subsequent derivation of a quantitative structure-activity relationship (QSAR) with the Abraham descriptors.
Yuan H. Zhao,Joelle Le,Michael H. Abraham,Anne Hersey,Peter J. Eddershaw,Chris N. Luscombe,Darko Boutina,Gordon Beck,Brad Sherborne,Ian Cooper,James Alexis Platts +10 more
TL;DR: The results show that Abraham descriptors can successfully predict human intestinal absorption if the human absorption data is carefully classified based on solubility and administration dose to humans.
Journal ArticleDOI
Chromatographic Hydrophobicity Index by Fast-Gradient RP-HPLC: A High-Throughput Alternative to log P/log D.
TL;DR: A new chromatographic hydrophobicity index (CHI) is described which can be used as part of a protocol for high-throughput (50-100 compounds/day) physicochemical property profiling for rational drug design and shows good correlation to the calculated octanol/water partition coefficient values.
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