Recent advances in lipophilicity measurement by reversed-phase high-performance liquid chromatography

Liang, Chao; Lian, Huibo

doi:10.1016/j.trac.2015.02.009

Cited by 65 publications

(48 citation statements)

References 99 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The partition coefficient (P) refers to the ratio of compound concentration in each phase and can be determined experimentally by a variety of methods including the well-known shake-flask method (EPA, 1996;OECD 107 Method, 1995), potentiometric methods (Avdeef, 1993(Avdeef, , 1992Ràfols et al, 2012;Takács-Novák and Avdeef, 1996), chromatographic methods (Donovan and Pescatore, 2002;Kaliszan et al, 2002;Liang and Lian, 2015;OECD 117 Method, 2004;Pallicer et al, 2012Pallicer et al, , 2010Wiczling et al, 2008) and others. Besides, lipophilicity can also be estimated using computer software and extensive studies about the accuracy of calculated log P values by different computer software has already been carried out (Chou and Jurs, 1979;Leo, 1987;Mannhold et al, 2009;Pallicer et al, 2014;Tetko et al, 2009).…”

Section: Introductionmentioning

confidence: 99%

Setup and validation of shake-flask procedures for the determination of partition coefficients (logD) from low drug amounts

Andrés

Rosés

Ràfols

et al. 2015

European Journal of Pharmaceutical Sciences

157

102

View full text Add to dashboard Cite

Several procedures based on the shake-flask method and designed to require a minimum amount of drug for octanol-water partition coefficient determination have been established and developed. The procedures have been validated by a 28 substance set with a lipophilicity range from -2.0 to 4.5 (logD7.4). The experimental partition is carried out using aqueous phases buffered with phosphate (pH 7.4) and n-octanol saturated with buffered water and the analysis is performed by liquid chromatography. In order to have accurate results, four procedures and eight different ratios between phase volumes are proposed. Each procedure has been designed and optimized (for partition ratios) for a specific range of drug lipophilicity (low, regular and high lipophilicity) and solubility (high and low aqueous solubility). The procedures have been developed to minimize the measurement in the octanolic phase. Experimental logD7.4 values obtained from different procedures and partition ratios show a standard deviation lower than 0.3 and there is a nice agreement when these values are compared with the reference literature ones.

show abstract

Section: Introductionmentioning

confidence: 99%

Setup and validation of shake-flask procedures for the determination of partition coefficients (logD) from low drug amounts

Andrés

Rosés

Ràfols

et al. 2015

European Journal of Pharmaceutical Sciences

157

102

View full text Add to dashboard Cite

show abstract

“…ILC has been reported as a promising method to investigate the partitioning of active substances into biomembranes [32], [33]. The thermodynamic parameters were analysed on the basis of capacity factor k , an index to assess the interaction between the liposome stationary phase and peptide (Table 2).…”

Section: Resultsmentioning

confidence: 99%

Interaction between Antibacterial Peptide Apep10 and Escherichia coli Membrane Lipids Evaluated Using Liposome as Pseudo-Stationary Phase

Tang¹,

Pu²,

Li³

2017

PLoS ONE

View full text Add to dashboard Cite

Liposomes constructed from Escherichia coli membrane lipids were used as a pseudo-stationary phase in capillary electrophoresis and immobilised liposome chromatography to evaluate the interaction between antibacterial peptide (ABP) Apep10 and bacterial membrane lipids. The peptide mobility decreased as the concentration of liposomes increased, providing evidence for the existence of this interaction. The binding constant between Apep10 and the Escherichia coli membranes lipid liposome was higher than that of Apep10 with a mixed phospholipids liposome at the same temperature. The capillary electrophoresis results indicate that the binding ability of Apep10 with a liposome was dependent on the liposome’s lipid compositions. Thermodynamic analysis by immobilised liposome chromatography indicated that hydrophobic and electrostatic effects contributed to the partitioning of Apep10 in the membrane lipids. The liposomes constructed from bacterial membrane lipid were more suitable as the model membranes used to study dynamic ABP/membrane interactions than those constructed from specific ratios of particular phospholipids, with its more biomimetic phospholipid composition and contents. This study provides an appropriate model for the evaluation of ABP-membrane interactions.

show abstract

“…It increases for acids and decreases for bases. To determine the aqueous pK a,chrom values an influence of organic modifier has been subtracted using the following formula: w w pK a,chrom = pK a,chrom − j · ˛p Ka · ϕ chrom (4) where j is an indicator variable, equal to 1 for acids and −1 for bases, ˛p Ka is a slope parameter. ϕ chrom denoted an average organic modifier content experienced by a given analyte at pH equal to pKa chrom .…”

Section: Theory/calculationmentioning

confidence: 99%

“…Lipophilicity is an important physicochemical parameter characterizing drug ability to penetrate cells membranes, plasma protein binding and tissue accumulation. The present methods for the determination of lipophilicity include the shake-flask method, potentiometric titration and chromatographic methods [3,4].…”

Section: Introductionmentioning

confidence: 99%

Simultaneous determination of hydrophobicity and dissociation constant for a large set of compounds by gradient reverse phase high performance liquid chromatography–mass spectrometry technique

Kubik

Struck-Lewicka

Kaliszan

et al. 2015

Journal of Chromatography A

View full text Add to dashboard Cite

Recent advances in lipophilicity measurement by reversed-phase high-performance liquid chromatography

Cited by 65 publications

References 99 publications

Setup and validation of shake-flask procedures for the determination of partition coefficients (logD) from low drug amounts

Setup and validation of shake-flask procedures for the determination of partition coefficients (logD) from low drug amounts

Interaction between Antibacterial Peptide Apep10 and Escherichia coli Membrane Lipids Evaluated Using Liposome as Pseudo-Stationary Phase

Simultaneous determination of hydrophobicity and dissociation constant for a large set of compounds by gradient reverse phase high performance liquid chromatography–mass spectrometry technique

Contact Info

Product

Resources

About