Use of reversed-phase liquid chromatography for determining the lipophilicity of α-aryl-N-cyclopropylnitrones

Balogh, György Tibor; Szántó, Z.; Forrai, Erika; Györffy, Werner; Lopata, Antal

doi:10.1016/j.jpba.2005.05.019

Cited by 13 publications

(5 citation statements)

References 30 publications

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“…where A and B are constant for a given compound and organic modifier. Numerous linear correlations between log P oct and log k w obtained in isocratic mode have been reported in the literature for different classes of compounds [161,162], as also shown in Fig. 3C.…”

Section: Theory and Principlesmentioning

confidence: 61%

Analytical tools for the physicochemical profiling of drug candidates to predict absorption/distribution

et al. 2009

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The measurement of physicochemical properties at an early phase of drug discovery and development is crucial to reduce attrition rates due to poor biopharmaceutical properties. Among these properties, ionization, lipophilicity, solubility and permeability are mandatory to predict the pharmacokinetic behavior of NCEs (new chemical entities). Due to the high number of NCEs, the analytical tools used to measure these properties are automated and progressively adapted to high-throughput technologies. The present review is dedicated to experimental methods applied in the early drug discovery process for the determination of solubility, ionization constants, lipophilicity and permeability of small molecules. The principles and experimental conditions of the different methods are described, and important enhancements in terms of throughput are highlighted.

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Section: Theory and Principlesmentioning

confidence: 61%

Analytical tools for the physicochemical profiling of drug candidates to predict absorption/distribution

et al. 2009

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“…Unfortunately, shake-flask method is extremely time-consuming and laborintensive, it requires a high purity of tested substances and often suffers from solubility and stability problems. Hence, nowadays this complicated approach was nearly completely substituted by modern chromatographic techniques [6][7][8][9][10][11][12]. Among them, HPLC is the leading and the most frequently used chromatographic method for the routine lipophilicity determination, since it enables rapid, accurate and highly reproducibility analysis of relatively large sets of samples.…”

Section: Introductionmentioning

confidence: 99%

Determination of lipophilicity of novel potential antituberculotic agents using HPLC on monolithic stationary phase and theoretical calculations

Mrkvičková

Kovařı́ková

Balíková

et al. 2008

Journal of Pharmaceutical and Biomedical Analysis

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“…This conventional shake-flask method is tedious and requires large amounts of compound. Other measurements, such as high performance liquid chromatography (HPLC), are based on partitioning small molecule analyte between an aqueous liquid and a solid surface. − The lipophilicity of a drug can be quantified by correlating the retention time on a HPLC column under certain conditions with similar compounds of known log P values, − most often with octanol in the mobile phase. , …”

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confidence: 99%

Measurement of Drug Lipophilicity and pK_a Using Acoustics

Cooper

2012

Anal. Chem.

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Lipophilicity of chemicals and drug candidates is normally described in terms of octanol/water partitioning and log P. We investigated an alternate approach to lipophilicity determination using a mimic of an alkyl alcohol with compound partitioning quantified using acoustic sensing. A self-assembled monolayer composed of HSC(10)(CH(2)CH(2)O)(6)C(18) was formed on planar gold electrodes of a piezoelectric acoustic sensor. The system was challenged with compounds covering a 4-log range of log D values. As compounds partitioned in the interfacial layer, changes in sensor resonant frequency were found to correlate with compound partition coefficients (log P) and with distribution coefficients (log D). Linear concordance (R(2) = 0.933) was established between log(-dF/M(w)t) and log P and with log D in both water and biological buffers at variant pH (pH 5.2 to 7.8). In turn, drug pK(a) could be determined by profiling log D changes during pH titration. The lipophilicity/pH profile of a weakly basic drug (quinine; pK(a) = 7.95) was sigmoidal with respect to -dF/M(w) values, with a profile inverse to that of a weakly acidic drug (naproxen; pK(a) = 4.15).

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Use of reversed-phase liquid chromatography for determining the lipophilicity of α-aryl-N-cyclopropylnitrones

Cited by 13 publications

References 30 publications

Analytical tools for the physicochemical profiling of drug candidates to predict absorption/distribution

Analytical tools for the physicochemical profiling of drug candidates to predict absorption/distribution

Determination of lipophilicity of novel potential antituberculotic agents using HPLC on monolithic stationary phase and theoretical calculations

Measurement of Drug Lipophilicity and pK_a Using Acoustics

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Use of reversed-phase liquid chromatography for determining the lipophilicity of α-aryl-N-cyclopropylnitrones

Cited by 13 publications

References 30 publications

Analytical tools for the physicochemical profiling of drug candidates to predict absorption/distribution

Analytical tools for the physicochemical profiling of drug candidates to predict absorption/distribution

Determination of lipophilicity of novel potential antituberculotic agents using HPLC on monolithic stationary phase and theoretical calculations

Measurement of Drug Lipophilicity and pKa Using Acoustics

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Product

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Measurement of Drug Lipophilicity and pK_a Using Acoustics