Bioautography detection in thin-layer chromatography

https://pubs.rsc.org/en/content/getauthorversionpdf/C4NP00068D

Chemo- and bioinformatics resources for in silico drug discovery from medicinal plants beyond their traditional use: a critical review

Lipophilicity and biomimetic properties measured by HPLC to support drug discovery.

Lipophilicity, quantified by the logarithm of the n-octanol/water partition coefficient (logP) or the distribution coefficient (logD), is a crucial parameter for modelling biological partition or distribution. As a maintream experimental method for lipophilicity measurement, reversed-phase high performance liquid chromatography (RP-HPLC) has attracted great interest and the attention of researchers throughout the world for its advantages including speed, reproducibility, insensitivity to impurities and degradation products, broad dynamic range, on-line detection, and reduced handling and sizes of samples. This review focuses on recent developments in lipophilicity measurement by RP-HPLC, both theoretical and experimental (mainly mobile and stationary phases).

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

Thin layer chromatography in drug discovery process.

Reversed-phase liquid chromatography with octadecylsilyl, immobilized artificial membrane and cholesterol columns in correlation studies with in silico biological descriptors of newly synthesized antiproliferative and analgesic active compounds

A (chromatographic) lipophilicity parameters of newly synthesized 2,4-bis(substituted)-6-chloro-s-triazines were studied. PCA-HCA were performed in order to classify and organize various chromatographic lipophilicity parameters that were determined by using different stationary and mobile phases and by various chromatographic techniques. The PCA-HCA indicates that for the set of investigated compounds, similar lipophilicity scales are given by chromatographic systems with covalently bonded hydrocarbons as a stationary phase and acetonitrile as a mobile phase modifier. Another cluster of lipophilicity scales forms cyano and octadecylsilica stationary phases with dioxane or tetrahydrofuran as a mobile phase modifiers. The general arrangement of investigated compounds along PC1 was according to the increase in lipophilicity forming two clusters (one of lower and the other of higher lipophilicity). PCA study of R M values underline the differences concerning solvent fraction. Also reveal that HPTLC systems on amino plates are distinguishable from the cyano and octadecylsilica supports, which were similar.

Chemometric characterization of (chromatographic) lipophilicity parameters of newly synthesized s‐triazine derivatives

High-performance liquid chromatography (HPLC), over-pressured-layer chromatography (OPLC) and thin-layer chromatography (TLC) techniques with micellar mobile phases were proposed to evaluate the lipophilicity of 21 newly synthesized 1,2,4-triazoles, compounds of potential importance in medicine or agriculture as fungicides. Micellar parameters log km were compared with extrapolated RM0 values determined from reversed-phase (RP) TLC experimental data obtained on RP-8 stationary phases as well as with log P values (Alog Ps, AClog P, Alog P, Mlog P, KowWin, xlog P2 and xlog P3) calculated from molecular structures of solutes tested. The results obtained by applying principal component analysis (PCA) and linear regression showed considerable similarity between partition and retention parameters as alternative lipophilicity descriptors, and indicated micellar chromatography as a suitable technique to study lipophilic properties of organic substances. In micellar HPLC, RP-8e column (Purospher) was applied, whereas in OPLC and TLC, RP-CN plates were applied, which was the novelty of this study and allowed the use of micellar effluents in planar chromatography measurements.

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Quantification of Lipophilicity of 1,2,4-Triazoles Using Micellar Chromatography.

The retention factors in pure water for a homologous series of s-triazines were calculated by a numerical method basing on Ościk's equation and were correlated with log k
 w
 values obtained by linear and parabolic extrapolation. Chromatographic data (log k
 w
 ) were compared with the software-calculated partition coefficients in the n-octanol/water system (Alog P, IAlog P, clog P, log P
 Kowin
 , xlog P, log P
 ACD
 and log P
 Chem.Off.) as alternative hydrophobicity indices. The effect of organic modifier (methanol and acetonitrile) and its concentration in the mobile phase used for log k
 w
 evaluation were investigated. Very good linear correlations were found between log k
 w
 values calculated by the numerical method and log P
 ACD
 , log P
 Chem.Off
 . and clog P values, independent of organic modifier type.

Determination of Retention Factors of s-Triazines Homologous Series in Water Using a Numerical Method Basing on Ościk's Equation

Micellar liquid chromatography (MLC) has been used to study the lipophilicity of eight newly synthesized N-phenyltrichloroacetamide derivatives. Because the lipophilicity of a substance determines its retention and its interactions with micelles, chromatographic data calculated from experimental results — km (log km) — were compared with partition coefficients log P calculated from the molecular structures of the solutes. Micellar mobile phases containing Brij 35 and tetrahydrofuran, alkyl-bonded stationary phases, and two planar chromatography techniques — thin-layer chromatography (TLC) and over-pressured-layer chromatography (OPLC) — were used in the experiments. According to results obtained from the OPLC studies, especially, log km values are excellent descriptors of the lipophilicity of the compounds. Very good linear relationships between log km and log P were obtained by use of this technique (R in the range 0.917–0.987).

Małgorzata Janicka

Papers

Reversed-phase liquid chromatography with octadecylsilyl, immobilized artificial membrane and cholesterol columns in correlation studies with in silico biological descriptors of newly synthesized antiproliferative and analgesic active compounds

Chemometric characterization of (chromatographic) lipophilicity parameters of newly synthesized s‐triazine derivatives

Quantification of Lipophilicity of 1,2,4-Triazoles Using Micellar Chromatography.

Determination of Retention Factors of s-Triazines Homologous Series in Water Using a Numerical Method Basing on Ościk's Equation

Chromatographic evaluation of the lipophilicity of N-phenyltrichloroacetamide derivatives using micellar TLC and OPLC