Assessment of Lipophilicity Indices Derived from Retention Behavior of Antioxidant Compounds in RP-HPLC

Abstract

Reverse phase high pressure liquid chromatography was employed in order to evaluate the lipophilicity of antioxidant compounds from different classes, such as phenolic acids, flavanones, flavanols, flavones, anthocyanins, stilbenes, xantonoids, and proanthocyanidins. The retention time of each compound was measured using five different HPLC columns: RP18 (LiChroCART, Purosphere RP-18e), C8 (Zorbax, Eclipse XDBC8), C16-Amide (Discovery RP-Amide C16), CN100 (Saulentechnik, Lichrosphere), and pentafluorophenyl (Phenomenex, Kinetex PFP), and the mobile phase consisted of methanol and water (0.1% formic acid) in different proportions. The measurements were conducted at two different column temperatures, room temperature (22 °C) and, in order to mimic the environment from the human body, 37 °C. Furthermore, principal component analysis (PCA) was used to obtain new lipophilicity indices and holistic lipophilicity charts. Additionally, highly representative depictions of the chromatographic behavior of the investigated compounds and stationary phases at different temperatures were obtained using two new chemometric approaches, namely two-way joining cluster analysis and sum of ranking differences.

Assessment of lipophilicity of newly synthesized celecoxib analogues using reversed-phase HPLC

“…Estimating log k w directly is often very difficult, and is nearly non-feasible, because it can produce elongated retention time and also extreme peak broadening. Hence, estimating k with various proportions of water-organic solvent combination as mobile phases is favored, then extrapolating the correlation between log k and percentage of organic modifier specifies the value of log k upon utilizing pure water as mobile phase [22]. log k was estimated for each of the new celecoxib analogues at different proportions of methanol.…”

“…It is calculated simply by the equation: 0 = − log k w /S. denotes the volume fraction of the organic modifier in the mobile phase at which equal partitioning of the solute between the mobile and stationary phases is obtained, that is, k = 1, log k = 0 [22]. The value of 0 is specific for each compound; it relies solely on the pH, organic modifier and temperature.…”

Mono-Alkylated Ligands Based on Pyrazole and Triazole Derivatives Tested Against Fusarium oxysporum f. sp. albedinis: Synthesis, Characterization, DFT, and Phytase Binding Site Identification Using Blind Docking/Virtual Screening for Potent Fophy Inhibitors

“…Table 6 shows the three best anti-Fusarium candidates IC 50 values, where the highest value is for ligand 5 having IC 50 = 18.8 µg/mL and IC 50 = 74.28 µmol/L, substituted pyridine ring with Brome. The lipophilicity (Veber et al, 2002;Leeson and Springthorpe, 2007;Podunavac-Kuzmanovic et al, 2008;Mannhold et al, 2009;Arnott and Planey, 2012;Hadda et al, 2014;Sima et al, 2017) characteristic of a ligand is the most important key in drug design and discovery, contributing to the ADMET-Tox (Gleeson et al, 2011;Glaab, 2016;Kauthale et al, 2017;Dhandapani and Balachandar, 2019) (administration, distribution, metabolism, excretion, and toxicity) of drugs and providing us insights about their solubility, cell membrane permeability, and so on (Arnott and Planey, 2012). It is expressed as the LogP of a compound with two different solvents: 1-octanol showing the lipid membrane and water as the model for cytoplasm (Holladay, 2015).…”

Chemometric study of chromatographic and computational bioactivity parameters of diphenylacetamides

“…The reason for this is the similarity in intermolecular interactions, which determine the chromatographic and biological behavior of one molecule . In practice, C‐18 phases are usually used for this purpose, although the tendency in using other modified stationary‐phase carriers is noted in the literature …”

“…10 In practice, C-18 phases are usually used for this purpose, although the tendency in using other modified stationary-phase carriers is noted in the literature. [11][12][13][14] It is a well-known fact that phenylacetamide derivatives exhibit analgesic properties. 15 Also, phenylacetamides possess a number of biological properties, and they have been applied as anticonvulsants, 16 antiarrhythmics, 17 antidepressants, 18 antipsychotics, 19 and antituberculotics.…”