Estimation of chromatographic lipophilicity of bile acids and their derivatives by reversed‐phase thin layer chromatography

Onişor, Cristina; Poša, Mihalj; Kevrešan, Slavko; Kuhajda, Ksenija; Sârbu, Costel

doi:10.1002/jssc.200900879

Cited by 22 publications

(15 citation statements)

References 31 publications

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“…In recent times to describe the molecules lipophilicity also used the chromatographic parameters φ0 which is the ratio of RM0 and the slope S (Fig. 2) [7,8].…”

Section: Chromatography -The Most Versatile Methods Of Chemical Analysmentioning

confidence: 99%

“…The logarithm of the retention coefficient logk is used as a parameter of hydrophobicity of chemical compound. An important chromatographic parameter of lipophilicity is logkw which were obtained an extrapolation of the linear equations (8) to the zero volume fraction φ of organic modifier in aqueous mobile phase.…”

Section: Chromatography -The Most Versatile Methods Of Chemical Analysmentioning

confidence: 99%

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Chromatographic Retention Parameters as Molecular Descriptors for Lipophilicity in QSA(P)R Studies of Bile Acid

Poša¹

2012

Chromatography - The Most Versatile Method of Chemical Analysis

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“…In recent times to describe the molecules lipophilicity also used the chromatographic parameters φ0 which is the ratio of RM0 and the slope S (Fig. 2) [7,8].…”

Section: Chromatography -The Most Versatile Methods Of Chemical Analysmentioning

confidence: 99%

Section: Chromatography -The Most Versatile Methods Of Chemical Analysmentioning

confidence: 99%

Chromatographic Retention Parameters as Molecular Descriptors for Lipophilicity in QSA(P)R Studies of Bile Acid

Poša¹

2012

Chromatography - The Most Versatile Method of Chemical Analysis

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“…It can be examined by using chromatographic parameters and over the partition coefficient. For hydrophilic subsystem there is an additional negative enthalpy H  0, which is distributed in the environment (interior solution), thereby giving a positive entropy change (environment) 11 .…”

Section: Physico-chemical Properties Of Bile Acidsmentioning

confidence: 99%

“…Between CMC values of bile salts and value of retention parameters (RPHPLC) there is a good correlation, indicating the importance of hydrophobicity (particularly hydrophobicity of β side by steroid nucleus.) amphiphilic in their selfassociation 11,12 .…”

Section: Physico-chemical Properties Of Bile Acidsmentioning

confidence: 99%

Untitled

2018

IJPSR

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ABSTRACT:The main roles of bile acids as amphiphilic molecules are the micellar solubilization of the lipids, in the course of the welding process and the regulation of cholesterol homeostasis, which is essential as a precursor for the synthesis of bile acids. From the hydrophobic and hydrophilic surfaces of bile acids directly depends the level of their attachment to the receptors, ion channels and their effectiveness in the solubilization of lipid (hydrophobic drugs). The toxicity of membrane of bile acids is mainly determined by their hydrophobicity. We have synthesized the methyl ester of 7α-hydroxy-3-oxo-5β-cholanoic acid. We have reviewed and discussed the effects of the structure of bile acids to their hydrophobicity, which is expressed by the retention parameters by reverse phase chromatography, and hydrophobic properties, which is represented by partition coefficient 1-octanol / water. It also discusses the role of the lipophilicity of bile acids in their interactions with biological systems.

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“…the first principal component scores (PC1/R M ) derived from principal component analysis (PCA) of multivariate retention data [30,31], and arithmetic means of R M values, more frequently denoted as mR M [23][24][25].…”

Section: Introductionmentioning

confidence: 99%

Multivariate assessment of lipophilicity scales—computational and reversed phase thin-layer chromatographic indices

Andrić

Bajusz

Rácz

et al. 2016

Journal of Pharmaceutical and Biomedical Analysis

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Needs for fast, yet reliable means of assessing the lipophilicities of diverse compounds resulted in the development of various in silico and chromatographic approaches that are faster, cheaper, and greener compared to the traditional shake-flask method. However, at present no accepted "standard" approach exists for their comparison and selection of the most appropriate one(s). This is of utmost importance when it comes to the development of new lipophilicity indices, or the assessment of the lipophilicity of newly synthesized compounds. In this study, 50 well-known, diverse compounds of significant pharmaceutical and environmental importance have been selected and examined. Octanol-water partition coefficients have been measured with the shake-flask method for most of them. Their retentions have been studied in typical reversed thin-layer chromatographic systems, involving the most frequently employed stationary phases (octadecyl-and cyano-modified silica), and acetonitrile and methanol as mobile phase constituents. Twelve computationally estimated logP-s and twenty chromatographic indices together with the shake-flask octanol-water partition coefficient have been investigated with classical chemometric approaches -such as principal component analysis (PCA), hierarchical cluster analysis (HCA), Pearson's and Spearman's correlation matrices, as well as novel non-parametric methods: sum of ranking differences (SRD) and generalized pairwise correlation method (GPCM). Novel SRD and GPCM methods have been introduced based on the Comparisons with One VAriable (lipophilicity metric) at a Time (COVAT). For the visualization of COVAT results, a heatmap format was introduced. Analysis of variance (ANOVA) was applied to reveal the dominant factors between computational logPs and various chromatographic measures. In consensusbased comparisons, the shake-flask method performed the best, closely followed by computational estimates, while the chromatographic estimates often overlap with in silico assessments, mostly with methods involving octadecylmodified silica stationary phases. The ones that employ cyano-modified silica perform generally worse. The introduction of alternative coloring schemes for the covariance matrices and SRD/GPCM heatmaps enables the discovery of intrinsic relationships among lipophilicity scales and the selection of best/worst measures. Closest to the recommended logK OW values are ClogP and the first principal component scores obtained on octadecyl-silica stationary phase in combination with methanol-water mobile phase, while the usage of slopes derived from Soczewinski-Matyisik equation should be avoided.

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Estimation of chromatographic lipophilicity of bile acids and their derivatives by reversed‐phase thin layer chromatography

Cited by 22 publications

References 31 publications

Chromatographic Retention Parameters as Molecular Descriptors for Lipophilicity in QSA(P)R Studies of Bile Acid

Chromatographic Retention Parameters as Molecular Descriptors for Lipophilicity in QSA(P)R Studies of Bile Acid

Untitled

Multivariate assessment of lipophilicity scales—computational and reversed phase thin-layer chromatographic indices

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