Modeling of Chromatographic Lipophilicity Indices of Quaternary Ammonium and Nitrone Derivatives and Their Thiazolic Salts Using Molecular Descriptors

Onişor, Cristina; Palage, Mariana; Sârbu, Costel

doi:10.1080/00032710903518575

Cited by 9 publications

(4 citation statements)

References 25 publications

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“…In comparison with parameter k m , which was calculated with one regression parameter, intercept, the micelle-water partition coefficient (P m/w ) was calculated using both parameters slope and intercept of regression analysis. This indicates that the micelle-water partition coefficient P m/w can be considered as analogous to C 0 in RP-TLC, initially introduced as a more reliable measure of lipophilicity by Bieganowska et al (31) and successfully applied (21,32).…”

Section: Discussionmentioning

confidence: 98%

Evaluation of Angiotensin-Converting Enzyme Inhibitor's Absorption with Retention Data of Micellar Thin-Layer Chromatography and Suitable Molecular Descriptor

et al. 2015

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Twelve angiotensin-converting enzyme (ACE) inhibitors were studied to evaluate correlation between their absorption (ABS) data available in the literature (22-96%) and hydrophobicity parameters (km and Pm/w) obtained in micellar thin-layer chromatography (MTLC) using Brij 35. The theoretical considerations showed that the geometric molecular descriptor-volume value (Vol) should be considered as an independent variable simultaneously with calculated hydrophobicity parameters in multiple linear regression analysis to obtain reliable correlation between ACE inhibitor's absorption and lipophilicity (calculated KOWWINlog P) and that captopril should be excluded from further correlations. The results of MTLC confirmed that between the two hydrophobicity parameters km and Pm/w, for absorption prediction of 11 ACE inhibitors, the micelle-water partition coefficient Pm/w provided higher correlation (R(2) = 0.756), while for the km parameter R(2) = 0.612 was obtained. The micelle-water partition coefficient Pm/w could be considered as analogous to hydrophobicity parameter C0 from reversed-phase thin-layer chromatography. Dissimilar retention behavior of lisinopril indicated its lowest non-polar interaction with micelle, because of its di-acid form. The proposed model which included ACE inhibitors on the opposite site of lipophilicity-lisinopril and fosinopril (KOWWINlog P = -0.96 and KOWWINlog P = 6.61, respectively), both with similar absorption values (25 and 36%, respectively), could indicate that absorption of investigated compounds occurs via two different mechanisms: active and passive transport.

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Section: Discussionmentioning

confidence: 98%

Evaluation of Angiotensin-Converting Enzyme Inhibitor's Absorption with Retention Data of Micellar Thin-Layer Chromatography and Suitable Molecular Descriptor

et al. 2015

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“…Therefore, the first component will be uncorrelated with the second component. For a better interpretation of the information, the matrices are graphically plotted in order to obtain a 2D plot and loading scores, which allows us to represent the relative position of the objects of the original variables (Ionuț, Tiperciuc, & Oniga, ; Onișor, Palage, & Sârbu, ; Palage et al, ; C. I. Stoica et al, ; Tiperciuc & Sârbu, ). PCA was performed using the XL‐STAT extension (XLSTAT, ).…”

Section: Methodsmentioning

confidence: 99%

“…The second component will account for the maximal amount of variance in the dataset that did not display strong correlation with the first component. Therefore, the first component will be uncorrelated with the second component.For a better interpretation of the information, the matrices are graphically plotted in order to obtain a 2D plot and loading scores, which allows us to represent the relative position of the objects of the original variables(Ionuț, Tiperciuc, & Oniga, 2017;Onișor, Palage, & Sârbu, 2010;Palage et al, 2011;C. I. Stoica et al, 2015;Tiperciuc & Sârbu, 2006).…”

mentioning

confidence: 99%

Lipophilicity evaluation of some thiazolyl‐1,3,4‐oxadiazole derivatives with antifungal activity

Stoica

Ionuț

Vlase

et al. 2018

Biomedical Chromatography

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The chromatographic behavior of a series of thiazolyl-1,3,4-oxadiazoles with antifungal activity was studied by reverse-phase thin-layer chromatography (RP-TLC). The lipophilicity parameters derived from RP-TLC were correlated with the data derived from liquid-chromatography mass-spectrometry. Good linear relationships were observed between the chromatographic lipophilicity parameters and the theoretical lipophilicity descriptors (logP) generated by various computer software and internet modules. Principal component analysis, applied on the experimental chromatographic lipophilicity indices and the theoretically calculated logP, enabled us to obtain a lipophilicity chart for better vizualization of the similarities and differences of the investigated compounds, which were grouped by k-means clustering in two congeneric classes.

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“…To this purpose, derivatization reactions have been used extensively to modify molecular characteristics in order to achieve allowing investigation through the establishment of Quantitative Structure-Retention Relationships (QSRR) [11]. Such models are useful for understanding the principal factors governing their retention, forming predictions or even characterizing chromatographic systems [12,13]. To achieve this goal, information inherent in the molecular structure needs to be transformed into a form compatible for use in statistical analysis and modelling.…”

Section: Introductionmentioning

confidence: 99%

Liquid chromatography coupled to quadrupole-time of flight tandem mass spectrometry based quantitative structure–retention relationships of amino acid analogues derivatized via n-propyl chloroformate mediated reaction

Kritikos

Tsantili‐Kakoulidou

Loukas

et al. 2015

Journal of Chromatography A

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Modeling of Chromatographic Lipophilicity Indices of Quaternary Ammonium and Nitrone Derivatives and Their Thiazolic Salts Using Molecular Descriptors

Cited by 9 publications

References 25 publications

Evaluation of Angiotensin-Converting Enzyme Inhibitor's Absorption with Retention Data of Micellar Thin-Layer Chromatography and Suitable Molecular Descriptor

Evaluation of Angiotensin-Converting Enzyme Inhibitor's Absorption with Retention Data of Micellar Thin-Layer Chromatography and Suitable Molecular Descriptor

Lipophilicity evaluation of some thiazolyl‐1,3,4‐oxadiazole derivatives with antifungal activity

Liquid chromatography coupled to quadrupole-time of flight tandem mass spectrometry based quantitative structure–retention relationships of amino acid analogues derivatized via n-propyl chloroformate mediated reaction

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