scholarly journals A Comparative Study of the Lipophilicity of Metformin and Phenformin

Molecules ◽  
2021 ◽  
Vol 26 (21) ◽  
pp. 6613
Author(s):  
Małgorzata Dołowy ◽  
Josef Jampilek ◽  
Katarzyna Bober-Majnusz
Keyword(s):  
Low Cost ◽  
Reversed Phase ◽  
Topological Indices ◽  
Qsar Study ◽  
Future Design ◽  
Mobile Phases ◽  
Lipophilicity Parameter ◽  
Anticancer Treatment ◽  
Tlc Analysis ◽  
Layer Chromatography

The results presented in this paper confirm the beneficial role of an easy-to-use and low-cost thin-layer chromatography (TLC) technique for describing the retention behavior and the experimental lipophilicity parameter of two biguanide derivatives, metformin and phenformin, in both normal-phase (NP) and reversed-phase (RP) TLC systems. The retention parameters (RF, RM) obtained under different chromatographic conditions, i.e., various stationary and mobile phases in the NP-TLC and RP-TLC systems, were used to determine the lipophilicity parameter (RMW) of metformin and phenformin. This study confirms the poor lipophilicity of both metformin and phenformin. It can be stated that the optimization of chromatographic conditions, i.e., the kind of stationary phase and the composition of mobile phase, was needed to obtain the reliable value of the chromatographic lipophilicity parameter (RMW) in this study. The fewer differences in the RMW values of both biguanide derivatives were ensured by the RP-TLC system composed of RP2, RP18, and RP18W plates and the mixture composed of methanol, propan-1-ol, and acetonitrile as an organic modifier compared to the NP-TLC analysis. The new calculation procedures for logP of drugs based on topological indices 0χν, 0χ, 1χν, M, and Mν may be a certain alternative to other algorithms as well as the TLC procedure performed under optimized chromatographic conditions. The knowledge of different lipophilicity parameters of the studied biguanides can be useful in the future design of novel and more therapeutically effective metformin and phenformin formulations for antidiabetic and possible anticancer treatment. Moreover, the topological indices presented in this work may be further used in the QSAR study of the examined biguanides.

scholarly journals Normal and reversed phase thin-layer chromatography of new 16, 17-secoestrone derivatives

2003 ◽  
Vol 68 (1) ◽  
pp. 57-64 ◽  
Author(s):  
Marijana Acanski ◽  
Suzana Jovanovic-Santa ◽  
Lidija Jevric
Keyword(s):  
Thin Layer ◽  
Stationary Phase ◽  
Thin Layer Chromatography ◽  
Silica Gel ◽  
Reversed Phase ◽  
Retention Behavior ◽  
Mobile Phases ◽  
Layer Chromatography

The retention behavior and separation ability of a series of new 16,17-secoestrone derivatives has been studied on silica gel, alumina and C-18 silica gel layers with non-aqueous and aqueous-organic mobile phases. The retention behavior and separation ability are discussed in terms of the nature of the solute, eluent and stationary phase.

scholarly journals Reversed-phase thin-layer chromatography behavior of aldopentose derivatives

2012 ◽  
Vol 66 (3) ◽  
pp. 365-372 ◽  
Author(s):  
Dragana Livaja-Popovic ◽  
Eva Loncar ◽  
Lidija Jevric ◽  
Radomir Malbasa
Keyword(s):  
Thin Layer ◽  
Thin Layer Chromatography ◽  
Stationary Phases ◽  
Reversed Phase ◽  
Chromatographic Behavior ◽  
Log P ◽  
Retention Factors ◽  
Mobile Phases ◽  
Acetone Water ◽  
Layer Chromatography

Quantitative structure-retention relationships (QSRR) have been used to study the chromatographic behavior of some aldopentose. The behavior of aldopentose derivatives was investigated by means of the reversed-phase thin-layer chromatography (RP TLC) on the silica gel impregnated with paraffin oil stationary phases. Binary mixtures of methanol-water, acetone-water and dioxane-water were used as mobile phases. Retention factors, RM0, corresponding to zero percent organic modifier in the aqueous mobile phase was determined. Lipophilicity C0 was calculated as the ratio of the intercept and slope values. There was satisfactory correlation between them and log P values calculated using different theoretical procedures. Some of these correlations offer very good predicting models, which are important for a better understanding of the relationships between chemical structure and retention. The study showed that the hydrophobic parameters RM0 and C0 can be used as a measures of lipophilicity of investigated compounds.

scholarly journals Evaluation of the Lipophilicity of New Anticancer 1,2,3-Triazole-Dipyridothiazine Hybrids Using RP TLC and Different Computational Methods

Processes ◽  
2020 ◽  
Vol 8 (7) ◽  
pp. 858
Author(s):  
Beata Morak-Młodawska ◽  
Krystian Pluta ◽  
Małgorzata Jeleń
Keyword(s):  
Computational Methods ◽  
Molecular Descriptors ◽  
Triazole Ring ◽  
Hydrophobic Surface ◽  
Acetone Concentration ◽  
Lipinski’S Rule ◽  
Mobile Phases ◽  
Lipophilicity Parameter ◽  
Lipinski’S Rule Of Five ◽  
Layer Chromatography

Two new anticancer-active 1,2,3-triazole-dipyridothiazine hybrids were evaluated for their lipophilicity using thin-layer chromatography (TLC) and computational methods. The experimental lipophilicity was evaluated with mobile phases (mixtures of TRIS buffer and acetone), exploiting a linear correlation between the retention parameter (RM) and the volume of acetone. The relative lipophilicity parameter (RM0) was obtained by extrapolation to 0% acetone concentration. This parameter was intercorrelated with a specific hydrophobic surface area (b) revealing two congeneric subgroups: hybrids of 1,2,3-triazole-2,7-diazaphenothiazines and 1,2,3-triazole-3,6-diazaphenothiazines. The parameter RM0 was converted into the absolute lipophilicity parameter logPTLC using a calibration curve prepared on the basis of compounds of known logP values. Triazole–dipyridothiazine hybrids turned out to be medium lipophilic with logPTLC values of 1.232–2.979. The chromatographically established parameter logPTLC was compared to the calculated lipophilic parameter logPcalcd obtained with various algorithms. The lipophilicity was correlated with molecular descriptors and ADME properties. The new triazole–dipyridothiazine hybrids followed Lipinski’s rule of five. The lipophilicity of these hybrids was dependent on the substituents attached to the triazole ring and the location of the azine nitrogen atoms.

scholarly journals Pressurized planar electrochromatography of DNS amino acids derivatives in silica gel and silanized silica gel systems with formic acid addition to the water mobile phase

2021 ◽  
Author(s):  
Adam Chomicki ◽  
Tadeusz H. Dzido
Keyword(s):  
Amino Acids ◽  
Silica Gel ◽  
High Performance ◽  
Reversed Phase ◽  
Mobile Phases ◽  
Phase Systems ◽  
Silanized Silica ◽  
Layer Chromatography ◽  
Derivatives Of ◽  
Electrophoretic Effect

AbstractPressurized planar electrochromatography (PPEC) of dansyl (DNS) derivatives of amino acids in normal- and reversed-phase systems is presented. The results have been obtained for mobile phases with different acetonitrile (ACN) concentrations (0–85%). The data obtained show differences in separation selectivity between high-performance thin-layer chromatography (HPTLC) and PPEC systems. These differences originate from the electrophoretic effect which is involved in the PPEC system, contrary to the HPTLC one.

scholarly journals Estimation of the correlation between the retention of s-triazine derivatives and some molecular descriptors

2011 ◽  
pp. 231-239 ◽  
Author(s):  
Lidija Jevric ◽  
Gordana Koprivica ◽  
Nevena Misljenovic ◽  
Aleksandra Tepic ◽  
Tatjana Kuljanin ◽  
...  
Keyword(s):  
Linear Regression ◽  
Molecular Descriptors ◽  
Reversed Phase ◽  
Quantitative Structure ◽  
Mobile Phases ◽  
Physico Chemical ◽  
Triazine Derivatives ◽  
Structure Retention ◽  
Layer Chromatography ◽  
Quantitative Structure Retention Relationship

In this study, 14 newly synthesized s-triazine derivatives were investigated by means of reversed-phase thin-layer chromatography (TLC) on C-18 stationary and two different mobile phases: acetonitrile-water and methanol-water. Quantitative structure-retention relationship (QSRR) was developed for a series of s-triazine compounds by the multiple linear regression (MLR) analysis. An MLR procedure was used to model the relationships between molecular descriptors and retention of s-triazine derivatives. Physico-chemical molecular descriptors were calculated from the optimized structures. Statistically significant and physically meaningful QSRRs were obtained.

scholarly journals Lipophilicity assessment of some 5,5-disubstituted hydantoins by the means of reversed phase liquid chromatography

2013 ◽  
Vol 19 (1) ◽  
pp. 1-6
Author(s):  
Vesna Despotovic ◽  
Nemanja Trisovic ◽  
Anamarija Mandic ◽  
Gordana Uscumlic ◽  
Tatjana Djakovic-Sekulic
Keyword(s):  
Liquid Chromatography ◽  
High Performance ◽  
Principal Component ◽  
Reversed Phase ◽  
Retention Data ◽  
Reversed Phase Liquid Chromatography ◽  
Mobile Phases ◽  
Statistical Level ◽  
Phase Liquid ◽  
Layer Chromatography

The retention of some 5,5-disubstituted hydantoins was investigated by reversed phase high performance thin-layer chromatography (RP HPTLC) and reversed phase high-pressure liquid chromatography (RP HPLC). The mobile phases were mixtures of methanol-water and acetonitrile-water in various volume fractions. In order to explore and visualize similarities and differences among the investigated compounds and chromatographic system Principal Component Analysis (PCA) was used. Results show that the experimental lipophilicity indices estimated from retention data (RM,W, logkw) and PC1 are directly correlated with logP values at a high significant statistical level.

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