Evaluation of lipophilicity of some benzimidazole and benztriazole derivatives by RP HPTLC and PCA

In this study 10 guaianolide-type sesquiterpene gamma-lactones named amphoricarpolides, isolated from the aerial parts of two endemic subspecies of Amphoricarpos neumayeri (ssp. neumayeri and ssp. murbeckii Bosnjak), were investigated by means of reversed-phase thin-layer chromatography. Methanol-water and tetrahydrofuran-water binary mixtures were used as mobile phase in order to determine lipophilicity parameters R (0) (M) and C(0). Some of the investigated compounds were screened for their cytotoxic activity against HeLa and B16 cells. Chromatographically obtained lipophilicity parameters were correlated with calculated logP values and IC(50) values. Principal component analysis identified the dominant pattern in the chromatographically obtained data.

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“…High correlation coefficient indicates that the investigated guaianolides behave as homologous compounds in chromatography (Sarbu et al, 2002).…”

Section: Lipophilicity Determination By Rp-tlcmentioning

confidence: 92%

Lipophilicity of some guaianolides isolated from two endemic subspecies of Amphoricarpos neumayeri (Asteraceae) from Montenegro

Atrrog

Natić

Tosti

et al. 2008

Biomedical Chromatography

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“…The correlation matrix depicted in Table 4 (Fig. 2), and it appears that the studied compounds form practically five different congeneric classes (from left to right) in a good agreement with their chemical structure: diacetoxy- (23,(25)(26)(27), oxo-derivatives (16)(17)(18)(19)(20)(21)(22)24), primary and secondary bile acids (1-7), and finally the glyco- (8,10,11,14) and tauro- (9, 12 13, 15) conjugates. The position of each compound within the graphs is also in a good agreement with the position and orientation of hydroxyls and the presence of polar groups -COOH, -SO À 3 , -C 5 O and -OCOCH 3 , respectively.…”

Section: Resultsmentioning

confidence: 65%

“…The slope of the linear regression equation is also considered as an alternative descriptor of lipophilicity. Much more, applying principal component analysis directly to the experimental R F and R M values, the loadings and scores of the covariance matrix were obtained [24,25] …”

Section: Rp-hptlcmentioning

confidence: 99%

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

Onişor

Poša

Kevrešan

et al. 2010

J of Separation Science

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The main goal of this study was to estimate the lipophilicity and investigate the molecular mechanism of retention of bile acids and their derivatives in order to find an objective manner of quantitative comparison of different chemically bonded stationary phases for high performance TLC in terms of their (dis)similarities. Highly significant correlations were obtained between different experimental indices of lipophilicity (R(M0), S and the scores corresponding to the first principal component) estimated on CN(F254s) and RP-18(F254s) and some computed log P values that combine electronic and topological aspects. The most statistically significant quantitative structure-property relationship models, using descriptors from Dragon software, multiple linear regression and genetic algorithm, were also obtained in the case of CN(F254s) and RP-18(F254s) stationary phases. Cross-validation suggests a good reliability of the results. The contribution of 2D and 3D descriptors, which are related to atomic mass, together with reactivity parameters such as polarizability and electronegativity seem to control the chromatographic mechanism (lipophilicity) on all stationary phases.

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“…The advantages of this method are: applicability to compounds with higher lipophilicity (log P ranging from 0 to 7), only a small amount of the sample required, low sensitivity to impurities, rapid determination, good accuracy and excellent reproducibility [4]. The estimation of lipophilicity parameter strongly varies depending on the type of chromatographic system employed, and a few multivariate statistical techniques can be used to select the most appropriate ones [5].…”

Section: Introductionmentioning

confidence: 99%

Correlation between structure, retention and activity of cholic acid derived cis–trans isomeric bis‐steroidal tetraoxanes

Šegan

Andrić

Radoičić

et al. 2011

J of Separation Science

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Both quantitative structure-retention (QSRR) and quantitative structure-activity relationship (QSAR) studies have been performed to correlate the molecular characteristics of seven pairs of cis-trans isomeric bis-steroidal tetraoxanes with their reversed-phase thin-layer chromatography (RPTLC) retention as well as with their antiproliferative activity. 2D and 3D molecular descriptors as whole molecule representations together with retention parameters as well as with biological activity data were subjected to the multivariate statistical analysis (principal component analysis--PCA and hierarchical cluster analysis--HCA) in order to determine the most influential factors governing the retention and activity against human cervix carcinoma (HeLa) and human malignant melanoma (Fem-X) cell lines. Both QSRR and QSAR models were built by means of the partial least-squares (PLS) statistical method. It was found that hydrogen bond donating (HBD), hydrogen bond accepting (HBAcc), hydrophilic surface percentage (%HS) and hydrophilic-lipophilic balance (HLB) exhibit the strongest influence on retention. The most prominent factors affecting antiproliferative activity of the investigated substances are those relating to the size and shape of a molecule such as: connectivity indices, refractivity (Ref), surface area (SA), molecular volume and weight, polarizability (Pol) and those regarding the ability of hydrogen bonding (HB).

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Evaluation of lipophilicity of some benzimidazole and benztriazole derivatives by RP HPTLC and PCA

Cited by 35 publications

References 22 publications

Lipophilicity of some guaianolides isolated from two endemic subspecies of Amphoricarpos neumayeri (Asteraceae) from Montenegro

Lipophilicity of some guaianolides isolated from two endemic subspecies of Amphoricarpos neumayeri (Asteraceae) from Montenegro

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

Correlation between structure, retention and activity of cholic acid derived cis–trans isomeric bis‐steroidal tetraoxanes

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