Role of stationary phase and eluent composition on the determination of log P values of N-hydroxyethylamide of aryloxyalkylen and pyridine carboxylic acids by reversed-phase high-performance liquid chromatography

G. Cimpan, F. Irimie, S. Gocan, H.A. Claessens

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Abstract

The partition coefficients, P, between n-octanol and water of a number of growth stimulating substances, N-hydroxyethylamide of aryloxyalkylen- and pyridine carboxylic acids were obtained from Pomona College (C log P), and Rekker's (log PRekker) revised fragmental constant system was used to calculate log P data sets. Both of these data sets were correlated with two different substance lipophilicity parameters, log kw and 0. Log kw was obtained by extrapolation of log retention factor (k) to 0% organic modifier measured in reversed-phase liquid chromatography (RPLC) systems. 0 values were obtained from the slopes and intercepts of these relationships. The RPLC experiments were performed on four commercially available reversed-phase columns. Binary mixtures of methanol–water, methanol–phosphate buffer (pH 7.0), methanol–tricine buffer (pH 7.0) and acetonitrile–water were used as mobile phases for the determination of log kw values. For the methanolic eluents linear regression provided satisfactory correlations (r>0.99) for the relationships log k vs. organic modifier content in the eluent, while for the acetonitrile-containing eluents a second-degree polynominal regression was necessary. For all four RPLC columns, by linear regression satisfactory correlations (r>0.99) were obtained between log kw and log P data using methanolic eluents. In such eluents 0 values were shown to be the second-best lipophilicity parameters. For acetonitrile-containing eluents the use of second-degree polynominal regression was necessary and, in contrast to methanol, significant influence of the applied column on regression results was observed. For acetonitrile-containing eluents the 0-index does not provide satisfactory results for our substances. No difference in regression results between the use of buffered and non-buffered eluents was observed.
Original languageEnglish
Pages (from-to)247-261
JournalJournal of Chromatography, B: Biomedical Sciences and Applications
Volume714
Issue number2
DOIs
Publication statusPublished - 1998

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Liquid chromatography
High performance liquid chromatography
Carboxylic Acids
Linear regression
Buffers
Chemical analysis
1-Octanol
Binary mixtures
Extrapolation
Methanol
Water
acetonitrile
pyridine
Experiments

Cite this

@article{33404c6f26b1493aa7c8d459a753ed89,
title = "Role of stationary phase and eluent composition on the determination of log P values of N-hydroxyethylamide of aryloxyalkylen and pyridine carboxylic acids by reversed-phase high-performance liquid chromatography",
abstract = "The partition coefficients, P, between n-octanol and water of a number of growth stimulating substances, N-hydroxyethylamide of aryloxyalkylen- and pyridine carboxylic acids were obtained from Pomona College (C log P), and Rekker's (log PRekker) revised fragmental constant system was used to calculate log P data sets. Both of these data sets were correlated with two different substance lipophilicity parameters, log kw and 0. Log kw was obtained by extrapolation of log retention factor (k) to 0{\%} organic modifier measured in reversed-phase liquid chromatography (RPLC) systems. 0 values were obtained from the slopes and intercepts of these relationships. The RPLC experiments were performed on four commercially available reversed-phase columns. Binary mixtures of methanol–water, methanol–phosphate buffer (pH 7.0), methanol–tricine buffer (pH 7.0) and acetonitrile–water were used as mobile phases for the determination of log kw values. For the methanolic eluents linear regression provided satisfactory correlations (r>0.99) for the relationships log k vs. organic modifier content in the eluent, while for the acetonitrile-containing eluents a second-degree polynominal regression was necessary. For all four RPLC columns, by linear regression satisfactory correlations (r>0.99) were obtained between log kw and log P data using methanolic eluents. In such eluents 0 values were shown to be the second-best lipophilicity parameters. For acetonitrile-containing eluents the use of second-degree polynominal regression was necessary and, in contrast to methanol, significant influence of the applied column on regression results was observed. For acetonitrile-containing eluents the 0-index does not provide satisfactory results for our substances. No difference in regression results between the use of buffered and non-buffered eluents was observed.",
author = "G. Cimpan and F. Irimie and S. Gocan and H.A. Claessens",
year = "1998",
doi = "10.1016/S0378-4347(98)00228-X",
language = "English",
volume = "714",
pages = "247--261",
journal = "Journal of Chromatography, B: Biomedical Sciences and Applications",
issn = "1387-2273",
publisher = "Elsevier",
number = "2",

}

TY - JOUR

T1 - Role of stationary phase and eluent composition on the determination of log P values of N-hydroxyethylamide of aryloxyalkylen and pyridine carboxylic acids by reversed-phase high-performance liquid chromatography

AU - Cimpan, G.

AU - Irimie, F.

AU - Gocan, S.

AU - Claessens, H.A.

PY - 1998

Y1 - 1998

N2 - The partition coefficients, P, between n-octanol and water of a number of growth stimulating substances, N-hydroxyethylamide of aryloxyalkylen- and pyridine carboxylic acids were obtained from Pomona College (C log P), and Rekker's (log PRekker) revised fragmental constant system was used to calculate log P data sets. Both of these data sets were correlated with two different substance lipophilicity parameters, log kw and 0. Log kw was obtained by extrapolation of log retention factor (k) to 0% organic modifier measured in reversed-phase liquid chromatography (RPLC) systems. 0 values were obtained from the slopes and intercepts of these relationships. The RPLC experiments were performed on four commercially available reversed-phase columns. Binary mixtures of methanol–water, methanol–phosphate buffer (pH 7.0), methanol–tricine buffer (pH 7.0) and acetonitrile–water were used as mobile phases for the determination of log kw values. For the methanolic eluents linear regression provided satisfactory correlations (r>0.99) for the relationships log k vs. organic modifier content in the eluent, while for the acetonitrile-containing eluents a second-degree polynominal regression was necessary. For all four RPLC columns, by linear regression satisfactory correlations (r>0.99) were obtained between log kw and log P data using methanolic eluents. In such eluents 0 values were shown to be the second-best lipophilicity parameters. For acetonitrile-containing eluents the use of second-degree polynominal regression was necessary and, in contrast to methanol, significant influence of the applied column on regression results was observed. For acetonitrile-containing eluents the 0-index does not provide satisfactory results for our substances. No difference in regression results between the use of buffered and non-buffered eluents was observed.

AB - The partition coefficients, P, between n-octanol and water of a number of growth stimulating substances, N-hydroxyethylamide of aryloxyalkylen- and pyridine carboxylic acids were obtained from Pomona College (C log P), and Rekker's (log PRekker) revised fragmental constant system was used to calculate log P data sets. Both of these data sets were correlated with two different substance lipophilicity parameters, log kw and 0. Log kw was obtained by extrapolation of log retention factor (k) to 0% organic modifier measured in reversed-phase liquid chromatography (RPLC) systems. 0 values were obtained from the slopes and intercepts of these relationships. The RPLC experiments were performed on four commercially available reversed-phase columns. Binary mixtures of methanol–water, methanol–phosphate buffer (pH 7.0), methanol–tricine buffer (pH 7.0) and acetonitrile–water were used as mobile phases for the determination of log kw values. For the methanolic eluents linear regression provided satisfactory correlations (r>0.99) for the relationships log k vs. organic modifier content in the eluent, while for the acetonitrile-containing eluents a second-degree polynominal regression was necessary. For all four RPLC columns, by linear regression satisfactory correlations (r>0.99) were obtained between log kw and log P data using methanolic eluents. In such eluents 0 values were shown to be the second-best lipophilicity parameters. For acetonitrile-containing eluents the use of second-degree polynominal regression was necessary and, in contrast to methanol, significant influence of the applied column on regression results was observed. For acetonitrile-containing eluents the 0-index does not provide satisfactory results for our substances. No difference in regression results between the use of buffered and non-buffered eluents was observed.

U2 - 10.1016/S0378-4347(98)00228-X

DO - 10.1016/S0378-4347(98)00228-X

M3 - Article

VL - 714

SP - 247

EP - 261

JO - Journal of Chromatography, B: Biomedical Sciences and Applications

JF - Journal of Chromatography, B: Biomedical Sciences and Applications

SN - 1387-2273

IS - 2

ER -