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Immobilized artificial membrane chromatography : quantitative structure-retention relationships of structurally diverse drugs

Luco, Juan M., Salinas, Adriana P., Torriero, Angel A. J., Vazquez, Rodolfo Nieto, Raba, Julio and Marchevsky, Eduardo 2003, Immobilized artificial membrane chromatography : quantitative structure-retention relationships of structurally diverse drugs, Journal of chemical information and computer science, vol. 43, no. 6, pp. 2129-2136, doi: 10.1021/ci034123p.

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Title Immobilized artificial membrane chromatography : quantitative structure-retention relationships of structurally diverse drugs
Author(s) Luco, Juan M.
Salinas, Adriana P.
Torriero, Angel A. J.ORCID iD for Torriero, Angel A. J. orcid.org/0000-0001-8616-365X
Vazquez, Rodolfo Nieto
Raba, Julio
Marchevsky, Eduardo
Journal name Journal of chemical information and computer science
Volume number 43
Issue number 6
Start page 2129
End page 2136
Total pages 8
Publisher American Chemical Society
Place of publication Washington, D. C.
Publication date 2003-11
ISSN 0095-2338
Keyword(s) biological membranes
drug products
electrons
high performance liquid chromatography
hydrophobicity
phospholipids
regression analysis
Summary The chromatographic capacity factors (log k‘) for 32 structurally diverse drugs were determined by high performance liquid chromatography (HPLC) on a stationary phase composed of phospholipids, the so-called immobilized artificial membrane (IAM). In addition, quantitative structure-retention relationships (QSRR) were developed in order to explain the dependence of retention on the chemical structure of the neutral, acidic, and basic drugs considered in this study. The obtained retention data were modeled by means of multiple regression analysis (MLR) and partial least squares (PLS) techniques. The structures of the compounds under study were characterized by means of calculated physicochemical properties and several nonempirical descriptors. For the carboxylic compounds included in the analysis, the obtained results suggest that the IAM-retention is governed by hydrophobicity factors followed by electronic effects due to polarizability in second place. Further, from the analysis of the results obtained of two developed quantitative structure-permeability studies for 20 miscellaneous carboxylic compounds, it may be concluded that the balance between polarizability and hydrophobic effects is not the same toward IAM phases and biological membranes. These results suggest that the IAM phases could not be a suitable model in assessing the acid-membrane interactions. However, it is not possible to generalize this observation, and further work in this area needs to be done to obtain a full understanding of the partitioning of carboxylic compounds in biological membranes. For the non-carboxylic compounds included in the analysis, this work shows that the hydrophobic factors are of prime importance for the IAM-retention of these compounds, while the specific polar interactions, such as electron pair donor−acceptor interactions and electrostatic interactions, are also involved, but they are not dominant.
Language eng
DOI 10.1021/ci034123p
Field of Research 030404 Cheminformatics and Quantitative Structure-Activity Relationships
030108 Separation Science
Socio Economic Objective 970103 Expanding Knowledge in the Chemical Sciences
HERDC Research category C1.1 Refereed article in a scholarly journal
Copyright notice ©2003, American Chemical Society
Persistent URL http://hdl.handle.net/10536/DRO/DU:30038923

Document type: Journal Article
Collection: Institute for Frontier Materials
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