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

Juan M Luco, Adriana P Salinas, Angel Alberto Jesus Torriero, Rodolfo Nieto Vazquez, Julio Raba, Eduardo Marchevsky

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The chromatog. capacity factors (log k ) for 32 structurally diverse drugs were detd. by high performance liq. chromatog. (HPLC) on a stationary phase composed of phospholipids, the so-called immobilized artificial membrane (IAM). In addn., quant. structure-retention relationships (QSRR) were developed in order to explain the dependence of retention on the chem. structure of the neutral, acidic, and basic drugs considered in this study. The obtained retention data were modeled by means of multiple regression anal. (MLR) and partial least squares (PLS) techniques. The structures of the compds. under study were characterized by means of calcd. physicochem. properties and several nonempirical descriptors. For the carboxylic compds. included in the anal., 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 anal. of the results obtained of two developed quant. structure-permeability studies for 20 misc. carboxylic compds., it may be concluded that the balance between polarizability and hydrophobic effects is not the same toward IAM phases and biol. 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 compds. in biol. membranes. For the non-carboxylic compds. included in the anal., this work shows that the hydrophobic factors are of prime importance for the IAM-retention of these compds., while the specific polar interactions, such as electron pair donor-acceptor interactions and electrostatic interactions, are also involved, but they are not dominant. [on SciFinder (R)]
Original languageEnglish
Pages (from-to)2129 - 2136
Number of pages8
JournalJournal of Chemical Information and Computer Sciences
Issue number6
Publication statusPublished - 2003
Externally publishedYes

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