Study of organic compounds-water interactions by partition in aqueous two-phase systems

abstract

Partition coefficients of fourteen organic compounds were determined in 10 or 20 different polymer/polymer aqueous two-phase systems (ATPS) all at physiological pH (0.15 M NaCl in 0.01 M phosphate buffer, pH 7.4). Solute-specific coefficients characterizing different types of solute-water interactions for the compounds examined were determined by the multiple linear regression analysis. It is shown that (i) the partition behavior for the polar organic compounds is affected not only by dipole-dipole and hydrogen-bond interactions with aqueous environment but, notably, in most cases also by dipole-ion interactions; (ii) it is possible to predict partition behavior for compounds with pre-determined solutespecific coefficients in ATPS with characterized solvent features; and (iii) linear combinations of the solute-specific coefficients for the organic compounds might be useful in the development of quantitative structure-activity relationship (QSAR) analysis to describe their odor detection threshold. (C) 2013 Elsevier By. All rights reserved.

keywords

SOLVATOCHROMIC COMPARISON METHOD; SOLVATION ENERGY RELATIONSHIP; SOLVENT PROPERTIES; ION INTERACTIONS; METHYLENE GROUP; PI-STAR; DRUGS; SALT; SOLUTES; BUFFER

subject category

Biochemistry & Molecular Biology; Chemistry

authors

Madeira, PP; Bessa, A; Teixeira, MA; Alvares-Ribeiro, L; Aires-Barros, MR; Rodrigues, AE; Zaslavsky, BY

our authors

acknowledgements

Financial support for this work was in part provided by national research grant PTDC/EQU-EQU/112812/2009 for which the authors are thankful. This work was co-financed by FCT and FEDER under Programe COMPETE (Project PEst-C/EQB/LA0020/2013). A. Bessa acknowledges the scholarship within the Project PTDC/EQU-EQU/112812/2009 from Fundacao para a Ciencia e a Tecnologia (FCT). P.P. Madeira acknowledges the financial support (Grant SFRH/BPD/45055/2008) from FCT. M.A. Teixeira acknowledges his post-doctoral grant from FCT (SFRH/BPD/76645/2011). The authors thank Prof. Manuel Coelho and Prof!. Maria do Carmo Pereira (Faculdade de Engenharia da Universidade do Porto) for the use of their UV-vis plate reader equipment.

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