Molecularly imprinted polymers as artificial steroid receptors

Abstract

The polymers selective to six different steroids (testosterone, Δ4-androstene-3,17-dione, 1,4-androstadiene-3,17-dione, β-estradiol, progesterone, testosterone propionate) have been synthesized using molecular imprinting based on noncovalent interactions. Analysis of the influence of structural features of the steroids under study has shown that molecules with a relatively rigid structure and the OH group at C-17 position are the most efficient templates for methacrylic acid-containing imprinted polymers. The chromatographic study of the polymers synthesized has demonstrated a strong dependence of the selectivity and intensity of interaction with analytes on the composition of solvents used both as porogen and chromatographic mobile phase. To obtain polymers with highly selective recognition sites and to create the optimal conditions for molecular recognition, all possible interactions (between template and functional monomer, template and solvent, solvent and functional monomer) should be taken into account. <?TF="palat-i"> The batch rebinding study of testosterone by the imprinted polymer in acetonitrile has revealed some heterogeneity of recognition sites, and permitted determination of Kass = 1.05 × 104 M−1, ΔG° = −5.4 kcal/mol and N = 1.2 μmol/g for high-affinity sites and Kass = 0.33 × 104 M−1, ΔG° = −4.8 kcal/mol and N = 2.2 μmol/g for low-affinity sites. <?TF="palat-i"> The results obtained show how it is possible to regulate in different modes the molecular recognition by imprinted polymers as well as to fabricate polymers possessing the necessary properties depending on their practical application.© 1998 John Wiley & Sons, Ltd.