Recognitive nano-thin-film composite beads for the enantiomeric resolution of the metastatic breast cancer drug aminoglutethimide.

Porkodi Kadhirvel, Manuel Azenha, Eric Schillinger, Mahadeo R Halhalli, António F Silva, Börje Sellergren

Index: J. Chromatogr. A. 1358 , 93-101, (2014)

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Abstract

Straightforward crushing and sieving bulk polymeric R-aminoglutethimide-imprinted materials were prepared by classical free radical polymerization, whereas nano thin walled grafted imprinted materials were prepared using RAFT mediated control polymerization technique. A stoichiometric non-covalent approach based on a triply hydrogen bonding functional monomer-template 1:1 complex (K=599mol(-1)L(-1)) led to chiral selectors far outperforming previously used selectors for resolving this racemate. The recognitive materials produced here (enantioselectivity factors, α∼10) also have no match within the previously reported enantioselective imprinted polymers (α 1.2-4.5). We here demonstrate a potentially generic solution to produce good quality grafted MIPs for templates interacting by hydrogen bonding alone, relying on solvent polarity tuning, significantly extending the range of templates compatible with this format. Copyright © 2014 Elsevier B.V. All rights reserved.