title: Recognitive nano-thin-film composite beads for the enantiomeric resolution of the metastatic breast cancer drug aminoglutethimide.
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.
authors.affiliation: CIQ-UP, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Portugal. Electronic address: kadhirvel@ipb.pt.
authors.forename: Porkodi
authors.initials: P
authors.lastname: Kadhirvel
authors.affiliation: CIQ-UP, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Portugal. Electronic address: mazenha@fc.up.pt.
authors.forename: Manuel
authors.initials: M
authors.lastname: Azenha
authors.affiliation: INFU, Faculty of Chemistry, Technical University of Dortmund, Otto-Hahn-Str. 6, Dortmund D-44221, Germany.
authors.forename: Eric
authors.initials: E
authors.lastname: Schillinger
authors.affiliation: INFU, Faculty of Chemistry, Technical University of Dortmund, Otto-Hahn-Str. 6, Dortmund D-44221, Germany.
authors.forename: Mahadeo R
authors.initials: MR
authors.lastname: Halhalli
authors.affiliation: CIQ-UP, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Portugal.
authors.forename: António F
authors.initials: AF
authors.lastname: Silva
authors.affiliation: INFU, Faculty of Chemistry, Technical University of Dortmund, Otto-Hahn-Str. 6, Dortmund D-44221, Germany; Department of Biomedical Sciences, Faculty of Health and Society, Malmö University, SE 20506 Malmö, Sweden.
authors.forename: Börje
authors.initials: B
authors.lastname: Sellergren
mesh_terms: D000616:Aminoglutethimide / Q000737:chemistry / Q000302:isolation & purification*; D018931:Antineoplastic Agents, Hormonal / Q000737:chemistry / Q000302:isolation & purification*; D001943:Breast Neoplasms; D002851:Chromatography, High Pressure Liquid; D005260:Female; D006801:Humans; D006860:Hydrogen Bonding; D053761:Nanocomposites / Q000737:chemistry*; D009362:Neoplasm Metastasis; D013237:Stereoisomerism; D013499:Surface Properties
chemical_list: D018931:Antineoplastic Agents, Hormonal; D000616:Aminoglutethimide
keywords: Aminoglutethimide; Molecular imprinting; RAFT; Racemic resolution; Stoichiometric imprinting