Molecular imprinting of cyclodextrin to physiologically active oligopeptides in water

Shi Hui Song, Kazumi Shirasaka, Yasuhito Hirokawa, Hiroyuki Asanuma, Takehiko Wada, Jun Sumaoka, Makoto Komiyama

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

β-Cyclodextrin (β-CyD)-based polymeric receptors for γ-endorphin (γ-endor, an opioid heptadecapeptide) were prepared using the molecular imprinting method. When mono-3-(N-acrylamido)-3-deoxy-β-CyD bearing a vinyl group in the secondary hydroxyl side of the cavity of β-CyD was polymerised in water in the presence of γ-endor, the binding activity of the β-CyD polymer to this peptide in water was enormously promoted by the imprinting. By contrast, the bindings towards methionine-enkephalin (N-terminal pentapeptide of γ-endor) and its homologue leucine-enkephalin were suppressed. Thus, the binding of γ-endor by the imprinted polymer was highly selective. The imprinting towards γ-endor was also successful with the use of the β-CyD monomer bearing a vinyl group in the primary hydroxyl side of the cavity, although the recognition was less strict. Various factors affecting the imprinting efficiency (kinds of β-CyD vinyl monomer and template, as well as the pH of imprinting mixture) are discussed.

Original languageEnglish
Pages (from-to)149-155
Number of pages7
JournalSupramolecular Chemistry
Volume22
Issue number3
DOIs
Publication statusPublished - 2010 Mar 1

Keywords

  • Column
  • Cyclodextrins
  • Molecular imprinting
  • Oligopeptides

ASJC Scopus subject areas

  • Chemistry(all)

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