Molecular recognition of deoxycholic acids by pyrene-appended γ- cyclodextrin connected with a rigid azacrown spacer

Iwao Suzuki, Maki Ito, Tetsuo Osa, Jun ichi Anzai

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

A γ-cyclodextrin (γ-CyD) derivative (1) having a pyrene moiety, connected through a 4,13-diaza-18-crown-6 ether moiety to γ-CyD, was synthesized and evaluated for guest binding and sensing properties. In aqueous solution, 1 existed as an association dimer in which the secondary hydroxyl sides faced each other to accommodate two pyrene moieties. Photo- induced electron transfer (PET) between the amino group and the excited pyrene moiety regulated the monomer fluorescence intensity of 1. The monomer- dimer equilibrium and the PET indicated that I may be used as a host capable of detecting guest complexation by changes in fluorescence intensity from the pyrene moiety. Deoxycholic acids were found to be good guests for detection by 1, and deoxycholic acid itself induced different fluorescence changes compared to the other deoxycholic acids. This indicated that 1 could recognize the position of the hydroxy groups on the steroidal framework. The azacrown part may participate in the guest selectivity for the deoxycholic acids by regulating the distance between the amino group and the pyrene moiety, modifying PET efficiency.

Original languageEnglish
Pages (from-to)151-155
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Volume47
Issue number2
DOIs
Publication statusPublished - 1999 Feb

Keywords

  • Azacrown ether
  • Fluorescent chemosensor
  • Photo-induced electron transfer
  • Pyrene
  • γ7-cyclodextrin

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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