Qualitative Determination of Bile Acids by Fluorescence Responses of Disubstituted γ-Cyclodextrins Having 2-(1-Naphthyl) propanoyl Residues

Iwao Suzuki, Yuki Kato, Tetsuo Osa, Junichi Anzai, Miyuki Narita, Fumio Hamada

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Eight γ-cyclodextrin (γ-CyD) derivatives having two optically active (R)-or (S)-2-(1-naphthyl) propanoyl residues at the primary hydroxyl sides, which are 6A,6B-, 6A,6C-, 6A,6D-, and 6A, 6Epositions (RR-AB, RR-AC, RR-AD, RR-AE, SS-AB, SS-AC, SS-AD, and SS-AE, respectively), were synthesized for investigating their fluorescence responses towards bile acids in a 10 vol.% ethylene glycol aqueous solutions. Strong intramolecular excimer fluorescence observed for RR-AD, RR-AE, SS-AD, and SS-AE is varied either strengthened or weakened direction based on the guest species. Although RR-AB, RR-AC, SS-AB, and SS-AC showed weak or no excimer fluorescence, some bile acids changed the monomer fluorescence intensity decreased, with excimer fluorescence being induced. By taking the fluorescence intensity changes as a sensitivity factor for detecting the guests, together with the shift in peak positions of the excimer fluorescence, one may qualitatively determine the type of bile acids in a solution at 50 mmol dm-3. No simple correlation is observed between the 1: 1 host-guest binding constants and the sensing factors, which indicated that not only the binding strength but also the binding conformation governed the sensitivity and selectivity of the hosts.

Original languageEnglish
Pages (from-to)64-68
Number of pages5
JournalInternational Journal of the Society of Materials Engineering for Resources
Volume8
Issue number2
DOIs
Publication statusPublished - 2000 Jan 1

Keywords

  • 2- (1-naphthyl) propanoic acid
  • bile acids
  • chemosensor
  • fluorescence
  • modified- γ-cyclodextrin

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Materials Science(all)
  • Mechanical Engineering

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