Enhanced ternary 1:2 host-guest complexation of amino-γ-cyclodextrins with 2-anthracenecarboxylic acid

Cheng Yang, Gaku Fukuhara, Asao Nakamura, Yumi Origane, Tadashi Mori, Takehiko Wada, Yoshihisa Inoue

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

The complexation behavior of 6-amino-6-deoxy-γ-cyclodextrin (CD), 6A,6X-diamino-6A,6X-deoxy-γ- CDs and 3A-amino-3A-deoxy-altro-γ-CD with 2-anthracenecarboxylic acid (AC) was studied by NMR, UV-vis and circular dichroism spectroscopy. These modified γ-CD derivatives were found to form stable 1:2 host-guest ternary complexes with AC in aqueous solution. Compared with native γ-CD, the primary-face-aminated γ-CDs exhibited remarkably enhanced overall association constants as a result of the additional electrostatic interactions between the oppositely charged host and guest. In contrast, the ternary complex formation of the secondary-face-aminated γ-CD with AC was hindered.

Original languageEnglish
Pages (from-to)433-437
Number of pages5
JournalJournal of Inclusion Phenomena and Macrocyclic Chemistry
Volume57
Issue number1-4
DOIs
Publication statusPublished - 2007 Apr 1
Externally publishedYes

Keywords

  • Amino-γ-cyclodextrin
  • Anthracenecarboxylic acid
  • Electrostatic interaction
  • Host-guest complex

ASJC Scopus subject areas

  • Food Science
  • Chemistry(all)
  • Condensed Matter Physics

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