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 journalArticle

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
Externally publishedYes

Fingerprint

cyclodextrins
Cyclodextrins
Complexation
acids
dichroism
circular dichroism spectroscopy
Circular dichroism spectroscopy
Acids
electrostatic interactions
electrostatics
aqueous solutions
nuclear magnetic resonance
Coulomb interactions
spectroscopy
chemical derivatives
Nuclear magnetic resonance
anthracene-1-carboxylic acid
Association reactions
interactions

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)
  • Condensed Matter Physics

Cite this

Enhanced ternary 1 : 2 host-guest complexation of amino-γ-cyclodextrins with 2-anthracenecarboxylic acid. / Yang, Cheng; Fukuhara, Gaku; Nakamura, Asao; Origane, Yumi; Mori, Tadashi; Wada, Takehiko; Inoue, Yoshihisa.

In: Journal of Inclusion Phenomena and Macrocyclic Chemistry, Vol. 57, No. 1-4, 04.2007, p. 433-437.

Research output: Contribution to journalArticle

Yang, Cheng ; Fukuhara, Gaku ; Nakamura, Asao ; Origane, Yumi ; Mori, Tadashi ; Wada, Takehiko ; Inoue, Yoshihisa. / Enhanced ternary 1 : 2 host-guest complexation of amino-γ-cyclodextrins with 2-anthracenecarboxylic acid. In: Journal of Inclusion Phenomena and Macrocyclic Chemistry. 2007 ; Vol. 57, No. 1-4. pp. 433-437.
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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.",
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T2 - 2 host-guest complexation of amino-γ-cyclodextrins with 2-anthracenecarboxylic acid

AU - Yang, Cheng

AU - Fukuhara, Gaku

AU - Nakamura, Asao

AU - Origane, Yumi

AU - Mori, Tadashi

AU - Wada, Takehiko

AU - Inoue, Yoshihisa

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N2 - 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.

AB - 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.

KW - Amino-γ-cyclodextrin

KW - Anthracenecarboxylic acid

KW - Electrostatic interaction

KW - Host-guest complex

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