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

doi:10.1007/s10847-006-9230-y

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 journal › Article › peer-review

3 Citations (Scopus)

Abstract

The complexation behavior of 6-amino-6-deoxy-γ-cyclodextrin (CD), 6^A,6^X-diamino-6^A,6^X-deoxy-γ- CDs and 3^A-amino-3^A-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 language	English
Pages (from-to)	433-437
Number of pages	5
Journal	Journal of Inclusion Phenomena and Macrocyclic Chemistry
Volume	57
Issue number	1-4
DOIs	https://doi.org/10.1007/s10847-006-9230-y
Publication status	Published - 2007 Apr 1
Externally published	Yes

Keywords

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

ASJC Scopus subject areas

Food Science
Chemistry(all)
Condensed Matter Physics

Access to Document

10.1007/s10847-006-9230-y

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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, 01.04.2007, p. 433-437.

Research output: Contribution to journal › Article › peer-review

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

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.",

keywords = "Amino-γ-cyclodextrin, Anthracenecarboxylic acid, Electrostatic interaction, Host-guest complex",

author = "Cheng Yang and Gaku Fukuhara and Asao Nakamura and Yumi Origane and Tadashi Mori and Takehiko Wada and Yoshihisa Inoue",

year = "2007",

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doi = "10.1007/s10847-006-9230-y",

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T1 - Enhanced ternary 1:2 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

PY - 2007/4/1

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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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