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

研究成果: Article

3 引用（Scopus）

抜粋

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.

元の言語	English
ページ（範囲）	433-437
ページ数	5
ジャーナル	Journal of Inclusion Phenomena and Macrocyclic Chemistry
巻	57
発行部数	1-4
DOI	https://doi.org/10.1007/s10847-006-9230-y
出版物ステータス	Published - 2007 4 1
外部発表	Yes

ASJC Scopus subject areas

Food Science
Chemistry(all)
Condensed Matter Physics

文献にアクセス

10.1007/s10847-006-9230-y

フィンガープリント Enhanced ternary 1:2 host-guest complexation of amino-γ-cyclodextrins with 2-anthracenecarboxylic acid' の研究トピックを掘り下げます。これらはともに一意のフィンガープリントを構成します。

これを引用

Yang, C., Fukuhara, G., Nakamura, A., Origane, Y., Mori, T., Wada, T., & Inoue, Y. (2007). Enhanced ternary 1:2 host-guest complexation of amino-γ-cyclodextrins with 2-anthracenecarboxylic acid. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 57(1-4), 433-437. https://doi.org/10.1007/s10847-006-9230-y

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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",

month = apr,

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

language = "English",

volume = "57",

pages = "433--437",

journal = "Journal of Inclusion Phenomena and Macrocyclic Chemistry",

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TY - JOUR

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

Y1 - 2007/4/1

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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DO - 10.1007/s10847-006-9230-y

M3 - Article

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VL - 57

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EP - 437

JO - Journal of Inclusion Phenomena and Macrocyclic Chemistry

JF - Journal of Inclusion Phenomena and Macrocyclic Chemistry

SN - 1388-3127

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