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
Y1 - 2007/4
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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U2 - 10.1007/s10847-006-9230-y
DO - 10.1007/s10847-006-9230-y
M3 - Article
AN - SCOPUS:34047214755
VL - 57
SP - 433
EP - 437
JO - Journal of Inclusion Phenomena and Macrocyclic Chemistry
JF - Journal of Inclusion Phenomena and Macrocyclic Chemistry
SN - 1388-3127
IS - 1-4
ER -