Molecular recognition thermodynamics of steroids by novel oligo(aminoethylamino)-β-cyclodextrins bearing anthryl : enhanced molecular binding ability by co-inclusion complexation

Molecular recognition thermodynamics of steroids by novel oligo(aminoethylamino)-β-cyclodextrins bearing anthryl : enhanced molecular binding ability by co-inclusion complexation

Three b-cyclodextrin (b-CD) derivatives bearing anthracene group (2–4) were synthesized by the condensation of...

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Main Authors: Liu, Yu, Zhao, Yanli, Yang, En Cui, Zhang, Heng Yi
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Published: 2011
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DRNTU::Science::Biological sciences::Biochemistry
Online Access:https://hdl.handle.net/10356/94265
http://hdl.handle.net/10220/7011
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spelling sg-ntu-dr.10356-942652023-02-28T19:38:59Z Molecular recognition thermodynamics of steroids by novel oligo(aminoethylamino)-β-cyclodextrins bearing anthryl : enhanced molecular binding ability by co-inclusion complexation Liu, Yu Zhao, Yanli Yang, En Cui Zhang, Heng Yi School of Physical and Mathematical Sciences DRNTU::Science::Biological sciences::Biochemistry Three b-cyclodextrin (b-CD) derivatives bearing anthracene group (2–4) were synthesized by the condensation of 9-anthracenecarboxylic acid with the corresponding oligo(aminoethylamino)-b-CDs in 33–36% yields and their original conformations and binding behavior with steroid molecules were investigated by using spectroscopic techniques and isothermal calorimeter. The combination of induced circular dichroism (ICD) and 2D NMR spectra reveals that the anthryl group attached to b-CD is itself included in cavity and the chain length of oligo(aminoethylamino) decides the orientation of the anthryl located in the cavity to some extent, directly affecting the binding ability with guest molecules. Calorimetric titration has been performed at buffer aqueous solution (pH 7.2) at 25 C to give the binding constants (KS) and thermodynamic parameters for 1:1 inclusion complexation of modified b-CDs 2–4 and representative steroids, i.e., cholate, deoxycholate, glycocholate, and taurocholate. Possessing the sidearm with appropriate length, 3 gives the highest stability constant of 22485 ± 15 M)1 for the complexation with deoxycholate molecule, which may be ascribed to the co-inclusion interactions between the host and guest. As compared with parent b-CD 1 upon complexation with steroids, hosts 2–4 with different chain lengths enhanced the binding ability and significant molecular discrimination, which are discussed comparatively and globally from the viewpoint of thermodynamics. Furthermore, we establish the correlation between the conformation of the resulting complexes and the thermodynamic parameters obtained. Accepted version 2011-09-07T08:58:41Z 2019-12-06T18:53:30Z 2011-09-07T08:58:41Z 2019-12-06T18:53:30Z 2004 2004 Journal Article Liu, Y., Zhao, Y. L., Yang, E. C., & Zhang, H. Y. (2004). Molecular recognition thermodynamics of steroids by novel oligo(aminoethylamino)-β-cyclodextrins bearing anthryl: Enhanced molecular binding ability by co-inclusion complexation. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 50, 3-11. https://hdl.handle.net/10356/94265 http://hdl.handle.net/10220/7011 10.1007/s10847-003-8826-8 159683 Journal of inclusion phenomena and macrocyclic chemistry © 2004 Kluwer Academic Publishers . This is the author created version of a work that has been peer reviewed and accepted for publication by Journal of Inclusion Phenomena and Macrocyclic Chemistry, Kluwer Academic Publishers.  It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document.  The published version is available at: http://dx.doi.org/10.1007/s10847-003-8826-8. 9 p. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
topic DRNTU::Science::Biological sciences::Biochemistry
spellingShingle DRNTU::Science::Biological sciences::Biochemistry
Liu, Yu
Zhao, Yanli
Yang, En Cui
Zhang, Heng Yi
Molecular recognition thermodynamics of steroids by novel oligo(aminoethylamino)-β-cyclodextrins bearing anthryl : enhanced molecular binding ability by co-inclusion complexation
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Liu, Yu
Zhao, Yanli
Yang, En Cui
Zhang, Heng Yi
format Article
author Liu, Yu
Zhao, Yanli
Yang, En Cui
Zhang, Heng Yi
author_sort Liu, Yu
title Molecular recognition thermodynamics of steroids by novel oligo(aminoethylamino)-β-cyclodextrins bearing anthryl : enhanced molecular binding ability by co-inclusion complexation
title_short Molecular recognition thermodynamics of steroids by novel oligo(aminoethylamino)-β-cyclodextrins bearing anthryl : enhanced molecular binding ability by co-inclusion complexation
title_full Molecular recognition thermodynamics of steroids by novel oligo(aminoethylamino)-β-cyclodextrins bearing anthryl : enhanced molecular binding ability by co-inclusion complexation
title_fullStr Molecular recognition thermodynamics of steroids by novel oligo(aminoethylamino)-β-cyclodextrins bearing anthryl : enhanced molecular binding ability by co-inclusion complexation
title_full_unstemmed Molecular recognition thermodynamics of steroids by novel oligo(aminoethylamino)-β-cyclodextrins bearing anthryl : enhanced molecular binding ability by co-inclusion complexation
title_sort molecular recognition thermodynamics of steroids by novel oligo(aminoethylamino)-β-cyclodextrins bearing anthryl : enhanced molecular binding ability by co-inclusion complexation
publishDate 2011
url https://hdl.handle.net/10356/94265
http://hdl.handle.net/10220/7011
_version_ 1759854577385996288
description Three b-cyclodextrin (b-CD) derivatives bearing anthracene group (2–4) were synthesized by the condensation of 9-anthracenecarboxylic acid with the corresponding oligo(aminoethylamino)-b-CDs in 33–36% yields and their original conformations and binding behavior with steroid molecules were investigated by using spectroscopic techniques and isothermal calorimeter. The combination of induced circular dichroism (ICD) and 2D NMR spectra reveals that the anthryl group attached to b-CD is itself included in cavity and the chain length of oligo(aminoethylamino) decides the orientation of the anthryl located in the cavity to some extent, directly affecting the binding ability with guest molecules. Calorimetric titration has been performed at buffer aqueous solution (pH 7.2) at 25 C to give the binding constants (KS) and thermodynamic parameters for 1:1 inclusion complexation of modified b-CDs 2–4 and representative steroids, i.e., cholate, deoxycholate, glycocholate, and taurocholate. Possessing the sidearm with appropriate length, 3 gives the highest stability constant of 22485 ± 15 M)1 for the complexation with deoxycholate molecule, which may be ascribed to the co-inclusion interactions between the host and guest. As compared with parent b-CD 1 upon complexation with steroids, hosts 2–4 with different chain lengths enhanced the binding ability and significant molecular discrimination, which are discussed comparatively and globally from the viewpoint of thermodynamics. Furthermore, we establish the correlation between the conformation of the resulting complexes and the thermodynamic parameters obtained.

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