Synthesis of novel indolyl modified β-cyclodextrins and their molecular recognition behavior controlled by the solution's pH value

In order to investigate the effects of substituent and tether length in molecular recognition, three novel indolylcontained...

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Main Authors: Liu, Yu, You, Chang Cheng, He, Song, Chen, Guo Song, Zhao, Yanli
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Published: 2011
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Online Access:https://hdl.handle.net/10356/92232
http://hdl.handle.net/10220/6999
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Institution: Nanyang Technological University
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spelling sg-ntu-dr.10356-922322023-02-28T19:34:07Z Synthesis of novel indolyl modified β-cyclodextrins and their molecular recognition behavior controlled by the solution's pH value Liu, Yu You, Chang Cheng He, Song Chen, Guo Song Zhao, Yanli School of Physical and Mathematical Sciences DRNTU::Science::Biological sciences::Biochemistry In order to investigate the effects of substituent and tether length in molecular recognition, three novel indolylcontained β-cyclodextrin derivatives were synthesized by the condensation of indol-3-ylbutyric acid with the corresponding oligo(aminoethylamino)-β-cyclodextrin in the presence of DCC. Their molecular recognition behavior with some representative dye guests, i.e. Acridine Red, Rhodamine B, Neutral Red, Brilliant Green and Methyl Orange, was studied by using absorption, fluorescence and circular dichroism spectrometry. From the results of induced circular dichroism spectra and two-dimensional NMR spectroscopy, it was found that the initial conformations of these compounds are dramatically different in aqueous buffers of pH 2.0 and 7.2, which intrinsically determine the molecular binding ability of the host. It was also revealed that both the guest structure and the host tether length were responsible for the inclusion complexation stability. Therefore, on the one hand the hydrophobicity and substituent effect of the guest simultaneously determine the stability of host–guest complex through hydrophobic, van der Waals, and electrostatic interactions. On the other hand, the size/shape-matching relationship and induced-fit concept working between host and guest also play crucial roles in the selective molecular binding process of cyclodextrin hosts. Accepted version 2011-09-06T00:54:16Z 2019-12-06T18:19:43Z 2011-09-06T00:54:16Z 2019-12-06T18:19:43Z 2002 2002 Journal Article Liu, Y., You, C. C., He, S., Chen, G. S., & Zhao, Y. L. (2002). Synthesis of novel indolyl modified β-cyclodextrins and their molecular recognition behavior controlled by the solution's pH value. Journal of the Chemical Society, Perkin Transactions 2, 2002, 463-469. 0300-922X https://hdl.handle.net/10356/92232 http://hdl.handle.net/10220/6999 10.1039/B110159E 159630 Journal of the chemical society-Perkin transactions 2 © 2002 Royal Society of Chemistry. This is the author created version of a work that has been peer reviewed and accepted for publication by Journal of the Chemical Society, Perkin Transactions 2, Royal Society of Chemistry. 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/10.1039/B110159E. 7 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
You, Chang Cheng
He, Song
Chen, Guo Song
Zhao, Yanli
Synthesis of novel indolyl modified β-cyclodextrins and their molecular recognition behavior controlled by the solution's pH value
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Liu, Yu
You, Chang Cheng
He, Song
Chen, Guo Song
Zhao, Yanli
format Article
author Liu, Yu
You, Chang Cheng
He, Song
Chen, Guo Song
Zhao, Yanli
author_sort Liu, Yu
title Synthesis of novel indolyl modified β-cyclodextrins and their molecular recognition behavior controlled by the solution's pH value
title_short Synthesis of novel indolyl modified β-cyclodextrins and their molecular recognition behavior controlled by the solution's pH value
title_full Synthesis of novel indolyl modified β-cyclodextrins and their molecular recognition behavior controlled by the solution's pH value
title_fullStr Synthesis of novel indolyl modified β-cyclodextrins and their molecular recognition behavior controlled by the solution's pH value
title_full_unstemmed Synthesis of novel indolyl modified β-cyclodextrins and their molecular recognition behavior controlled by the solution's pH value
title_sort synthesis of novel indolyl modified β-cyclodextrins and their molecular recognition behavior controlled by the solution's ph value
publishDate 2011
url https://hdl.handle.net/10356/92232
http://hdl.handle.net/10220/6999
_version_ 1759857371200356352
description In order to investigate the effects of substituent and tether length in molecular recognition, three novel indolylcontained β-cyclodextrin derivatives were synthesized by the condensation of indol-3-ylbutyric acid with the corresponding oligo(aminoethylamino)-β-cyclodextrin in the presence of DCC. Their molecular recognition behavior with some representative dye guests, i.e. Acridine Red, Rhodamine B, Neutral Red, Brilliant Green and Methyl Orange, was studied by using absorption, fluorescence and circular dichroism spectrometry. From the results of induced circular dichroism spectra and two-dimensional NMR spectroscopy, it was found that the initial conformations of these compounds are dramatically different in aqueous buffers of pH 2.0 and 7.2, which intrinsically determine the molecular binding ability of the host. It was also revealed that both the guest structure and the host tether length were responsible for the inclusion complexation stability. Therefore, on the one hand the hydrophobicity and substituent effect of the guest simultaneously determine the stability of host–guest complex through hydrophobic, van der Waals, and electrostatic interactions. On the other hand, the size/shape-matching relationship and induced-fit concept working between host and guest also play crucial roles in the selective molecular binding process of cyclodextrin hosts.