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Positive and negative allosteric effects of thiacalix[4]arene-based receptors having urea and crown-ether moieties

Teate, Simon J.; Elsegood, Mark R. J.; Tomiyasu, Hirotsugu; Zhao, Jiang-Lin; Ni, Xin-Long; Ni, Xin Long; Zeng, Xi; Elsegood, Mark R. J.; Jones, Beth; Redshaw, Carl; Teat, Simon J.; Yamato, Takehiko; Zhao, Jiang Lin

Authors

Simon J. Teate

Mark R. J. Elsegood

Hirotsugu Tomiyasu

Jiang-Lin Zhao

Xin-Long Ni

Xin Long Ni

Xi Zeng

Mark R. J. Elsegood

Beth Jones

Professor Carl Redshaw C.Redshaw@hull.ac.uk
Professor of Inorganic Materials Chemistry and REF Lead for Chemistry

Simon J. Teat

Takehiko Yamato

Jiang Lin Zhao

Abstract

Heteroditopic receptors (4ₐ₋ₑ) based on a thiacalix[4]arene in the 1,3-alternate conformation, which have two urea moieties linking various phenyl groups substituted with either electron-donating or -withdrawing groups at their m-, or p-positions with a crown-ether moiety at the opposite side of the thiacalix[4]arene cavity, have been synthesized. The two examples with p-CH₃– (4b) and p-NO₂-substituted (4ₑ) phenyl groups have been characterized by X-ray crystallography. The binding properties of receptor 4ₑ were investigated by means of ¹H NMR spectroscopic and absorption titration experiments in CHCl₃–DMSO (10:1, v/v) solution in the presence of K⁺ ions and various anions. Interestingly, it was found that receptor 4ₑ, which possesses two p-nitrophenyl ureido moieties, can complex most efficiently in the urea cavity or the crown-ether moiety; and the plausible allosteric effect of receptor 4ₑ was also studied.

Journal Article Type Article
Publication Date Jan 1, 2015
Journal RSC advances
Print ISSN 2046-2069
Electronic ISSN 2046-2069
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 5
Issue 19
Pages 14747-14755
Institution Citation Tomiyasu, H., Zhao, J., Ni, X., Zeng, X., Elsegood, M. R. J., Jones, B., …Yamato, T. (2015). Positive and negative allosteric effects of thiacalix[4]arene-based receptors having urea and crown-ether moieties. RSC advances, 5(19), 14747-14755. doi:10.1039/c4ra15905e
DOI https://doi.org/10.1039/c4ra15905e
Keywords Allosteric effects; Thiacalix[4]arene-based receptors; Urea moieties
Publisher URL http://pubs.rsc.org/en/Content/ArticleLanding/2015/RA/C4RA15905E#!divAbstract
Additional Information This is a description of an article which has been published in: RSC advances, 2015, v.5 at http://pubs.rsc.org/en/...C4RA15905E#!divAbstract

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