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

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

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.

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. https://doi.org/10.1039/c4ra15905e

• Journal Article Type: Article
• Acceptance Date: Jan 22, 2015
• Online Publication Date: Jan 22, 2015
• Publication Date: Jan 1, 2015
• Deposit Date: Jul 8, 2015
• Publicly Available Date: Jul 16, 2018
• 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
• DOI: https://doi.org/10.1039/c4ra15905e
• Keywords: Allosteric effects; Thiacalix[4]arene-based receptors; Urea moieties
• Public URL: https://hull-repository.worktribe.com/output/376091
• 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/Content/ArticleLanding/2015/RA/C4RA15905E#!divAbstract