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.-L., Ni, X.-L., Zeng, X., Elsegood, M. R. J., Jones, B., Redshaw, C., Teat, S. J., & 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
• Contract Date: Jul 8, 2015