Imidazolium p-tert-Butylthiacalix[4]arene Amphiphiles—Aggregation in Water Solutions and Binding with Adenosine 5′-Triphosphate Dipotassium Salt

被引：4

作者：

Burilov V.A. ^{[1
]}

Mironova D.A. ^{[1
]}

Ibragimova R.R. ^{[1
]}

Evtugyn V.G. ^{[2
]}

Osin Y.N. ^{[2
]}

Solovieva S.E. ^{[1
,3
]}

Antipin I.S. ^{[1
,3
]}

机构：

[1] Department of Organic Chemistry, Kazan Federal University, 18 Kremlevskaya St., Kazan

[2] Interdisciplinary Center for Analytical Microscopy, Kazan Federal University, 18 Kremlevskaya St., Kazan

[3] A.E. Arbuzov Institute of Organic and Physical Chemistry of Kazan Scientific Centre of Russian Academy of Science, Arbuzov str. 8, Kazan

来源：

BioNanoScience | 2018年 / 8卷 / 01期

基金：

俄罗斯科学基金会;

关键词：

ATP; Eosin Y; Imidazolium salts; Pyrene; Supramolecular amphiphile; Thiacalix[4]arene;

D O I：

10.1007/s12668-017-0484-1

中图分类号：

学科分类号：

摘要：

Aggregation properties of water-soluble cationic amphiphilic p-tert-butylthiacalix[4]arene derivatives adopting 1,3-alternate stereoisomeric form with methylimidazolyl headgroups were studied. It was found that derivatives 1 and 2 form stable aggregates in water solutions. The size and shape of aggregates were defined using DLS and TEM techniques. Critical aggregation concentration (CAC) of methylimidazolyl derivatives was calculated using dye micellization method. It was found that correct CAC determination of cationic amphiphiles using anionic xanthene dyes should be considered carefully in respect with electrostatic interactions. Using indicator displacement procedure, DLS studies, and 31P NMR spectroscopy, it was found that macrocycles 1 and 2 bind with ATP with 1:1 stoichiometry. It was found that ATP causes eosin Y release from binary thiacalixarene-eosin Y system up from 3 to 12 μM of ATP in the case of macrocycles 1 and 2, respectively. © 2017, Springer Science+Business Media, LLC, part of Springer Nature.

引用

页码：337 / 343

页数：6

共 34 条

[1]

Gale P.A., Anion receptor chemistry: highlights from 2008 and 2009, Chemical Society Reviews, 39, pp. 3746-3771, (2010)

[2]

Kim S.K., Sessler J.L., Ion pair receptors, Chemical Society Reviews, 39, pp. 3784-3809, (2010)

[3]

Li A.F., Wang J.H., Wang F., Jiang Y.B., Anion complexation and sensing using modified urea and thiourea-based receptors, Chemical Society Reviews, 39, pp. 3729-3745, (2010)

[4]

Zhou Y., Xu Z., Yoon Y., Fluorescent and colorimetric chemosensors for detection of nucleotides, FAD and NADH: highlighted research during 2004–2010, Chemical Society Reviews, 40, pp. 2222-2235, (2011)

[5]

Ng S., Lim H.S., Ma Q., Gao Z., Optical aptasensors for adenosine triphosphate, Theranostics, 6, 10, pp. 1683-1702, (2016)

[6]

Gourine A.V., Llaudet E., Dale N., Spyer K.M., ATP is a mediator of chemosensory transduction in the central nervous system, Nature, 436, pp. 108-111, (2005)

[7]

Wenz G., Han B.H., MSller A., Cyclodextrin rotaxanes and polyrotaxanes, Chemical Reviews, 106, pp. 782-817, (2006)

[8]

Lagona J., Mukhopadhyay P., Chakrabarti S., Isaacs L., The cucurbit[n]uril family, Angewandte Chemie, 44, 31, pp. 4844-4870, (2005)

[9]

Wang K., Yang Y.W., Zhang S.X.A., Research progress on the synthesis of pillar[n]arenes and their host-guest chemistry, Chemical Journal of Chinese Universities, 33, 2, pp. 1-13, (2012)

[10]

Solovieva S.E., Burilov V.A., Antipin I.S., Thiacalix[4]arene’s lower rim derivatives: synthesis and supramolecular properties, Macroheterocycles, 10, 2, pp. 134-146, (2017)

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