Amphiphilic N-Oligoethyleneglycol-imidazolium Derivatives of p-tert-Butylthiacalix[4]arene: Synthesis, Aggregation and Interaction with DNA

IF 1 4区化学 Q4 CHEMISTRY, MULTIDISCIPLINARY

Macroheterocycles Pub Date : 2021-01-01 DOI:10.6060/mhc210439s

B. Gafiatullin, D. Radaev, M. V. Osipova, E. Sultanova, V. Burilov, S. Solovieva, I. Antipin

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引用次数: 5

Abstract

New water-soluble derivatives of p-tert-butylthiacalix[4]arene have been synthesized in the stereoisomeric form 1,3-alternate with butyl and tetradecyl groups on one side of the macrocyclic platform and tri/tetraethylene glycol substituents on the other. The aggregation characteristics of macrocycles in the aquatic environment (CAC, aggre-gate size, zeta potential) have been studied. It has been demonstrated that the resulting aggregates have the ability to solubilize the lipophilic azo dye Orange OT, and the solubilizing ability significantly increases on going from butyl to tetradecyl derivatives. Using the methods of dynamic and electrophoretic light scattering and fluorimetry with ethidium bromide as a probe, it was shown that the obtained macrocycles interact with the DNA of the calf thymus. It was found that the efficiency of the interaction is greatly influenced by the length of the oxyethyl fragments: macrocycles containing tetraethylene glycol fragments are more effective than triethylene glycol analogs, causing a 2-fold compaction of DNA.

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对叔丁基噻唑芳烃的两亲性n -聚乙二醇-咪唑衍生物:合成、聚集及与DNA的相互作用

合成了对叔丁基噻唑芳烃的新的水溶性衍生物，其立体异构体形式为1,3-交替，大环平台一侧为丁基和十四烷基，另一侧为三/四乙二醇取代基。研究了大环在水生环境中的聚集特性(CAC、聚集门大小、zeta电位)。结果表明，所得到的聚集体具有增溶亲脂偶氮染料Orange OT的能力，并且从丁基衍生物到十四烷基衍生物的增溶能力显著提高。采用动态光散射、电泳光散射和以溴化乙啶为探针的荧光法，证实了所获得的大环与小牛胸腺DNA的相互作用。研究发现，相互作用的效率很大程度上受到氧乙基片段长度的影响:含有四甘醇片段的大环比三甘醇类似物更有效，导致DNA的2倍压实。

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来源期刊

Macroheterocycles CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

2.30

自引率

21.40%

发文量

期刊介绍： The journal is a forum for the specialists investigating macroheterocyclic compounds. It publishes original experimental and theoretical works (full papers and short communications) and reviews on synthesis, structural characterization, physical and coordination chemistry as well as practical application of macroheterocycles.