Complexation of water-soluble phosphorylated calixarenes with uracils. Stability constants and DFT study of the supramolecular complexes

IF 2.3 4区 化学 Q2 Agricultural and Biological Sciences Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2023-08-19 DOI:10.1007/s10847-023-01198-x
O.I. Kalchenko, A.B. Rozhenko, S.O. Cherenok, A.I. Selikhova, S.Yu. Suikov, A.A. Kyrylchuk, V.I. Kalchenko
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Abstract

Modification of the upper rim of the lipophilic cone-shaped tetrapropoxycalix [4]arene with hydrophilic phosphine oxide groups or phosphinic acid groups yielded nano-sized water-soluble calixarenes that form supramolecular complexes with uracils, including active pharmaceutical ingredients of 5-Fluorouracil and 5-Methyluracil drugs. Stability constants of the formed complexes in an aqueous-organic medium were determined by the HPLC method. The most favored structures of the calixarenes and their uracil complexes were optimized at the DFT level of approximation. In the most favored structures of all adducts, the uracil molecules coordinate via hydrogen bonding with the phosphorus-containing groups on the upper rim of the calixarene ligands.

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水溶性磷酸化杯芳烃与尿嘧啶的络合。超分子配合物的稳定性常数及DFT研究
用亲水的氧化膦基团或磷酸基团修饰亲脂锥形四丙氧基杯芳烃的上缘,得到纳米级水溶性杯芳烃,与尿嘧啶形成超分子配合物,包括5-氟尿嘧啶和5-甲基尿嘧啶药物的活性药物成分。用高效液相色谱法测定了所形成的配合物在有机水介质中的稳定性常数。在近似DFT水平上对杯芳烃及其尿嘧啶配合物的最优结构进行了优化。在所有加合物的最有利的结构中,尿嘧啶分子通过氢键与杯芳烃配体上边缘的含磷基团配合。
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来源期刊
CiteScore
3.30
自引率
8.70%
发文量
0
审稿时长
3-8 weeks
期刊介绍: The Journal of Inclusion Phenomena and Macrocyclic Chemistry is the premier interdisciplinary publication reporting on original research into all aspects of host-guest systems. Examples of specific areas of interest are: the preparation and characterization of new hosts and new host-guest systems, especially those involving macrocyclic ligands; crystallographic, spectroscopic, thermodynamic and theoretical studies; applications in chromatography and inclusion polymerization; enzyme modelling; molecular recognition and catalysis by inclusion compounds; intercalates in biological and non-biological systems, cyclodextrin complexes and their applications in the agriculture, flavoring, food and pharmaceutical industries; synthesis, characterization and applications of zeolites. The journal publishes primarily reports of original research and preliminary communications, provided the latter represent a significant advance in the understanding of inclusion science. Critical reviews dealing with recent advances in the field are a periodic feature of the journal.
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