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
{"title":"Complexation of water-soluble phosphorylated calixarenes with uracils. Stability constants and DFT study of the supramolecular complexes","authors":"O.I. Kalchenko,&nbsp;A.B. Rozhenko,&nbsp;S.O. Cherenok,&nbsp;A.I. Selikhova,&nbsp;S.Yu. Suikov,&nbsp;A.A. Kyrylchuk,&nbsp;V.I. Kalchenko","doi":"10.1007/s10847-023-01198-x","DOIUrl":null,"url":null,"abstract":"<div><p>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.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"103 9-10","pages":"369 - 383"},"PeriodicalIF":2.3000,"publicationDate":"2023-08-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s10847-023-01198-x","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"Agricultural and Biological Sciences","Score":null,"Total":0}
引用次数: 0

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.

Abstract Image

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
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。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 去求助
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.
期刊最新文献
Correction: X-ray structures, thermal stabilities and kinetics of guest desolvation of complexes of three fluorenone-derived host compounds with the polar aprotic guest solvent, tetramethylurea Asymmetric direct Aldol reaction between acetone and aromatic aldehydes catalyzed by diazadioxocalix[2]arene[2]triazine derivatives X-ray structures, thermal stabilities and kinetics of guest desolvation of complexes of three fluorenone-derived host compounds with the polar aprotic guest solvent, tetramethylurea Development and characterization of a cyclodextrin-based delivery system for enhanced pharmacokinetic and safety profile of oseltamivir Retraction Note: Soft nanotube hosts for capsulation and release of molecules, macromolecules, and nanomaterials
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1