Stability constants and DFT calculations of anionic calixarene complexes with antiretroviral drugs Tenofovir and Emtricitabine

IF 1.6 4区化学 Q2 Agricultural and Biological Sciences

Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2025-01-08 DOI:10.1007/s10847-024-01273-x

Olga I. Kalchenko, Alexander B. Rozhenko, Serhii O. Cherenok, Anna I. Selikhova, Andriy B. Drapailo, Pilar López-Cornejo, Vitaly I. Kalchenko

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引用次数: 0

Abstract

Stability constants of supramolecular host-guest complexes between water-soluble sodium salts of thiacalix[4]arene sulfonic acid (TCS), thiacalix[4]arene methylphosphonic acid (TCPA), calix[4]arene methylene-bisphosphonic acid (CMBPA) (hosts) and the antiretroviral drugs Tenofovir (TFV) and Emtricitabine (FTC) (guests) were determined by HPLC method in 90/10, (v/v) water/acetonitrile solution (K_A values 1.2 × 10³ − 9.3 × 10³ M^− 1). DFT calculations show that the conformationally flexible calixarenes adopt the conformation (cone or 1,3-alternate preferably) suitable to form a number of intermolecular hydrogen bonds with the guest molecules. The water-soluble, low cytotoxic, synthetically available anionic calixarenes TCSA, TCPA and CMBPA with practically unlimited possibilities of chemical modification have the prospect of application in formulations of the antiretroviral drugs and the creation of vectors for their delivery systems.

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阴离子杯芳烃配合物与抗逆转录病毒药物替诺福韦和恩曲他滨的稳定性常数和DFT计算

在90/10，（v/v）水/乙腈溶液中（KA值1.2 × 103−9.3 × 103 M−1），采用高效液相色谱法（HPLC）测定了巯基芳烃磺酸（TCS）、巯基芳烃甲基膦酸（TCPA）、巯基芳烃亚甲基膦酸（CMBPA）水溶性钠盐（宿主）与抗逆转录病毒药物替诺福韦（TFV）和恩曲他滨（FTC）之间的超分子主-客配合物的稳定性常数。DFT计算表明，构象柔性杯芳烃采用适合与客体分子形成多个分子间氢键的构象（锥或1,3-交替）。水溶性、低细胞毒性、可合成的阴离子杯芳烃TCSA、TCPA和CMBPA具有几乎无限的化学修饰可能性，在抗逆转录病毒药物的配方和其递送系统载体的创建中具有应用前景。

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来源期刊

Journal of Inclusion Phenomena and Macrocyclic Chemistry 化学-化学综合

CiteScore

3.30

自引率

8.70%

发文量

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.