Structure, stability, and dynamics of inclusion complexes formed from auranofin derivatives and hydroxypropyl-β-cyclodextrin

IF 2.3 4区化学 Q2 Agricultural and Biological Sciences

Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2024-07-12 DOI:10.1007/s10847-024-01252-2

Hélio F. Dos Santos, Cleber P. A. Anconi

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Abstract

The inclusion compounds of auranofin (AF) and its iodide derivative (AF-I) with HP-β-CD were recently identified and characterized experimentally. In the present work, classical molecular dynamics and the quantum computational GFN2-xTB method were applied to investigate the inclusion processes. As a result, both approaches identified AF-I@HP-β-CD as the most favourable system, as observed experimentally. The higher stability of AF-I@HP-β-CD was explained by entropy and solvation factors, with the GFN2-xTB method providing a stability constant (logK_1:1) in good agreement with the experimental results: 0.21–1.21 for AF@HP-β-CD and 1.31–2.33 for AF-I@HP-β-CD (the experimental values are 1.48 and 2.52, respectively). The preferred inclusion mode for AF-I@HP-β-CD has a triethylphosphine (-PEt₃) group pointed towards the head portion of the HP-β-CD where the HP groups are attached (labelled P2). The P2 mode showed short contacts between -CH₂CH₃ groups (-PEt₃) and -H-3 only (inside the CD cavity), which is also supported by ROESY experiments.

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呋喃丹衍生物与羟丙基-β-环糊精形成的包合物的结构、稳定性和动力学特性

最近发现了呋喃丹（AF）及其碘化物衍生物（AF-I）与 HP-β-CD 的包合物，并对其进行了实验表征。本研究采用经典分子动力学和量子计算 GFN2-xTB 方法来研究其包合过程。结果，这两种方法都发现 AF-I@HP-β-CD 是最有利的体系，与实验观察结果一致。AF-I@HP-β-CD 较高的稳定性可以用熵和溶解因子来解释，GFN2-xTB 方法提供的稳定性常数（logK1:1）与实验结果非常吻合：AF@HP-β-CD 为 0.21-1.21，AF-I@HP-β-CD 为 1.31-2.33（实验值分别为 1.48 和 2.52）。AF-I@HP-β-CD 的首选包合模式是三乙基膦（-PEt3）基团指向 HP-β-CD 的头部，HP 基团附着在头部（标记为 P2）。P2 模式显示了 -CH2CH3 基团（-PEt3）和 -H-3 之间的短接触（CD 腔内），这也得到了 ROESY 实验的支持。

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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.