羧基化柱[5]芳烃遇到药用双胍：在晶体和溶液/气相中与阿列克西定和苯乙双胍形成主客体复合物,Crystal Growth & Design

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羧基化柱[5]芳烃遇到药用双胍：在晶体和溶液/气相中与阿列克西定和苯乙双胍形成主客体复合物
Crystal Growth & Design ( IF 3.2 ) Pub Date : 2023-10-12 , DOI: 10.1021/acs.cgd.3c00942
Helena Butkiewicz ₁ , Sandra Kosiorek ₁ , Volodymyr Sashuk ₁ , Magdalena M. Zimnicka ₂ , Oksana Danylyuk ₁

Affiliation

在这里，我们讨论了羧化柱[5]芳烃与两种阳离子客体（alexidine 和 phenformin）的晶体和溶液/气相复合物，揭示了主客体和组装好奇心、氢键的作用以及空腔包含与外型结合的关系。我们表明，羧基化的柱[5]芳烃与双（双胍）客体阿来西定的结合导致了开放型超分子结构的结晶。这也是有史以来第一个报道的alexidine的晶体结构。柱[5]芳烃与双胍药物苯乙双胍的结晶会影响一种罕见的固态复合物，该复合物在同一晶格内包含两种空腔包含模式。乙醇分子和有机阳离子（苯乙双胍）之间争夺柱[5]芳烃空腔的竞争的获胜者尚未确定，可视化为一个晶体结构中这两种包含可能性的“快照”。我们的结果表明，羧化柱[ n ]芳烃可以作为大环工具包的有用补充，以促进生物（大）分子的结晶。此外，柱[5]芳烃主体和双胍客体的预结晶溶液的 IM-MS 分析表明存在与晶型中观察到的结构和构象密切相关的结构和构象。柱[5]芳烃-alexidine 复合物获得的最有趣的结果表明该复合物在 24 小时内发生了构象演化。IM-MS 分析辅以理论计算，可用于预测和检查主客体系统的结晶过程，补充晶体学研究。

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Carboxylated Pillar[5]arene Meets Medicinal Biguanides: Host–Guest Complexes with Alexidine and Phenformin in the Crystal and Solution/Gas Phase

Here, we discuss crystal and solution/gas-phase complexes of carboxylated pillar[5]arene with two cationic guests, alexidine and phenformin, revealing host–guest and assembly curiosities, the role of hydrogen bonding, and cavity inclusion versus exo-mode binding. We show that the combination of carboxylated pillar[5]arene with bis(biguanidinium) guest alexidine results in the crystallization of open-type supramolecular architecture. This is also the first crystal structure of alexidine ever reported. The crystallization of pillar[5]arene with biguanidinium drug phenformin affects a rare solid-state complex comprising two cavity inclusion modes within the same crystal lattice. The winner in the competition between ethanol molecules and an organic cation (phenformin) for access to the cavity of pillar[5]arene is undecided, visualized as a “snapshot” of these two inclusion possibilities in one crystal structure. Our results demonstrate that carboxylated pillar[n]arenes can be a useful addition to the macrocyclic toolkit for the facilitation of the crystallization of bio(macro)molecules. Moreover, the IM-MS analysis of the precrystallization solutions of pillar[5]arene host and biguanide guests has shown the presence of structures and conformations closely related to those observed in the crystal forms. The most intriguing results obtained for a pillar[5]arene–alexidine complex imply a conformational evolution of the complex over 24 h. The IM-MS analysis complemented by theoretical calculations may be applied to predict and examine the crystallization process of host–guest systems, complementing crystallographic studies.

更新日期：2023-10-12

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