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

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dc.contributor.authorButkiewicz, Helena
dc.contributor.authorKosiorek, Sandra
dc.contributor.authorSashuk, Volodymyr
dc.contributor.authorZimnicka, Magdalena
dc.contributor.authorDanylyuk, Oksana
dc.contributor.organizationInstitute of Physical Chemistry Polish Academy of Sciencesen
dc.contributor.organizationInstitute of Organic Chemistry, Polish Academy of Sciencesen
dc.date.accessioned2023-10-17T16:06:59Z
dc.date.available2023-10-17T16:06:59Z
dc.date.issued2023-10-12
dc.description.abstractHere we discuss crystal and solution/gas phase complexes of carboxylated pillar[5]arene with two cationic guests, alexi-dine 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 effects a rare solid state complex comprising two cavity inclusion modes within the same crystal lattice. The winner in the competition between ethanol molecules and organic cation (phenformin) for the access to the cavity of pillar[5]arene is undecided, visualized as ‘snapshot’ of these two inclusion possibilities in one crystal structure. Our results demonstrate that carbox-ylated pillar[n]arenes can be useful addition to the macrocyclic toolkit for the facilitation of the crystallization of bio(macro)molecules. Moreover, the IM-MS analysis of the pre-crystallization solutions of pillar[5]arene host and bigua-nide guests have shown the presence of structures and conformations closely related to those observed in the crystal forms. The most intriguing results obtained for 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 studiesen
dc.description.sponsorshipNCN PRELUDIUM 14 nr 2017/27/N/ST5/01931
dc.identifier.citationCryst. Growth Des. 2023. Publication Date: October 12, 2023. https://doi.org/10.1021/acs.cgd.3c00942en
dc.identifier.doi10.1021/acs.cgd.3c00942
dc.identifier.issn1528-7505
dc.identifier.urihttps://open.icm.edu.pl/handle/123456789/22955
dc.language.isoen
dc.publisherAmerican Chemical Societyen
dc.rightsUznanie autorstwa 4.0 Międzynarodowe*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.titleCarboxylated Pillar[5]arene Meets Medicinal Biguanides: Host−Guest Complexes with Alexidine and Phenformin in the Crystal and Solution/Gas Phaseen
dc.typearticleen
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