The solid-state structures of organic salts formed by calixarene dihydroxyphosphonic acid with nucleic bases cations: adeninium, cytosinium, guaninium and uracilium
Lazar, Adina N.
Coleman, Anthony W.
KAUST DepartmentAdvanced Membranes and Porous Materials Research Center
Physical Sciences and Engineering (PSE) Division
Functional Materials Design, Discovery and Development (FMD3)
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AbstractCalixarene dihydroxyphosphonic acid has been demonstrated to possess an interesting range of biological properties, including atypical anti-cancer activity. The robustness of calixarene dihydroxyphosphonic acid and its ubiquitous dimeric motif offers perspectives for pre-defined solid state complexation with small molecules. In the current article we describe co-crystals (organic salts) of calixarene dihydroxyphosphonic acid with four nucleic base cations: adeninium, cytosinium, guaninium and uracilium. A number of characteristic interactions between the components in the four co-crystals are pointed out also using the Hirshfeld surface analysis. All the four co-crystals are based on layers of calixarene dimers, alternating with layers of nucleic acid molecules. Two of the reported crystal structures (cytosinium and guaninium) are 1D channel-type structures, while the two others (adeninium and uracilium) represent 2D channel-type structures. In three out of four reported structures, interactions between the cations of nucleic bases are present generating 1D chains of cations. A constant motif is that the nucleic base is present in a type of cavity formed by one aromatic ring and a phosphonic acid moiety.
CitationShkurenko A, Lazar AN, Collard D, Navaza A, Kim B, et al. (2018) The solid-state structures of organic salts formed by calixarene dihydroxyphosphonic acid with nucleic bases cations: adeninium, cytosinium, guaninium and uracilium. Supramolecular Chemistry 30: 545–559. Available: http://dx.doi.org/10.1080/10610278.2018.1439171.
SponsorsWe thank the Plateforme Lyonnaise d’Analyses Thermiques du LMI (PLAT) for the TG analyses and for help in interpreting the data.
PublisherInforma UK Limited