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
Functional Materials Design, Discovery and Development (FMD3)
Physical Science and Engineering (PSE) Division
Online Publication Date2018-02-18
Print Publication Date2018-06-03
Permanent link to this recordhttp://hdl.handle.net/10754/627282
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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