Carbohydrates play a critical role in myriad biological processes in both health and disease. Thus, there is an increasing impetus to develop novel materials with well-defined structures that either contain or respond to carbohydrates. The former offer the opportunity to develop probes for biological studies while the latter could be used to develop smart delivery systems (e.g., glucose/insulin). Our group developed non-polymeric thermo- and pH-responsive supramolecular G-Quadruplexes (SGQs) composed of 8-aryl-2’-deoxyguanosine (8ArG) as an alternative to current polymeric systems. In this presentation we will demonstrate how the presence of monosaccharides (e.g., glucose, mannose) affect the properties of SGQs (e.g., thermodynamic stability, dynamics). We will start by presenting the results from model compounds, lacking the guanosine moiety, prepared to optimize the synthetic protocols and used to determine critical chemical properties like pKa values. For example, we synthesized, with reasonable yields, six chalcone derivatives containing boronic acid (BA) moieties via the Claisen-Schmidt condensation of acetophenone and various BA-containing aldehydes. NMR was used to the determine the pKa values of these compounds to be in the range of 6.5–9, and to determine the affinity for various sugars (e.g., glucose). The results of parallel studies to incorporate monosaccharides into 8ArG derivatives, and how those impact the corresponding SGQs will also be presented (and rationalized using molecular modeling studies).

Development of sugar-containing & sugar-responsive supramolecular G-quadruplexes

251st National Meeting (2016)

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