Bicyclic guanidinium oligomers for recognition, cell delivery, and molecular materials

Identifier:  TDX:1049

Handle: https://hdl.handle.net/20.500.11797/TDX1049

Authors:  Valero Moreno, Julián

Abstract:
Nature frequently uses guanidinium group (mainly found in the amino acid arginine) to bind via ion pairing and hydrogen bonding different anions (mostly oxoanions), thus facilitating interactions between different macromolecules. This manuscript is divided into two clearly defined sections. The first one is based on the development of a robust and reliable synthetic methodology for the construction of bicyclic guanidinium oligomers of different lengths and functionalization degree and the study of the binding properties of these oligoguanidinium compounds with biologically relevant molecules such as p53 or targeted DNA sequences. Attributable to their cationic nature and hence similarity with cell penetrating peptides, bicyclic guanidinium oligomers were also explored as cell membrane carriers. The second part explores the self-assembly of bicyclic guanidines for calix[4]arene complexation and expansion of their cavities, multiporphyrin-fullerene dyad arrays, and their properties and potential applications as organogelators.