Synthesis and supramolecular assembly of 1,3-bis(1′-uracilyl)-2-propanone

Abstract

In this research work, we investigated the properties of a novel heterocyclic molecule, named by us U₂CO, whose structure consists of two uracil rings connected by a 2-propanone moiety. We studied by UV the spectroscopic characteristics of U₂CO as a function of temperature and ionic strength of the solution. Furthermore, dynamic light scattering (DLS) studies conducted on samples containing the uracil-containing derivative indicated the formation of non-covalent supramolecular networks based on multiple U₂CO units. These aggregates contained hydrophobic cavities able to encapsulate drugs such as doxorubicin, as evidenced by fluorescence studies. This property, together with the good stability in human serum of U₂CO, determined by HPLC analysis, could be an interesting feature in developing new drug delivery systems. Interestingly, UV studies suggested that U₂CO is able to form complexes with copper(II) cations, which is a useful characteristic in view of potential anti-oxidant approaches.