Self-Assembled Biradical Ureabenzene Nanoparticles for Magnetic Resonance Imaging

Abstract

As part of a series of investigations related to the construction of metal-free magnetic resonance imaging (MRI) contrast agents as alternatives to gadolinium agents, water-soluble biradicals, denoted as 1-AMP and 2-HEG, were prepared, in which two stable radicals were introduced to a ureabenzene framework. We found that 1-AMP possessed an amphiphilic side chain that consisted of an alkyl group and a hexaethylene glycol (HEG) chain, whereas 2-HEG possessed only an HEG chain. Accordingly, the biradicals showed self-assembly behavior due to multiple intermolecular interactions through which nanoparticles were formed in a water solution. Magnetic interaction took place in both biradicals, and the estimated interaction strength was J = 5.4 mT. Through MRI measurement, the water proton relaxivities, r1, were estimated to be 0.12 and 0.41 mM–1 s–1 for 1-AMP and 2-HEG, respectively; in other words, the r1 value for 2-HEG was approximately twice as high as that of monoradical-based contrast agents.