Synthesis and characterization of a new class of glycopolymer MRI contrast agents

CHED 810

Michael W. Robinson, robins_mw@denison.edu1, Theresa M. Reineke, theresa.reineke@uc.edu2, Christopher G. Gulgas, gulgascg@email.uc.edu2, and Robie L. Lucas, robie.lucas@uc.edu2. (1) Department of Chemistry and Biochemistry, Denison University, Ebaugh Laboratories, Granville, OH 43023, (2) Department of Chemistry, University of Cincinnati, 2901 Campus Drive, Cincinnati, OH 45221
Glycopolymeric compounds introduce new benefits to typical organic MRI contrast agents, such as increased relaxivity, low toxicity, and improved solubility. The polymers reported here, bis-amide derivatives of DTPA that incorporate a thiourea moiety, were polymerized with a meso-glucarate or L- tartrate monomer to form two classes of polymers with degrees of polymerization approaching thirty repeat units. Structurally similar polymers, although significantly shorter and lacking a thiourea moiety in the repeat unit, have shown up to a three-fold increase in relaxivity compared with Magnevist, a commonly used MRI contrast agent. The synthesis and characterization of these new glycopolymer contrast agents will be presented.