Hyperpolarization of 15N-pyridinium and 15N-aniline derivatives by using parahydrogen: new opportunities to store nuclear spin polarization in aqueous media

Abstract

Hyperpolarization techniques hold the promise to improve the sensitivity of magnetic resonance imaging (MRI) contrast agents by over 10 000-fold. Among these techniques, para-hydrogen induced polarization (PHIP) allows for generating contrast agents within seconds. Typical hyperpolarized contrast agents are traceable for 2–3 minutes only, thus prolonging tracking-times holds great importance for the development of new ways to diagnose and monitor diseases. Here, we report on the design of perdeuterated ¹⁵N-containing molecules with longitudinal relaxation times (T₁) of several minutes. T₁ is a measure for how long hyperpolarization can be stored. In particular, we introduce two new hyperpolarizable families of compounds that we signal enhanced with para-hydrogen: tert-amine aniline derivatives and a quaternary pyridinium compound with ¹⁵N-T₁ of about 8 minutes. Especially the latter compound has great potential for applicability since we achieved ¹⁵N-polarization up to 8% and the pyridinium motif is contained in a variety of drug molecules and is also used in drug delivery systems.