Molecular oxygen (O2) is a vital component of aerobic respiration, and thus its partial pressure (pO2) in various tissues can be considered a key physiological biomarker for pathologies known to alter the normal metabolic process. In particular, inadequate levels of tissue oxygenation have been linked to a variety of afflictions, including myocardial infarction, ischemic stroke, cancer, peripheral artery disease, deep vein thrombosis, and metabolic syndrome. Furthermore, tumor oxygenation has been identified as a significant factor affecting the efficacy of cancer therapy. Spatiotemporal mapping of tissue pO2, therefore, holds the potential to guide decision-making in the crucial early stages of treatment for various disease states. Oxygen quantification in vivo, however, remains a significant challenge for which there is an opportunity for more sensitive, universal, and versatile contrast agents. Magnetic resonance imaging (MRI) methods for interrogating tissue oxygenation are attractive due to the wide availability of MRI equipment and avoidance of expensive and short-lived radiopharmaceuticals. Specifically, 19F MRI has transformative potential to dynamically map oxygenation in tissue. The spin lattice relaxation rate (T1) of 19F is exquisitely sensitive to O2 concentration and it offers high spatial and temporal resolution and arbitrary tissue depth penetration. We report the synthesis of partially fluorinated epoxide monomers and their polymerization into partially fluorinated polyethers for use as 19F MR imaging agents. These novel polyether (co)polymers have a high density of chemically equivalent fluorine nuclei to ensure MRI sensitivity and have a low chemical shift dispersion for high resolution spatiotemporal mapping of tissue oxygenation. With this synthetic platform established, we will discuss current efforts in understanding the critical structure–property relationships for eventual translation to medical imaging.

Partially fluorinated polyethers for spatiotemporal mapping of tissue oxygenation

254th National Meeting (2017)

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