A Superfluorinated Molecular Probe for Highly Sensitive in Vivo¹⁹F-MRI

Abstract

(19)F-MRI offers unique opportunities to image diseases and track cells and therapeutic agents in vivo. Herein we report a superfluorinated molecular probe, herein called PERFECTA, possessing excellent cellular compatibility, and whose spectral properties, relaxation times, and sensitivity are promising for in vivo (19)F-MRI applications. The molecule, which bears 36 equivalent (19)F atoms and shows a single intense resonance peak, is easily synthesized via a simple one-step reaction and is formulated in water with high stability using trivial reagents and methods.

Fluorine MR Imaging of Inflammation in Atherosclerotic Plaque in Vivo

“…It should also be noted that because of the slow clearance kinetics of the crown ether used in this study (30), other PFCs might be more suitable for human applications. PFCs with a single resonance, such as perfluoropolyether (34) or "Perfecta" (35), might have different kinetics and allow for fewer injections, although this remains to be tested. Furthermore, given that the voxel size in humans is often more than two orders of magnitude larger than that used in EXPERIMENTAL STUDIES: Fluorine MR Imaging of Inflammation in Atherosclerotic Plaque in Vivo van Heeswijk et al mice here (up to 2 3 2 3 8 mm 3 or 32 mL vs 0.22 mL used in this study), a smaller dose may in fact be sufficient for initial plaque macrophage visualization in human carotid arteries.…”

Design and Synthesis of Fluorinated Dendrimers for Sensitive 19F MRI

“…To a stirring mixture of diol 5 (41.0 g, 76.5 mmol) and K 2 CO 3 (26.4 g, 191.0 mmol) 12 in DMF (300 mL) at rt was added MeI (11.9 mL,27.1 g,190.8 mmol 13 (m), 83. 8,89.8,122.2 (q,J = 288.5 Hz),124.7,128.1,129.6,133.2;19 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 14 bromide 9 as an example). 1,32.4,34.2,54.3,61.7,65.7,122.5 (q,J = 287.5 Hz),125.6,126.4,129.3,129.5,130.0,130.3,143.0,144.0 33.9,34.0,54.4...…”

“…1 However, it is a very challenging task to image a drug in vivo with 19 F MRI because it has such a low sensitivity that a high 19 F concentration, a typical concentration of 89 mM for an example, 8 is generally required which is far beyond the in vivo concentration of most drugs. In addition, the 19 F NMR signal splitting and relatively long relaxation times of perfluorocarbons emulsion-based 19 F MRI agents, which are the most used imaging agents for 19 F MRI, further deteriorates the sensitivity of 19 F MRI.…”

Organic Nanoprobes for Fluorescence and 19F Magnetic Resonance Dual‐Modality Imaging

“…Alternatively, 19 F MRI holds several unique advantages such as low endogenous background signals, high signal-to-noise ratio (SNR), 100% natural isotopic abundance, relatively high sensitivity (83% of proton) and broad range of chemical shifts. [26][27][28][29] To date, some exogenous contrast agents such as molecular probes with a number of equivalent fluorine atoms, [27,[30][31][32][33][34][35] polymeric tracers containing high numbers of fluorine atoms, [28,[36][37][38][39][40][41][42] and fluorinated metallic nanoparticles [43][44][45][46] have been developed and employed for 19 F MRI. Despite great successes, it is highly desirable and still challenging to develop suitable 19 F MRI contrast agents with satisfied performance as well as multi-modalities.…”