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J Nucl Med. 2008; 49 (Supplement 1):302P
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Radiopharmaceutical Chemistry: New Chemistry-Other

New Chemistry-Other Posters

Synthesis and initial in vivo characterization of 18F-labeled rhodamine B: A potential PET myocardial perfusion agent

Tobias Heinrich1, Frederic Fahey1, Patricia Dunning1, Erin Snay1, S. Treves1 and Alan Packard1

1 Nuclear Medicine, Children's Hospital Boston/Harvard Medical School, Boston, Massachusetts

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Objectives: The objective of this project is the development of a myocardial perfusion agent based on 18F-labeled rhodamine derivatives. Rhodamines are lipophilic cations, a property they share with the myocardial perfusion agents 99mTc-MIBI and 99mTc-tetrofosmin. Some rhodamines are also used as mitochondrial dyes, another property they share with 99mTc-MIBI and 99mTc-tetrofosmin. Additionally, there are reports that non-radioactive rhodamines accumulate in the myocardium. As functional analogs of 99mTc-MIBI, these compounds are also presumptive markers of multidrug resistance (MDR1).

Methods: The 18F-labeled 2-fluoroethylester of rhodamine B was prepared from rhodamine B lactone using 2-[18F]fluoroethyltosylate and DIPEA in CH3CN using a "one-pot" synthesis (figure) and purified by semi-preparative HPLC. The product was characterized by HPLC and TLC using the 19F compound as a reference. The biodistribution was evaluated in mice using microPET.

Results: The synthesis of [18F]fluoroethyl rhodamine B proceeds rapidly (45 min.), reproducibly, in good yield (35%), and high radiochemical purity (>95%) producing the first example of a radiofluorinated rhodamine. The microPET study revealed significant accumulation of the tracer in the gall bladder with minimal uptake in the myocardium. It is possible that this is the result of in vivo hydrolysis of the ester, despite previous studies suggesting that rhodamine esters are stable in vivo in rodents. Studies are currently underway to address this question.

Conclusions: We have developed a rapid, high-yield synthesis of 18F-labeled rhodamine B. MicroPET evaluation of the biodistribution suggests possible hydrolysis of the 2-[18F]fluoroester, and this issue is now being addressed.

Research Support: NIH CA094338





This Article
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Right arrow Articles by Packard, A.