Dose-on-demand of diverse 18F-fluorocholine derivatives through a two-step microfluidic approach

Nuclear Medicine and Biology

Volumn 38, Issue 5, 2011, Pages 637-644

  Pascali, Giancarlo ^a   Nannavecchia, Giovanni ^a,b   Pitzianti, Sabrina ^a,c   Salvadori, Piero A ^a  

^a INSTITUTE OF CLINICAL PHYSIOLOGY   (Italy)

^b SCUOLA UNIVERSITARIA SUPERIORE IUSS PAVIA   (Italy)

^c UNIVERSITY OF PISA   (Italy)

Author keywords

Dose on demand; Fluorocholine; Microfluidic radiochemistry; PET; Radiotracers

Indexed keywords

DEANOL; FLUOROETHYLCHOLINE F 18; FLUOROMETHYLCHOLINE F 18; FLUOROPROPYLCHOLINE F 18; RADIOPHARMACEUTICAL AGENT; TRACER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; DRUG DISTRIBUTION; DRUG PURIFICATION; DRUG RESPONSE; DRUG SYNTHESIS; FLUORINATION; MICROFLUIDICS; POSITRON EMISSION TOMOGRAPHY; PROCESS OPTIMIZATION; RADIOACTIVITY; RADIOCHEMISTRY; RADIOSYNTHESIS; REACTION TIME;

CHOLINE; HALOGENATION; MICROFLUIDIC ANALYTICAL TECHNIQUES; POSITRON-EMISSION TOMOGRAPHY; RADIOCHEMISTRY; SOLID PHASE EXTRACTION;

EID: 79959639639     PISSN: 09698051     EISSN: 18729614     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2011.01.005     Document Type: Article

References (35)

1. Hara T., Kosaka N., Shinoura N., Kondo T. PET imaging of brain tumor with [methyl-11C]choline. J Nucl Med 1997, 38:842-847.
2. Hara T., Kosaka N., Kondo T., Kishi H., Kobori O. Imaging of brain tumor, lung cancer, esophagus cancer, colon cancer, prostate cancer, and bladder cancer with [11C-]choline. J Nucl Med 1997, 38S:250.
3. Czernin J., Benz M.R., Allen-Auerbach M.S. PET imaging of prostate cancer using 11C-acetate. PET Clinics 2009, 4(2):163-172.
4. Felicini C., Någren K., Berton A., Pascali G., Salvadori P.A. Development of an automated modular system for the synthesis of [11C]acetate. Nucl Med Comm 2010, 31(12):1033-1039.
5. Lindhe Ö., Sun A., Ulin J., Rahman O., Långström B., Sörensen J. [18F]Fluoroacetate is not a functional analogue of [11C]acetate in normal physiology. Eur J Nucl Med Mol Imaging 2009, 36(9):1453-1459.
6. DeGrado T.R., Baldwin S.W., Wang S., Orr M.D., Liao R.P., Friedman H.S., et al. Synthesis and evaluation of 18F-labeled choline analogs as oncologic PET tracers. J Nucl Med 2001, 42:1805-1814.
7. Yu K.H., Park J.H., Yang S.D. Synthesis of [18F]fluorocholine analogues as a potential imaging agent for PET studies. Bull Korean Chem Soc 2004, 25:506-510.
8. Hara H. 18F-fluorocholine: a new oncologic PET tracer. J Nucl Med 2001, 42:1815-1817.
9. Pascali G., D'Antonio L., Bovone P., Gerundini P., August T. Optimization of automated large-scale production of [18F]fluoroethylcholine for PET prostate cancer imaging. Nucl Med Biol 2009, 36:569-574.
10. Asti M., Farioli D., Iori M., Guidotti C., Versari A., Salvo D. Efficient automated one-step synthesis of 2-[18F]fluoroethylcholine for clinical imaging: optimized reaction conditions and improved quality controls of different synthetic approaches. Nucl Med Biol 2010, 37:309-315.
11. Farsad M., Allegri V., Castellucci P. "PET-CT beyond FDG: a quick guide to image interpretation" 2010, 13-47. Springer, Berlin Heidelberg. S. Fanti, M. Farsad, L. Mansi (Eds.).
12. Watanabe H., Kanematsu M., Kondo H., Kako N., et al. Preoperative detection of prostate cancer: a comparison with 11C-choline PET, 18F-fluorodeoxyglucose PET and MR imaging. J Magn Res Imag 2010, 31:1151-1156.
13. Beheshti M., Imamovic L., Broinger G., Vali R., Waldenberger P., et al. 18F choline PET/CT in the preoperative staging of prostate cancer in patients with intermediate or high risk of extracapsular disease: a prospective study of 130 patients. Radiology 2010, 254:925-933.
14. Uusijärvi H., Nilsson L.E., Bjartell A., Mattsson S. Biokinetics of 18F-choline studied in four prostate cancer patients. Radiat Prot Dosimetry 2010, 139:240-244.
15. Filice A., Asti M., Roncali M., Fraternali A., Casali M., Di Paolo M., et al. Comparison between the physiological distribution of 18F-FMCH and 18F-FECH. Eur J Nucl Med Mol Imaging 2010, 37(S2):S333-S481.
16. Lu S.Y., Watts P., Chin F.T., Hong J., Musachio J.L., Briard E., et al. Syntheses of 11C- and F-labeled carboxylic esters within a hydrodynamically-driven micro-reactor. Lab Chip 2004, 4:523-525.
17. Lee C.C., Sui G.D., Elizarov A., Shu C.Y., Shin J., et al. Multistep synthesis of a radiolabeled imaging probe using integrated microfluidics. Science 2005, 310:1793-1796.
18. Gillies J.M., Prenant C., Chimon G.N., Smethurst G.J., Perrie W., Hamblett I., et al. Microfluidic reactor for the radiosynthesis of PET radiotracers. Appl Radiat Isot 2006, 64:325-332.
19. Steel C.J., O'Brien A.T., Luthra S.K., Brady F.J. Automated PET radiosyntheses using microfluidic devices. Label Compd Radiopharm 2007, 50:308-311.
20. Elizarov A. Microreactors for radiopharmaceutical synthesis. Lab on Chip 2009, 9:1326-1333.
21. Nordberg A. PET imaging of amyloid in Alzheimer's disease. Lancet Neurol 2004, 3:519-527.
22. Zeng F., Mun J., Jarkas N., Stehouwer J.S., Voll R.J., et al. Synthesis, radiosynthesis, and biological evaluation of carbon-11 and fluorine-18 labeled reboxetine analogues: potential positron emission tomography radioligands for in vivo imaging of the norepinephrine transporter. J Med Chem 2009, 52:62-73.
23. Mindt T.L., Müller C., Stuker F., Salazar J.F., Hohn A., et al. A "click chemistry" approach to the efficient synthesis of multiple imaging probes derived from a single precursor. Bioconjugate Chem 2009, 20:1940-1949.
24. Evens N., Muccioli G.G., Houbrechts N., Lambert D.M., Verbruggen A.M., et al. Synthesis and biological evaluation of carbon-11- and fluorine-18-labeled 2-oxoquinoline derivatives for type 2 cannabinoid receptor positron emission tomography imaging. Nucl Med Biol 2009, 36:455-465.
25. Emmons W.D., Ferris A.F. Metathetical reactions of silver salts in solution. II. The synthesis of alkyl sulfonates. J Am Chem Soc 1953, 75(9):2257.
26. Pascali G., Kiesewetter D.O., Salvadori P.A., Eckelman W.C. Use of 1,8-bis-(dimethylamino)-naphthalene/(HF)-F-18 complex as new radiofluorinating agent. J Label Compd Radiopharm 2004, 47:373-383.
27. Zuhayra M., Alfteimi A., Papp L., Lützen U., Lützen A., VonForstner C., et al. Simplified fast and high yielding automated synthesis of [18F]fluoroethylcholine for prostate cancer imaging. Bioorg Med Chem 2008, 16:9121-9126.
28. Kryza D., Tadino V., Filannino M.A., Villeret G., Lemoucheux L. Fully automated [18F]fluorocholine synthesis in the TracerLab MX FDG Coincidence synthesizer. Nucl Med Biol 2008, 35:255-260.
29. Pascali G., Mazzone G., Saccomanni G., Manera C., Salvadori P.A. Microfluidic approach for fast labeling optimization and dose-on-demand implementation. Nucl Med Biol 2010, 37:547-555.
30. Neal T.R., Apana S., Berridge M.S. Improved synthesis of [18F]fluoromethyl tosylate, a convenient reagent for radiofluoromethylations. J Label Compd Radiopharm 2005, 48:557-568.
31. Smith G., Zhao Y., Leyton J., Shan B., Nguyen Q., Perumal M., et al. Radiosynthesis and pre-clinical evaluation of [18F]fluoro-[1,2-2H4]choline. Nucl Med Biol 2011, 38(1):39-51.
32. Chun J.H., Lu S., Lee Y.S., Pike V.W. Fast and high-yield microreactor syntheses of ortho-substituted [18F]fluoroarenes from reactions of [18F]fluoride ion with diaryliodonium salts. J Org Chem 2010, 75:3332-3338.
33. Kwee S.A., DeGrado T.R., Talbot J.N., Gutman F., Coel M.N. Cancer imaging with fluorine-18-labeled choline derivatives. Semin Nucl Med 2007, 37:420-428.
34. Li Z., Vance D.E. Phosphatidylcholine and choline homeostasis. J Lipid Res 2008, 49:1187-1194.
35. Salvadori P.A. Radiopharmaceuticals, drug development and pharmaceutical regulations in Europe. Curr Radioph 2008, 1:7-11.