PET radiochemistry automation: State of the art and Future trends in 18F-nucleophilic fluorination

Current Organic Chemistry

Volumn 17, Issue 19, 2013, Pages 2097-2107

  Krasikova, Raisa ^a,b  

^a Institute of the Human Brain Russian Academy of Sciences   (Russian Federation)

^b ST PETERSBURG STATE UNIVERSITY   (Russian Federation)

Author keywords

Automation; F 18; Nucleophilic fluorination; PET radiopharmaceuticals; Synthesis modules

Indexed keywords

FLUORINATION; HALOGENATION; RADIOACTIVE TRACERS;

'CURRENT; AUTOMATED SYNTHESIS; AUTOMATION SOLUTIONS; F-18; FUTURE TRENDS; GENERAL ASPECTS; NUCLEOPHILIC FLUORINATION; PET RADIOPHARMACEUTICAL; STATE OF THE ART; SYNTHESIS MODULE;

AUTOMATION;

EID: 84893187224     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/13852728113179990102     Document Type: Review

References (47)

1. Krug, B.; Van Zanten, A.; Pirson A.S.; Crott, B.; Vander Borght, T. Activity-based costing evaluation of [(18)F]-fludeoxyglucose production. Eur. J. Nucl. Med. Mol. Imaging., 2008, 35, 80-8.
2. Padgett, H.C.; Schmidt, D.G.; Luxen, A.; Bida, G.T.; Satyamurthy, N.; Barrio, J.R. Computer-controlled radiochemical synthesis: a chemistry process control unit for the automated production of radiopharmaceuticals. Appl. Radiat. Isot., 1989, 40, 433-445.
3. Alexoff, D.L. Automation for the synthesis and application of PET radio-pharmaceuticals. In: Handbook of Radiopharmaceuticals. Radiochemistry and Application; Welch, M.J.; Redvanly C.S.; Eds.; Wiley, 2003; pp 283-305.
4. Satyamurthy, N.; Phelps, M.E.; Barrio J.R Electronic generators for the production of positron emitter labelled radiopharmaceuticals: Where would PET be without them? Clin. Posit. Imag., 1999, 2, 233-253.
5. Krasikova, R.N. Synthesis Modules and Automation in F-18 labeling. In: PET chemistry: the driving force in molecular imaging. Schubiger, P.A.; Lehmann, L.; Fribe, M., Eds.; Ernst Schering Research Foundation Workshop 62, Springer-Verlag Berlin, 2007, pp. 290-316.
6. Sachinidis, J.I.; Poniger, S.; Tochon-Danguy, H.J. Automation for Optimised Production of Fluorine-18-Labelled Radiopharmaceuticals. Cur. Radiopharm., 2010, 3, 248-253.
7. 18F]fluoride. Int. J. Rad. Appl. Instrum. A., 1988, 39, 699-703.
8. Krasikova, R. Robotic synthesis of radiopharmaceuticals for positron emission tomography. Radiochemistry, 1998, 40, 364-372.
9. 18F]Fluoride Ion. Eur. J. Org. Chem., 2008, 2853-2873.
10. 18F]fluoro-2-deoxy-D-glucose using aminopolyether supported nucleophilic substitution. J. Nucl. Med., 1986, 27, 235-238.
11. 14C-2-deoxy-2-fluoro-d-glucose. J. Label. Compd. Radiopharm., 1977, 14, 175-183.
12. Fuchetner, F.; Steinbach, J.; Mading, P.; Johannsen, B. Basic hydrolysis of 2[18F]Fluoro-1,3,4,6-tetra-O-acetyl-d-glucose in the preparation of 2[18F]Fluoro-2-deoxy-D-glucose. Appl. Rad. Isot., 1996, 47, 61-66.
13. Schlyer, D.J.; Bastos, M.A.V.; Alexoff, D.; Wolf, A.P. Separation of [18F]fluoride from [18O]water using anion exchange resin. Appl. Radiat. Isot., 1990, 41, 531-533.
14. Gomzina, N.A.; Zaitsev, V.V.; Krasikova, R.N. Optimization of nucleophilic fluorination step in the synthesis of various compounds labelled with fluorine-18 for their use as PET radiotracers. J. Label. Compds. Radiopharm., 2001, 44, Suppl 1, S895-897.
15. 18F]fluoro-2-deoxy-D-glucose based on alkali hydrolysis. Radiochemistry, 2002, 44, 366-372.
16. 18F]flumazenil and its evaluation in cynomolgus monkey by positron emission tomography. Nucl. Med. Biol. 2005, 32,109-116.
17. 18Ffluorinated alpha-amino acids under phase-transfer conditions using (S)NOBIN. Nucl. Med. Biol., 2004, 31, 597-603.
18. 18F-fluorination without azeotropic drying. Nuklearmedizin, 2012, 51, 1-8.
19. 18F-fluoride from an anion exchange resin in an organic medium suitable for radiolabelling without any evaporation step by the use of strong organic bases. 2009, WO2009003251 (A1).
20. 18F]Fluoride for the Labeling of Radiopharmaceuticals. Angew. Chem. Int. Ed., 2010, 49, 3161-3164.
21. Mercier, F.; Paris, J.; Kaisin, G., Thonon, D.; Flagothier, J.; Teller, N.; Lemaire, C.; Luxen, A. General Method for Labeling siRNA by Click Chemistry with Fluorine-18 for the Purpose of PET Imaging. Bioconjugate Chem., 2011, 22, 108-114.
22. 18F]Fluoride Using Polymer Cartridge. Bull. Korean Chem. Soc., 2011, 32, 71-76.
23. 18O-water and subsequent no carrier added nucleophilic fluorination. Appl. Radiat. Isot., 2002, 56, 519-523.
24. 18F]fluoro-D-glucose by direct nucleophilic exchange on a quaternary 4-aminopyridinium resin. Int. J. Rad. Appl. Instrum. B., 1990, 17, 273-279.
25. 18F-FDG with FDG MicroLab system: basic studies for clinical application. Jpn. J. Nucl. Med., 1999, 36, 873-878.
26. 18F]-2-fluoro2-deoxy-D-glucose from resin-bound perfluoroalkylsulfonates. Org. Biomol. Chem., 2009, 7, 564-575.
27. 18F]FDG using an alkaline hydrolysis on solid support. J. Label. Compds. Radiopharm., 1999, 42:515-516.
28. 18F]FDG synthesis by alkaline hydrolysis on a low polarity solid phase support. J. Label. Compds. Radiopharm., 2002, 45, 435-447.
29. 18F]fluoroacetate a simple and fast method using a commercial synthesizer. Nucl. Med. Biol., 2006, 33, 153-158.
30. Lemaire, C.; Plenevaux, A.; Aerts, G.; Del Fiore, G.; Brihaye, C.; Le Bars, D.; Comar, D.; Luxen, A. Solid phase extraction an alternative to the use of rotary evaporators for solvent removal in the rapid formulation of PET radiopharmaceuticals. J. Label. Compds. Radiopharm. 1999, 42, 63-75.
31. 18F]fluorocholine. Appl. Radiat. Isot., 2002, 57, 347-52.
32. Pascali, G.; D'Antonio, L.; Bovone, P.; Gerundini, P.; August, T. Optimization of automated large-scale production of [(18)F]fluoroethylcholine for PET prostate cancer imaging. Nucl. Med. Biol., 2009, 36, 569-74.
33. Schmaljohann, J.; Schirrmacher, E.; Wängler, B.; Wängler, C.; Schirrmacher, R.; Guhlke, S. Fully automated SPE-based synthesis and purification of 2[18F]fluoroethyl-choline for human use. Nucl. Med. Biol., 2011, 38, 165-70.
34. Mueller, D.; Klette, I.; Kalb, F.; Baum, R.P. Synthesis of O-(2[18F]fluoroethyl)-L-tyrosine based on a cartridge purification method. Nucl. Med. Biol., 2011, 38, 653-8.
35. Pascali, C.; Bogni, A.; Fugazza, L.; Cucchi, C.; Crispu, O.; Laera, L.; Iwata, R.; Maiocchi, G.; Crippa, F.; Bombardieri, E. Simple preparation and purification of ethanol-free solutions of 3'-deoxy-3'-[(18)F]fluorothymidine by means of disposable solid-phase extraction cartridges. Nucl Med Biol., 2012, 39, 540-550.
36. 18F]FMISO based upon a modified Explora FDG4 module. J. Radioanal. Nucl. Chem. 2009, 280, 149-155.
37. Mori, T.; Kasamatsu, S.; Mosdzianowski, C.; Welch, M.J.; Yonekura, Y.; Fujibayashi,Y.; Automatic synthesis of 16 alpha-[(18)F]fluoro-17betaestradiol using a cassette-type [(18)F]fluorodeoxyglucose synthesizer. Nucl. Med. Biol., 2006, 33, 281-286.
38. 18F]fluoroestradiol using a conventional [18F]FDG module with a disposable cassette system. Appl. Radiat. Isot., 2007, 65, 676-681.
39. Mourtada, F.; Sims-Mourtada, J.; Azhdarinia, A.; Yang, D.J. Regulatory Requirements for PET Radiopharmaceuticals Production: Is Automation an Answer? Curr. Med. Imag. Revs., 2008, 4, 28-33.
40. Couturier, O.; Luxen, A.; Chatal, J.F.; Vuillez, J.P.; Rigo, P.; Hustinx, R. Fluorinated tracers for imaging cancer with positron emission tomography. Eur. J. Nucl. Med. Molec. Imag., 2004, 31, 1182-1206.
41. 18F]FDG for use in oncology and neurosciences. Nucl. Med. Biol., 2010, 37, 727-740.
42. Någren, K.; Halldin, C.; Rinne, J.O. Radiopharmaceuticals for positron emission tomography investigations of Alzheimer's disease. Eur. J. Nucl. Med. Mol. Imag., 2010, 37, 1575-1593.
43. 18F]labelled radiopharmaceuticals using a Tracerlab FXFN. J. Label. Compds. Radiopharm., 2011, 54, 292-307.
44. 18F]SFB) with RGD Peptide Using a GE FASTlab™ Synthesizer. Mol. Imag. Biol., 2011, 13, 1088-1095.
45. 18F]fluorobenzoate on an IBA Synthera module. J. Label. Compd. Radiopharm., 2011, 54, 671-673.
46. 18F]fluorocholine using a multipurpose chemistry module. J. Label. Compd. Radiopharm., 2009, 52, S267.
47. 18F]gefitinib on a modular system. Appl. Radiat. Isot., 2012, 70, 205-209.