Abstract
Potential of electrophilic and nucleophilic methods of radiofluorination in the synthesis of fluorine-18-labeled fluorinated amino acid analogs, radiotracers for positron emission tomography (PET), is considered. The synthesis of 6-L-[18F]FDOPA ((S)-2-amino-3-(6-[18F]fluoro-3,4-dihydroxyphenyl)propionic acid) was used as an example to discuss new elaborations in this field directed on both the improvement of already existing methods and the development of fundamentally new approaches to the introduction of a fluorine-18 label into the nonactivated aromatic ring of amino acids using nucleophilic methods.
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M. E. Phelps, J. C. Maziotta, H. R. Schelbert, Positron Emission Tomography and Autoradiography. Principles and Application for the Brain and Heart, Raven Press, New York, 1985, 704.
R. L. Wahl, J. W. Buchanan, Principles and Practice of Positron Emission Tomography, Williams & Wilkins, Lippincott, Philadelphia, 2002, 462.
S. V. Medvedev, T. Yu. Skvortsova, R. N. Krasikova, PET v Rossii: pozitronno-emissionnaya tomografiya v klinike i fiziologii [PET in Russia: Positron-Emission Tomography in Clinic and Physiology], Astrel´-SPb, St.-Petersburg, 2008, 319 pp. (in Russian).
T. Beyer, D. W. Townsend, T. Brun, P. E. Kinahan, M. Charron, R. Roddy, J. Jerin, J. Young, L. Byars, R. Nutt, J. Nucl. Med., 2000, 41, 1369.
Cyclotron Produced Radionuclides: Guidelines for Setting up a Facility, Technical Report Series No. 471, IAEA, Vienna, 2009.
K. A. Wood, P. J. Hoskin, M. L. Saunders, J. Clin. Oncol., 2007, 19, 237.
G. V. Heller, D. Calnon, S. Dorbala, J. Nucl. Cardiol., 2009, 16, 962.
C. M. Lee, L. Farde, Trends Pharmacol. Sci., 2006, 27, 310.
A. K. Buck, K. Herrmann, T. Stargardt, T. Dechow, B. J. Krause, J. Schrey, J. Nucl. Med., 2010, 51, 401.
R. N. Krasikova, Abstr. of the First Russian-Nordic Symposium on Radiochemistry (Moscow, 21-24 October 2013), 99.
G. M. Gallagher, J. S. Fowler, N. I. Gutterson, R. R. MacGregor, C. N. Wan, A. P. Wolf, J. Nucl. Med., 1978, 19, 1154.
O. Warburg, The Metabolism of Tumors, Constabel & Co, London, 1930, 327.
M. Guillaume, A. Luxen, B. Nebeling, M. Argentini, J. C. Clark, V. W. Pike, Appl. Radiat. Isot., 1991, 42, 749.
M. V. Korsakov, Osnovy PET radiokhimii [Principles of PET of Radiochemistry], TEZA, St.-Petersburg, 2002, 180 pp. (in Russian).
S. Eberl, T. Eriksson, O. Svedberg, Appl. Radiat. Isot., 2012, 70, 922.
J. I. Sachinidis, S. Poniger, H. J. Tochon-Danguy, Curr. Radiopharm., 2010, 3, 248.
R. Krasikova, Curr. Org. Chem., 2013, 17, 2097.
G. E. Kodina, R. N. Krasikova, Metody polucheniya radiofarmatsevticheskikh preparatov i radionuklidnykh generatorov dlya yadernoi meditsiny. Uchebnoe posobie dlya vuzov [Methods for Preparation of Radiopharmaceutical Agents and Radionuclide Generators for Nuclear Medicine. Textbook for Higher Education Institutions, ID MEI, Moscow, 2014, 281 pp. (in Russian).
K. Hamacher, H. H. Coenen, G. Stocklin, J. Nucl. Med., 1986, 27, 235.
M.-C. Lasne, C. Perrio, J. Rouden, L. Barré, D. Roeda, F. Dollé, C. Crouzel, Top. Curr. Chem., 2002, 222, 201.
H. H. Coenen, Fluorine-18 Labelling Methods in PET Chemistry, The Driving Force in Molecular Imaging, Springer, Berlin, 2007, 50 p.
L. Cai, S. Lu, V. W. Pike, Eur. J. Org. Chem., 2008, 17, 2853.
M. Attina, F. Cacace, A. P. Wolf, J. Label. Compd. Radiopharm., 1983, 20, 501.
R. Rengan, P. K. Chakraborty, M. R. Kilbourn, J. Label. Compd. Radiopharm., 1993, 33, 563.
G. Angelini, M. Speranza, A. P. Wolf, J. Fluor. Chem., 1985, 27, 177.
C. Lemaire, in PET Studies on Amino Acid Metabolism and Protein Synthesis. Developments in Nuclear Medicine, Vol. 23, Kluwer Publishing, France, 1993, p. 89.
P. L. Jager, W. Vaalburg, J. Pruim, E. G. de Vries, K. J. Langen, D. A. Piers, J. Nucl. Med., 2001, 42, 432.
P. Laverman, O. C. Boerman, F. H. M. Corstens, J. G. W. Oyen, Eur. J. Nucl. Med., 2002, 29, 681.
C. Huang, J. McConathy, Curr. Top. Med. Chem., 2013, 13, 871.
E. S. Garnett, G. Firnau, C. Nahmias, Nature, 1983, 305, 137.
J. R. Barrio, S.-C. Huang, M. E. Phelps, Biochem. Pharmacol., 1997, 54, 341.
N. D. Volkow, J. S. Fowler, G. J. Wang, J. M. Swanson, F. Telang, Arch. Neurol., 2007, 64, 1575.
J. P. Seibyl, W. Chen, D. H. S. Silverman, Sem. Nucl. Med., 2007, 37, 440.
H. Minn, S. Kauhanen, M. Seppanen, P. Nuutila, J. Nucl. Med., 2009, 50, 1915.
M. Pretze, C. Wängler, B. Wängler, in Recent Trends in Pharmaceutical Radiochemistry for Molecular PET Imaging, BioMed Research International, 2014, DOI 10.1155/2014/674063.
R. M. Lambrecht, R. Neirinkhx, A. P. Wolf, Int. J. Appl. Rad. Isot., 1978, 29, 175.
M. Guilliame, A. Luxen, B. Nebeling, Int. J. Radiat. Appl. Instrum. Part A, 1991, 42, 749.
R. J. Nickles, M. E. Daube, T. J. Ruth, Int. J. Appl. Rad. Isot., 1984, 35, 117.
K. P. Koopmans, A. H. Brouwers, M. N. de Hooge, A. N. van der Horst-Schrivers, I. P. Kema, B. H. Wolffenbuttel, E. G. de Vries, P. L. Jager, J. Nucl. Med., 2005, 7, 1240.
G. Firnau, R. Chiracal, E. S. Garnett, J. Nucl. Med., 1984, 25, 1228.
J. R. Barrio, S.-C. Huang, M. E. Phelps, Biochem. Pharmacol., 1997, 54, 34.
R. E. Ehrenkaufer, J. F. Potocki, D. M. Jewett, J. Nucl. Med., 1984, 25, 333.
R. D. Neirincks, R. M. Lambrecht, A. P. Wolf, Int. J. Appl. Rad. Isot., 1978, 29, 323.
R. E. Ehrenkaufer, R. R. MacGregor, Int. J. Appl. Rad. Isot., 1983, 34, 613.
R. Chiracal, G. Firnau, J. G. Schrobilgen, J. McKay, E.S. Gamlett, Int. J. Appl. Rad. Isot., 1984, 35, 401.
F. Oberdorfer, E. Hoffman, W. Maier-Borst, J. Label. Compd. Radiopharm., 1988, 25, 999.
F. Oberdorfer, E. Hoffman, W. Maier-Borst, Appl. Radiat. Isot., 1988, 39, 685.
N. Satyamurthy, G. T. Bida, M. E. Phelps, J. R. Barrio, Appl. Radiat. Isot., 1990, 41, 733.
A. Jordanova, J. Steinbach, B. Johannsen, J. Label. Compd. Radiopharm., 2001, 44, S901.
M. Constantinou, F. I. Aigbirhio, R. G. Smith, C. A. Ramsden, V. W. Pike, J. Am. Chem. Soc., 2001, 123, 1780.
H. Teare, E. G. Robins, E. Arstad, S. K. Luthra, V. Gouverneur, Chem. Commun., 2007, 2330.
H. Teare, E. G. Robins, A. Kirjavainen, S. Forsback, G. Sandford, O. Solin, S. K. Luthra, V. Gouverneur, Angew. Chem., Int. Ed., 2010, 49, 6821.
I. S. R. Stenhagen, A. K. Kirjavainen, S. J. Forsback, C. G. Jorgensen, E. G. Robins, S. K. Luthra, O. Solin, V. Gouverneur, Chem. Commun., 2013, 49, 1386.
M. Diksic, S. Farrokhzad, J. Nucl. Med., 1985, 26(11), 1314.
A. Luxen, M. Perlmutter, G. T. Bida, G. Van Moffaert, J. C. Cook, N. Satyamurthy, M. E. Phelps, J. R. Barrio, Appl. Radiat. Isot., 1990, 41, 275.
M. Namavari, A. Bishop, N. Satyamurthy, G. Bida, J. R. Barrio, Appl. Radiat. Isot., 1992, 43(8), 989.
C.-H. K. Kao, W.-L. Hsu, H.-L. Xie, M.-C. Lin, W.-C. Lan, H.-Y. Chao, Ann. Nucl. Med., 2011, 25, 309.
E. F. J. de Vries, G. Luurstema, M. Brussermann, P. H. Elsinga, W. Vaalburg, Appl. Radiat. Isot., 1999, 51, 389.
M. Diksic, S. Farrokhzad, J. Nucl. Med., 1985, 26 (11), 1314.
M. J. Adam, S. Jivan, Appl. Radiat. Isot., 1988, 39, 1203.
T. Chaly, J. R. Dahl, R. Matacchieri, D. Bandyopadhyay, A. Belakhlef, V. Dhawan, S. Takikawa, W. Robeson, D. Margouleff, D. Eidelberg, Appl. Radiat. Isot., 1993, 44, 869.
C. W. Chang, H. E. Wang, H. M. Lin, C. S. Chtsai, J. B. Chen, R. S. Liu, Nucl. Med. Commun., 2000, 21, 799.
M. Namavari, A. Bishop, N. Satyamurthy, G. Bida, J. R. Barrio, Appl. Radiat. Isot., 1992, 43, 989.
F. Dolle, S. Demphel, F. Hinnen, D. Fournier, F. Vaufrey, C. Crouzel, J. Label. Compd. Radiopharm., 1998, 41, 105.
F. Fuchtner, J. Zesslin, P. Mading, F. Wust, Nuclearmedizin, 2008, 47, 62.
J. Bergman, O. Solin, Nucl. Med. Biol., 1997, 24, 677.
S. Forsback, O. Eskola, M. Haaparanta, J. Bergman, O. Solin, Radiochim. Acta, 2008, 96, 845.
A. S. Kamlet, C. N. Neumann, E. Lee, S. M. Carlin, C. K. Moseley, N. Stephenson, J. M. Hooker, T. Ritter, PLOS One, 2013, 8(3), e59187.
E. Lee, J. M. Hooker, T. Ritter, J. Am. Chem. Soc., 2012, 134, 17456.
D. J. Schlyer, M. A. V. Bastos, D. Alexoff, A. P. Wolf, Appl. Radiat. Isot., 1990, 41, 531.
N. A. Gomzina, D. A. Vasil´ev, R. N. Krasikova, Radiochemistry (Engl. Transl.), 2002, 44, 403 [Radiokhim., 2002, 44, 366].
D. Block, B. Klatte, A. Knochel, J. Label. Compd. Radiopharm., 1986, 23, 467.
K. Hamacher, H. H. Coenen, G. Stocklin, J. Nucl. Med., 1986, 27, 235.
M. S. Haka, M. R. Kilbourn, G. L. Watkins, S. A. Toorongian, J. Label. Compd. Radiopharm., 1989, 27, 823.
H. Sun, S. G. DiMagno, J. Fluorine Chem., 2007, 128, 806.
H. H. Coenen, J. Ermert, Curr. Radiopharm., 2010, 3, 163.
V. V. Zaitsev, O. S. Fedorova, I. K. Mosevich, O. F. Kuznetsova, N. A. Gomzina, R. N. Krasikova, Radiochemistry (Engl. Transl.), 2002, 44, 394 [Radiokhim., 2002, 44, 358].
Y.-S. Ding, C.-Y. Shiue, J. S. Fowler, A. P. Wolf, A. Plenevaux, J. Fluorine Chem., 1990, 48, 189.
C. Lemaire, M. Guillaume, R. Cantineau, A. Plenevaux, Appl. Radiat. Isot., 1991, 42, 629.
A. Najafi, J. Nucl. Med. Biol., 1995, 22, 395.
R. Iwata, C. Pascali, A. Bogni, G. Horvath, Z. Kovacs, K. Yanai, T. Ido, Appl. Radiat. Isot., 2000, 52, 87.
R. N. Krasikova, O. F. Kuznetsova, O. S. Fedorova, I. K. Mosevich, V. I. Maleev, Yu. N. Belokon´,T. F. Savel´eva, A. S. Sagiyan, S. A. Dadayan, A. A. Petrosyan, Radiochemistry (Engl. Transl.), 2007, 49, 449 [Radiokhim., 2007, 49, 512].
C. Lemaire, S. Gillet, S. Guillouet, A. Plenevaux, J. Aerts, A. Luxen, Eur. J. Org. Chem., 2004, 2899.
L. C. Libert, X. Franci, A. R. Plenevaux, J. Nucl. Med., 2013, 54, 1154.
C. Lemaire, P. Damhaut, A. Plenevaux, D. Comar, J. Nucl. Med., 1994, 35, 1996.
L. Zhang, G. Tang, D. Yin, X. Tang, Y. Wang, Appl. Radiat. Isot., 2002, 57, 145.
B. Shen, W. Ehrlichmann, M. Uebele, H.-J. Machulla, G. Reischl, Appl. Radiat. Isot., 2009, 67, 1650.
S. Kaneko, K. Ishiwata, K. Hatano, H. Omura, K. Ito, M. Senda, Appl. Radiat Isot., 1999, 50, 1025.
D. Morrison, G. Mosher, Assymmetric Organic Reactions, Prentice Hall, Englewood Cliffs, NJ, 1971, 465.
K. A. Kochetkov, V. M. Belikov, Russ. Chem. Rev., 1987, 56, 1045.
V. I. Maleev, Dr. of Sci. Thesis (Chem.), A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, 2006, 331 pp. (in Russian).
C. Lemaire, A. Plenevaux, R. Cantineau, Appl. Radiat. Isot., 1993, 44, 737.
C. Lemaire, A. Plenevaux, D. Coman, J. Nucl. Med., 1992, 19, 591.
D. Seebach, M. Boes, R. Naef, W. B. Schweizer., J. Am. Chem. Soc., 1983, 105, 5390.
Y. N. Belokon, V. I. Bakhmutov, N. I. Chernoglasova, J. Chem. Soc., Perkin. Trans., 1988, 1, 305.
Y. N. Belokon, Pure and Appl. Chem., 1992, 64, 1917.
K. Fasth, B. Langstrom, Acta Chem. Scand., 1990, 44, 720.
I. K. Mosevich, O. F. Kuznetsova, M. V. Korsakov, Radiochemistry (Engl. Transl.), 1996, 38, 511 [Radiokhim., 1996, 38, 542].
R. N. Krasikova, O. S. Fedorova, I. K. Mosevich, O. F. Kuznetsova, M. V. Korsakov, S. M. Ametamey, P. A. Schubiger, J. Label. Compd. Radiopharm., 1999, 42, 102.
Yu. N. Belokon´, V. I. Maleev, A. A. Petrosyan, T. F. Savel´eva, N. S. Ikonnikov, A. S. Peregudov, V. N. Khrustalev, A. S. Sagiyan, Russ. Chem. Bull. (Int. Ed.), 2002, 51, 1593 [Izv. Akad. Nauk, Ser. Khim., 2002, 1464].
U -H. Dolling, P. Davis, E. J. J. Grabowski, J. Am. Chem. Soc., 1984, 106, 446.
E. J. Corey, M. C. Noe, F. Xu, Tetrahedron Lett., 1998, 39, 5347.
Y. N. Belokon, K. A. Kochetkov, N. S. Ikonnikov, O. V. Larionov, S. Harutyunyan, M. North, S. Vyskocil, H. B. Kagan, Angew. Chem., Int. Ed. Engl., 2001, 40, 1948.
R. N. Krasikova, V. V. Zaitsev, S. M. Ametamey, O. F. Kuznetsova, O. S. Fedorova, I. K. Mosevich, Yu. N. Belokon, Š. Vyskoil, S. V. Shatik, M. Nader, P. A. Schubiger, J. Nucl. Med. Biol., 2004, 31, 597.
T. Tierling, K. Hamacher, H. H. Coenen, J. Label. Compd., 2001, 44, suppl.146.
F. M. Wagner, J. Ermert, H. H. Coenen, J. Nucl. Med., 2009, 50, 1724.
Patent EP 2 746 250 A1.
M. S. Yusubov, D. Yu. Svitich, M. S. Larkina, V. V. Zhdankin, ARKIVOC, 2013, 364.
M. R. Zhang, K. Kumata, K. Suzuki, Tetrahedron Lett., 2007, 48, 8632.
J.-H. Chun, S. Telu, S. Lu, V. W. Pike, Org. Biomolec. Chem., 2013, 11, 5094.
N. Ichiishi, A. F. Brooks, J. J. Topczewski, M. E. Rodnick, M. S. Sanford, P. J. H. Scott, J. Am. Chem. Soc., 2014, 16, 3224.
M. Tredwell, S. M. Preshlock, N. J. Taylor, S. Gruber, M. Huiban, J. Passchier, J. Mercier, Ch. Genicot, V. Gouverneur, Angew. Chem., Int. Ed., 2014, 53, 1.
P. Lam, Ch. Clark, S. Saubern, J. Adams, M. Winters, D. Chan, A. Combs, Tetrahedron Lett., 1998, 39, 2941.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1518–1535, July, 2015.
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Orlovskaya, V.V., Fedorova, O.S. & Krasikova, R.N. Methods for the synthesis of fluorine-18-labeled aromatic amino acids, radiotracers for positron emission tomography (PET). Russ Chem Bull 64, 1518–1535 (2015). https://doi.org/10.1007/s11172-015-1037-9
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DOI: https://doi.org/10.1007/s11172-015-1037-9