No carrier added synthesis of O-(2′-[18F]fluoroethyl)-l-tyrosine via a novel type of chiral enantiomerically pure precursor, NiII complex of a (S)-tyrosine Schiff base

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 9, 2008, Pages 4994-5003

  Krasikova, Raisa N ^a   Kuznetsova, Olga F ^a   Fedorova, Olga S ^a   Maleev, Victor I ^b   Saveleva, Tatyana F ^b   Belokon, Yuri N ^b  

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

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

Asymmetric synthesis; Fluorine 18; Labeling precursor; O (2 18F fluoroethyl) l tyrosine

Indexed keywords

[N 2 (N' BENZYLPROLYL)AMINO]BENZOPHENONE; BENZOPHENONE DERIVATIVE; NITROGEN; RADIOPHARMACEUTICAL AGENT; SCHIFF BASE; TETRABUTYLAMMONIUM; TRACER; TYROSINE;

ALLOGRAFT; ANALYTIC METHOD; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CHIRALITY; CONTROLLED STUDY; ENANTIOMER; FLUORINATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MALE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; RACEMIC MIXTURE; RADIOCHEMISTRY; RAT;

ANIMALS; BENZOPHENONES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DISEASE MODELS, ANIMAL; GLIOMA; MOLECULAR CONFORMATION; NICKEL; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; RATS; RATS, WISTAR; SCHIFF BASES; SKIN NEOPLASMS; STEREOISOMERISM; TYROSINE;

RATTUS; RATTUS NORVEGICUS;

EID: 43049181572     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.03.040     Document Type: Article

References (36)

1. Chen W. J. Nucl. Med. 48 (2007) 1468
2. Reske S.N., and Kotzerke J. Eur. J. Nucl. Med. 28 (2001) 1707
3. Gallagher B.M., Fowler J.S., Gutterson N.I., MacGregor R.R., Wan C.N., and Wolf A.P. J. Nucl. Med. 19 (1978) 1154
4. Cook G.J.R., Wegner E.A., and Foegelman I. Semin. Nucl. Med. 34 (2004) 122
5. Strauss L.G. Eur. J. Nucl. Med. 23 (1996) 1409
6. Jager P.L., Vaalburg W., Pruim J., de Vries E.G., Langen K.J., and Piers D.A. J. Nucl. Med. 42 (2001) 432
7. Laverman P., Boerman O.C., Corstens F.H.M., and Oyen J.G.W. Eur. J. Nucl. Med. 29 (2002) 681
8. Couturier O., Luxen A., Chatal J.-F., Vuillez J.-P., Rigo P., and Hustinx R. Eur. J. Nucl. Mol. Imaging 31 (2004) 1182
9. Lemaire C., Damhaut P., Plenevaux A., and Comar D. J. Nucl. Med. 35 (1994) 1996
10. Lemaire C., Gillet S., Guillouet S., Plenevaux A., Aerts J., and Luxen A. Eur. J. Org. Chem. (2004) 2899
11. Krasikova R.N., Zaitsev V.V., Ametamey S.M., Kuznetsova O.F., Fedorova O.S., Mosevich I.K., Belokon Yu.N., Vyskočil S., Shatik S.V., Nader M., and Schubiger P.A. Nucl. Med. Biol. 31 (2004) 597
12. Wester H., Herz M., Weber W., Heiss P., Senekovitsch-Schmidtke R., Schwaiger M., and Stocklin G. J. Nucl. Med. 40 (1999) 205
13. Tang G.H., Wang M.F., Tang X.L., Luo L., and Gan M.Q. Nucl. Med. Biol. 30 (2003) 733
14. Iwata R., Furumoto S., Pascali C., Bogni A., and Ishiwata K. J. Label. Compd. Radiopharm. 46 (2003) 555
15. Weber W.A., Wester H.J., Grosu A.L., Herz M., Dzewas B., Feldmann H.J., Molls M., Stocklin G., and Schwaiger M. Eur. J. Nucl. Med. 27 (2000) 542
16. Heiss P., Mayer S., Herz M., Wester H.J., Schwaiger M., and Senekovitsch-Schmidtke R. J. Nucl. Med. 40 (1999) 1367
17. Langen K.J., Hamacher K., Weckesser M., Floeth F., Stoffels G., Bauer D., Coenen H.H., and Pauleit D. Nucl. Med. Biol. 33 (2006) 287
18. Popperl G., Gotz C., Rachinger W., Gildehaus F.J., Tonn J.C., and Tatsch K. Eur. J. Nucl. Med. Mol. Imaging 31 (2004) 1464
19. Weckesser M., Langen K.J., Rickert C.H., Kloska S., Straeter R., Hamacher K., Kurlemann G., Wassmann H., Coenen H.H., and Schober O. Eur. J. Nucl. Med. Mol. Imaging 32 (2005) 422
20. Rachinger W., Goetz C., Popperl G., Gildehaus F.J., Kreth F.W., Holtmannspotter M., Herms J., Koch W., Tatsch K., and Tonn J.C. Neurosurgery 57 (2005) 505
21. Floeth F.W., Pauleit D., Sabel M., Stoffels G., Reifenberger G., Riemenschneider M.J., Jansen P., Coenen H.H., Steiger H.J., and Langen K.J. J. Nucl. Med. 48 (2007) 519
22. Pauleit D., Stoffels G., Schaden W., Hamacher K., Bauer D., Tellmann L., Herzog H., Broer S., Coenen H.H., and Langen K.J. J. Nucl. Med. 46 (2005) 411
23. Rau F.C., Weber W.A., Wester H.J., Herz M., Becker I., Kruger A., Schwaiger M., and Senekowitsch-Schmidtke R. Eur. J. Nucl. Med. Mol. Imaging 29 (2002) 1039
24. Kaim A.H., Weber B., Kurrer M.O., Westera G., Schweitzer A., Gottschalk J., von Schulthess G.K., and Buck A. Eur. J. Nucl. Med. Mol. Imaging 29 (2002) 648
25. Pauleit D., Zimmermann A., Stoffels G., Bauer D., Risse J., Fluss M.O., Hamacher K., Coenen H.H., and Langen K.J. J. Nucl. Med. 47 (2006) 256
26. Tsukada H., Sato K., Fukumoto D., and Kakiuchi T. Eur. J. Nucl. Med. Mol. Imaging 33 (2006) 1017
27. Hamacher K., and Coenen H.H. Appl. Radiat. Isot. 57 (2002) 853
28. Hamacher K., Blessing G., and Nebeling B. App. Radiat. Isot. 41 (1990) 49
29. Wang H.-E., Wu S.-Y., Chang C.-W., Liu R.-S., Hwang L.-C., Lee T.-W., Chen J.-C., and Hwang J.-J. Nucl. Med. Biol. 32 (2005) 367
30. Belokon Yu.N. Pure Appl. Chem. 64 (1992) 1917
31. Belokon Yu.N., Tararov V.I., Maleev V.I., Saveleva T.F., and Ryzhov M.G. Tetrahedron: Asymm. (1998) 4249
32. Krasikova R.N., Fedorova O.S., Mosevich I.K., Kuznetsova O.F., Korsakov M.V., Ametamey S.M., and Schubiger P.A. J. Label. Compd. Radiopharm. 42 1 (1999) S102
33. Krasikova R.N., Kuznetsova O.F., Fedorova O.S., Mosevich I.K., Maleev V.I., Belokon Yu.N., Saveleva T.F., Sagyan A.S., Dadayan S.A., and Petrosjan A.A. Radiochemistry 49 (2007) 512
34. Kuznetsova, O. F.; Krasikova, R. N.; Fedorova, O. S.; Maleev, V. I.; Saveleva, T. F.; Pripadchev, D. A.; Babayan, E. P.; Belokon, Yu. N. Quart. J. Nucl. Med. Mol. Imag., 2006, 50, 42.
35. Yamada S., Hongo C., Yoshioka R., and Chibata I. J. Org. Chem. 48 (1983) 843
36. Krasikova R.N. Radiochemistry 40 4 (1998) 364