History of the first synthesis of 2-deoxy-2-fluoro-D-glucose the unlabeled forerunner of 2-deoxy-2-[18F]fluoro-D-glucose

Molecular Imaging and Biology

Volumn 4, Issue 5, 2002, Pages 352-354

  Pacák, Josef ^a   Černý, Miloslav ^a  

^a CHARLES UNIVERSITY   (Czech Republic)

Author keywords

2 deoxy 2 fluoro D glucose; 19FDG; FDG PET; Positron emission tomography

Indexed keywords

ANTINEOPLASTIC AGENT; FLUORODEOXYGLUCOSE; FLUORODEOXYGLUCOSE F 18; GLUCOSE; HEXOKINASE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL PROLIFERATION; CHEMICAL REACTION; DRUG MARKETING; DRUG RESEARCH; DRUG SYNTHESIS; GLUCOSE METABOLISM; GLYCOLYSIS; HYDROGEN BOND; INTRACELLULAR TRANSPORT; MITOSIS INHIBITION; NUCLEAR MAGNETIC RESONANCE; PHOSPHORYLATION; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL;

EID: 0036765213     PISSN: 15361632     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1536-1632(02)00083-5     Document Type: Article

References (28)

1. Nutt, R. The history of positron emission tomography. Mol. Imag. Biol. 4:11-26; 2002.
2. Phelps, M.E. Positron emission tomography provides molecular imaging of biological processes. Proc. Natl. Acad. Sci. U. S. A. 97:9226-9233; 2000.
3. Alavi, A.; Reivich, M. The conception of FDG-PET imaging. Semin. Nucl. Med. 32:2-5; 2002.
4. 14C-2-deoxy-2-fluoro-D-glucose. J. Labelled Compd. Radiopharm. 14:175-183; 1978.
5. 18FDG. Semin. Nucl. Med. 32:6-12; 2002.
6. Beuthien-Baumann, B.; Hamacher, K.; Oberdorfer, F.; Steinbach, J. Preparation of fluorine-18 labelled sugars and derivatives and their application as tracer for positron-emission-tomography. Carbohydr. Res. 327:107-118; 2000.
7. Stöcklin, G. Fluorine-18 compounds. In: Wagner Jr., H.N., Szabo, Z., Buchanan, J.W., eds. Principles of nuclear medicine. Philadelphia: W.B. Saunders Co.; 1995: 178-194.
8. Penglis, A.A.E. Fluorinated carbohydrates. Adv. Carbohydr. Chem. Biochem. 38:195-285;1981.
9. Tsuchiya, T. Chemistry and developments of fluorinated carbohydrates. Adv. Carbohydr. Chem. Biochem. 48:91-277; 1990.
10. Helferich, B.; Gnüchtel, A. Glukose-6-fluorhydrin und einige seiner Derivate. Berichte 74:1035-1039; 1941.
11. Taylor, N.F.; Kent, P.W. Fluorocarbohydrates. Part 1. The synthesis of 6-deoxy-6-fluoro-α-D-galactose and 5-deoxy-5-fluoro-β-D-ribose. J. Chem. Soc. 872-875;1958.
12. Černy, M.; Staněk Jr., J. 1,6-Anhydro derivatives of aldohexoses. Adv. Carbohydr. Chem. Biochem. 34:23-177; 1977.
13. Pacák, J.; Halásková, J.; Štěpán, V.; Černý, M. Synthesis of 1,6-dideoxy-1,6-difluoro-D-fructose. Coll. Czech. Chem. Commun. 37: 3646-3651; 1972.
14. Pacák, J.; Podešva, J.; Černý, M. 2,4-Dideoxy-2,4-difluoro-D-glucose. Chem. & Ind. (London) 1970: 929.
15. Buděšínsky, M.; Černý, M.; Doležalová, J.; Kulhánek, M.; Pacák, J.; Tadra, M. 4-Deoxy-4-fluoro-D-fructose: preparation and structure. Coll. Czech. Chem. Commun. 49:267-274;1984.
16. Černý, M.; Doležalová, J.; Mácová,J.; Pacák, J.;Trnka, T.; Buděšínsky, M. Preparation of 3-deoxy-3-fluoro-D-mannose and corresponding hexitol. Coll. Czech. Chem. Commun. 48:2693-2700;1983.
17. Kulhánek, M.; Tadra, M.; Pacák, J.; Trejbalová, H.; Černý, M. 5-Deoxy-5-fluoro-L-sorbose. Originating from 2-deoxy-2-fluoro-D-glucitol by fermentation with Acetomonas oxydans. Folia Microbiol. (Praha).22:295-297;1977.
18. Pacḱ, J.; Drašar, P.; Štropová, D.; Černý, M.; Buděšínský, M. Syntheses with anhydro sugars XVIII. Aminodideoxy-fluorine derivatives of D-glucose. Coll. Czech. Chem. Commun. 38:3936-3939; 1973.
19. Delbeke, D. Oncological applications of FDG-PET imaging: brain tumors, colorectal cancer, lymphoma, and melanoma. J. Nucl. Med. 40: 591-603; 1999.
20. Pacák, J.; Točík, Z.; Černý, M. Synthesis of 2-deoxy-2-fluoro-D-glucose. Chem. Commun. 1969:77.
21. Pacák, J.; Podešva, J.; Točík, Z.; Černý, M. Syntheses with anhydro sugars XI. Preparation of 2-deoxy-2-fluoro-D-glucose and 2,4-dideoxy-2,4-difluoro-D-glucose. Coll. Czech. Chem. Commun. 37:2589-2599; 1972.
22. Adamson, J.; Foster, A.B.; Hall, L.D.; Hesse, R.H. 2-Deoxy-2-fluoro-D-glucose. Chem. Commun. 309-310;1969.
23. Bessel, E.M.; Courtenay, D.V.; Foster, A.B.; et al. Some in vivo and in vitro antitumor effects of the deoxyfluoro-D-glucopyranoses. Eur. J. Cancer. 9:463-470; 1973.
24. Berkowitz, B.A.; Ackerman, J.J.H. Proton decoupled fluorine nuclear magnetic resonance spectroscopy in situ. Biophys.J. 151:681-685; 1987.
25. Nakada, T.; Kwee, I.L.; Griffey, B.V.; Griffey, R.H. F-19 2-FDG NMR imaging of the brain in rat. Magn. Reson. Imag. 6:633-635;1988.
26. Kanazawa, Y.; Yamane, H.; Shinohara, S.; et al. 2-Deoxy-2-fluoro-D-glucose as functional probe for NMR: The unique metabolism beyond its 6-phosphate. J. Neurochem. 66:2113-2120; 1996.
27. 19F magnetic resonance spectroscopy in vivo predict response of murine RIF-1 tumors. Cancer Res. 60:2122-2127; 2000.
28. Wiebe, L.I. FDG metabolism: quaecumque sunt vera.... J. Nucl. Med. 42:1679-1681; 2001.