Abstract
The use of radiotracers labeled with the positron-emitting radionuclides carbon-11, nitrogen-13, oxygen-15 and fluorine-18 for studying alterations of physiologic and chemical processes that underlie the onset and progression of brain disorders in conjunction with the medical imaging technique positron emission tomography (PET) has been well documented1,2. The hallmark of PET is that it permits the use of positron emitting isotopes of the elements carbon, nitrogen, oxygen and fluorine (a hydrogen or hydroxyl substitute) that are the building blocks of the biochemicals that regulate and sustain biologic processes. The role positron labeled radiotracers has played in basic research and diagnostic nuclear medicine has experienced a rapid growth over the past decade due primarily to the development of a new generation of medical cyclotrons.3–5 These machines are computer-controlled, compact, self-shielded, moderate energy (11 to 18 MeV) accelerators designed to support either a University based innovative research or a clinical diagnostic program located at moderate sized (600–1000 bed) medical centers. These single or dual particle, negative or positive ion, isochronous accelerators are capable of producing nitrogen-13, fluorine-18, carbon-11 and oxygen-15 in sufficient quantities, 0.2 to 2.0 Ci (Table 1), for the labeling of radiotracers by currently available synthetic methods.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
M.E. Phelps, J.C. Mazziotta, and S.C. Huang, Study of cerebral function with positron computed tomography, J. Cereb. Blood Flow Metab. 2:113–162 (1982).
M.E. Phelps and J.C. Maziotta, Positron emission tomography brain function and biochemistry, Science 228:799–809 (1985).
A.P. Wolf and W.B. Jones, Cyclotrons for biomedical radioisotope production, Radiochim. Acta. 34:1–7 (1983).
J.R. Barrio, G. Bida, N. Satyamuithy and et al, A mini cyclotron based technology for the production of positron-emitting labeled radiopharmaceuticals, in: “The Metabolism of the Human Brain Studied with Positron Emission Tomography,” Greitz, et al, eds., Raven Press, New York, pp 113–121 (1986).
H.G. Jacobson, Cyclotrons and radiopharmaceuticals in positron emission tomography. Council on scientific affairs. Report of the positron emission tomography panel, JAMA 259:1854–1860 (1988).
M.E. Phelps, S.C. Huang, E.J. Hoffman, C. Selin,and D.E. Kuhl, Tomographic measurement of local cerebral glucose metabolic rate in humans with (F-18) 2-fluoro-2-deoxyglucose: validation of the method. Ann. Neurol. 6:371–388 (1979).
M. Reivich, A. Alavi, A.P. Wolf, J.S. Fowler, J. Russel, C. Arnett, C.Y. Shiue, H. Atkins, A. Anand, R. Dann, and J.H. Greenberg, Glucose metabolic rate kinetic model parameter determination in humans: the lumped constants and rate constants for [18F]fluorodeoxyglucose and [11C]deoxy glucose, J. Cereb. Blood Flow Metab. 5:179–192 (1985).
K.J. Kearfott, D.R. Elmaleh, M.M. Goodman, J.A. Correia, N.M. Alpert, R.H. Ackerman, G.L. Brownell, and W.H. Strauss, Comparison of 2-and 3–18F-Fluoro-deoxy-D-glucose for studies of tissue of tissue metabolism, International Journal of Nuclear Biology 1(1): 15–22 (1984).
A. Luxen, N. Satyamurthy, G.T. Bida, and J.R. Barrio, Stereospecific approach to the synthesis of [18F]2- deoxy-2-fluoro-D-mannose, Appl. Radiat. Isot. 37:409 (1986).
K. Hamacher, H.H. Coenen, and G. Stocklin, Efficient stereospecific synthesis of no carrier-added 2-[18F]- fluoro-2-deoxy-D-glucose using aminopolyether supported nucleophilic substitution, J. Nucl. Med. 7:235–238 (1986).
11.J. Engel, D.E. Kuhl, and M.E. Phelps, Patterns of human local cerebral glucose metabolism during epileptic seizures, Science 218(4567):64–66 (1982).
G. DiChiro, R. De Lapaz, B. Smith, et al, J.Cereb. Blood Flow Metab. 1:S11-S-12 (1981).
F. Fazekas, A. Alavi, J.B. Chawluk, R.A. Zimmerman, D. Hackney, L. Bilaniuk, M. Rosen, W.M. Alves, H.I. Hurtig, D.G. Jamieson, et al., Comparison of CT, MR and PET in Alzheimer’s dementia and normal aging, J. Nucl. Med. 30(10): 1607–1615 (1989).
E.M. Bessell, A.B. Foster, and J.H. Westwood, Biochem. J. 128:199–204 (1972).
M.M. Goodman, G.W. Kabalka, and C.P.D. Longford, Synthesis of fluorine labeled 4-fluoro-4-deoxy-D- glucose as a potential brain, heart and tumor imaging agent, in: “Proceedings, Ninth International Symposium on Radiopharmaceutical Chemistry,” Paris, France, 568–569, (April 6–10, 1992).
T.G. Bidder, Hexose translocation across the blood-brain interface: configurational aspects, J. Neurochem. 15:867–874 (1968).
W.M. Partridge and W.H. Olendorf, Kinetics of blood-brain barrier transport of hexoses, Biochem. Biophysics Acta. 382:377–392 (1975).
A.L. Betz, J. Gsejtey, and G.W. Goldstein, Hexose transport and phosphorylation by capillaries isolated from rat brain, Am. J. Physiol. 236:C96–C102 (1979).
G. Kloster, C. Muller-Platz, and P. Laufer, 3-[11C]-Methyl-D-Glucose, a potential agent for regional cerebral glucose utilization studies: Synthesis, chromatography and tissue distribution studies in mice, J. Labeled Cmpd. Radiopharm. 18:855–863 (1981).
D.J. Brooks, A.A. Beaney, A. Lammerstsma, S. Herold, D.R. Turton, S.K. Luthra, R.S.J. Frackowiak, D.G.T. Thomas, J. Marshall, and T. Jones, Glucose transport across the blood-brain barrier in normal human subjects and patients with cerebral tumours studied using [11C]3-O-methyl-D-glucose and positron emission tomography, J. Cereb. Blood Flow Metab. 6:230–239 (1986).
DJ. Brooks, J.S.R. Gibbs, S. Herold, D.R. Turton, S.K. Luthra, D.G.T. Thomas, S.R. Bloom, and T. Jones, Regional cerebral glucose transport in insulin-dependent diabetic patients studied using [11C]3–0- methyl-D-glucose and positron emission tomography J. Cereb. Blood Flow Metab. 6:240–244 (1986).
T.D. Reisine, J.Z. Fields, H.I. Yamamura, E.D. Bird, E. Spokes, P.S. Schreiner, and S.J. Enna, Neurotransmitter receptor alterations in Parkinson’s disease, Life Science. 21:335–344 (1977).
P. Seeman and Tardive Dyskinesia, Dopamine receptors and neurologic damage to cell membranes, J. Clin. Pyschopharmacol. 8(suppl):35–95 (1988).
S.H. Snyder, Dopamine receptors, Neuroleptics and Schizophrenia, Am. J. Psychiatry. 138:460–464 (1981).
F.I. Carroll, A.H. Lewin, J.W. Boja, M.J. Kuhar, Cocaine receptor: Biochemical characterization and structure-activity relationships of cocaine analogues at the dopamine transporter, J. Med. Chem. 35:969–981 (1992).
M.M. Goodman, G.W. Kabalka, T.L. Collier, and C.P.D. Longford, Radioiodinated 2ß-carbomethoxy-3ß-(4-chlorophenyl)-8-(3E-and 3Z-iodopropen-2-yl)nortropanes. Synthesis of potential radioligands for mapping cocaine receptor sites by SPECT, J. Nucl. Med. (5)33:890(1992).
M.M. Goodman, M.P. Kung, and H.F. Kung, Unpublished results.
R.H. Kline, J. Wright, A.J. Eshleman, K.M. Fox, and M.E. Eldefrawi, Syntheseis of 3-carbamoylecogonine methyl ester analogues as inhibitors of cocaine binding and dopamine uptake, J. Med. Chem. 34:702–705 (1991).
T.L. Collier, M.M. Goodman, G.W. Kabalka, and C.P.D. Longford, Rapid microwave radiofluorination of (lR-2-exo-3-exo)-2ß-carbomethoxy-8-azabicyclo[3.2.1]octyl-3-N-(4’-[18F]fluoro-3’- nitrophenyl)carbamate. A potential PET cocaine receptor imaging agent, J. Nucl. Med. 33(5): 1025 (1992).
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1995 Springer Science+Business Media New York
About this chapter
Cite this chapter
Goodman, M.M., Kabalka, G.W., Longford, D., Collier, T.L., Gotsick, T. (1995). Synthesis of Fluorine-18 Labeled Compounds for Brain Imaging. In: Emran, A.M. (eds) Chemists’ Views of Imaging Centers. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-9670-4_39
Download citation
DOI: https://doi.org/10.1007/978-1-4757-9670-4_39
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4757-9672-8
Online ISBN: 978-1-4757-9670-4
eBook Packages: Springer Book Archive