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Seminars in Nuclear Medicine
Volume 37, Issue 6
, Pages 400-419
, November 2007
18F-Labeled Positron Emission Tomographic Radiopharmaceuticals in Oncology: An Overview of Radiochemistry and Mechanisms of Tumor Localization
References
- . The hallmarks of cancer. Cell. 2000;100:57–70
- . The metabolism of cancer cells. Biochem Zeitschr. 1924;152:129–169
- . On the origin of cancer cells. Science. 1956;123:309–314
- . Mammalian hexokinases and their abnormal expression in cancer. Br J Biomed Sci. 2000;57:170–178
- . Effects of glucose analogues (2-deoxy-D-glucose, 2-deoxy-D-galactose) on experimental tumors. J Natl Cancer Inst. 1960;24:267–281
- . History of the First Synthesis of 2-Deoxy-2-Fluoro-D-Glucose the Unlabeled Forerunner of 2-Deoxy-2-[18F]Fluoro-D-Glucose. Mol Imaging Biol. 2002;4:353–354
- Labeled 2-deoxy-D-glucose analogs: 18F labeled 2-deoxy-2-fluoro-D-glucose, 2-deoxy-2-fluoro-D-mannose and 14C-2-deoxy-2-fluoro-D-glucose. J Label Compd Radiopharmacol. 1978;14:175–183
- . The history of positron emission tomography (PET). Mol Imag Biol. 2002;4:11–26
- . Food and Drug Administration [Docket No. 00N–0553] Positron Emission Tomography Drug Products; Safety and Effectiveness of Certain PET Drugs for Specific Indications. Federal Register. 2000;65(48):12999–13010
- . Principles of cancer imaging with fluorodeoxyglucose. In: Wahl RL, Buchanan JW editor. Principles and Practice of Positron Emission Tomography. Lippincott: Williams & Wilkins; 2002;
- . Beyond Detection: Novel applications for PET Imaging to guide cancer therapy. J Nucl Med. 2007;48:855–856
- . Is there a future for clinical fluorine-18 radiopharmaceuticals (excluding FDG)?. Eur J Nucl Med. 1998;25:1612–1616
- 18F-labeled radiopharmaceuticals for PET in oncology, excluding FDG. Nuc Med Biol. 2000;27:103–112
- . Update on PET radiopharmaceuticals: Life beyond fluorodeoxyglucose. Radiol Clin N Am. 2004;42:1033–1053
- Fluorinated tracers for imaging cancer with positron emission tomography. Eur J Nucl Med Mol Imag. 2004;31:1182–1206
- Vallabhajosula S. Radiopharmaceuticals for PET, in Biersack HJ, Freeman L (eds.) Practical Nuclear Medicine, in press
- . Substrate specificity of brain hexokinase. J Biol Chem. 1954;210:581–595
- . Imaging of malignant bone involvement by morphologic, scintigraphic, and hybrid modalities. J Nucl Med. 2005;46:1356–1367
- Bone imaging in metastatic breast cancer. J Clin Oncol. 2004;22:2942–2953
- The absorption of fluorides by enamel, dentin, bone, and hydroxyapatite as shown by the radioactive isotope. J Biol Chem. 1940;134:543–548
- . A new isotope for bone scanning. J Nucl Med. 1962;3:332–334
- Quantitative studies of bone with the use of 18F-fluoride and 99mTc-methylene diphosphonate. Semin Nucl Med. 2001;31:28–49
- Fluoride kinetics of the axial skeleton measured in vivo with fluorine-18-fluoride PET. J Nucl Med. 1997;38:1970–1976
- Assessment of malignant skeletal disease with 18F-fluoride PET/CT. J Nucl Med. 2004;45:272–278
- . Thymidine metabolism and cell kinetics. Front Biol. 1967;6:43–100
- . Regulation of human thymidine kinase during the cell cycle. J Biol Chem. 1988;263:8350–8358
- In vitro determination of thymidine-[H-3] labeling index in human solid tumors. Cancer Res. 1974;34:1376–1380
- Detection of DNA synthesis in intact organisms with positron-emitting methyl-[C-11]-thymidine. Proc Natl Acad Sci USA. 1972;69:988–992
- Studies on 18F-labeled pyrimidines III (Biochemical investigation of 18F-labeled pyrimidines and comparison with 3H-deoxythymidine in tumor-bearing rats and mice). Eur J Nucl Med. 1985;10:39–44
- Development of labeled thymidine analogs for imaging tumor proliferation. Nucl Med Biol. 1996;23:17–22
- Imaging proliferation in vivo with [F-18]FLT and positron emission tomography. Nat Med. 1998;4:1334–1336
- Evaluation of pyrimidine metabolising enzymes and in vitro uptake of 3′-[18F]fluoro-3′-deoxythymidine ([18F]FLT) in pancreatic cancer cell lines. Eur J Nucl Med Mol Imaging. 2002;29:1174–1181
- Metabolism of 3′-deoxy-3′-[F-18]fluorothymidine in proliferating A549 cells: Validations for positron emission tomography. Nucl Med Biol. 2004;31:829–837
- 18F-5-Fluorouridine, a new probe for measuring the proliferation of tissue in vivo. Adv Enz Regul. 1982;20:3–22
- . PET imaging with 18F-FLT and thymidine analogs: Promise and pitfalls. J Nucl Med. 2003;44:1432–1434
- . Dietary choline: Biochemistry, physiology, and pharmacology. Annu Rev Nutr. 1981;1:95–121
- . Dietary Reference Intakes for Thiamin, Riboflavin, Niacin, Vitamin B6, Folate, Vitamin B12, Pantotheni Acid, Biotin and Choline. Washington, DC: National Academy Press; 1998;
- Substrate specificity of choline kinase. Arch Biochem Biophys. 1987;254:214–221
- Betaine as an osmolyte in rat liver: metabolism and cell-to-cell interactions. Hepatology. 1998;27:787–793
- Blood metabolism of [methyl-11C]choline; implications for in vivo imaging with positron emission tomography. Eur J Nucl Med. 2000;27:25–32
- . Coordination of membrane phospholipid synthesis with the cell cycle. J Biol Chem. 1994;269:3858–3867
- Lipid requirement for cell cycling: The effect of selective inhibition of lipid synthesis. Exp Cell Res. 1997;109:299–307
- Increased choline signal coinciding with malignant degeneration of cerebral gliomas: A serial proton magnetic resonance spectroscopy imaging study. J Neurosurg. 1997;87:516–524
- PET imaging of brain tumor with [methyl-11C] choline. J Nucl Med. 1997;38:842–847
- . Development of [18F]-Fluoroethylcholine for cancer imaging with PET: Synthesis, biochemistry, and prostate cancer imaging. J Nucl Med. 2002;43:187–199
- Synthesis and evaluation of 18F labeled choline as an oncologic tracer for positron emission tomography: Initial findings in prostate cancer. Cancer Res. 2001;61:110–117
- Synthesis and preclinical evaluation of the choline transport tracer deshydroxy-[18F]fluorocholine ([18F]dOC). Nucl Med Biol. 2004;31:851–858
- . Lipids in normal and tumor cells in culture. Prog Biochem Pharmacol. 1975;10:135–166
- Fatty acid synthase drives the synthesis of phospholipids partitioning into detergent-resistant membrane microdomains. Biochem Biophys Res Commun. 2003;302:898–903
- 11C-acetate PET imaging of prostate cancer: Detection of recurrent disease at PSA relapse. J Nucl Med. 2003;44:549–555
- [18F]-Fluoroacetate, an analogue of C-11 acetate for tumor imaging. J Nucl Med. 2003;44:296p
- . Positron emission tomography for prostate, bladder, and renal cancer. Semin Nucl Med. 2004;34:274–292
- Radiolabeled choline as a proliferation marker: Comparison with radiolabeled acetate. Nuclear Medicine andNucl Med Biol. 2004;31:859–865
- Radiolabeled amino acids: Basic aspects and clinical applications in oncology. J Nucl Med. 2001;42:432–445
- Comparison of fluorotyrosines and methionine uptake in F98 rat gliomas. Nucl Med Biol. 2003;30:501–508
- Neutral amino acid transport systems in animal cells: Potential targets of oncogene action and regulators of cellular growth. J Membr Biol. 1988;104:1–20
- . Dopamine visualized in the basal ganglia of living man. Nature. 1983;305:137–138
- Remote, semiautomated production of 6-[18F]fluoro-L-dopa for human studies with PET. Int J Rad Appl Instrum A. 1990;41:275–281
- Production of 6-[18F]fluoro-L-dopa and its metabolism in vivo—a critical review. Int J Rad Appl Instrum B. 1992;19:149–158
- 18F-DOPA positron emission tomography for tumor detection in patients with medullary thyroid carcinoma and elevated calcitonin levels. Eur J Nucl Med. 2001;28:64–71
- Pheochromocytomas: Detection with 18F DOPA whole body PET—initial results. Radiology. 2002;222:507–512
- Imaging of advanced neuroendocrine tumors with [18]F-FDOPA PET. J Nucl Med. 2004;45:1161–1167
- Expression of neuroendocrine cell markers L-dopa decarboxylase, chromogranin A, and dense core granules in human tumors of endocrine and nonendocrine origin. Cancer Res. 1988;48:4078–4082
- : Biodistribution studies on L-3-[18F]fluoro-α-methyl tyrosine: A potential tumor-detecting agent. J Nucl Med. 1998;39:663–667
- Synthesis and evaluation of [18F] 1-amino-3-fluorocyclobutane-l-carboxylic acid to image brain tumors. J Nucl Med. 1999;40:331–338
- . Blood flow and tissue oxygenation of human tumors: An update. Adv Exp Med Biol. 1992;317:139–151
- Functional imaging of intra-tumoral hypoxia. Mol Imaging Biol. 2004;6:291–305
- . A marker for hypoxic cells in tumours with potential clinical applicability. Br J Cancer. 1981;43:546–550
- . The biological properties of reduced nitroheterocyclics and possible underlying biochemical mechanisms. Biochem. Pharmacol. 1986;35:97–103
- Characterization of radiolabeled fluoromisonidazole as a probe for hypoxic cells. Radiat Res. 1987;111:292–304
- Tumor hypoxia imaging with [F-18] fluoromisonidazole positron emission tomography in head and neck cancer. Clin Cancer Res. 2006;12:5435–5441
- Pharmacokinetics of [18F]FETNIM: A potential marker for PET. J Nucl Med. 2001;42:1397–1404
- Characterization of [18F]fluoroetanidazole, a new radiopharmaceutical for detecting tumor hypoxia. J Nucl Med. 1999;40:1072–1079
- Hypoxia-specific tumor imaging with 18F-fluoroazomycin arabinoside. J Nucl Med. 2005;46:106–113
- Pretreatment 18F-FAZA PET predicts success of hypoxia-directed radiochemotherapy using tirapazamine. J Nucl Med. 2007;48:973–980
- Radiolabeled estradiol derivatives to predict response to hormonal treatment in breast cancer: Areview. Eur J Nucl Med. 2000;27:1421–1433
- . ERβ identification and characterisation of a novel human estrogen receptor. FEBS Lett. 1996;392:49–53
- The predictive value of estrogen and progesterone receptors’ concentrations on the clinical behavior of breast cancer in women: Clinical correlation on 547 patients. Cancer. 1986;57:1171–1180
- . Estrogen receptors in hormone-responsive tissue and tumors. In: Wissler RW, Dao TL, Wood S editor. Endogenous factors influencing host tumor balance. Chicago: University of Chicago Press; 1967;
- . PET imaging of cellular proliferation. Radiol Clin N Am. 2005;43:153–167
- Preparation of four fluorine-18-labeled estrogens and their selective uptakes in target tissues of immature rats. J Nucl Med. 1984;25:1212–1221
- . Analysis of blood clearance and labeled metabolites for the estrogen receptor tracer [F-18]-16α-fluoroestradiol (FES). Nucl Med Biol. 1997;24:341–348
- Automated synthesis of 11β-methoxy-4-16α-[16α-18F]difluoroestradiol (4F-M[18F]FES) for estrogen receptor imaging by positron emission tomography. Nucl Med Biol. 2007;34:459–464
- . Synthesis of 2, 16α- and 4,16α difluoroestradiols and their 11β-methoxy derivatives as potential estrogen receptor-binding radiopharmaceuticals. J Chem Soc Perkin Trans. 2002;1:657–663
- . Absolute cross section for the production of 18F via the 18O(p,n)18F reaction. Radiochimica Acta. 1979;26:21–24
- . Production of radionuclides in accelerators. In: Welch MJ, Redvanley CS editor. Handbook of Radiopharmaceuticals, Radiochemistry and Applications. New York: John Wiley & Sons Inc; 2003;
- An 18O target for the high yield production of 18F fluoride. Int J Appl Rad Isotop. 1983;34:625–629
- . An oxygen target for the production of [18F]F2. Appl Radiat Isot. 1984;35:117-112
- . Fluorine-I8 labeling of radiopharmaceuticals (Nuclear Science Series no. NAS-NS-3203). Washington, DC: National Academy of Sciences, National Academy Press; 1990;
- The NCA nucleophilic 18F-fluorination of I,N-disubstituted alkanes as fluoralkylation agents. J Label Compd Radiopharm. 1987;24:1029–1042
- . The preparation of [18F]5-fluoro-DOPA with reactor produced fluorine-18. Int J Appl Radiat Isot. 1973;24:182–184
- . Aromatic radiofluorination with 18F fluorine gas: 6-[18F]fluoro-L-dopa. J Nucl Med. 1984;25:1228–1233
- Routine synthesis of L-[18F]6-fluorodopa with fluorine-18 acetyl hypofluorite. J Nucl Med. 1986;27:1462–1466
- Regioselective radiofluorodestannylation with [18F]F2 and [18F]CH3COOF (A high yield synthesis of 6-[18F]Fluoro-L-DOPA). Int J Rad Appl Instrum. 1992;43:989–996
- 6-[18F]Fluoro-L- DOPA by Radiofluoro-destannylation: A short and simple synthesis of a new labeling precursor. J Label Compd Radiopharm. 1998;41:105–114
- . The use of 3′-fluoro-3′-deoxythymidine and studies of its 18F-radiolabeling, as a tracer for the non-invasive monitoring of the biodistribution of drugs against AIDS. J Fluorine Chem. 1991;55:283–289
- . An improved radiosynthesis of [F-18]FLT. J Labelled Compd Radiopharm. 1999;42:S525–S526
- . Radiosynthesis of 3′-Deoxy-3′-[18F]fluoro thymidine:[18F]FLT for imaging of cellular proliferation in vivo. Nucl Med Biol. 2000;27:143–156
- A new precursor for the radiosynthesis of [18F]FLT. Nucl Med Biol. 2002;29:263–273
- High radiochemical yield synthesis of 3′-deoxy-3′-[18F]Fluorothymidine using (5′-O-dimethoxytirtyl-2′-deoxy-3′-Onosyl-D-threo-pentofuranosyl)thymine and its 3-N-BOC protected analogue as a labeling precursor. Nucl Med Biol. 2003;30:151–157
- Suehiro M, Vallabhajosula S, Goldsmith SJ, et al: Investigation of the role of the base in the synthesis of [18F]FLT. Applied Radiat Isotop 2007 (in Press)
- Fully automated synthesis system of 3′-deoxy-3′-[18F]fluorothymidine. Nucl Med Biol. 2004;31:803–809
- Synthesis and biodistribution of 18F labeled fluoronitroimidazoles: Potential in vivo markers of hypoxic tissue. Int J Radiat Appl Instrum. 1986;37:599–605
- A radiosynthesis of fluorine-18 fluoromisonidazole. J Nucl Med. 1989;30:343–350
- . An efficient radiosynthesis of [18F]fluoromisonidazole. Appl Radiat Isot. 1993;44:1085–1091
- Rapid synthesis of 3-[18F]fluoro-1-(2′-nitro-1′-imidazolyl)-2-propanol [18F]fluoromisonidazole). Pharm Res. 1994;11:466–469
- . Preparation of [18F]fluoromisonidazole by nucleophilic substitution on THP-protected precursor: Yield dependence on reaction parameters. J Radioanal Nucl Chem. 1999;240:925–927
- Preparation of fluorine-18-labelled fluoromisonidazole using different synthesis methods. J Label Compd Radiopharm. 2004;47:37–45
- . Fully automated one-pot synthesis of [18F]fluoromisonidazole. Nucl Med Biol. 2005;32:553–558
- Preparation of four fluorine-18 labeled estrogens and their selective uptakes in target tissues of immature rats. J Nucl Med. 1984;25:1212–1221
- . Synthesis of 16α-fluoroestradiol using fluoride ion as a source of fluorine. J Nucl Med. 1983;24:P52
- The use of 3-methoxymethyl-l6β, 17β-epiestriol-O-cyclic sulfone as the precursor in the synthesis of F-l 8-16α-fluoroestradiol. Nucl Med Biol. 1996;23:911–915
- Automated production of 16α-[18F]fluoroestradiol for breast cancer imaging. Nucl Med Biol. 1999;26:473–479
- . Automated synthesis of fluorine-18 labeled choline analogue: 2-fluoroethyl-dimethyl-2-oxyethylammonium. [abstract] J Nucl Med. 1997;38:44P
- Synthesis and evaluation of 18F-labeled choline as an oncologic tracer for positron emission tomography: Initial findings in prostate cancer. Cancer Res. 2001;61:110–117
- Synthesis and evaluation of [18]F-labeled choline analogs as oncologic PET tracers. J Nucl Med. 2001;42:1805–1814
- [18F]-Fluoroalkylation using the “Loop” System. J Nucl Med. 2004;45:P445
- Pharmacokinetics and Biodistribution of Radiolabelled Choline in human Subjects: Comaprison of [11C]Choline and [18F]Fluorocholine. J Label Compd Radiopharm. 2005;48:S281
- [18F]Fluoromethyl triflate, a novel and reactive [18F]fluoromethylating agent: Preparation and application to the on-column preparation of [18F]fluorocholine. Appl Radiat Isot. 2002;57:347–352
- The radiation dosimetry of 2-[F-18]fluoro-2-deoxy-D-glucose in man. J Nucl Med. 1982;23:613–617
- MIRD Dose Estimate Report No. 19: Radiation Absorbed Dose Estimates from 18F-FDG J Nucl Med. 2002;43:210–214
- Radiation exposure of patients undergoing whole-body dual-modality 18F-FDG PET/CT examinations. J Nucl Med. 2005;46:608–613
- ICRP Publication 53: [18F]Fluoride radiation dosimetry. Volume. 1987;18:73–74
- Absorbed dose estimates in positron emission tomography studies based on the administration of 18Flabeled radiopharmaceuticals. J Radiat Res. 1991;32:243–261
- . Estimation of the radiation dose in man due to 6-[18F]fluoro-L-dopa. J Nucl Med. 1985;26:931–935
- 18F-fluorothymidine radiation dosimetry in human PET imaging studies. J Nucl Med. 2003;44:1482–1488
- 18F-Fluoroerythronitroimidazole radiation dosimetry in cancer studies. J Nucl Med. 2002;43:1674–1680
- [18F]fluoroestradiol radiation dosimetry in human PET studies. J Nucl Med. 2001;42:679–684
- Pharmacokinetics and radiation dosimetry of 18F-fluorocholine. J Nucl Med. 2002;43:92–96
- . Food and Drug Administration [Docket Nos. 94D–0422 and 93N–0005] Revocation of Certain Guidance Documents on Positron Emission Tomography Drug Products. Federal Register. 1997;62(244):66636
- . Food and Drug Administration [Docket No. 1998D-0266] Draft Guidance on Current Good Manufacturing Practice for Positron Emission Tomography Drug Products. Federal Register. 2005;70(181):55038-55062 and 55145
PII: S0001-2998(07)00090-6
doi: 10.1053/j.semnuclmed.2007.08.004
© 2007 Elsevier Inc. All rights reserved.
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Seminars in Nuclear Medicine
Volume 37, Issue 6
, Pages 400-419
, November 2007
