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Radiolabeling Methods Used for Preparation of Molecular Probes  

Choe, Yearn-Seong (Department of Nuclear Medicine, Samsung Medical Center, Sungkyunkwan University School of Medicine)
Publication Information
The Korean Journal of Nuclear Medicine / v.38, no.2, 2004 , pp. 121-130 More about this Journal
Abstract
Molecular imaging visualizes cellular processes at a molecular or genetic level in living subjects, and diverse molecular probes are used for this purpose. Radiolabeling methods as well as radioisotopes are very important in preparation of molecular probes, because they can affect the biodistribution in tissues and the excretion route. In this review, the molecular probes are divided into small organic molecules and macromolecules such as peptides and proteins, and their commonly used radiolabeling methods are described.
Keywords
Molecular probe; Radioisotope; Radiolabeling method; Small organic molecules; Proteins; Peptides; PET; SPECT;
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1 Radiotracer production. In: Wagner HN, Szabo Z, Buchanan JW, editiors. Principles of Nuclear Medicine Philadelphia: W.B. Saunders; 1995
2 Pike VW, Eakins MN, Allan RM, Selwyn AP. Preparation of [$1-^{11}C$]acetate - an agent for the study of myocardial metabolism by positron emission tomography. Int J Appl Radiat Isot 1982; 33:505-12   DOI   ScienceOn
3 N$\aa$gren K, Muller L, Halldin C, Swahn CG, Leuhkoinen P. Improved synthesis of some commonly used PET radioligands by the use of [$^{11}$C]methyl triflate. Nucl Med Biol 1995;22:235-9   DOI   ScienceOn
4 Iwata R, Pascali C, Bogni A, Miyake Y, Yanai K, Ido T. A simple loop method for the automated preparation of [11C]raclopride from [11C]methyl triflate. Appl Radiat Isot 2001;55:17-22   DOI   ScienceOn
5 Alberto R, Schibli R, Egli A, Schubiger AP. A novel organometallic aqua complex of technetium for the labeling of biomolecules: synthesis of [$^{99m}Tc(OH_2)_3(CO)_3$]$^+$- in aqueous solution and its reaction with a bifunctional ligand. J Am Chem Soc 1998;120:7987-8   DOI   ScienceOn
6 Kung MP. Stevenson DA, Pl$\ddot{o}$ssel K, Meegalla SK, Beckwith A, Essman WD, Mu M, Lucki I, Kung HF. [$^{99m}$Tc]TRODAT-1: A novel technetium-99m complex as a dopamine transporter imaging agent. Eur J Nucl Med 1997;24:372-80
7 Rennen HJ, Boerman OC, Koenders EB, Oyen WJ, Corstens FH. Labeling proteins with Tc-99m via hydrazinonicotinamide (HYNIC): optimization of the conjugation reaction. Nucl Med Biol 2000; 27:599-604   DOI   ScienceOn
8 Russell J, O'Donoghue JA, Finn R, Koziorowski J, Ruan S, Humm JL, et al. Iodination of annexin V for imaging apoptosis. J Nucl Med 2002;43:671-7   PUBMED
9 Larsen P, Ulin J, Dahlström K, Jensen M. Synthesis of [$^{11}$C]iodomethane by iodination of [11C]methane. Appl Radiat Isot 1997;48:153-7   DOI   ScienceOn
10 Wester H-J, Hamacher K, St$\ddot{o}$cklin G. A comparative study of N.C.A. fluorine-18 labeling of proteins via acylation and photochemical conjugation. Nucl Med Biol 1996;23:365-72
11 Spradau TW, Katzenellenbogen JA. Preparation of cyclopentadienyltricarbonylrhenium complexes using a double ligand transfer reaction. Organometallics 1998;17:2009-17   DOI   ScienceOn
12 Bolton AM, Hunter RM. The labeling of proteins to high specific radioactivities by conjugation to I-125 containing acylating agent. Biochem J 1973;133:529-39   DOI
13 Hamacher K, Coenen HH, Stöcklin G. Efficient stereospecific synthesis of no-carrier-added 2-[$^{18}$F]fluoro-2-deoxy-D-glucose using aminopolyether supported nucleophilic substitution. J Nucl Med 1986;27:235-8   PUBMED
14 Alauddin MM, Conti PS, Mazza SM, Hamzeh FM, Lever JR. 9-[(3-[$^{18}$F]-Fluoro-1-hydroxy-2-propoxy)methyl]guanine ([$^{18}$F]-FHPG): a potential imaging agent of viral infection and gene therapy using PET. Nucl Med Biol 1996;23:787-92   DOI   ScienceOn
15 Fischman AJ, Babich JW. Radiolabeled paptides: a new class of imaging agents. In: Freeman LM, editor. Nuclear Medicine Annual. New York: Raven Press; 1997. p. 103
16 Snyder SE, Kilbourn MR. Chemistry of fluorine-18 radiopharmaceuticals. In: Welch MJ, Redvanly CS, editors. Handbook of Radiopharmaceuticals Chichester: Wiley; 2003. p 195-227
17 Ido T, Wan CN, Casella V, Fowler JS, Wolf AP, Reivich M, et al. Labeled 2-deoxy-2-fluoro-D-glucose analogs. $^{18}$F-Labeled 2-deoxy-2-fluoro-D-glucose, 2-deoxy-2-fluoro-D-mannose and $^{14}$C-2-deoxy- 2-fluoro-D-glucose. J Labelled Cpd Radiopharm 1978;14:171-83
18 Goodman MM, Kung M-P, Kabalka GW, Kung HF, Switzer R. Synthesis and characterization of radioiodinated N-(3-iodopropen-1-yl) 2$\beta$-carbomethoxy-3$\beta$-(4-chlorophenyl)tropanes: potential dopamine reuptake site imaging agents. J Med Chem 1994;37:1535-42   DOI   ScienceOn
19 Coenen HH. New radiohalogenation methods: An overview. In: Cox PH, Mather SJ, Sampson CB, Lazarus CR, editors. Progress in Radiopharmacy. Boston: Martinus Nijhoff; 1986. p 196-220
20 Jonson SD, Welch MJ. Synthesis, biological evaluation, and baboon PET imaging of the potential adrenal agent cholesteryl-p-[$^{18}$F] fluorobenzoate. Nucl Med Biol 1999;26:131-8   DOI   ScienceOn
21 Neumeyer JL, Wang S, Milius RA. Baldwin RM, Zea-Ponce Y, Hofer PB, et al. [$^{123}$I]-2$\beta$-Carbomethoxy-3$\beta$-(4-iodophenyl)tropane: high-affinity SPECT radiotracer of monoamine reuptake sites in brain. J Med Chem 1991;34:3144-6   DOI   PUBMED
22 Parker CW. Radiolabeling of proteins. Methods Enzymol 1990; 182:721-31   DOI   PUBMED
23 Blok D, Feitsma RIJ, Vermeij P, Pauwels EJK. Peptide radiopharmaceuticals in nuclear medicine. Eur J Nucl Med 1999; 26:1511-1519   DOI   ScienceOn
24 Rennen HJ, Boerman OC, Oyen WJ, van der Meer JW, Corstens FH. Specific and rapid scintigraphic detection of infection with $^{99m}$Tc-labeled interleukin-8. J Nucl Med 2001;42:117-23   PUBMED
25 Haka MS, Kilbourn MR, Watkins GL, Toorongian SA. Aryltrimethylammonium trifluoromethanesulfonates as precursors to aryl [$^{18}$F]fluoride: Improved synthesis of [$^{18}$F]GBR-13119. J Labelled Cpd Radiopharm 1989;27:823-33   DOI   ScienceOn
26 Lee SY, Choe YS, Kim YR, Choi BW, Kim SE, Choi Y, Lee KH, Lee J, Kim BT. Synthesis and evaluation of $^{18}$F-labeled N-benzylpiperidine benzisoxazole for acetylcholinesterase mapping. J Nucl Med 2002;43S:358P
27 Su Z-F, He J, Rusckowski M, Hnatowich. In vitro cell studies of technetium-99m labeled RGD-HYNIC peptide, a comparison of tricine and EDDA as co-ligands. Nucl Med Biol 2003;30:141-9   DOI   ScienceOn
28 Crouzel C, L$\aa$ngstr$\ddot{o}$m B, Pike VW, Coenen HH. Recommendations for a practical production of [$^{11}$C]methyl iodide. Appl Radiat Isot 1987;38:601-3   DOI   ScienceOn
29 Le Bars D, Lemaire C, Ginovart N, Plenevaux A, Aerts J, Brihaye C, et al. High-yield radiosynthesis and preliminary in vivo evaluation of p-[$^{18}$F]MPPF, a fluoro analog of WAY-100635. Nucl Med Biol 1998;25:343-50   DOI   ScienceOn
30 Diksic M, Farrokhzad S, Yamamoto YL, Feindel W. A simple synthesis of $^{18}$F-labelled 5-fluorouracil using acetylhypofluorite. Int J Nucl Med Biol 1984;11:141-2   DOI   ScienceOn
31 King TP, Zhao SW, Lam T. Preparation of protein conjugates via intermolecular hydrazone linkage. Biochemistry 1986;25:5774-9   DOI   ScienceOn
32 Fowler JS, Finn RD, Lambrecht RM, Wolf AP. The synthesis of $^{18}$F-5-fluorouracil. J Nucl Med 1973;14:63-4   PUBMED
33 Moerlein SM. Regiospecific aromatic radioiodination via n.c.a. copper (I) assisted iododebromination. Radiochim Acta 1990; 50:55-61
34 Comar D, Carton JC, Maziere M, Marazano C. labelling and metabolism of methionine-methyl-$^{11}$C. Eur J Nucl Med 1976; 1:11-4   PUBMED
35 Jewett DM. A simple synthesis of [$^{11}$C]methyl triflate. Appl Radiat Isot 1992;43:1383-5   DOI   ScienceOn
36 Jurisson SS, Lydon JD. Potential technetium small molecule radiopharmaceuticals. Chem Rev 1999;99:2205-18   DOI   ScienceOn
37 Adam MJ, Jivan S. Synthesis and purification of L-6-[$^{18}$F] fluorodopa. Appl Radiat Isot 1988;39:1203-10   DOI   ScienceOn
38 Zalutsky MR, Narula AS. A method for the radiohalogenation of proteins resulting in decreased thyroid uptake of radioiodine. Appl Radiat Isot 1987;38:1051-5   DOI   ScienceOn
39 Kim DW, Choe YS, Chi DY. A new nucleophilic fluorine-18 labeling method for aliphatic mesylates: reaction in ionic liquids shows tolerance for water. Nucl Med Biol 2003;30:345-50   DOI   ScienceOn
40 Hom RK, Katzenellenbogen JA. Technetium-99m-labeled receptorspecific small-molecule radiopharmaceuticals: recent developments and encouraging results. Nucl Med Biol 1997;24:485-98   DOI   ScienceOn