대한핵의학회지 (The Korean Journal of Nuclear Medicine)

대한핵의학회 (The Korean Society of Nuclear Medicine)
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분자영상 방사성추적자의 생산에 사용되는 방사성동위 원소 표지방법

Radiolabeling Methods Used for Preparation of Molecular Probes

  • 최연성 (성균관대학교 의과대학 삼성서울병원 핵의학과)
  • Choe, Yearn-Seong (Department of Nuclear Medicine, Samsung Medical Center, Sungkyunkwan University School of Medicine)
  • 발행 : 2004.04.30
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초록

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.

키워드

참고문헌

  1. Radiotracer production. In: Wagner HN, Szabo Z, Buchanan JW, editiors. Principles of Nuclear Medicine Philadelphia: W.B. Saunders; 1995
  2. Snyder SE, Kilbourn MR. Chemistry of fluorine-18 radiopharmaceuticals. In: Welch MJ, Redvanly CS, editors. Handbook of Radiopharmaceuticals Chichester: Wiley; 2003. p 195-227
  3. 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 https://doi.org/10.1016/0020-708X(82)90003-5
  4. 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 https://doi.org/10.1016/0883-2889(87)90123-7
  5. 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 https://doi.org/10.1016/S0969-8043(96)00177-7
  6. Jewett DM. A simple synthesis of [$^{11}$C]methyl triflate. Appl Radiat Isot 1992;43:1383-5 https://doi.org/10.1016/0883-2889(92)90012-4
  7. 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 https://doi.org/10.1016/0969-8051(94)00083-V
  8. Comar D, Carton JC, Maziere M, Marazano C. labelling and metabolism of methionine-methyl-$^{11}$C. Eur J Nucl Med 1976; 1:11-4
  9. 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 https://doi.org/10.1016/S0969-8043(00)00368-7
  10. 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
  11. 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 https://doi.org/10.1016/S0969-8051(03)00017-9
  12. 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
  13. 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 https://doi.org/10.1016/0969-8051(96)00075-3
  14. 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 https://doi.org/10.1002/jlcr.2580270711
  15. 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
  16. 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 https://doi.org/10.1016/S0969-8051(97)00229-1
  17. 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 https://doi.org/10.1016/S0969-8051(98)00081-X
  18. 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
  19. Fowler JS, Finn RD, Lambrecht RM, Wolf AP. The synthesis of $^{18}$F-5-fluorouracil. J Nucl Med 1973;14:63-4
  20. 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 https://doi.org/10.1016/0047-0740(84)90049-4
  21. Adam MJ, Jivan S. Synthesis and purification of L-6-[$^{18}$F] fluorodopa. Appl Radiat Isot 1988;39:1203-10 https://doi.org/10.1016/0883-2889(88)90100-1
  22. Hom RK, Katzenellenbogen JA. Technetium-99m-labeled receptorspecific small-molecule radiopharmaceuticals: recent developments and encouraging results. Nucl Med Biol 1997;24:485-98 https://doi.org/10.1016/S0969-8051(97)00066-8
  23. Jurisson SS, Lydon JD. Potential technetium small molecule radiopharmaceuticals. Chem Rev 1999;99:2205-18 https://doi.org/10.1021/cr980435t
  24. Spradau TW, Katzenellenbogen JA. Preparation of cyclopentadienyltricarbonylrhenium complexes using a double ligand transfer reaction. Organometallics 1998;17:2009-17 https://doi.org/10.1021/om971018u
  25. 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 https://doi.org/10.1021/ja980745t
  26. 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
  27. Moerlein SM. Regiospecific aromatic radioiodination via n.c.a. copper (I) assisted iododebromination. Radiochim Acta 1990; 50:55-61
  28. 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 https://doi.org/10.1021/jm00114a027
  29. 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 https://doi.org/10.1021/jm00036a020
  30. Parker CW. Radiolabeling of proteins. Methods Enzymol 1990; 182:721-31 https://doi.org/10.1016/0076-6879(90)82056-8
  31. Blok D, Feitsma RIJ, Vermeij P, Pauwels EJK. Peptide radiopharmaceuticals in nuclear medicine. Eur J Nucl Med 1999; 26:1511-1519 https://doi.org/10.1007/s002590050488
  32. 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
  33. 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
  34. King TP, Zhao SW, Lam T. Preparation of protein conjugates via intermolecular hydrazone linkage. Biochemistry 1986;25:5774-9 https://doi.org/10.1021/bi00367a064
  35. 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 https://doi.org/10.1016/S0969-8051(00)00134-7
  36. 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
  37. 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 https://doi.org/10.1016/S0969-8051(02)00390-6
  38. 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
  39. 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 https://doi.org/10.1042/bj1330529
  40. 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 https://doi.org/10.1016/0883-2889(87)90069-4