대한방사성의약품학회지 (Journal of Radiopharmaceuticals and Molecular Probes)

  • 제2권1호
  • /
  • Pages.9-16
  • /
  • 2016
  • /
  • 2384-1583(pISSN)
  • /
  • 2508-3848(eISSN)
대한방사성의약품학회 (Korean Society of Radiopharmaceuticals and Molecular Probes)
권호 표지
DOI QR코드

DOI QR Code

Recent advances in carbon-11 chemistry

  • Lu, Yingqing (Department of Nuclear Medicine, Seoul National University Bundang Hospital, Seoul National University College of Medicine) ;
  • Lee, Byung Chul (Department of Nuclear Medicine, Seoul National University Bundang Hospital, Seoul National University College of Medicine) ;
  • Kim, Sang Eun (Department of Nuclear Medicine, Seoul National University Bundang Hospital, Seoul National University College of Medicine)
  • 투고 : 2016.04.21
  • 심사 : 2016.05.19
  • 발행 : 2016.06.30
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

Carbon-11 is one of the most sensitive and desirable positron emission tomography radio-isotope, which offers the capacity to be incorporated, through a covalent bond, into biologically active molecules without altering their biological properties. Carbon-11 can be obtained from the cyclotron with two different chemical forms: $[^{11}C]CO_2$ and $[^{11}C]CH_4$. [$^{11}C$]Methyl iodide has been widely used as a highly reactive labelling precursor that can be applied to label carbon-11 with biologically active molecules via alkylation of N-, O-, or S-nucleophiles. A more recent and still challenging labeling method is transition metal mediated $^{11}C$-carbonylation. Advances in organic chemistry, radiochemistry and improved automated techniques greatly encourage researchers to develop more carbon-11 labelled radiotracers for molecular imaging studies. This mini-review will introduce a historical track of carbon-11 chemistry combining with examples and its role in near future.

키워드

참고문헌

  1. Blake P, Johnson B, VanMeter JW. Positron emission tomography (PET) and single photon emission computed tomography (SPECT): Clinical applications. J Neuroophthalmol 2003;23:34-41. https://doi.org/10.1097/00041327-200303000-00009
  2. Ametamey SM, Honer M, Schubiger PA. Molecular imaging with PET. Chem Rev 2008;108:1501-1516. https://doi.org/10.1021/cr0782426
  3. Ruben S, Hassid WZ, Kamen MD. Radioactive carbon in the study of photosynthesis. J Am Chem Soc 1939;61:661-663. https://doi.org/10.1021/ja01872a034
  4. Tobias CA, Lawrence JH, Roughton FJW, Root WS, Gregersen MI. The elimination of carbon monoxide from the human body with reference to the possible conversion of CO to $CO_2$. Am J Physiol 1945;145:253-263. https://doi.org/10.1152/ajplegacy.1945.145.2.253
  5. Winstead MB, Winchell HS, Fawwaz R, The use of sodium $^{11}C$-benzoate in renal visualization. Int J Appl Radiat Isot 1969; 20:859-863. https://doi.org/10.1016/0020-708X(69)90111-2
  6. Tang DY, Lipman A, Meyer G-J, Wan C-N, Wolf AP. $^{11}C$-labeled octanal and benzaldehyde. J Label Compd Radiopharm 1979;16: 435-440. https://doi.org/10.1002/jlcr.2580160309
  7. Raichle ME, Eichling JO, Straatmann MG, Welch MJ, Larson KB, Ter-Pogossian MM. Blood-brain barrier permeability of $^{11}C$-labeled alcohols and $^{15}O$-labeled water. Am J Physiol 1976; 230:543-552.
  8. Langstrom B, Lundqvist H. The preparation of $^{11}C$-methyl iodide and its use in the synthesis of $^{11}C$-methyl-L-methionine. Int J Appl Radiat Isot 1976;27:357-363. https://doi.org/10.1016/0020-708X(76)90088-0
  9. Comar D, Cartron JC, Maziere M, Marazano C. Labelling and metabolism of methionine-methyl-$^{11}C$. Eur J Nucl Med 1976;1: 11-14.
  10. Wilson AA, Garcia A, Jin L, Houle S. Radiotracer synthesis from [$^{11}C$]-iodomethane: a remarkably simple captive solvent method. Nucl Med Biol 2000;27:529-532. https://doi.org/10.1016/S0969-8051(00)00132-3
  11. Alauddin MM, Conti PS, Fissekis JD. Synthesis of [$^{18}F$]-labeled 2'-deoxy-2'-fluoro-5-methyl-1-${\beta}$-D-arabinofuranosyluracil ([$^{18}F$]-FMAU). J Label Compd Radiopharm 2002;45:583-590. https://doi.org/10.1002/jlcr.549
  12. Hughes JA, Hartman NG, Jay M. Preparation of [$^{11}C$]-thymidine and [$^{11}C$]-2'-arabino-2'-fluoro-${\beta}$-5-methyl-uridine (FMAU) using a hollow fiber membrane bioreactor system. J Label Compd Radiopharm 1995;36:1133-1145. https://doi.org/10.1002/jlcr.2580361204
  13. Samuelsson L, Langstrom B. Synthesis of 1-(2'-deoxy-2'‐fluoro- ${\beta}$-D-arabinofuranosyl)-[Methyl-$^{11}C$]thymine ([$^{11}C$]FMAU) via a Stille cross‐coupling reaction with [$^{11}C$]methyl iodide. J Label Compd Radiopharm 2003;46:263-272. https://doi.org/10.1002/jlcr.668
  14. Nagren K, Muller L, Halldin C, Swahn CG, Lehikoinen P. Improved synthesis of some commonly used PET radioligands by the use of [$^{11}C$]methyl triflate. Nucl Med Biol 1995;22:235-239. https://doi.org/10.1016/0969-8051(94)00083-V
  15. Nagren K, Halldin C. Methylation of amide and thiol functions with [$^{11}C$]methyl triflate, as exemplified by [$^{11}C$]NMSP, [$^{11}C$]flumazenil and [$^{11}C$]methionine. J Label Compd Radiopharm 1998; 41:831-841. https://doi.org/10.1002/(SICI)1099-1344(1998090)41:9<831::AID-JLCR129>3.0.CO;2-E
  16. Iwata R, Pascali C, Bogni A, Miyake Y, Yanai K, Ido T. A simple loop method for the automated preparation of [$^{11}C$]raclopride from [$^{11}C$]methyl triflate. Appl Radiat Isot 2001;55:17-22.
  17. Brinkman GA, Hass-Lisewska I, Veenboer JTh, Lindner L. Preparation of $^{11}COCl_2$. Int J Appl Radiat Isot 1978;29:701-702.
  18. Roeda D, Westera G. A u.v.-induced on-line synthesis of $^{11}C$phosgene and the preparation of some of its derivatives. Int J Appl Radiat Isot 1981;32:931-932.
  19. Diksic M, Jolly D, Farrokhzad S. An on-line synthesis of "no-carrier- added" [$^{11}C$]phosgene. Int J Nucl Med Biol 1982;9:283-285. https://doi.org/10.1016/0047-0740(82)90089-4
  20. Landais P, Crouzel C. A new synthesis of carbon-11 labelled phosgene. Appl Radiat Isot 1987;38:297-300. https://doi.org/10.1016/0883-2889(87)90042-6
  21. Ogawa M, Takada Y, Suzuki H, Nemoto K. Fukumura T. Simple and effective method for producing [$^{11}C$] phosgene using an environmental $CCl_4$ gas detection tube. Nucl Med Biol 2010;37:73-76. https://doi.org/10.1016/j.nucmedbio.2009.08.008
  22. Kihlberg T, Karimi F, Langstrom B. [$^{11}C$]Carbon monoxide in selenium- mediated synthesis of $^{11}C$-carbamoyl compounds. J Org Chem 2002;67:3687-3692. https://doi.org/10.1021/jo016307d
  23. Rahman O, Llop J, Langstrom B. Organic bases as additives to improve the radiochemical yields of [$^{11}C$]ketones prepared by the Suzuki coupling reaction. Eur J Org Chem 2004;2004:2674-2678. https://doi.org/10.1002/ejoc.200400038
  24. Rahman O, Kihlberg T, Langstrom B. Synthesis of $^{11}C$-/$^{13}C$-ketones by suzuki coupling. Eur J Org Chem 2004;2004:474-478. https://doi.org/10.1002/ejoc.200300527
  25. Eriksson J, Aberg O, Langstrom B. Synthesis of [$^{11}C$]/[$^{13}C$]acrylamides by palladium-mediated carbonylation. Eur J Org Chem 2007;2007:455-461. https://doi.org/10.1002/ejoc.200600700
  26. Miller PW, Long NJ, de Mello AJ, Vilar R, Audrain H, Bender D, Passchier J, Gee A. Rapid multiphase carbonylation reactions by using a microtube reactor: applications in positron emission tomography $^{11}C$-radiolabeling. Angew Chem Int Ed 2007;46:2875-2878. https://doi.org/10.1002/anie.200604541
  27. 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: 505-512. https://doi.org/10.1016/0020-708X(82)90003-5
  28. Lerch RA, Bergmann SR. Assessment of myocardial metabolism with $^{11}C$-palmitate. Comparison with $^{123}I$-heptadecanoic acid. Eur Heart J 1985;6(Suppl B):21-27.
  29. van der Meij M, Carruthers NI, Herscheid JDM, Jablownowski JA, Leysen JE, Windhorst AD. Reductive N-alkylation of secon dary amines with [2-$^{11}C$]acetone. J Labelled Compd Radiopharm 2003;46:1075-1085. https://doi.org/10.1002/jlcr.740
  30. Bolster JM, Vaalburg W, Elsinga PhH, Woldring MG, Wynberg H. Synthesis of carbon-11 labelled glycine and the dipeptides L-phenylalanylglycine and L-leucylglycine. Int J Rad Appl Instrum A 1986;37:985-987. https://doi.org/10.1016/0883-2889(86)90251-0
  31. Chakraborty PK, Mangner TJ, Chugani HT. The synthesis of no-carrier-added [$^{11}C$]urea from [$^{11}C$] carbon dioxide and application to [$^{11}C$]uracil synthesis. Appl Radiat Isot 1997;48:619-621.
  32. Hooker JM, Reibel AT, Hill SM, Schueller MJ, Fowler JS. One-Pot, direct incorporation of [$^{11}C$]$CO_2$ into carbamates. Angew Chem Int Ed 2009;48:3482-3485. https://doi.org/10.1002/anie.200900112
  33. Wilson AA, Garcia A, Houle S, Vasdev N. Direct fixation of [$^{11}C$]-$CO_2$ by amines: formation of [$^{11}C$-carbonyl]-methylcarbamates. Org Biomol Chem 2010;8:428-432. https://doi.org/10.1039/B916419G
  34. Wilson AA, Garcia A, Houle S, Sadovski O, Vasdev N. Synthesis and application of isocyanates radiolabeled with carbon-11. Chemistry 2011;17:259-264. https://doi.org/10.1002/chem.201002345
  35. Hooker JM, Kim SW, Reibel AT, Alexoff D, Xu Y, Shea C. Evaluation of [$^{11}C$]metergoline as a PET radiotracer for 5HTR in nonhuman primates. Bioorg Med Chem 2010;18:7739-7745. https://doi.org/10.1016/j.bmc.2010.04.039
  36. Hooker JM, Kim SW, Alexoff D, Xu Y, Shea C, Reid A, Volkow N, Fowler JS. Histone deacetylase inhibitor, MS-275, exhibits poor brain penetration: PK studies of [$^{11}C$]MS-275 using Positron Emission Tomography. ACS Chem Neurosci 2010;1:65-73. https://doi.org/10.1021/cn9000268
  37. Vasdev N, Garcia A, Stableford WT, Young AB, Meyer JH, Houle S, Wilson AA. Synthesis and ex vivo evaluation of carbon-11 labelled N-(4-methoxybenzyl)-N'-(5-nitro-1,3-thiazol-2-yl)urea ([$^{11}C$]AR-A014418): a radiolabelled glycogen synthase kinase- 3beta specific inhibitor for PET studies. Bioorg Med Chem Lett 2005;15:5270-5273. https://doi.org/10.1016/j.bmcl.2005.08.037
  38. Hicks JW, Wilson AA, Rubie EA, Woodgett JR, Houle S, Vasdev N. Towards the preparation of radiolabeled 1-aryl-3-benzyl ureas: Radiosynthesis of [$^{11}C$-carbonyl] AR-A014418 by [$^{11}C$]$CO_2$ fixation. Bioorg Med Chem Lett 2012;22:2099-2101. https://doi.org/10.1016/j.bmcl.2011.12.139
  39. Hicks JW, Parkes J, Sadovski O, Tong J, Houle S, Vasdev N, Wilson AA. Synthesis and preclinical evaluation of [$^{11}C$-carbonyl] PF-04457845 for neuroimaging of fatty acid amide hydrolase. Nucl Med Biol 2013;40:740-746. https://doi.org/10.1016/j.nucmedbio.2013.04.008
  40. Wilson AA, Garcia A, Houle S, Vasdev N. Direct fixation of [$^{11}C$]-$CO_2$ by amines: formation of [$^{11}C$-carbonyl]-methylcarbamates Org Biomol Chem 2010;8:428-432. https://doi.org/10.1039/B916419G
  41. Wilson AA, Garcia A, Parkes J, Houle S, Tong J, Vasdev N. [$^{11}C$]CURB: Evaluation of a novel radiotracer for imaging fatty acid amide hydrolase by positron emission tomography. Nucl Med Biol 2011;38:247-253. https://doi.org/10.1016/j.nucmedbio.2010.08.001
  42. Riss PJ, Lu S, Telu S, Aigbirhio FI, Pike VW. Cu(I)-catalyzed $^{11}C$-carboxylation of boronic acid esters: a rapid and convenient entry to $^{11}C$-labeled carboxylic acids, esters and amides. Angew Chem Int Ed 2012; 51: 2698-2702. https://doi.org/10.1002/anie.201107263
  43. Vasdev N, Sadovski O, Garcia A, Dolle F, Meyer JH, Houle S, Wilson AA. Radiosynthesis of [$^{11}C$]SL25.1188 via [$^{11}C$]$CO_2$ fixation for imaging monoamine oxidase B. J Labelled Compd Radiopharm 2011;54:678-680. https://doi.org/10.1002/jlcr.1908