[13N] Labeled Tracers, Synthesis and Applications

  • R. S. Tilbury
  • A. M. Emran

Abstract

This article presents a review of the methods of production and yields of 13N and [13N]-labeled compounds, and their use in medicine and other biosciences. New techniques have been developed for the preparation of pure samples of [13N]-NH3, [13N]-NO3 and [13N]-NO2 using a recirculating water target. A number of methods have been developed for the enzymatic synthesis of [13N]-labeled amino acids (glutamine, glutamate, asparagine, and citrulline) and the distribution and metabolic fate of many of these have been determined in animals. Some studies in humans have also been performed. Chemical methods have been devised for the synthesis of [13N]-labeled nitroso compounds, biogenic amines, and for cis-platin.

Keywords

Glutamate Dehydrogenase Radiochemical Yield Label Amino Acid Asparagine Synthetase Carbamyl Phosphate 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. Austin, S.M., Galonsky, A., Bortins, J. and Wolk, C.P., 1975, Nucl. Instr. Meth. 126:373.Google Scholar
  2. Barrio, J.R., Baumgartner, F.J., Eberhard, H., Stauber, M.S., Egbert, J.E., MacDonald, N.S., Schelbert, H.R., Phelps, M.E., Liu, F.T., 1983, J. Nucl. Med. 24:937.Google Scholar
  3. Bergman, S.R., Fox, K.A., Geltman, E.M., Sobel, B.E. 1985 Progress In Cardiovascular Diseases 28:165.Google Scholar
  4. Buckingham, P.D. and Forse, G.R., 1963, Int. J. Appl. Radiat. Isot. 14:439.Google Scholar
  5. Calderon, J., Cooper, A.J., Gelbard, A.S., Mora, J., 1989, J. of Bacteriol. 171: 1772.Google Scholar
  6. Ciofetta, G., Ronchettì, R., Silverman, M., 1989, Europ. Respir. J. Suppl. 2:171S.Google Scholar
  7. Cohen, M.B., Spolter, L., Chang, C.C., MacDonald, N.S., Takahashi, J., Bobinet, D.D., 1974, J. Nucl. Med. 15:1192.Google Scholar
  8. Cohen, M.B., Spolter, L., MacDonald, N., Chang, C.C., Takahashi, J., 1975, in Radiopharmaceuticals, Society of Nuclear Medicine, New York.Google Scholar
  9. Cohen, M.B., Spolter, L., MacDonald, N., Masuoka, D.T., Laws, S., Neely, H.H., Takahashi, J., 1973, Radiopharmaceuticals Labelled Compounds IAEA, Vienna, Vol. 1, 483–490.Google Scholar
  10. Conlon, K.C., Bading, J.R., DiResta, G.R., Corbally, M.T., Gelbard, A.S., Brennan, M.F., 1989, Life Sciences 44:847–859.Google Scholar
  11. Cooper, A.J., Nieves, E., Rosenspire, K.C., Filc-DeRicco, S., Gelbard, A.S., Brusilow, S.W., 1988, J. Biol. Chem. 263:12268.Google Scholar
  12. Cooper, A.J.L., McDonald, J.M., Gelbard, A.S., Gledhill, R.F., Duffy, T.E., 1979, J. Biol. Chem. 254:4982–4992.Google Scholar
  13. Curie, I. and Joliot, F., 1934, Compt. Rendu. 198, 254. Daube, M.E., Nickles, R.J., 1985, Int. J. Nucl. Med. Biol. 12:303.Google Scholar
  14. De Spiegeleer, B., Slegers, G., Vandecasteele, C., VanDenBossche, W., Schelstraete, K., Claeys, A., DeMoerloose, P., 1986, J. Nucl. Med. 27:399.Google Scholar
  15. DeVis, K., Schelstraete, K., Deman, J., Vermeulen, F.L., Sambre, J., Goethals, P., VanHaver, D., Siegers, G., Vandecasteele, C., DeSchryver, A., Acta Oncologica 26:105.Google Scholar
  16. Digenis, G.A., Cheng, Y.C., McQuinn, R.L., Freed, B.R., Tilbury, R.S., 1980, in Short-Lived Radionuclides in Chemistry and Biology, J.W. Root., Ed., American Chemical Society, Washington, D.C.Google Scholar
  17. Digenis, G.A., McQuinn, R.L., Freed, B., Tilbury, R.S., Reiman, R.E., Cheng, Y.C., 1979, J. Lab. Compds. Radiopharm. 16:95.Google Scholar
  18. Elmaleh, D.R., Hantowich, D.J, Kulprathipanja, S., 1979, J. Lab. Compds. Radiopharm. 16: 92.Google Scholar
  19. Emran, A.M., “Synthesis of 13N and/or 11C single or doubly labelled urea”, in Proceedings of the 197th. ACS National Meeting, Dallas, Texas, April, 1989.Google Scholar
  20. Emran, A.M., Vora, M.M., Finn, R.D., Carroll, S.T., Boothe, T.E., and Kothari, P.J., 1984 “Synthesis of Nitrogen13-labelled Diphenylhydantoin (DPH) Radiopharmaceutical” in Proceedings of the American Pharmaceutical Association, Philadelphia, PA.Google Scholar
  21. Ferrieri, R.A., Schlyer, D.J., Wieland, B.W., Wolf, A.P., 1983, Int. J. Appl. Radiat. Isot. 34:897.Google Scholar
  22. Finn, R.D., Christman, D.R., Wolf, A.P., 1980, J. Lab. Compds. Radiopharm. 18:909.Google Scholar
  23. Fowler, J.S. and Wolf, A.P. “Positron Emitter-labeled compounds: Priorities and Problems,” in Positron Emission Tomography and Autoradiography:Principles and Appications for the Brain and Heart; M. Phelps, J. Mazziotta and H. Schelbert, Eds., Raven Press, New York.Google Scholar
  24. Freed, B.R., McQuinn, R.L., Tilbury, R.S., Digenis, G.A., 1982, Cancer Chemother. Pharmacol. 10:21.Google Scholar
  25. Fudo, T., Kambara, H., Hashimoto, T., Hayashi, M., Kawai, C., Senda, M., Tamaki, N., Yonekura, Y., 1989, J. Cardiol. 18: 13.Google Scholar
  26. Fudo, T., Kambara, H., Hashimoto, T., Hayashi, M., Nohara, R., Tamaki, N., Yonekura, Y., Senda, M., Konishi, J., Kawai, C., 1988, Amer. J. Cardiol. 61:1191–1197.Google Scholar
  27. Gawlinski, A., 1987, Heart and Lung 16:756–9.Google Scholar
  28. Gelbard, A.S., Clarke, L.P., Laughlin, J.S., 1974, J. Nucl. Med. 15:1223.Google Scholar
  29. Gelbard, A.S., Hara, T., Tilbury, R.S. and Laughlin, J.S., 1973, in “Radiopharmaceuticals and Labelled Compounds”, Volume I, I.A.E.A., Vienna.Google Scholar
  30. Gelbard, A.S., 1981, J. Lab. Compds. Radiopharm. 18:933.Google Scholar
  31. Gelbard, A.S., Kaseman, D.S., Rosenspire, K.C., Meister, A., 1985, Int. J. Nucl. Med. Biol. 12:235.Google Scholar
  32. Ginos, J.Z., Cooper, A.J., Dhawan, V., Lai, J.C., Strother, S.C., Alcock, N.,Rottenberg, D.A., 1987, J. Nucl. Med. 28:1844.Google Scholar
  33. Goldstein, R.A., Kirkeeide, R.L., Smalling, R.W., Nishikawa, A., Merhige, M.E., Demer, L.L., Mullani, N.A., Gould, K.L., 1987, J. Nucl. Med. 28:1262.Google Scholar
  34. Gould, K.L., Goldstein, R.A., Mullani, N.A., Kirkeeide, R.L., Wong, W.H., Tewson, T.J., Berridge, M.S., Bolomey, L.A., Hartz, R.K., Smalling, R.W., 1986, J. Amer. Coll. Cardiol. 7: 775.CrossRefGoogle Scholar
  35. Haber, M.T., Cooper, A.J.L., Rosenspire, K.C., Ginos, J.Z., Rottenberg, D.A., 1984, J. Lab. Compds. Radiopharm. 22:509.Google Scholar
  36. Harper, P.V., Lathrop, K.A., Krizek, H., Lembares, N., Dinwoodie, R. 1975 in “Radiopharmaceuticals,” Subramanian G., Editor, Society of Nuclear Medicine, N.Y.Google Scholar
  37. Harper, P.V., Lathrop, K.A., Krizek, H., Lembares, N., Stark, V, Hoffer, P.B. 1971, J. of Nucl. Med. 13:278.Google Scholar
  38. Harper, P.V., Schwartz, J., Beck, R.N., Lathrop, K.A., Lembares, N., Krizek, H., Gloria, I., Dinwoodie, R., McLauglin, A., Stark, V.J., Bekerman, C., Hoffer, P.B., Gottschalk, A., Resnekov, L., Al-Sadir, J., Mayorga, A., Brooks, H.L. 1973, Radiology 108: 613.Google Scholar
  39. Heselius, S.J., Schlyer, D.J., Wolf, A.P., 1989, Int. J. Radiat. Applic. Instrum. 40:663.Google Scholar
  40. Himi, T., Kagaya, A., Yoshida, K., Morooka, N., Watanabe, S., Masuda, Y., Inagaki, Y., Endo, M., Yamazaki, T., Tateno, Y., 1987, J. of Cardiol. 17: 831.Google Scholar
  41. Irie, T., Inoue, O., Suzuki, K., Tominaga, T., 1985, Int. J. Appl. Radiat. Isot. 36:345.Google Scholar
  42. Jones, S.C., Bucelewicz, W.M., Brissette, R.A., Subramanyam, R., Hoop, B. Jr., 1977, Int. J. Appl. Radiat. Isot. 28:25.Google Scholar
  43. Kambara, H., Nohara, R., Kawai, C., Yonekura, Y., Senda, M., Torizuka, K., 1986, J. Cardiography 16:519.Google Scholar
  44. Kaseman, D.S., Cooper, A.J.L., Meister, A., 1984, J. Lab. Compds. Radiopharm. 21:803.Google Scholar
  45. Kazemi, H., 1987, Europ. J. Nucl. Med. 13:S42.Google Scholar
  46. Knapp, W.H., Helus, F., Layer, K., Panzer, M., Hover, K.H., Ostertag, H., 1986, J. Nucl. Med. 27:1604.Google Scholar
  47. Knapp, W.H., Helus, F., Sinn, H., Ostertag, H., Georgi, P., Brandeis, W-E, Braun, A., 1984, J. Nucl. Med. 25:989.Google Scholar
  48. Knapp, W.H., Panzer, M., Helus, F., Layer, K., Sinn, H.J., Ostertag, H., 1988, J. Nucl. Med. 29:208.Google Scholar
  49. Kothari, P.J., Finn, R.D., Kabalka, G.W., Vora, M.M., Boothe, T.E., Emran, A.M., 1986, Int. J. Radiat. Applic. Instrum. 37:469.Google Scholar
  50. Krivokapich, J., Keen, R.E., Phelps, M.E., Shine, K.I., Barrio, J.R., 1987, Circ. Res. 60:505.Google Scholar
  51. Krizek, H, Lembares, N., Dinwoodie, I., Gloria, I, Lathrop, K.A., Harper, P.V., 1973, J. Nucl. Med. 14:629.Google Scholar
  52. Lambrecht, R.H.D., Slegers, A., Claeys, A., Gillis, E., Vandecasteele, C., 1983, J. Radiochem. Radioanal. Let. 58:39.Google Scholar
  53. Lambrecht, R.H.D., Siegers, G., Mannens, G., Claeys, A., 1987, Enzyme Microbial Technology 9: 221.Google Scholar
  54. Lambrecht, R.M and Sajjad, M., 1988, “Radiochemistry of Carbon, Nitrogen and Oxygen” Office of Scientific and Technical Information, U.S. Department of Energy, Washington, D.C.Google Scholar
  55. Lathrop, K.A., Harper, P.V., Rich, B.H., Dinwoodie, R., Krizek, H., Lembares, N. and Gloria, I 1973, in “Radiopharmaceuticals Labelled Compounds”, Volume I, I.A.E.A., Vienna.Google Scholar
  56. Lembares, N, Dinwoodie, R., Gloria, I., Lathrop, K.A., Bautovich, G., Harper, P.V., 1973, Rapid Incorporation of Short-Lived Cyclotron-Produced Radionuclides into Radiopharmaceuticals. J. Nucl. Med. 14:630.Google Scholar
  57. Lockwood, A.H., McDonald, J.M.,Reiman, R.E., Gelbard, A.S., Laughlin, J.S.,Duffy, T.E., Plum, F., 1979, J. Clin. Invest. 63:449.Google Scholar
  58. Majumdar, C., Lathrop, K.A., Harper, P.V., 1977, J. Lab. Compl. Radiopharm. 13:206.Google Scholar
  59. Mellenberg, D.E., Tilbury, R.S., Hogstrom, K.R., 1988, Int. J. Radiat. Applic. Instrum. 15: 631.CrossRefGoogle Scholar
  60. Mulholland, G.K., 1990, Appl. Radiat. Isot. in press. Murata, K., Itoh, H., Senda, M., Todo, G., Vonekura, Y., Torizuka, K., 1986, Radiology 158:303.Google Scholar
  61. Nickles, R.J., Gatley, S.J., Hichwa, R.D., Simpkin, D.J., Martin, J.L., 1978, Int. J. Appl. Radiat. Isot. 29:225.Google Scholar
  62. Nickles, R.J., Gatley, S.J., Madsen, M.T., Hichwa, R.D., Martin, J.L., Simpkin, D.J., Halama, J.R., 1979, J. Lab. Compds. Radiopharm. 16:90.Google Scholar
  63. Nieves, E., Rosenspire, K.C., Filc-DeRicco, S., Gelbard, A.S., Cooper, A.J., 1986, J. Chrom. 383:325.Google Scholar
  64. Parks, N.J. and Krohn, K.A., 1978, Int. J. Appl. Radiat. Isot. 29, 754.Google Scholar
  65. Parks, N.J. Appl. Nucl., 1982, Appl. Nucl. Radiochem. 15.Google Scholar
  66. Patt, J.T., Nebelling, B. and Stocklin, G., 1990, in Proceedings of Eighth Symposium on Radiopharmaceutical Chemistry. J. Lab. Compds. Radiopharm., in press. Google Scholar
  67. Pettit, W.A., 1979, IEEE Transactions on Nuclear Science NS-26:1718.Google Scholar
  68. Pettit, W.A., Tilbury, R.S., Digenis, G.A., Mortara, R.H., 1977, J. Lab. Compds. Radiopharm. 13:119.Google Scholar
  69. Schelbert, H.R., 1985, Circulation 72:122.Google Scholar
  70. Schwaiger, M., Brunken, R., Grover-McKay, M., Krivokapich, J., Child, J., Tillisch, J.H., Phelps, M.E., Schelbert, H.R., 1986, J. Amer. Col. Cardiol. 8:800–808.Google Scholar
  71. Schwaiger, M., 1986, Europ. J. Nucl. Med. 12:54.Google Scholar
  72. Senda, M., Murata, K., Itoh, H., Yonekura, Y., Torizuka, K., 1986, J. Nucl. Med. 27:268.Google Scholar
  73. Shibata, T., Yamamoto, K., Hayashi, N., Yonekura, Y., Nagara, T., Saji, H, Mukai, T., Konishi, J., 1988, Europ. J. Nucl. Med. 14:607.Google Scholar
  74. Slegers, G., Van Decasteele, C., Sambre J., 1980, Farmaceutisch Tijdschrift Voor Belgie 57: 369.Google Scholar
  75. Siegers, G., Van Decasteele, Sambre J., 1980, J. of Radioanal. Chem. 59:2585.Google Scholar
  76. Sordillo, P.P., Benua, R.S., Gelbard, A.S., Bading J., Reiman, R.E., Magill, G.B., Laughlin, J.S., 1986, Amer. J. Physiologic Imaging 1:195.Google Scholar
  77. Spolter, L., Cohen, M.B., Chang, C.C., MacDonald, N.S., 1977, J. Lab. Compds. Radiopharm. 13:204.Google Scholar
  78. Straatmann, M.G., 1977, Int. J. Appl. Radiat. Isot. 28:13.Google Scholar
  79. Suzuki, K., Iwata, R., 1977, Radiochem. Radioanal. 28:263.Google Scholar
  80. Suzuki, K., Tamate, K., 1984, Int. J. Appl. Radiat. Isot. 35:771.Google Scholar
  81. Tamaki, N., Yonekura, Y., Kodama, S., Senda, M., Saji, H., Torizuka, K., Kambara, H., Kawai, C., Konishi, Y., Ban, T., 1985, J. Cardiography 15:553.Google Scholar
  82. Tamaki, N., Yonekura, Y., Senda, M., Kureshi, S.A., Saji, H., Kodema, S., Konishi, Y., Ban, T., Kambara, H., Kawai, C, 1985, Europ. J. Nucl. Med. 11:246.Google Scholar
  83. Tamaki, N., Yonekura, Y., Senda, M., Yamashita, K., Koide, H., Saji, H., Hashimoto, T., Fudo, T., Kambara, H., Kawai, C, 1988, J. Nucl. Med. 29:1181.Google Scholar
  84. Tamaki, N., Yonekura, Y., Yamashita, K., Senda, M., Saji, H., Hashimoto, T., Fudo, T., Kambara, H., Kawai, C., Ban, T., 1988, Amer. J. Cardiol. 62:202.Google Scholar
  85. Tamaki, N., Yonekura, Y., Yamashita, K., Senda, M., Saji, H., Konishi, Y., Hirata, K., Ban, T., Konishi, J., 1989, J. Nucl. Med. 30:1302.Google Scholar
  86. Thomas, D.G., Gibbs, J.M., Wise, R.J., 1985, Clin. Neurosurg. 32:51.Google Scholar
  87. Tilbury, R.S., Dahl, J.R., Monahan, W.G., Laughlin, J.S., 1971, Radiochem. Radioanal. Let. 8:317.Google Scholar
  88. Tilbury, R.S., Dahl, J.R., 1979, Radiat. Res. 79:22.Google Scholar
  89. Tillisch, J., Brunken, R., Marshall, R., Schwaiger, M., Mandelkern, M., Phelps, M., Schelbert, H., 1986, New Engl. J. Med. 314: 884.PubMedCrossRefGoogle Scholar
  90. Tominaga, T., Inoue, O., Irie, T., Suzuki, K., Yamasaki, T., Hirobe, M., 1985, Int. J. Appl. Radiat. Isot. 36:555.Google Scholar
  91. Tominaga, T., Inoue, O., Suzuki, K., Yamasaki, T., Hirobe, M., 1987, Biochem. Pharmcol. 36:3671.Google Scholar
  92. Tominaga, T., Inoue, O., Suzuki, K., Yamasaki, T., Hirobe, M., 1986, Int. J. Appl. Radiat. Isot. 1209.Google Scholar
  93. Tominaga, T., Inoue, O., Suzuki, K., Yamazasi, T., Hirobe, M., 1987, Int. J. Radiat. Applic. Instrum. 14:485.Google Scholar
  94. Tominaga, T., Inoue, E., Suzuki, K., Yamazaki, T., Hirobe, M., 1987, Int. J. Radiat. Applic. Instrum. 14:491.Google Scholar
  95. Torizuka, K., 1987, J. Cardiography 17:107.Google Scholar
  96. Torizuka, K., Koga, S., 1987, J. Cardiology 17:51.Google Scholar
  97. Vaalburg, W. Kamphuis, J.A.A., Beerling-Van-Der, Molen, H.D., Reiffers, S., Rijskamp, A. and Woldring, M.G., 1975, Int. J. Appl. Radiat. Isot. 26:316.Google Scholar
  98. Vaalburg, W., Steenhoek, A., Paans, A.M.J., Peset, R., Reiffers, S., Woldring, M.G., 1981, J. Lab. Compds. Radiopharm., 18:303.Google Scholar
  99. Vandecasteele, C., 1981, IEEE Transaction on Nuclear Science NS-28:1928.Google Scholar
  100. Weinberg, I.N., Huang, S.C., Hoffman, E.J., Araujo, L., Nienaber, C., Grover-McKay, M., Dahlbom, M., Schelbert, H., 1988, J. Nucl. Med. 29: 241.PubMedGoogle Scholar
  101. Welch, M.J., 1986, Chem. Commun. 1354.Google Scholar
  102. Yonekura, Y., Senda, M., Torizuka, K., 1987, J. Cardiol. 17:65.Google Scholar
  103. Yonekura, Y., Tamaki, N., Senda, M., Nohara, R., Kambara, H., Konishi, Y., Koide, H., Kureshi, S.A., Saji, H., Ban, T., 1987, Amer. Heart J. 113:645.Google Scholar
  104. Yoshida, K., Himi, T., Imai, H., Shukuya, M., Masuda, Y., Inagaki, Y., Yamasaki, T., Tateno, Y., 1985, J. Cardiography 15: 377.Google Scholar
  105. Yoshida, K., Himi, T., Shukuya, M., Masuda, Y., Inagâki, Y., Endo, M., Fukuda, N., Yamasaki, T., Iinuma, T., Tateno, Y., 1986, Eur. J. Nucl. Med. 12:226.Google Scholar
  106. Yoshida, K., Himi, T., Shukuya, M., Masuda, Y., Inagaki, Y., Endo, M., Yamasaki, T., Tateno, Y., 1987, J. of Cardiol. 17: 55.Google Scholar
  107. Zimmerman, R., Tillmanns, H., Knapp, W.H., Helus, F., Georgi, P., Rauch, B., Neumann, F.J., Girgensohn, S., Maier-Bosrt, W., Kubler, W., 1988, J. Amer. Col. Cardiol. 11:549.Google Scholar

Copyright information

© Springer Science+Business Media New York 1991

Authors and Affiliations

  • R. S. Tilbury
    • 1
  • A. M. Emran
    • 2
  1. 1.Division of Diagnostic ImagingThe University of Texas M.D. Anderson Cancer CenterHoustonUSA
  2. 2.Cyclotron Facility, Positron Diagnostic and Research CenterThe University of Texas Health Science CenterHoustonUSA

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