Journal of Nuclear Science, Engineering and Technology (JONSAT)
In cooperation with the Iranian Nuclear Society

Investigation of Radioiodination of Meta-Iodobenzylguanidine Compound with 131I Isotope in Solid Phase Using Cu Catalyser

Document Type : Research Paper

Authors

M.R Davarpanah
S Attar Nosrati
H.A Khoshhosn
M Kazemi Boudani
M Fazlali
M Ghannadi Maragheh
Abstract
In this study the radioiodination process of meta-iodobenzylguanidine with 131I isotope in presence of ammonium sulphate and Cu(II) Catalyser was investigaded. In order to optimize the process, the influence of different parameters on labeling yield was studied. The results of experiments showed that the use of oil bath with temperature of 160˚C is necessary. After the labeling process, purification step of the final product was carried out using Dowex-1x8 resin. The mean labeling yield was 97.2%. In this method radiolabelling of MIBG with 131I (185 MBq for diagnostic dose and 3330 MBq for therapeutic dose) is quite simple and it complies with the requirements of routine production of 131I-MIBG radiopharmaceutical for diagnostic and therapeutic purposes. This paper is a narration of industrial scale production of 131I-MIBG radiopharmaceutical

Highlights

  1. 1.    B. Kimming, W.E. Brandeis, M. Eisenhut, “Scintigraphy of a neuroblastoma with I-I31 meta-iodobenzylguanidine,” J. Nucl. Med., 25, 773-775 (1984).

 

  1. 2.    L. Troncone, V. Rufini, P. Montemaggi, “The diagnostic and therapeutic utility of radioiodinated MIBG,” Eur. J. Nucl. Med, 16, 325-350 (1989).

 

  1. 3.    M. Nakajo, B. Shapiro, J. Glowniak, “Inverse relationship of 1311-meta iodobenzylguanidine (131I-MIBG) heart accumulation to circulating catecholamines: Observations in patients suspected of having pheochromocytoma,” J. Nucl. Med, 24, 1127-1134 (1983).

 

  1. 4.    D.M. Wieland, J. Wu, L.E. Brown, T.J. Mangner, “Radioiodinated adrenergic neuron-blocking agents: adrenomedullary imaging [131I] iodobenzylguanidine,” J. Nucl. Med, 21, 349-353 (1980).

 

  1. 5.    J.C. Sisson, B.C. Shapiro, W.H. Beierwaltes, “Radiopharmaceutical treatment of malignant pheochromocytoma,” J. Nucl. Med, 25, 197-206 (1983).

 

  1. 6.    W.H. Beierwaltes, “Applications of [131I] m-iodobenzylguanidine (131I-MIBG),” Nucl. Med. Biol, 14, 183-189 (1987).

 

  1. 7.    J.C. Sisson, M.S. Frager, T.W. Valk, “Scintigraphic localization of pheochromocytoma,” Eng.J. Med, 305, 12-17 (1981).

 

  1. 8.    M. Nakajo, B. Shapiro, J. Copp, “The normal and abnormal distribution of the adrenomedullary imaging agent m- [131I]-iodobenzylguanidine (I-I31 MIBG) in man: Evaluation by scintigraphy,” J. Nucl. Med, 24, 672-682 (1983).

 

  1. 9.    C.A. Hoefnagel, “Metaiodobenzylguanidine and somatostatin in oncology: role in the management of neural crest tumours,” Eur. J. Nucl. Med, 21, 561-581 (1994).

 

 

  1. T.W. Valk, M.S. Frager, M.D. Gross, “Spectrum of pheochromocytomas in multiple endocrine neoplasia. A scintigraphic portrayal using 131I-meta-iodobenzyl guanidine,” Ann Intern. Med, 94,762-767 (1981).

     

  2. A.R. Wafelman, M.C. Konings, C.A. Hoefnagel, R.A. Maes, J.H. Beijnen, “Synthesis, radiolabelling and stability of radioiodinated m iodobenzylguanidine, a review,” Appl. Radiat. Isot, 45, 997–1007 (1994).

 

  1. B.J. McBride, R.M. Baldwin, J.M. Kerr, J.L. Wu, “A simple method for the preparation of 123I- and 125I-labelled iodobenzodiazepines,” Appl. Radiat. Isot, 42, 173–175 (1990).

 

  1. G. Vaidyanathan, M.R. Zalutsky, “No-carrier-added meta [123I] iodobenzylguanidine: synthesis and preliminary evaluation,” Nucl. Med. Biol, 22, 61–64 (1995).

 

  1. G. Vaidyanathan, M.R. Zalutsky, “No-carrier-added synthesis of meta [131I]iodobenzylguanidine,” Appl. Radiat. Isot., 44, 621–628 (1993).

 

  1. C. Krummeich, M. Holschbach, G. Stocklin, “Direct n.c.a. electrophilic radioiodination of tyrosine analogues; their in vivo stability and brain-uptake in mice,” Appl. Radiat. Isot., 45, 929–935 (1994).

 

  1. B.F. Francis, W.J. Rzeszotarski, W.C. Eckelman, R.C. Reba, “Nucleophilic iodination of 3 quinuclidinyl benzilates,” J. Label. Comp. Radiopharm, 19, 1499–1500 (1982).

 

  1. J. Grassi, P. Pradelles, “Radioiodination and other labelling techniques,” Springer-Verlag, Berlin Heidelberg, New York, 91–141 (1987).

  2. T.J. Mangner, J.L. Wu, D.M. Wieland, “Solid-phase cxchange radioiodination of aryl iodides, Facilitation by ammonium sulfate,” J. Org. Chem, 47, 1484-1488 (1982).

 

  1. S. Chattopadhyay, N. Ramamoorthy, G. Prabhakar, S. Mehra Kiran, “Stabilisation of [131I]meta-iodobenzylguanidine at room temperature as organic extract in ethyl acetate/chloroform,” Appl. Radiat. Isot, 54, 241–244 (2001).

 

  1. J.J.R. Mertens, W. Vanryckeghem, M. Gysemans, “New fast preparation of 123I labelled radiopharmaceuticals,” Eur. J. Nucl. Med, 13, 380-381 (1987).

 

  1. A.S. ElWetery, A.A. ElMohty, S. Ayyoub, M. Raieh, “Catalytic effect of copper(II) chloride on the radioiodination of L-p-iodophenylalanine,” J. Labelled. Compd. Rad, 39, 631–644 (1997).

 

  1. M. Neves, A. Paulo, L. Patricio, “A kit formulation of [131I] meta-iodobenzylguanidine (MIBG) using Cu(I) generated `in situ' by sodium disulphite,” Appl. Radiat. Isot, 43, 737-740 (1992).

 

  1. V.I. Stanko, N.G. Iroshnikova, A.F. Volkov,  A.I. Klimova, “Copper catalyst on isotopic exchange as a novel approach to incorporating iodine and bromine into benzene derivatives,” Appl. Radiat. Isot., 35, 1129-1132 (1984).

 

G. Prabhakara, “Evaluation of radioiodination of meta-iodobenzylguanidine (MIBG) catalysed by in situ generated Cu(I) and directly added Cu(II),” Appl. Radiat. Isot, 50, 1011-1014 (1999).

Keywords

Meta-Iodobenzylguanidine
131I
Radioiodination
Radiolabelling
Radiopharmacetical
  1. 1.    B. Kimming, W.E. Brandeis, M. Eisenhut, “Scintigraphy of a neuroblastoma with I-I31 meta-iodobenzylguanidine,” J. Nucl. Med., 25, 773-775 (1984).

 

  1. 2.    L. Troncone, V. Rufini, P. Montemaggi, “The diagnostic and therapeutic utility of radioiodinated MIBG,” Eur. J. Nucl. Med, 16, 325-350 (1989).

 

  1. 3.    M. Nakajo, B. Shapiro, J. Glowniak, “Inverse relationship of 1311-meta iodobenzylguanidine (131I-MIBG) heart accumulation to circulating catecholamines: Observations in patients suspected of having pheochromocytoma,” J. Nucl. Med, 24, 1127-1134 (1983).

 

  1. 4.    D.M. Wieland, J. Wu, L.E. Brown, T.J. Mangner, “Radioiodinated adrenergic neuron-blocking agents: adrenomedullary imaging [131I] iodobenzylguanidine,” J. Nucl. Med, 21, 349-353 (1980).

 

  1. 5.    J.C. Sisson, B.C. Shapiro, W.H. Beierwaltes, “Radiopharmaceutical treatment of malignant pheochromocytoma,” J. Nucl. Med, 25, 197-206 (1983).

 

  1. 6.    W.H. Beierwaltes, “Applications of [131I] m-iodobenzylguanidine (131I-MIBG),” Nucl. Med. Biol, 14, 183-189 (1987).

 

  1. 7.    J.C. Sisson, M.S. Frager, T.W. Valk, “Scintigraphic localization of pheochromocytoma,” Eng.J. Med, 305, 12-17 (1981).

 

  1. 8.    M. Nakajo, B. Shapiro, J. Copp, “The normal and abnormal distribution of the adrenomedullary imaging agent m- [131I]-iodobenzylguanidine (I-I31 MIBG) in man: Evaluation by scintigraphy,” J. Nucl. Med, 24, 672-682 (1983).

 

  1. 9.    C.A. Hoefnagel, “Metaiodobenzylguanidine and somatostatin in oncology: role in the management of neural crest tumours,” Eur. J. Nucl. Med, 21, 561-581 (1994).

 

 

  1. T.W. Valk, M.S. Frager, M.D. Gross, “Spectrum of pheochromocytomas in multiple endocrine neoplasia. A scintigraphic portrayal using 131I-meta-iodobenzyl guanidine,” Ann Intern. Med, 94,762-767 (1981).

     

  2. A.R. Wafelman, M.C. Konings, C.A. Hoefnagel, R.A. Maes, J.H. Beijnen, “Synthesis, radiolabelling and stability of radioiodinated m iodobenzylguanidine, a review,” Appl. Radiat. Isot, 45, 997–1007 (1994).

 

  1. B.J. McBride, R.M. Baldwin, J.M. Kerr, J.L. Wu, “A simple method for the preparation of 123I- and 125I-labelled iodobenzodiazepines,” Appl. Radiat. Isot, 42, 173–175 (1990).

 

  1. G. Vaidyanathan, M.R. Zalutsky, “No-carrier-added meta [123I] iodobenzylguanidine: synthesis and preliminary evaluation,” Nucl. Med. Biol, 22, 61–64 (1995).

 

  1. G. Vaidyanathan, M.R. Zalutsky, “No-carrier-added synthesis of meta [131I]iodobenzylguanidine,” Appl. Radiat. Isot., 44, 621–628 (1993).

 

  1. C. Krummeich, M. Holschbach, G. Stocklin, “Direct n.c.a. electrophilic radioiodination of tyrosine analogues; their in vivo stability and brain-uptake in mice,” Appl. Radiat. Isot., 45, 929–935 (1994).

 

  1. B.F. Francis, W.J. Rzeszotarski, W.C. Eckelman, R.C. Reba, “Nucleophilic iodination of 3 quinuclidinyl benzilates,” J. Label. Comp. Radiopharm, 19, 1499–1500 (1982).

 

  1. J. Grassi, P. Pradelles, “Radioiodination and other labelling techniques,” Springer-Verlag, Berlin Heidelberg, New York, 91–141 (1987).

  2. T.J. Mangner, J.L. Wu, D.M. Wieland, “Solid-phase cxchange radioiodination of aryl iodides, Facilitation by ammonium sulfate,” J. Org. Chem, 47, 1484-1488 (1982).

 

  1. S. Chattopadhyay, N. Ramamoorthy, G. Prabhakar, S. Mehra Kiran, “Stabilisation of [131I]meta-iodobenzylguanidine at room temperature as organic extract in ethyl acetate/chloroform,” Appl. Radiat. Isot, 54, 241–244 (2001).

 

  1. J.J.R. Mertens, W. Vanryckeghem, M. Gysemans, “New fast preparation of 123I labelled radiopharmaceuticals,” Eur. J. Nucl. Med, 13, 380-381 (1987).

 

  1. A.S. ElWetery, A.A. ElMohty, S. Ayyoub, M. Raieh, “Catalytic effect of copper(II) chloride on the radioiodination of L-p-iodophenylalanine,” J. Labelled. Compd. Rad, 39, 631–644 (1997).

 

  1. M. Neves, A. Paulo, L. Patricio, “A kit formulation of [131I] meta-iodobenzylguanidine (MIBG) using Cu(I) generated `in situ' by sodium disulphite,” Appl. Radiat. Isot, 43, 737-740 (1992).

 

  1. V.I. Stanko, N.G. Iroshnikova, A.F. Volkov,  A.I. Klimova, “Copper catalyst on isotopic exchange as a novel approach to incorporating iodine and bromine into benzene derivatives,” Appl. Radiat. Isot., 35, 1129-1132 (1984).

 

G. Prabhakara, “Evaluation of radioiodination of meta-iodobenzylguanidine (MIBG) catalysed by in situ generated Cu(I) and directly added Cu(II),” Appl. Radiat. Isot, 50, 1011-1014 (1999).

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