Nuclear Medicine and Biology
Volume 35, Issue 7 , Pages 741-746 , October 2008

A convenient solution-phase method for the preparation of meta-iodobenzylguanidine in high effective specific activity

Received 17 April 2008 ,Revised 14 July 2008 ,Accepted 24 July 2008.

References 

  1. Eckelman WC. Radiolabeling with technetium-99m to study high-capacity and low-capacity biochemical systems. Eur J Nucl Med. 1995;22:249–263
  2. Eckelman WC, Gibson RE. The Design of site-directed radiopharmaceuticals for use in drug discovery. In:  Burns HD,  Gibson RE,  Dannals RF,  Siegl PKS editor. Nuclear imaging in drug discovery, development and approval. Boston: Birkhäusser; 1993;p. 113–134
  3. Vaidyanathan G, Zalutsky MR. No-carrier-added Synthesis of meta-[131I]Iodobenzylguanidine. Appl Radiat Isotopes. 1993;44:621–628
  4. Mairs RJ, Russel J, Cunningham S, O'Donoghue JA, Gaze MN, Owens J, et al. Enhanced tumour uptake and in vitro radiotoxicity of no-carrier-added [131I]meta-iodobenzylguanidine: implications for the targeted radiotherapy of neuroblastoma. Eur J Cancer Res. 1995;31A:576–581
  5. Eersels JLH, Travis MJ, Herscheid JDM. Manufacturing I-123-labelled radiopharmaceuticals. Pitfalls and solutions. J Label Compd Radiopharm. 2005;48:241–257
  6. Tepmongkol S, Heyman S. 131I MIBG Therapy in neuroblastoma: mechanisms, rationale, and current status. Med Pediatr Oncol. 1999;32:427–431
  7. Mairs RJ, Gaze MN, Watson DG, Skellern GG, Constable P, McKellar K, et al. Carrier-free 131I-meta-iodobenzylguanidine: comparison of production from meta-diazobenzylguanidine and from meta-trimethylsilylbenzylguanidine. Nucl Med Commun. 1994;15:268–274
  8. Vaidyanathan G, Affleck DJ, Alston KL, Zalutsky MR. A tin precursor for the synthesis of no-carrier-added [*I]MIBG and [211At]MABG. J Label Compd Radiopharm. 2007;50:177–182
  9. Hunter DH, Xizhen Z. Polymer-supported radiopharmaceuticals: [131]MIBG and [123]MIBG. J Label Compd Radiopharm. 1999;42:653–661
  10. Donovan A, Forbes J, Dorff P, Schaffer P, Babich J, Valliant JF. A new strategy for preparing molecular imaging and therapy agents using fluorine-rich (fluorous) soluble supports. J Am Chem Soc. 2006;128:3536–3537
  11. Vaidyanathan G, Affleck DJ, Alston KL, Zhao XG, Hens M, Hunter DH, et al. A kit method for the high level synthesis of [211At]MABG. Bioorg Med Chem. 2007;15:3430–3436
  12. Shah VP, Midha KK, Findlay JWA, Hill HM, Hulse JD, McGilveray IJ, et al. Bioanalytical method validation — a revisit with a decade of progress. Pharm Res. 2000;17:1551–1557
  13. Djuric S, Venit J, Magnus P. Silicon in synthesis: Stabase adducts — a new primary amine protecting group: alkylation of ethy glycinate. Tetrahedron Lett. 1981;22:1787–1790
  14. Kabalka GW, Namboodiri V, Akula MR. Synthesis of 123I labeled Congo red via solid-phase organic chemistry. J Label Compd Radiopharm. 2001;44:921–929
  15. Coenen HH, Morelein SM, Stöcklin G. No-carrier-added radiohalogenation methods with heavy halogens. Radiochim Acta. 1983;34:47–68
  16. Coenen HH, Mertens J, Mazière B. Radioiodination reactions for radiopharmaceuticals. Dordrecht: Springer; 2006;
  17. Clayden J. Organolithiums: selectivity for synthesis. New York: Pergamon; 2002;
  18. Maryanoff CA, Stanzione RC, Plampin JN, Mills JE. A convenient synthesis of guanidines from thioureas. J Org Chem. 1986;51:1882–1884
  19. Kim K, Lin YT, Mosher HS. Monosubsitituted guanidines from primary amines and aminoiminomethanesulfonic acid. Tetrahedron Lett. 1988;29:3183–3186
  20. Bernatowicz MS, Wu Y, Matsueda GR. 1H-Pyrazole-1-carboxamidine hydrochloride: an attractive reagent for guanylation of amines and its application to peptide synthesis. J Org Chem. 1992;57:2502–2504
  21. Robinson S, Roskamp EJ. Solid phase synthesis of guanidines. Tetrahedron. 1997;53:6697–6705
  22. Fui Y, Kowalski JA, Thoen JC, Lipton MA. A new reagent for solid and solution phase synthesis of protected guanidines from amines. Tetrahedron Lett. 1999;40:53–56
  23. Marcel P, Smrcina M, Nakanishi E, Izawa H. Solid-phase synthesis of substituted guanidines using a novel acid labile linker. J Comb Chem. 2000;2:370–377
  24. Linton BR, Carr AJ, Orner BP, Hamilton AD. A versatile one-pot synthesis of 1,3-substituted guanidines from carbamoyl isothiocyanates. J Org Chem. 2000;65:1566–1568
  25. Li M, Wilson LJ, Portlock DE. A simple solid-phase synthesis of disubstituted guanidines using rink amide resin as an amine component. Tetrahedron Lett. 2001;42:2273–2275
  26. Permittivity (dielectric constant) of liquids. In: Lide DR, editor. CRC Handbook of Chemistry and Physics. 88th ed. Boca Raton (Fla): CRC Press/Talor and Francis; Internet Version 2008.
  27. Beekman FJ, McElroy DP, Berger F, Gambir SS, Hoffman EJ, Cherry SR. Towards in vivo nuclear microscopy: iodine-125 imaging in mice using micro-pinholes. Eur J Nucl Med. 2002;29:933–938
  28. Salacinski PR, McLean C, Sykes JE, Clement-Jones VV, Lowry PJ. Iodination of proteins, glycoproteins, and peptides using a solid-phase oxidizing agent, 1,3,4,6-tetrachloro-3α-6α-diphenyl glycoluril (iodogen). Anal Biochem. 1981;117:136–146

PII: S0969-8051(08)00175-3

doi: 10.1016/j.nucmedbio.2008.07.006

Nuclear Medicine and Biology
Volume 35, Issue 7 , Pages 741-746 , October 2008

Article Tools

* Image Usage & Resolution