Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2012; 44(21): 3387-3391
DOI: 10.1055/s-0032-1316789
DOI: 10.1055/s-0032-1316789
paper
Improved Synthesis of No-Carrier-Added [*I]MIBG and Its Precursor
Further Information
Publication History
Received: 09 July 2012
Accepted after revision: 10 September 2012
Publication Date:
28 September 2012 (online)
† Deceased December 29, 2010
Abstract
3-(Trimethylstannyl)benzyl alcohol was coupled in a Mitsunobu reaction with bis(Boc)-guanidine to give bis(Boc)-protected 3-(trimethylstannyl)benzylguanidine used as precursor for [*I]MIBG. Radioiodination with [131I]iodine generated from [131I]NaI and chloramine-T, removal of Boc groups, and purification by HPLC gave no-carrier-added tracer [*I]MIBG (81% radiochemical yield, 99% chemical purity) used for imaging tumors of neuroendocrine origin. The structures of bis(Boc)-guanidine and bis(Boc)-protected 3-(trimethylstannyl)benzylguanidine were secured by single crystal X-ray structure analyses.
-
References
- 1 Nakajo M, Shapiro B, Copp J, Kalff V, Gross MD, Sisson JC, Beierwaltes WH. J. Nucl. Med. 1983; 24: 672
- 2 Wafelman AR, Hoefnagel CA, Maes RA. A, Beijnen JH. Eur. J. Nucl. Med. 1994; 21: 545
- 3 Shapiro B, Gross MD. Med. Pediatr. Oncol. 1987; 15: 170
- 4 Rubello D, Bui C, Casara D, Gross MD, Fig LM, Shapiro B. Eur. J. Endocrinol. 2002; 147: 13
- 5 Valdes Olmos RA, Hoefnagel CA, van der Schoot JB. Eur. J. Nucl. Med. Mol. Imaging 1993; 20: 515
- 6 Howard JP, Maris JM, Kersun LS, Huberty JP, Cheng SC, Hawkins RA, Matthay KK. Pediatr. Blood Cancer 2005; 44: 232
- 7 Hunter HD, Zhu X. J. Labelled Compd. Radiopharm. 1999; 42: 653
- 8 Mangner TJ, Wu J.-L, Wieland DM, Beierwaltes WH. J. Nucl. Med. 1981; 22: P12
- 9 Mertens J, Vanryckeghem W, Gysemans M, Eersels J, Finda-Panek E, Carlsen L. Eur. J. Nucl. Med. Mol. Imaging 1987; 13: 380
- 10 Verbruggen RF. Appl. Radiat. Isot. 1987; 38: 303
- 11 Amartey JK, Al-Jammaz I, Lambrecht RM. Appl. Radiat. Isot. 2001; 54: 711
- 12 Neves M, Paulo A, Patricio L. Appl. Radiat. Isot. 1992; 43: 337
- 13 Vaidyanathan G, Zalutsky MR. Appl. Radiat. Isot. 1992; 44: 621
- 14 Rossouw DD, Macheki L. J. Labelled Compd. Radiopharm. 2009; 52: 499
- 15 Vaidyanathan G, Affleck DJ, Alston KL, Zalutsky MR. J. Labelled Compd. Radiopharm. 2007; 50: 177
- 16 Hunter DH, Goel A, Flanagan RJ. US Patent 5565185, 1996 ; Chem. Abstr. 1996, 124, 260616.
- 17 Koldobsky AB, Vakhmistrov VE, Shilova OS, Kalinin VN, Tehrani KA, De Kimpe N. Org. Prep. Proced. Int. 1998; 30: 447
- 18 Efange SM. N, Michelson RH, Khane AB, Thomas JR. J. Med. Chem. 1993; 36: 1754
- 19 Kumara Swamy KC, Bhuvan Kumar NN, Balaraman E, Pavan Kumar KV. P. Chem. Rev. 2009; 109: 2551
- 20 Yong YF, Kowalski JA, Lipton MA. J. Org. Chem. 1997; 62: 1540
- 21 Feichtinger K, Sings HL, Baker TJ, Matthews K, Goodman M. J. Org. Chem. 1998; 63: 8432
- 22 Dodd DS, Kozikowski AP. Tetrahedron Lett. 1994; 35: 977
- 23 Vaidyanathan G, Zalutsky MR. J. Org. Chem. 1997; 62: 4867
- 24 Bergeron RJ, McManis JS. J. Org. Chem. 1987; 52: 1700
- 25 Kessler RM, Ansari MS, de Paulis T, Schmidt DE, Clanton JA, Smith HE, Manning RG, Gillespie D, Ebert MH. J. Nucl. Med. 1991; 32: 1593
- 26 Schirbel A, Zolle I, Hammerschmidt F, Berger ML, Schiller D, Kvaternik H, Reiners C. Radiochim. Acta 2004; 92: 297
- 27 Wafelman AR, Suchi R, Hoefnagel CA, Beijnen JH. Eur. J. Nucl. Med. Mol. Imaging 1993; 20: 614
- 28 Chattopadhyay S, Das MK, Sarkar BR, Prabhakar G, Mehra KS, Ramamoorthy N. Appl. Radiat. Isot. 2000; 54: 241
- 29 Mikenda W. Vib. Spectrosc. 1992; 3: 327
- 30 CCDC 873052 (9a) and 859313 (10) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.ac.uk/data_request/cif.
- 31 SHELXTL Version 2008 . Bruker AXS Inc; Madison WI: 2008