Download PDF
Synthesis 2010(21): 3700-3704  
DOI: 10.1055/s-0030-1258269
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A New and Improved Synthesis of the Precursor of the Hypoxia Marker [¹8F]-FMISO

Elena Nietoa, Ramón Alajarína, Julio Álvarez-Builla*a, Ignacio Larrañagab, Elena Gorospeb, Miguel A. Pozoc
a Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Alcalá, Ctra. Madrid-Barcelona km 33.6, 28871 Alcalá de Henares, Madrid, Spain
Fax: +34918854686; e-Mail: julio.alvarez@uah.es;
b Instituto Tecnológico PET, Manuel Bartolomé Cossío, 28040 Madrid, Spain
c Instituto Pluridisciplinar, Universidad Complutense de Madrid, Paseo Juan XXIII, 28040 Madrid, Spain
Further Information

Publication History

Received 23 June 2010
Publication Date:
28 September 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

A new synthetic approach to the precursor of the hypoxia marker [¹8F]-FMISO has been developed. Three different tosylation methods were studied for the preparation of the key intermediate. The overall yield is markedly higher than the yields reported for previous syntheses. The precursor was used to prepare [¹8F]-FMISO and the results were comparable to those obtained when a commercial precursor was used.

Key words

[¹8F]-FMISO - hypoxia - radiopharmaceutical - regioselective tosylation

    References

  • 1a Lee ST. Scott AM. Semin. Nucl. Med.  2007,  37:  451 
    Google Scholar
  • 1b Hicks RJ. Dorow D. Roselt P. Cancer Imaging  2006,  6:  S102 
    Google Scholar
  • 2a Krohn KA. Link JM. Mason RP. J. Nucl. Med.  2008,  49:  129S 
    Google Scholar
  • 2b Rasey JS. Martin VG. Krohn KA. In Imaging of Hypoxia   Machulla H.-J. Kluwer Academic Publishers; Dordrecht: 1999.  p.85-117  
    Google Scholar
  • 2c Grierson J. Patt M. In Imaging of Hypoxia   Machulla H.-J. Kluwer Academic Publishers; Dordrecht: 1999.  p.75-84  
    Google Scholar
  • 3a Tatum JL. Kelloff GJ. Gillies RJ. Arbeit JM. Brown JM. Chao KSC. Chapman JD. Eckelman WC. Fyles AW. Giaccia AJ. Hill RP. Koch CJ. Krishna MC. Krohn KA. Lewis JS. Mason RP. Melillo G. Padhani AR. Powis G. Rajendran JG. Reba R. Robinson SP. Semenza GL. Swartz HM. Vaupel P. Yang D. Croft B. Hoffman J. Liu G. Stone H. Sullivan D. Int. J. Radiat. Biol.  2006,  82:  699 
    Google Scholar
  • 3b Foo SS. Abbott DF. Lawrentschuk N. Scott AM. Mol. Imaging Biol.  2004,  6:  291 
    Google Scholar
  • 4a Prekeges JL. Rasey JS. Grunbaum Z. Krohn KH. Biochem. Pharmacol.  1991,  42:  2387 
    Google Scholar
  • 4b McClelland RA. Panicucci R. Rauth AM. J. Am. Chem. Soc.  1987,  109:  4308 
    Google Scholar
  • 5a Grierson JR. Link JM. Mathis CA. Rasey JS. Krohn KA. J. Nucl. Med.  1989,  30:  343 
    Google Scholar
  • 5b Tada M. Iwata R. Sugiyama H. Sato K. Kubota K. Kubota R. Takahashi H. Fukuda H. Ido T. J. Labelled Compd. Radiopharm.  1996,  38:  771 
    Google Scholar
  • 5c McCarthy TJ. Dence CS. Welch MJ. Appl. Radiat. Isot.  1993,  44:  1129 
    Google Scholar
  • 6 Kämäräinen E.-L. Kyllönen T. Nihtilä O. Björk H. Solin O. J. Labelled Compd. Radiopharm.  2004,  47:  37 
    CrossrefGoogle Scholar
  • 8a Lim J.-L. Berridge MS. Appl. Radiat. Isot.  1993,  44:  1085 
    Google Scholar
  • 8b Patt M. Kuntzsch M. Machulla H.-J.
    J. Radioanal. Nucl. Med.  1999,  240:  925 
    Google Scholar
  • 8c Adamsen TCH. Grierson JR. Krohn KA. J. Labelled Compd. Radiopharm.  2005,  48:  923 
    Google Scholar
  • 8d Tang G. Wang M. Tang X. Gan M. Luo L. Nucl. Med. Biol.  2005,  32:  553 
    Google Scholar
  • 8e Oh SJ. Chi DY. Mosdzianowski C. Kim JY. Gil HS. Kang SH. Ryu JS. Moon DH. Nucl. Med. Biol.  2005,  32:  899 
    Google Scholar
  • 8f Kim DW. Ahn D.-S. Oh Y.-H. Lee S. Kil HS. Oh SJ. Lee SJ. Kim JS. Ryu JS. Moon DH. Chi DY. J. Am. Chem. Soc.  2006,  128:  16394 
    Google Scholar
  • 9 Cherif A. Yang DJ. Tansey W. Kim EE. Wallace S. Pharm. Res.  1994,  11:  466 
    CrossrefGoogle Scholar
  • 13 Ho P.-T. Tetrahedron Lett.  1978,  1623 
    CrossrefGoogle Scholar
  • 14 Beaman AG. Tautz W. Duschinsky R. Antimicrob. Agents Chemother.  1968,  520 
    Google Scholar
  • 15 Takano S. Moriya M. Suzuki M. Iwabuchi Y. Sugihara T. Ogasawara K. Heterocycles  1990,  31:  1555 
    CrossrefGoogle Scholar
  • 16 Wu Q.-P. Zhou M.-X. Xi X.-D. Song D. Wang Y. Liu H.-X. Li Y.-Z. Zhang Q.-S. Tetrahedron Lett.  2008,  49:  2714 
    CrossrefGoogle Scholar
  • 17 Poon KWC. Lovell KM. Dresner KN. Datta A.
    J. Org. Chem.  2008,  73:  752 
    CrossrefGoogle Scholar
  • 18 Martinelli MJ. Vaidyanathan R. Pawlak JM. Nayyar NK. Dhokte UP. Doecke CW. Zollars LMH. Moher ED. Khau VV. Košmrlj B. J. Am. Chem. Soc.  2002,  124:  3578 
    CrossrefGoogle Scholar
  • 19 Reginato G. Ricci A. Roelens S. Scapecchi S. J. Org. Chem.  1990,  55:  5132 
    CrossrefGoogle Scholar
  • 20 Li X. Manjunatha UH. Goodwin MB. Knox JE. Lipinski CA. Keller TH. Barry CE. Dowd CS. Bioorg. Med. Chem. Lett.  2008,  18:  2256 
    CrossrefGoogle Scholar
7

ABX Advanced Biochemical Compounds, Germany (3500 ı/1 g).

10

Aldrich Co. (317.5 ı/1 g).

11

Website of multiMag research group:
http://www.multimag.es.

12

Aldrich Co. (46.2 ı/10 g).