Download PDF
Synlett 2011(12): 1697-1700  
DOI: 10.1055/s-0030-1260942
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

SiFA Azide: A New Building Block for PET Imaging Using Click Chemistry

Lutz F. Tietze*, Kianga Schmuck
Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen, Tammannstr. 2, 37077 Göttingen, Germany
Fax: +49(551)399476; e-Mail: ltietze@gwdg.de;
Further Information

Publication History

Received 12 May 2011
Publication Date:
05 July 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

We present a new highly potent building block for PET imaging based on silicon fluoride acceptors (SiFA) which can easily be coupled to bioactive compounds by means of click chemistry. Owing to a remarkable chemoselectivity, short reaction times, and high yields the labeling reactions thoroughly meet the stringent demands for PET investigations.

Key words

azides - cancer - click chemistry - fluorine labeling - PET

    References

  • 1a Agarwal A. Tripathi PK. Tripathi S. Jain NK. Curr. Drug Targets  2008,  9:  895 
    Google Scholar
  • 1b Alves F. Dullin C. Napp J. Missbach-Guentner J. Jannasch K. Mathejczyk J. Pardo LA. Stühmer W. Tietze LF. Eur. J. Radiol.  2009,  70:  286 
    Google Scholar
  • 2 Zweifel M. Padhani AR. Eur. J. Nucl. Med. Mol. Imaging  2010,  37:  164 
    CrossrefGoogle Scholar
  • 3 Gomes CM. Abrunhosa AJ. Ramos P. Pauwels EK. Adv. Drug Delivery Rev.  2011,  63:  547 
    CrossrefGoogle Scholar
  • 4a Miller PW. Long NJ. Vilar R. Gee AD. Angew. Chem. Int. Ed.  2008,  47:  8998 
    Google Scholar
  • 4b Li Z. Conti PS. Adv. Drug Delivery Rev.  2010,  62:  1031 
    Google Scholar
  • 5a Tietze LF. Krewer B. Chem. Biol. Drug. Des.  2009,  74:  205 
    Google Scholar
  • 5b Bagshawe KD. Curr. Drug Targets  2009,  10:  152 
    Google Scholar
  • 5c Bagshawe KD. Expert Rev. Anticancer Ther.  2006,  6:  1421 
    Google Scholar
  • 6a Tietze LF. Panknin O. Krewer B. Major F. Schuberth I. Int. J. Mol. Sci.  2008,  9:  821 
    Google Scholar
  • 6b Tietze LF. Schuster HJ. Schmuck K. Schuberth I. Alves F. Bioorg. Med. Chem.  2008,  16:  6312 
    Google Scholar
  • 6c Bosslet K. Straub R. Blumrich M. Czech J. Gerken M. Sperker B. Kroemer HK. Gesson J.-P. Koch M. Monneret C. Cancer Res.  1998,  58:  1195 
    Google Scholar
  • 6d Bosslet K. Czech J. Hoffmann D. Tumor Target.  1995,  1:  45 
    Google Scholar
  • 7a Tietze LF. Schmuck K. Schuster HJ. Müller M. Schuberth I. Chem. Eur. J.  2011,  17:  1922 
    Google Scholar
  • 7b Tietze LF. von Hof JM. Müller M. Krewer B. Schuberth I. Angew. Chem. Int. Ed.  2010,  49:  7336 
    Google Scholar
  • 7c Schuster HJ. Krewer B. von Hof JM. Schmuck K. Schuberth I. Alves F. Tietze LF. Org. Biomol. Chem.  2010,  8:  1833 
    Google Scholar
  • 7d Tietze LF. Krewer B. Anti-Cancer Agents Med. Chem.  2009,  9:  304 
    Google Scholar
  • 7e Tietze LF. Schuster HJ. Krewer B. Schuberth I. J. Med. Chem.  2009,  52:  537 
    Google Scholar
  • 7f Tietze LF. Krewer B. von Hof JM. Frauendorf H. Schuberth I. Toxins  2009,  1:  134 
    Google Scholar
  • 7g Tietze LF. von Hof JM. Krewer B. Müller M. Major F. Schuster HJ. Schuberth I. ChemMedChem  2008,  3:  1946 
    Google Scholar
  • 7h Tietze LF. Krewer B. Frauendorf H. Major F. Schuberth I. Angew. Chem. Int. Ed.  2006,  45:  6570 
    Google Scholar
  • 7i Tietze LF. Major F. Schuberth I. Angew. Chem. Int. Ed.  2006,  45:  6574 
    Google Scholar
  • 7j Tietze LF. Major F. Eur. J. Org. Chem.  2006,  2314 
    Google Scholar
  • 8a Iovkova L. Wängler B. Schirrmacher E. Schirrmacher R. Quandt G. Boening G. Schürmann M. Jurkschat K. Chem. Eur. J.  2009,  15:  2140 
    Google Scholar
  • 8b Schirrmacher E. Wängler B. Cypryk M. Bradtmöller G. Schäfer M. Eisenhut M. Jurkschat K. Schirrmacher R. Bioconjugate Chem.  2007,  18:  2085 
    Google Scholar
  • 8c Schirrmacher R. Bradtmöller G. Schirrmacher E. Thews O. Tillmanns J. Siessmeier T. Buchholz HG. Bartenstein P. Wängler B. Niemeyer CM. Jurkschat K. Angew. Chem. Int. Ed.  2006,  45:  6047 
    Google Scholar
  • 9a Huisgen R. Angew. Chem., Int. Ed. Engl.  1963,  2:  565 
    Google Scholar
  • 9b Rostovtsev VV. Green LG. Fokin VV. Sharpless KB. Angew. Chem. Int. Ed.  2002,  41:  2596 
    Google Scholar
  • 9c Tornøe CW. Christensen C. Meldal M. J. Org. Chem.  2002,  67:  3057 
    Google Scholar