Nuclear Medicine and Biology
Volume 35, Issue 6 , Pages 725-731 , August 2008

Automated synthesis of the generic peptide labelling agent N-succinimidyl 4-[18F]fluorobenzoate and application to 18F-label the vasoactive transmitter urotensin-II as a ligand for positron emission tomography

  • Peter Johnström

      Affiliations

    • Clinical Pharmacology Unit, University of Cambridge, Addenbrooke's Hospital, Cambridge, UK
    • Wolfson Brain Imaging Centre, University of Cambridge, Addenbrooke's Hospital, Cambridge, UK
    • ,
  • John C. Clark

      Affiliations

    • Wolfson Brain Imaging Centre, University of Cambridge, Addenbrooke's Hospital, Cambridge, UK
    • ,
  • John D. Pickard

      Affiliations

    • Wolfson Brain Imaging Centre, University of Cambridge, Addenbrooke's Hospital, Cambridge, UK
    • ,
  • Anthony P. Davenport

      Affiliations

    • Clinical Pharmacology Unit, University of Cambridge, Addenbrooke's Hospital, Cambridge, UK
    • Corresponding Author InformationCorresponding author. Clinical Pharmacology Unit, University of Cambridge, Addenbrooke's Centre for Clinical Investigation, Box 110, Addenbrooke's Hospital, Cambridge, CB2 2QQ, UK. Tel.: +44 1223 336899; fax: +44 1223 762576.

Received 13 March 2008 ,Accepted 14 April 2008.

References 

  1. Foord SM, Bonner TI, Neubig RR, Rosser EM, Pin JP, Davenport AP, et al. International Union of Pharmacology. XLVI. G protein-coupled receptor list. Pharmacol Rev. 2005;57:279–288
  2. Maguire JJ, Davenport AP. Regulation of vascular reactivity by established and emerging GPCRs. Trends Pharmacol Sci. 2005;26:448–454
  3. Ames RS, Sarau HM, Chambers JK, Willette RN, Aiyar NV, Romanic AM, et al. Human urotensin-II is a potent vasoconstrictor and agonist for the orphan receptor GPR14. Nature. 1999;401:282–286
  4. Douglas SA, Dhanak D, Johns DG. From ‘gills to pills’: urotensin-II as a regulator of mammalian cardiorenal function. Trends Pharmacol Sci. 2004;25:76–85
  5. Maguire JJ, Kuc RE, Davenport AP. Orphan-receptor ligand human urotensin II: receptor localization in human tissues and comparison of vasoconstrictor responses with endothelin-1. Br J Pharmacol. 2000;131:441–446
  6. Ng LL, Loke I, O'Brien RJ, Squire IB, Davies JE. Plasma urotensin in human systolic heart failure. Circulation. 2002;106:2877–2880
  7. Bousette N, Pottinger J, Ramli W, Ohlstein EH, Dhanak D, Douglas SA, et al. Urotensin-II receptor blockade with SB-611812 attenuates cardiac remodeling in experimental ischemic heart disease. Peptides. 2006;27:2919–2926
  8. Maguire JJ, Kuc RE, Wiley KE, Kleinz MJ, Davenport AP. Cellular distribution of immunoreactive urotensin-II in human tissues with evidence of increased expression in atherosclerosis and a greater constrictor response of small compared to large coronary arteries. Peptides. 2004;25:1767–1774
  9. Vaidyanathan G, Zalutsky MR. Labeling proteins with fluorine-18 using N-succinimidyl 4-[18F]fluorobenzoate. Int J Rad Appl Instrum B. 1992;19:275–281
  10. Wester HJ, Hamacher K, Stöcklin G. A comparative study of N.C.A. fluorine-18 labeling of proteins via acylation and photochemical conjugation. Nucl Med Biol. 1996;23:365–372
  11. Johnström P, Aigbirhio FI, Clark JC, Downey SP, Pickard JD, Davenport AP. Syntheses of the first endothelin-A- and -B-selective radioligands for positron emission tomography. J Cardiovasc Pharmacol. 2000;36:S58–S60
  12. Johnström P, Harris NG, Fryer TD, Barret O, Clark JC, Pickard JD, et al. 18F-Endothelin-1, a positron emission tomography (PET) radioligand for the endothelin receptor system: radiosynthesis and in vivo imaging using microPET. Clin Sci. 2002;103(Suppl 48):4S–8S
  13. Johnström P, Richards H, Fryer T, Barret O, Clark J, Pickard J, et al. Radiosynthesis and in vivo biodistribution of [18F]-Big ET-1, a potential PET radioligand for the study of enzyme conversion of Big ET-1 to ET-1. Br J Pharmacol. 2002;137:63P
  14. Johnström P, Fryer TD, Richards HK, Harris NG, Barret O, Clark JC, et al. Positron emission tomography using 18F-labelled endothelin-1 reveals prevention of binding to cardiac receptors owing to tissue-specific clearance by ETB receptors in vivo. Br J Pharmacol. 2005;144:115–122
  15. Johnström P, Rudd JH, Richards HK, Fryer TD, Clark JC, Weissberg PL, et al. Imaging endothelin ETB receptors using [18F]-BQ3020: in vitro characterization and positron emission tomography (microPET). Exp Biol Med. 2006;231:736–740
  16. Le Bars D, Bonmarchand G, Alvarez JM, Lemaire C, Mosdzianowski C. New automation of [18F]MPPF using a Coincidence synthesizer. J Label Compnd Radiopharm. 2001;44(Suppl. 1):S1045–S1046
  17. Oh SJ, Mosdzianowski C, Chi DY, Kim JY, Kang SH, Ryu JS, et al. Fully automated synthesis system of 3′-deoxy-3′-[18F]fluorothymidine. Nucl Med Biol. 2004;31:803–809
  18. Oh SJ, Chi DY, Mosdzianowski C, Kim JY, Gil HS, Kang SH, et al. Fully automated synthesis of [18F]fluoromisonidazole using a conventional [18F]FDG module. Nucl Med Biol. 2005;32:899–905
  19. Sun LQ, Mori T, Dence CS, Ponde DE, Welch MJ, Furukawa T, et al. New approach to fully automated synthesis of sodium [18F]fluoroacetate — a simple and fast method using a commercial synthesizer. Nucl Med Biol. 2006;33:153–158
  20. Oh SJ, Chi DY, Mosdzianowski C, Kil HS, Ryu JS, Moon DH. The automatic production of 16α-[18F]fluoroestradiol using a conventional [18F]FDG module with a disposable cassette system. Appl Radiat Isot. 2007;65:676–681
  21. Kryza D, Tadino V, Filannino MA, Villeret G, Lemoucheux L. Fully automated [18F]fluorocholine synthesis in the TracerLab MXFDG Coincidence synthesizer. Nucl Med Biol. 2008;35:255–260
  22. Haka MS, Kilbourn MR, Watkins GL, Toorongian SA. Aryltrimethylammonium trifluoromethanesulfonates as precursors to aryl [18F]fluorides: improved synthesis of [18F]GBR-13119. J Label Compnd Radiopharm. 1989;27:823–833
  23. Johnström P, Davenport AP. Imaging and characterization of radioligands for positron emission tomography using quantitative phosphor imaging autoradiography. Methods Mol Biol. 2005;306:203–216
  24. Munson PJ, Rodbard D. Ligand: a versatile computerized approach for characterization of ligand-binding systems. Anal Biochem. 1980;107:220–239
  25. Gaudriault G, Vincent JP. Selective labeling of α- or ε-amino groups in peptides by the Bolton–Hunter reagent. Peptides. 1992;13:1187–1192
  26. Mäding P, Füchtner F, Wüst F. Module-assisted synthesis of the bifunctional labelling agent N-succinimidyl 4-[18F]fluorobenzoate ([18F]SFB). Appl Radiat Isot. 2005;63:329–332
  27. Marik J, Sutcliffe JL. Fully automated preparation of n.c.a. 4-[18F]fluorobenzoic acid and N-succinimidyl 4-[18F]fluorobenzoate using a Siemens/CTI chemistry process control unit (CPCU). Appl Radiat Isot. 2007;65:199–203
  28. Zijlstra S, Gunawan J, Burchert W. Synthesis and evaluation of a 18F-labelled recombinant annexin-V derivative, for identification and quantification of apoptotic cells with PET. Appl Radiat Isot. 2003;58:201–207
  29. Wester HJ, Krummeich C, Fixmann A, Förmer W, Müller-Gärtner HW, Stöcklin G. 18F- and 131I-labeling of the octadecapeptide apamin: a selective blocker of the Ca2+ dependent K+-channel. Syntheses and in-vivo evaluation in NMRI mice. J Label Compnd Radiopharm. 1995;37:513–515
  30. Flohr S, Kurz M, Kostenis E, Brkovich A, Fournier A, Klabunde T. Identification of nonpeptidic urotensin II receptor antagonists by virtual screening based on a pharmacophore model derived from structure–activity relationships and nuclear magnetic resonance studies on urotensin II. J Med Chem. 2002;45:1799–1805
  31. Kinney WA, Almond HR, Qi J, Smith CE, Santulli RJ, de Garavilla L, et al. Structure–function analysis of urotensin II and its use in the construction of a ligand–receptor working model. Angew Chem Int Ed Engl. 2002;41:2940–2944
  32. Lavecchia A, Cosconati S, Novellino E. Architecture of the human urotensin II receptor: comparison of the binding domains of peptide and non-peptide urotensin II agonists. J Med Chem. 2005;48:2480–2492
  33. Guhlke S, Wester HJ, Bruns C, Stöcklin G. (2-[18F]Fluoropropionyl-(d)phe1)-octreotide, a potential radiopharmaceutical for quantitative somatostatin receptor imaging with PET: synthesis, radiolabeling, in vitro validation and biodistribution in mice. Nucl Med Biol. 1994;21:819–825

PII: S0969-8051(08)00102-9

doi: 10.1016/j.nucmedbio.2008.04.005

Nuclear Medicine and Biology
Volume 35, Issue 6 , Pages 725-731 , August 2008

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