Skip to main content
SpringerLink
Log in
Book cover

PET Chemistry pp 79–111Cite as

Fluorine-18 Labeling of Peptides and Proteins

  • Conference paper

Part of the book series: Ernst Schering Research Foundation Workshop ((SCHERING FOUND,volume 64))

Abstract

The pool of promising peptides worthy of investigation and evaluation for clinical use is continuously filled from different sources. Driven by the promising results obtained with peptides addressing somatostatin-2 receptor positive (sst2+) neuroendocrine tumours, other peptides targeting further receptor systems are being studied and evaluated. Progress in profiling the density and incidence of peptide hormone receptors in human cancer has initiated and will further promote research on the corresponding peptidic binders. In addition, industrial pharmaceutical research will be another significant source of peptides in the future. A recent prognosis revealed that about 50% of the drugs entering clinical trials in the next years will be peptides. The extensive research activities in genomics and proteomics will point out and quantify new and already known target structures upregulated in specific diseases. Based on the knowledge of their endogenous ligands or via selection of suitable candidates by phage display, suitable peptide ligands for e.g. membrane associated receptors can be identified and thus allow targeting of such binding sites. Thus, bioactive peptides specifically addressing relevant molecular targets are expected to become an important class of tracers, also due to the possibility of bridging imaging with therapeutic approaches. In this brief overview a summary of methods and strategies for the 18F-labeling of peptides and proteins is given.

This is a preview of subscription content, log in via an institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Aloj L, Lang L, Jagoda E, Neumann RD, Eckelman WC (1996) Evaluation of human transferrin radiolabeled with N-succinimidyl 4-[fluorine-18](fluoromethyl) benzoate. J Nucl Med 37:1408–1412

    PubMed  CAS  Google Scholar 

  • Beer AJ, Haubner R, Goebel M, Luderschmidt S, Spilker ME, Wester HJ, Weber WA, Schwaiger M (2005) Biodistribution and pharmacokinetics of the avb3-selective tracer 18F-galacto-RGD in cancer patients. J Nucl Med 46:1333–1341

    PubMed  CAS  Google Scholar 

  • Bergmann R, Scheunemann M, Heichert C, Mading P, Wittrisch H, Kretzschmar M, Rodig H, Tourwe D, Iterbeke K, Chavatte K, Zips D, Reubi JC, Johannsen B (2002) Biodistribution and catabolism of 18F-labelled neurotensin (8–13) analogs. Nucl Med Biol 29:61–72

    Article  PubMed  CAS  Google Scholar 

  • Block D, Coenen HH, Stöcklin G. (1988) N.c.a. 18F-fluoroacylation via fluorocarboxylic acid esters. J Lab Compd Radiopharm 25:185

    Article  CAS  Google Scholar 

  • Bock, M., Haubner, R., Senekowitsch-Schmidtke, R., Kessler, H., Stöcklin, G., Schwaiger, M., Wester, H.J (1999) Homo-and heteromultimeric ligand systems as tracers for tumorimaging und endoradiotherapy. Nuclear Med 38:A44 (abstract)

    Google Scholar 

  • Bruus-Jensen K, Poethko T, Schottelius M, Hauser A, Schwaiger M, Wester HJ (2006) Chemoselective hydrazone formation between HYNICfunctionalized peptides and 18F-fluorinated aldehydes. Nucl Med Biol 33:173–183

    Article  PubMed  CAS  Google Scholar 

  • Chang YS, Jeong JM, Lee YS, Kim HW, Rai GB, Lee SJ, Lee DS, Chung JK, Lee MC. (2005) Preparation of 18F-human serum albumin: a simple and efficient protein labeling method with 18F using a hydrazone-formation method. Bioconjugate Chem 16:1329–1333

    Article  CAS  Google Scholar 

  • Chen X, Park R, Hou Y, Khankaldyyan V, Gonzales-Gomez I, Tohme M, Bading JR, Laug WE, Conti PS (2004b) MicroPET imaging of brain tumor angiogenesis with 18F-labeled PEGylated RGD peptide Eur J Nucl Med Mol Imaging 31:1081–1089

    Article  PubMed  CAS  Google Scholar 

  • Chen X, Park R, Shahinian AH, Tohme M, Khankaldyyan V, Bozorgzadeh MH, Bading JR, Moats R, Laug WE, Conti PS (2004c) 18F-labeled RGD peptide: initial evaluation for imaging brain tumor angiogenesis. Nucl Med Biol 31:179–189

    Article  PubMed  CAS  Google Scholar 

  • Chen X, Park R, Tohme M, Shahinian AH, Bading JR, Conti PS (2004d) MicroPET and autoradiographic imaging of breast cancer alpha v-integrin expression using 18F-and 64Cu-labeled RGD peptide. Bioconjug Chem 15:41–49

    Article  PubMed  CAS  Google Scholar 

  • de Bruin B, Kuhnast B, Hinnen F, Yaounancq L, Amessou M, Johannes L, Samson A, Boisgard R, Tavitian B, Dollé F (2005) 1-[3-(2-[18F]fluoropyridin-3-yloxy)propyl]pyrrole-2,5-dione: design, synthesis and radiosynthesis of a new[18F]fluoropyridine-based maleimide reagent for the labeling of peptides and proteins. Bioconjug Chem 16:406–420

    Article  PubMed  CAS  Google Scholar 

  • Downer JB, McCarthy TJ, Edwards WB, Anderson CJ, Welch MJ (1993) Reactivity of ρ-[18F]fluorophenacyl bromide for radiolabeling of proteins and peptides. Appl Radiat Isot 48:907–916

    Article  Google Scholar 

  • Fredriksson A, Johnström P, Stone-Elander S, Jonasson P, Nygren PA, Ekberg K, Johansson BL, Wahren J (2001) Labeling of human c-peptide by conjugation with N-succinimidyl-4-[18F]fluorobenzoate. J Label Compounds Radiopharm. 44:509–519

    Article  CAS  Google Scholar 

  • Garg PK, Garg S, Zalutsky MR (1991) Fluorine-18 labeling of monoclonal antibodies and fragments with preservation of immunoreactivity. Bioconjugate Chem 2:44–49

    Article  CAS  Google Scholar 

  • Glaser M, Karlsen H, Solbakken M, Arukwe J, Brady F, Luthra SK, Cuthbertson A (2004) 18F-fluorothiols: a newapproach to label peptides chemoselectively as potential tracers for positron emission tomography. Bioconjugate Chem 15:1447–1453

    Article  CAS  Google Scholar 

  • Guhlke S, Coenen HH, Stöcklin G. (1994) Fluoroacylation agents based on small n.c.a. [18F]fluorocarboxylic acids. Appl Radiat Isot 45:715–727

    Article  CAS  Google Scholar 

  • Guhlke S, Wester HJ, Bruns C, Stocklin G. (1994) (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 216:819–825

    Article  Google Scholar 

  • Hashizume K, Hashimoto N, Miyake Y (1995) Synthesis of positron labeled photoactive compounds: 18F labeled aryl azides for positron labeling of biochemical molecules J Org Chem 60:6680–6681

    Article  CAS  Google Scholar 

  • Haubner R, Weber WA, Beer AJ, Vabuliene E, Reim D, Sarbia M, Becker KF, Goebel M, Hein R, Wester HJ, Kessler H, Schwaiger M (2005) Noninvasive visualization of the activated alphavbeta3 integrin in cancer patients by positron emission tomography and [18F]Galacto-RGD. PLoS Med 2:e70

    Article  PubMed  CAS  Google Scholar 

  • Haubner R, Wester HJ (2004) Radiolabeled tracers for imaging of tumor angiogenesis and evaluation of anti-angiogenic therapies. Curr Pharm Des 10:1439–1455

    Article  PubMed  CAS  Google Scholar 

  • Haubner R, Wester HJ, Weber WA, Mang C, Ziegler SI, Goodman SL, Senekowitsch-Schmidtke R, Kessler H, Schwaiger M (2001a) Noninvasive imaging of alpha(v)beta3 integrin expression using 18F-labeled RGDcontaining glycopeptide and positron emission tomography. Cancer Res 61:1781–1785

    PubMed  CAS  Google Scholar 

  • Haubner R, Wester HJ, Burkhart F, Senekowitsch-Schmidtke R, Weber W, Goodman S, Kessler H and Schwaiger M (2001b) Glycosylated RGD-containing peptides: tracer for tumor targeting and angiogenesis imaging with improved biokinetics. J Nucl Med 42:326–336

    PubMed  CAS  Google Scholar 

  • Haubner R, Wester HJ, Reuning U, Senekowitsch-Schmidtke R, Diefenbach B, Kessler H, Stocklin G, Schwaiger M (1999) Radiolabeled αvβ3 integrin antagonists: a new class of tracers for tumor targeting. J Nucl Med 40:1061

    PubMed  CAS  Google Scholar 

  • Haubner RH, Wester HJ, Weber WA, Schwaiger M (2003) Radiotracer-based strategies to image angiogenesis. Q J Nucl Med 47:189

    PubMed  CAS  Google Scholar 

  • Hebel D, Kirk KL, Cohen LA, Labroo VM (1990) First direct fluorination of tyrosine-containing biologically active peptides. Tetrahedron Lett 31:619–622

    Article  CAS  Google Scholar 

  • Hostetler ED, Edwards WB, Anderson CJ, Welch MJ (1999) J Label Compounds Radiopharm 42(Suppl I); S720 (abstract)

    Google Scholar 

  • Jakobson K, Furlano DC, Kirk KL (1988) A prosthetic group for the rapid introduction of fluorine into peptides and functionalized drugs. J Fluor Chem 39:339–347

    Article  Google Scholar 

  • Jelinski M, Hamacher K, Coenen HH (2002) C-Terminal 18F-fluoroethylamidation exemplified on [Gly-OH9] oxytocin. J Label Compd Radiopharm 45:217–229

    Article  CAS  Google Scholar 

  • Johnstrom P, Fryer TD, Richards HK, Harris NG, Barret O, Clark JC, Pickard JD, Davenport AP (2005) Positron emission tomography using 18F-labelled endothelin-1 reveals prevention of binding to cardiac receptors owing to tissue-specific clearance by ETBreceptors in vivo. Br J Pharmacol 144:115–122

    Article  PubMed  CAS  Google Scholar 

  • Kilbourn MR, Dence CS, Welch MJ, Mathias CJ. (1987) Fluorine-18 labeling of proteins. J Nucl Med 28:462–470

    PubMed  CAS  Google Scholar 

  • Kuhnast B, Dolle F, Terrazzino S, Rousseau B, Loc’h C, Vaufrey F, Hinnen F, Doignon I, Pillon F, David C, Crouzel C, Tavitian B. (2000) Generalmethod to label antisense oligonucleotides with radioactive halogens for pharmacological and imaging studies. Bioconjugate Chem 11:627–636

    Article  CAS  Google Scholar 

  • Kurth M, Pelegrin A, Rose K, Offord RE, Pochon S, Mach JP, Buchegger F (1993) Site-specific conjugation of a radioiodinated phenethylamine derivative to a monoclonal antibody results in increased radioactivity localization in tumor. J Med Chem 36:1255–1261

    Article  PubMed  CAS  Google Scholar 

  • Labroo VM, Hebel D, Kirk KL, Cohen LA, Lemieux C, Schiller PW. (1991) Direct electrophilic fluorination of tyrosine in dermorphin analogues and its effect on biological activity, receptor affinity and selectivity. Int J Pept Protein Res 37:430–439

    Article  PubMed  CAS  Google Scholar 

  • Lang L, Eckelman WC (1994) One-step synthesis of 18F labeled [18F]-Nsuccinimidyl 4-(fluoromethyl)benzoate for protein labeling. Appl Radiat Isot 45:1155–1163

    Article  PubMed  CAS  Google Scholar 

  • Lang L, Eckelman WC (1997) Labeling proteins at high specific activity using N-succinimidyl 4-[18F](fluoromethyl) benzoate. Appl Radiat Isot 48:169–173

    Article  PubMed  CAS  Google Scholar 

  • Lange CW, VanBrocklin HF, Taylor SE (2002) Photoconjugation of 3-azido-5-nitrobenzyl-[18F]fluoride to an oligonucleotide aptamer. J Label Compd Radiopharm 45:257–268

    Article  CAS  Google Scholar 

  • Leisner M, Kessler H, Schwaiger M, Wester HJ (1999) Synthesis of Nα-d-Phe1-Amadori derivatives of Tyr3-octreotide: Precursors for 123I-/18F-labeled sstr-binding SPECT/PET tracers with improved biodistribution. J Label Compd Radiopharm. 42:549–551 (abstract)

    Google Scholar 

  • Magata Y, Lang L, Kiesewetter DO, Jagoda EM, Channing MA, Eckelman WC (2000) Biologically stable [(18)F]-labeled benzylfluoride derivatives. Nucl Med Biol 27:163–168

    Article  PubMed  CAS  Google Scholar 

  • Mading P, Fuchtner F, Wust F (2005) Module-assisted synthesis of the bifunctional labelling agent N-succinimidyl 4-[(18)F]fluorobenzoate ([(18)F]SFB). Appl Radiat Isot 63:329–332

    Article  PubMed  CAS  Google Scholar 

  • Maschauer S, Pischetsrieder M, Kuwert T, Prante O (2005) Utility of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-[18F]fluoroglucopyranoside for no-carrier-added 18F-glycosylation of amino acids. J Label Compd Radiopharm 48:701–719

    Article  CAS  Google Scholar 

  • Moody TW, Leyton J, Unsworth E, John C, Lang L, Eckelman W. (1998) (Arg15, Arg21)VIP: Evaluation of biological activity and localization to breast cancer tumors. Peptides 19:585–592

    Article  PubMed  CAS  Google Scholar 

  • Murakami Y, Takamatsu H, Taki J, Tatsumi M, Noda A, Ichise R, Tait JF, Nishimura S. (2004) 18F-labelled annexin V: a PET tracer for apoptosis imaging. Eur J Nucl Med Mol Imaging 31:469–474

    Article  PubMed  CAS  Google Scholar 

  • Neumaier B, Mahren B, Solbach C, Vogg ATJ, Rattat D, Buchmann I, Kotzerke J, Reske SN (2002) 18F-radiolabelled anti CD-66 for quantitative dosimetry in radioimmunotherapy. Eur J Nucl Med 29: 92 (abstract)

    Google Scholar 

  • Ogawa M, Hatano K, Oishi S, Kawasumi Y, Fujii N, Kawaguchi M, Doi R, Imamura M, Yamamoto M, Ajito K, Mukai T, Saji H, Ito K (2003) Direct electrophilic radiofluorination of a cyclic RGD peptide for in vivo αvβ3 integrin related tumor imaging. Nucl Med Biol 30:1–9

    Article  PubMed  CAS  Google Scholar 

  • Okarvi SM (2001) Recent progress in fluorine-18 labelled peptide radiopharmaceuticals. Eur J Nucl Med 28: 929–938

    Article  PubMed  CAS  Google Scholar 

  • Page RL, Garg PK, Vaidyanathan G, Zalutsky MR (1994) Preclinical evaluation and PET imaging of 18F-labeled Mel-14 F(ab′)2 fragment in normal dogs. Nucl Med Biol 21:911–919

    Article  PubMed  CAS  Google Scholar 

  • Poethko T, Schottelius M, Thumshirn G, Hersel U, Herz M, Henriksen G, Kessler H, Schwaiger M, Wester HJ (2004a) Two-step methodology for high-yield routine radiohalogenation of peptides: (18)F-labeled RGD and octreotide analogs. J Nucl Med 45:892–902

    PubMed  CAS  Google Scholar 

  • Poethko T, Schottelius M, Thumshirn G, Herz M, Haubner R, Henriksen G, Kessler H, Schwaiger M, Wester HJ (2004b) Chemoselective pre-conjugate radiohaloge-nation of unprotected mono-and multimeric peptides via oxime formation. Radiochim Acta 92:317–328

    Article  CAS  Google Scholar 

  • Prante O, Hamacher K, Coenen HH (1999) Chemo-enzymatic n.c.a. synthesis of the coenzyme uridine diphospho-2-deoxy-2-[18F]fluoro-D-glucose. J Label Compds Radiopharm 42:S111

    Google Scholar 

  • Schottelius M, Poethko T, Herz M, Reubi JC, Kessler H, Schwaiger M, Wester HJ (2004) First (18)F-labeled tracer suitable for routine clinical imaging of sst receptor-expressing tumors using positron emission tomography. Clin Cancer Res 10:3593–3606

    Article  PubMed  CAS  Google Scholar 

  • Schottelius M, Reubi JC, Eltschinger V, Schwaiger M, Wester HJ. (2005a) N-terminal sugar conjugation and C-terminal Thr-for-Thr(ol) exchange in radioiodinated Tyr3-octreotide: effect on cellular ligand trafficking in vitro and tumor accumulation in vivo. J Med Chem 48:2778–2789

    Article  PubMed  CAS  Google Scholar 

  • Schottelius M, Rau F, Reubi JC, Schwaiger M, Wester HJ (2005b) Modulation of pharmacokinetics of radioiodinated sugar-conjugated somatostatin analogues by variation of peptide net charge and carbohydration chemistry. Bioconjug Chem 16:429–437

    Article  PubMed  CAS  Google Scholar 

  • Schottelius M, Wester HJ, Reubi JC, Senekowitsch-Schmidtke R, Schwaiger M. (2002) Improvement of pharmacokinetics of radioiodinated Tyr(3)-octreotide by conjugation with carbohydrates. Bioconjug Chem 13:1021–1030

    Article  PubMed  CAS  Google Scholar 

  • Shai Y, Kirk KL, Channing MA, Dunn BB, Lesniak MA, Eastman RC, Finn RD, Roth J, Jacobson KA (1989) 18F-labeled insulin: a prosthetic group methodology for incorporation of a positron emitter into peptides and proteins. Biochemistry 28:4801–4806

    Article  PubMed  CAS  Google Scholar 

  • Shao J, Tam JP (1995) Unprotected peptides as building blocks for the synthesis of peptide dendrimers with oxime, hydrazone and thiazolidine linkages. J Am Chem Soc 117:3893–3898

    Article  CAS  Google Scholar 

  • Shiue CY, Wolf AP, Hainfeld JF (1989) Synthesis of 18F-labeled N-(p-[18F]fluorophenyl)-maleimide and its derivatives for labeling monoclonal antibody with 18F. J Labelled Compd Radiopharm 26:287–289

    Google Scholar 

  • Stöcklin G, Wester HJ (1998) Strategies for radioligand development: Peptides for tumor targeting. In: Gulyas B, Müller-Gärtner HW (eds) Positron emission tomography: a critical assessment of recent trends. Kluwer Academic Publishers, the Netherlands, pp 57–90

    Google Scholar 

  • Sutcliffe-Goulden JL, O’Doherty MJ, Bansal SS (2000) Solid phase synthesis of [18F]labelled peptides for positron emission tomography. Bioorg Med Chem Lett 10:1501–1503

    Article  PubMed  CAS  Google Scholar 

  • Sutcliffe-Goulden JL, O’Doherty MJ, Marsden PK, Hart IR, Marshall JF, Bansal SS (2002) Rapid solid phase synthesis and biodistribution of 18F-labelled linear peptides. Eur J Nucl Med Mol Imaging 29:754–759

    Article  PubMed  CAS  Google Scholar 

  • Tavitian B, Terrazzino S, Kuhnast B, Marzabal S, Stettler O, Dolle F, Deverre JR, Jobert A, Hinnen F, Bendriem B, Crouzel C, Di Giamberardino L (1998) In vivo imaging of oligonucleotides with positron emission tomography. Nat Med 4:467–471

    Article  PubMed  CAS  Google Scholar 

  • Tavitian B (2003) In vivo imaging with oligonucleotides for diagnosis and drug development. Gut 52:40

    Article  Google Scholar 

  • Thumshirn G, Hersel U, Goodman SL, Kessler H (2003) Multimeric cyclic RGD peptides as potential tools for tumor targeting: solid-phase peptide synthesis and chemoselective oxime ligation. Chemistry 9:2717–2725

    Article  PubMed  CAS  Google Scholar 

  • Toretsky J, Levenson A, Weinberg IN, Tait JF, Uren A, Mease RC. (2004) Preparation of F-18 labeled annexin V: a potential PET radiopharmaceutical for imaging cell death. Nucl Med Biol 31:747–752

    Article  PubMed  CAS  Google Scholar 

  • Toyokuni T, Walsh JC, Dominguez A, Phelps ME, Barrio JR, Gambhir SS, Satyamurthy N (2003) Synthesis of a new heterobifunctional linker, N-[4-(aminooxy)butyl]maleimide, for facile access to a thiol-reactive 18F-labeling agent. Bioconjugate Chem 14:1253–1259

    Article  CAS  Google Scholar 

  • Vaidyanathan G, Bigner DD, Zalutsky MR (1992) Fluorine-18-labeled monoclonal antibody fragments: a potential approach for combining radioimmunoscintigraphy and positron emission tomography. J Nucl Med 33:1535–1541

    PubMed  CAS  Google Scholar 

  • Vaidyanathan G, Zalutsky MR (1992) Labeling proteins with fluorine-18 using N-succinimidyl 4-[18F]fluorobenzoate. Nucl Med Biol 19:275–281

    CAS  Google Scholar 

  • Vaidyanathan G, Zalutsky MR (1994) Improved synthesis of N-succinimidyl 4-[18F]fluorobenzoate and its application to the labeling of a monoclonal antibody fragment. Bioconjugate Chem 54:352–356

    Article  Google Scholar 

  • Vaidyanathan G, Zalutsky MR (1997) Fluorine-18-labeled [Nle4,D-Phe7]-alpha-MSH, an alpha-melanocyte stimulating hormone analogue. Nucl Med Biol 24:171–178

    Article  PubMed  CAS  Google Scholar 

  • Vaidyanathan G, Affleck D, Welsh P, Srinivasan A, Schmidt M, Zalutsky MR (2000) Radioiodination and astatination of octreotide by conjugation labeling. Nucl Med Biol 27:329–337.

    Article  PubMed  CAS  Google Scholar 

  • Vaidyanathan G, Friedman HS, Affleck DJ, Schottelius M, Wester HJ, Zalutsky MR (2003) Specific and high-level targeting of radiolabeled octreotide analogues to human medulloblastoma xenografts. Clin Cancer Res 9:1868–1876

    PubMed  CAS  Google Scholar 

  • Wester HJ, Brockmann J, Rosch F, Wutz W, Herzog H, Smith-Jones P, Stolz B, Bruns C, Stocklin G (1997) PET-pharmacokinetics of 18F-octreotide: a comparison with 67Ga-DFO-and 86Y-DTPA-octreotide. Nucl Med Biol 24:275–286

    Article  PubMed  CAS  Google Scholar 

  • Wester HJ, Schottelius M, Poethko T, Bruus-Jensen K, Schwaiger M. (2004) Radiolabeled carbohydrated somatostatin analogs: a review of the current status. Cancer Biother Radiopharm 19:231–244

    Article  PubMed  CAS  Google Scholar 

  • Wester HJ, Schottelius M, Scheidhauer K, Reubi JC, Wolf I, Schwaiger M (2002) Comparison of radioiodinated TOC, TOCA and Mtr-TOCA: the effect of carbohydration on the pharmacokinetics. Eur J Nucl Med Mol Imaging 29:28–38

    Article  PubMed  CAS  Google Scholar 

  • Wester HJ, Hamacher K, Stöcklin G (1996) A comparative study of N.C.A. fluorine-18 labeling of proteins via acylation and photochemical conjugation. Nucl Med Biol 23:365.

    Article  PubMed  CAS  Google Scholar 

  • Wester HJ, Schottelius M, Scheidhauer K, Meisetschläger G, Herz M, Rau FC., Reubi JC, and Schwaiger M (2003) PET imaging of somatostatin receptors: design, synthesis and preclinical evaluation of a novel 18F-labelled, carbohydrated analogue of octreotide. Eur J Nucl Med 30:117–122

    Article  CAS  Google Scholar 

  • Wester HJ, Kessler H (2005) Molecular targeting with peptides or peptidepolymer-conjugates: just a question of size ? J Nucl Med 46:1940–1945

    PubMed  CAS  Google Scholar 

  • Wilbur DS (1992) Radiohalogenation of proteins: an overview of radionuclides, labeling methods, and reagents for conjugate labeling. Bioconjugate Chem. 3:433–470

    Article  CAS  Google Scholar 

  • Wüst F, Hultsch C, Bergmann R, Johannsen B, Henle T (2003) Radiolabelling of isopeptide N epsilon-(gamma-glutamyl)-L-lysine by conjugation with N-succinimidyl-4-[18F]fluorobenzoate. Appl Radiat Isot 59:43–48

    Article  PubMed  CAS  Google Scholar 

  • Yagle KJ, Eary JF, Tait JF, Grierson JR, Link JM, Lewellen B, Gibson DF, Krohn KA (2005) Evaluation of 18F-annexin V as a PET imaging agent in an animal model of apoptosis. J Nucl Med 46:658–666

    PubMed  CAS  Google Scholar 

  • Zalutsky MR, Garg PK, Johnson SH, Utsunomiya H, Coleman RE (1992) Fluorine-18-antimyosin monoclonal antibody fragments: preliminary investigations in a canine myocardial infarct model. J Nucl Med 33:575–580

    PubMed  CAS  Google Scholar 

  • Zijlstra S, Gunawan J, Burchert W. (2003) Synthesis and evaluation of a 18F-labelled recombinant annexin-V derivative, for identification and quantification of apoptotic cells with PET. Appl Radiat Isot 58:201–207

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Nuklearmedizinische Klinik und Poliklinik und Institut für Radiochemie, Technische Universität München, Ismaninger Str. 22, 81675, Munich, Germany

    H. J. Wester & M. Schottelius

Authors
  1. H. J. Wester
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. Schottelius
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Animal Imaging Center — PET, Center for Radiopharmaceutical Science of ETH, PSI and USZ, ETH Hönggerberg D-CHAB, Wolfgang-Pauli Str. 10, 8093, Zürich, Switzerland

    P. A. Schubiger

  2. Corporate Research, Schering AG, Müller Str. 178, 13342, Berlin, Germany

    L. Lehmann  & M. Friebe  & 

Rights and permissions

Reprints and permissions

Copyright information

© 2007 Springer-Verlag Berlin Heidelberg

About this paper

Cite this paper

Wester, H.J., Schottelius, M. (2007). Fluorine-18 Labeling of Peptides and Proteins. In: Schubiger, P.A., Lehmann, L., Friebe, M. (eds) PET Chemistry. Ernst Schering Research Foundation Workshop, vol 64. Springer, Berlin, Heidelberg . https://doi.org/10.1007/978-3-540-49527-7_4

Download citation

  • DOI: https://doi.org/10.1007/978-3-540-49527-7_4

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-32623-6

  • Online ISBN: 978-3-540-49527-7

  • eBook Packages: MedicineMedicine (R0)

Publish with us

Policies and ethics

Search

Navigation