Automated radiosynthesis of the thiol-reactive labeling agent N-[6-(4-[18F]fluorobenzylidene)aminooxyhexyl]maleimide ([18F]FBAM)

Applied Radiation and Isotopes

Volumn 69, Issue 9, 2011, Pages 1226-1230

  Kniess, Torsten ^a   Kuchar, Manuela ^a   Pietzsch, Jens ^a  

^a INSTITUTE OF ION BEAM PHYSICS AND MATERIALS RESEARCH   (Germany)

Author keywords

18F labeling; Maleimide; Michael addition; Module assisted synthesis; Peptide radiolabeling; Positron emission tomography (PET)

Indexed keywords

18F-LABELING; MALEIMIDES; MICHAEL ADDITIONS; MODULE ASSISTED SYNTHESIS; RADIOCHEMICAL PURITY; RADIOCHEMICAL YIELD; RADIOSYNTHESIS; REACTION CONDITIONS; SOLID-PHASE EXTRACTION; SPECIFIC ACTIVITY; TOTAL SYNTHESIS;

ADDITION REACTIONS; EXTRACTION; SYNTHESIS (CHEMICAL);

POSITRON EMISSION TOMOGRAPHY;

FLUORINE 18; N [6 (4 FLUOROBENZYLIDENE)AMINOOXYLHEXYL]MALEIMIDE F 18; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG;

ARTICLE; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; RADIOCHEMISTRY; REACTION OPTIMIZATION; SOLID PHASE EXTRACTION;

AUTOMATION, LABORATORY; FLUORINE RADIOISOTOPES; ISOTOPE LABELING; MALEIMIDES; RADIOPHARMACEUTICALS; SULFHYDRYL REAGENTS;

EID: 79957625365     PISSN: 09698043     EISSN: 18729800     Source Type: Journal    
DOI: 10.1016/j.apradiso.2011.03.043     Document Type: Article

References (24)

1. Berndt M., Pietzsch J., Wuest F. Labeling of low-density lipoproteins using the 18F-labeled thiol-reactive reagent N-[6-(4-[18F]fluorobenzylidene)aminooxyhexyl]maleimide. Nucl. Med. Biol. 2007, 34:5-15.
2. Bi Y., Bailly L., Marsais F., Levacher V., Papamicael C., Dupas G. Chemoselective, accelerated and stereoselective aza-Michael addition of amines to N-phenylmaleimide by using TMADE based receptors. Tetrahedron Asymmetry 2004, 15:3703-3706.
3. Cai W., Zhang Y., Wu X., Chen A. A thiol-reactive 18F-labelling agent, N-[2-(4-18F-fluorobenzamido)ethyl]maleimide, and synthesis of RGD peptide-based tracer for PET imaging of avb3 intergrin expression. J. Nucl. Med. 2006, 47:1172-1180.
4. De Bruin B., Kuhnast F., Hinnen L., Yaouancq L., Amessou M., Johannes L., Samson A., Boisgard R., Tavitian B., Dollè F. 1-[3-(2-[18F]Fluoropyridin-3-yloxy)]pyrrole-2,5-dione: design, synthesis, and radiosynthesis of a new [18F]fluoropyridine-based maleimide reagent for the labelling of peptides and proteins. Bioconjugate Chem. 2005, 16:406-420.
5. Glaser M., Robins E.G. Click labelling in PET radiochemistry. J. Labelled Compd. Radiopharm. 2009, 52:407-414.
6. Heppeler A., Froidevaux S., Ebele A.N., Maecke H.R. Receptor targeting for tumor localisation and therapy with radiopeptides. Curr. Med. Chem. 2000, 7:971-994.
7. Höhne A., Mu L., Honer M., Schubiger P.A., Ametamey S.M., Graham K., Stellfield T., Borkowski S., Berndorff D., Klar U., Voigtmann U., Cyr J.E., Friebe M., Dinkelborg L., Srinivasan A. Synthesis, F-18-labeling, and in vitro and in vivo studies of bombesin peptides modified with silicon-based building blocks. Bioconjugate Chem. 2008, 19:1871-1879.
8. Iwata R., Pascali C., Bogni A., Horvath G., Kovàcs Z., Yanai K., Ido T. A new, convenient method for the preparation of 4-[18F]fluorobenzyl halides. Appl. Radiat. Isot. 2000, 52:87-92.
9. Koslowsky I., Mercer J., Wuest F. Synthesis and application of 4-[18F]fluorobenzylamine: a versatile building block for the preparation of PET radiotracers. Org. Biomol. Chem. 2010, 8:4730-4735.
10. Lemaire C., Damhaut P., Plenevaux A., Cantineau R., Christiaens L., Guillaume M. Synthesis of fluorine-18 substituted aromatic aldehydes and benzyl bromides, new intermediates for n.c.a. 18F-fluorination. Appl. Radiat. Isot. 1992, 43:485-494.
11. Maeding P., Fuechtner F., Wuest F. Module-assisted synthesis of the bifunctional labelling agent N-succinimidyl-4-[18F]fluorobenzoate ([18F]SFB). Appl. Radiat. Isot. 2005, 63:329-332.
12. Mc Bride W.J., Sharky R.M., Karacay H., D'Souza C.A.D., Rossi E.A., Laverman P., Chang C.H., Boerman O.C., Goldenberg D.M. A novel method of 18F radiolabeling for PET. J. Nucl. Med. 2009, 50:991-998.
13. Poethko T., Schottelius M., Thumshim G., Hersel U., Herz M., Hendriksen G., Kessler H., Schwaiger M., Wester H.J. Two-step methodology for high-yield routine radiohalogenation of peptides: F-18-labeled RGD and octreotide analogs. J. Nucl. Med. 2004, 45:892-902.
14. Shiue C.Y., Wolf A.P., Hainfield J.F. Synthesis of 18F-labeled N-(p-[18F]fluorophenyl)maleide and its derivatives for labelling monoclonal antibody with 18F. J. Labelled Compd. Radiopharm. 1989, 26:287-289.
15. Ting R., Adam M.J., Ruth T.J., Perrin D.M. Arylfluoroborates and alkylfluorosilicates as potential PET imaging agents: high-yielding aqueous biomolecular F-18-labelling. J. Am. Chem. Soc. 2005, 127:13094-13095.
16. Toyokuni T., Walsh J.C., Dominguez A., Phelps M.E., Barrio J.R., Gambhir S.S., Satyamurthy N. Synthesis of a new heterobifunctional linker, N-[4-(aminooxy)butyl]maleimide, for facile access to a thiol-reactive 18F-labeling agent. Bioconjugate Chem. 2003, 14:1253-1259.
17. Tolmachev V., Stone-Elander S. Radiolabelled proteins for positron emission tomography: pros and cons of labelling methods. Biochim. Biophys. Acta 2010, 1800:487-510.
18. Vaidyanthan G., Zalutsky M.R. Synthesis of N-succinimidyl-4-[18F]fluorobenzoate an agent for labelling proteins and peptides with 18F. Nat. Protoc. 2006, 1655-1661.
19. Wängler C., Waser B., Alke A., Iovkova L., Buchholz H.G., Niedermoser S., Jurkschat K., Fottner C., Bartenstein P., Schirrmacher R., Reubi J.C., Wester H.J., Wängler B. Bioconjugate Chem. 2010, 21:2289-2296.
20. Wester H.J., 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.
21. Wilson A.A., Dannals R.F., Ravert H.T., Wagner H.N. Reductive amination of [18F]fluorobenzaldehyde: radiosynthesis of [2-18F]-and [4-18F]fluorodexetomides. J. Labelled Compd. Radiopharm. 1990, 28:1189-1199.
22. Wuest F., Hultsch C., Bergmann R., Johannsen B., Henle T. Radiolabelling of isopeptide Nε-(γ-glutamyl)-l-lysine by conjugation with N-succinimidyl-4-[18F]fluorobenzoate. Appl. Radiat. Isot. 2003, 59:43-48.
23. Wuest F., Berndt M., Bergmann R., van den Hoff J., Pietzsch J. Synthesis and application of [18F]FDG-maleimidehexyloxime ([18F]FDG-MHO): a [18F]FDG-based prosthethic group for the chemoselective 18F-labeling of peptides and proteins. Bioconjugate Chem. 2008, 19:1202-1210.
24. Wuest F., Koehler L., Berndt M., Pietzsch J. Systematic comparison of two novel thiol-reactive prosthetic groups for 18F labelling of peptides and proteins with the acylation agent succinimidyl-4-[18F]fluorobenzoate ([18F]FSB). Amino Acids 2009, 36:283-295.