Systematic comparison of two novel, thiol-reactive prosthetic groups for 18F labeling of peptides and proteins with the acylation agent succinimidyl-4-[18F]fluorobenzoate ([18F]SFB)

Amino Acids

Volumn 36, Issue 2, 2009, Pages 283-295

  Wuest, Frank ^a   Köhler, Lena ^a   Berndt, Mathias ^a   Pietzsch, Jens ^a  

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

Author keywords

18F labeled prosthetic groups; Apolipoproteins; LDL; Peptides; Positron emission tomography (PET)

Indexed keywords

4 FLUOROBENZALDEHYDE O [2 [2 [2 (PYRROL 2,5 DIONE 1 YL)ETHOXY]ETHOXY]ETHYL]OXIME F 18; 4 FLUOROBENZALDEHYDE O [6 (2,5 DIOXO 2,5 DIHYDROPYRROL 1 YL)HEXYL]OXIME F 18; APOLIPOPROTEIN A1; APOLIPOPROTEIN B100; APOLIPOPROTEIN E; CYSTEINE; GLUTATHIONE; LOW DENSITY LIPOPROTEIN; NEUROTENSIN DERIVATIVE; RADIOPHARMACEUTICAL AGENT; SUCCINIMIDYL 4 FLUOROBENZOATE F 18; THIOL GROUP; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; ISOTOPE LABELING; LIPOPHILICITY; PRIORITY JOURNAL; PROTEIN BINDING; RADIOACTIVITY; RADIOCHEMISTRY;

ACYLATION; BENZOATES; CHOLESTEROL, LDL; FLUORINE RADIOISOTOPES; HUMANS; ISOTOPE LABELING; MALEIMIDES; NEUROTENSIN; OXIMES; PEPTIDES; PROTEINS; RADIOPHARMACEUTICALS; SUCCINIMIDES;

EID: 59449084092     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-008-0065-2     Document Type: Article

References (43)

1. J Becaud M Karramkam L Mu PA Schubiger S Ametamey R Smits B Koksch K Graham JE Cyr L Dinkelborg D Suelzle T Stellfeld T Brumby L Lehmann A Srinivasan 2007 Development of a new direct method for 18F-labeling of peptides J Label Compd Radiopharm 50 S215
2. R Bergmann M Scheunemann C Heichert P Mäding H Wittrisch M Kretzschmar H Rodig D Tourwé K Iterbeke K Chavatte D Zips JC Reubi B Johannsen 2002 Biodistribution and catabolism of (18)F-labeled neurotensin(8-13) analogs Nucl Med Biol 29 61 72
3. M Berndt J Pietzsch F Wuest 2007 Labeling of low-density lipoproteins using the 18F-labeled thiol-reactive reagent N-[6-(4-[18F]fluorobenzylidene) aminooxyhexyl]maleimide Nucl Med Biol 34 5 15
4. L Bodei M Cremonesi C Grana P Rocca M Bartolomei M Chinol G Paganelli 2004 Receptor radionuclide therapy with 90Y-[DOTA]0-Tyr3-octreotide (90Y-DOTATOC) in neuroendocrine tumours Eur J Nucl Med Mol Imaging 31 1038 1046
5. W Cai T Olafsen X Zhang Q Cao SS Gambhir LE Williams AM Wu X Chen 2007 PET imaging of colorectal cancer in xenograft-bearing mice by use of an 18F-labeled T84.66 anti-carcinoembryonic antigen diabody J Nucl Med 48 304 310
6. I Carrió PL Pieri J Narula L Prat P Riva L Pedrini E Pretolani G Caruso G Sarti M Estorch L Berná V Riambau X Matías-Guiu C Pak C Ditlow F Chen BA Khaw 1998 Noninvasive localization of human atherosclerotic lesions with indium 111-labeled monoclonal Z2D3 antibody specific for proliferating smooth muscle cells J Nucl Cardiol 5 551 557
7. PC Chinn JE Leonard J Rosenberg N Hanna DR Anderson 1999 Preclinical evaluation of 90Y-labeled anti-CD20 monoclonal antibody for treatment of non-Hodgkin's lymphoma Int J Oncol 15 1017 1025
8. B de Bruin B Kuhnast F Hinnen L Yaouancq M Amessou L Johannes A Samson R Boisgard B Tavitian F Dollé 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
9. M de Jong WH Bakker EP Krenning WA Breeman ME van der Pluijm BF Bernard TJ Visser E Jermann M Béhé P Powell HR Mäcke 1997 Yttrium-90 and indium-111 labelling, receptor binding and biodistribution of [DOTA0,d-Phe1,Tyr3]octreotide, a promising somatostatin analogue for radionuclide therapy Eur J Nucl Med 24 368 371
10. 18F]fluoropyridine-based maleimide reagent for protein labelling J Label Compd Radiopharm 46 S15
11. CA Fisher V Narayanaswami RO Ryan 2000 The lipid-associated conformation of the low density lipoprotein receptor binding domain of human apolipoprotein E J Biol Chem 275 33601 33606
12. M Glaser E Arstad 2007 "Click labeling" with 2-[18f]fluoroethylazide for positron emission tomography Bioconjug Chem 18 989 993
13. DM Goldenberg 2001 The role of radiolabeled antibodies in the treatment of non-Hodgkin's lymphoma: the coming of age of radioimmunotherapy Crit Rev Oncol Hematol 39 195 201
14. S Hoppmann B Steiniger K Strobel C Haase J Pietzsch 2006
15. C Hultsch M Berndt R Bergmann F Wuest 2007 Radiolabeling of multimeric neurotensin(8-13) analogs with the short-lived positron emitter fluorine-18 Appl Radiat Isot 65 818 826
16. HA Jacene R Filice W Kasecamp RL Wahl 2007 Comparison of 90Y-ibritumomab tiuxetan and 131I-tositumomab in clinical practice J Nucl Med 48 1767 1776
17. F Jamar PT Chapman DH Manicourt DM Glass DO Haskard AM Peters 1997 A comparison between 111In-anti-E-selectin mAb and 99Tcm-labelled human non-specific immunoglobulin in radionuclide imaging of rheumatoid arthritis Br J Radiol 70 473 481
18. G Karabatsos N His 1967 Structural studies by nuclear magnetic resonance-XI: conformations and configurations of oxime O-methyl ethers Tetrahedron Lett 23 1079 1095
19. EP Krenning DJ Kwekkeboom WH Bakker WA Breeman PP Kooij HY Oei M van Hagen PT Postema M de Jong JC Reubi 1993 Somatostatin receptor scintigraphy with [111In-DTPA-D-Phe1]- and [123I-Tyr3]-octreotide: the Rotterdam experience with more than 1,000 patients Eur J Nucl Med 20 716 731
20. ZB Li Z Wu K Chen FT Chin X Chen 2007 Click chemistry for (18)F-labeling of RGD peptides and microPET imaging of tumor integrin alphavbeta3 expression Bioconjug Chem 18 1987 1994
21. 13C NMR characterization of lysine residues in apolipoprotein B and their role in binding to the low density lipoprotein receptor J Biol Chem 263 13831 13838
22. P Mäding F Füchtner F Wuest 2005 Module-assisted synthesis of the bifunctional labelling agent N-succinimidyl 4-[(18)F]fluorobenzoate ([(18)F]SFB) Appl Radiat Isot 63 329 332
23. 18F]fluoropeptides using Cu(I) catalyzed 1,3-dipolar cycloaddition Tetrahedron Lett 47 6881 6884
24. J Pietzsch R Bergmann 2004 Analysis of 6-hydroxy-2-aminocaproic acid (HACA) as a specific marker of protein oxidation: the use of N(O,S)-ethoxycarbonyl trifluoroethyl ester derivatives and gas chromatography/mass spectrometry Amino Acids 26 45 51
25. J Pietzsch R Bergmann K Rode C Hultsch B Pawelke F Wuest J van den Hoff 2004 Fluorine-18 radiolabeling of low-density lipoproteins: a potential approach for characterization and differentiation of metabolism of native and oxidized low-density lipoproteins in vivo Nucl Med Biol 31 1043 1050
26. T Ramenda R Bergmann F Wuest 2007 Synthesis of 18F-labeled neurotensin(8-13) via copper-mediated 1,3-dipolar [3 + 2]cycloaddition reaction Lett Drug Des Discov 4 279 285
27. J Scott 1989 The molecular and cell biology of apolipoprotein-B Mol Biol Med 6 65 80
28. JP Segrest MK Jones VK Mishra GM Anantharamaiah DW Garber 1994 apoB-100 has a pentapartite structure composed of three amphipathic alpha-helical domains alternating with two amphipathic beta-strand domains. Detection by the computer program LOCATE Arterioscler Thromb 14 1674 1685
29. JP Segrest MK Jones H De Loof N Dashti 2001 Structure of apolipoprotein B-100 in low density lipoproteins J Lipid Res 42 1346 1367
30. J Shepherd DK Bedfordm HG Morgan 1976 Radioiodination of human low density lipoprotein: a comparison of four methods Clin Chim Acta 66 97 109
31. 18F J Label Compd Radiopharm 26 287 289
32. JE Shively 2007 F-18 labeling for immuno-PET: where speed and contrast meet J Nucl Med 48 170 172
33. T Toyokuni JC Walsh A Dominguez ME Phelps JR Barrio SS Gambhir 2003 Synthesis of a new heterobifunctional linker, N-[4-(aminooxy)butyl]maleimide, for facile access to a thiol-reactive F-18-labeling agent Bioconjug Chem 14 1253 1259
34. 18F Nat Protoc 1 1655 1661
35. MA Walker 1994 The Mitsunobu reaction - a novel method for the synthesis of bifunctional maleimid linkers Tetrahedron Lett 35 665 668
36. MA Walker 1995 A high yielding synthesis of N-alkyl maleinides using a novel modification of the Mitsunobu reaction J Org Chem 60 5352 5355
37. HJ Wester M Schottelius 2007 Fluorine-18 labeling of peptides and proteins Ernst Schering Res Found Workshop 62 79 111
38. HJ Wester K Hamacher G Stöcklin 1996 A comparative study of N.C.A. fluorine-18 labeling of proteins via acylation and photochemical conjugation Nucl Med Biol 23 365 372
39. AA Wilson L Jin A Garcia JN DaSilva S Houle 2001 An admonition when measuring the lipophilicity of radiotracers using counting techniques Appl Radiat Isot 54 203 208
40. 90Y-labeled anti-CD20 monoclonal antibody Clin Cancer Res 53 3281s 3286s
41. 18F]fluorobenzoate Appl Radiat Isot 59 43 48
42. C Yang ZW Gu M Yang AM Gotto Jr 1994 Primary structure of apoB-100 Chem Phys Lipids 67-68 99 104
43. CY Yang ZW Gu M Yang SN Lin AJ Garcia-Prats LK Rogers SE Welty CV Smith 1999 Selective modification of apoB-100 in the oxidation of low density lipoproteins by myeloperoxidase in vitro J Lipid Res 40 686 698