New F-18 prosthetic group via oxime coupling

Bioconjugate Chemistry

Volumn 22, Issue 4, 2011, Pages 642-653

  Carberry, Patrick ^a   Lieberman, Brian P ^a   Ploessl, Karl ^a   Choi, Seok R ^c   Haase, Danniebelle N ^a   Kung, Hank F ^a,b  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

^c AVID RADIOPHARMACEUTICALS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINE COMPOUNDS; GLYCOPROTEINS; MOLECULES; PROSTHETICS; PROTEINS; SYNTHESIS (CHEMICAL);

AMYLOID PLAQUES; BLOOD-BRAIN BARRIER; FLUORINE-18; ORGANIC COMPLEX; POST INJECTION; PROSTHETIC GROUPS; RADIOCHEMICAL PURITY; RADIOCHEMICAL YIELD; SHORT REACTION TIME; SYNTHESISED;

LIGANDS;

2 [6 [2 [2 (2 FLUOROETHOXY)ETHOXY]ETHOXY]PYRIDIN 3 YL]METHYLENEAMINOOXY] N [17 [5 [4 (METHYLAMINO)STYRYL]PYRIDIN 2 YLOXY] 3,6,9,12,15 PENTAOXAHEPTADECYL]ACETAMIDE F 18; 2 [6 [2 [2 (2 FLUOROETHOXY)ETHOXY]ETHOXY]PYRIDIN 3 YL]METHYLENEAMINOOXY] N [2 [2 [2 [5 [4 (METHYLAMINO)STYRYL]PYRIDIN 2 YLOXY]ETHOXY]ETHOXY]ETHYL]ACETAMIDEF 18; 4 [2 [6 [2 [2 (2 FLUOROETHOXY)ETHOXY]ETHOXY]PYRIDINE 3 YL]VINYL] N METHYL BENZENAMINE F 18; AMYLOID BETA PROTEIN; OXIME; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; BLOOD; BLOOD BRAIN BARRIER; BONE; BRAIN; DRUG BLOOD LEVEL; DRUG BONE LEVEL; DRUG BRAIN LEVEL; DRUG DISTRIBUTION; DRUG LIVER LEVEL; DRUG MUSCLE LEVEL; DRUG PENETRATION; DRUG SYNTHESIS; DRUG TISSUE LEVEL; DRUG UPTAKE; HEART; HUMAN; HUMAN TISSUE; IN VIVO STUDY; ISOTOPE LABELING; KIDNEY; LIVER; LUNG; MALE; MOUSE; MUSCLE; NONHUMAN; PANCREAS; REACTION TIME; SKIN; SPLEEN;

MUS;

EID: 79955026635     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc1004262     Document Type: Article

References (49)

1. Tolmachev, V. and Stone-Elander, S. (2010) Radiolabelled proteins for positron emission tomography: Pros and cons of labelling methods Biochim. Biophys. Acta, Gen. Subj. 1800, 487-510
2. Cherry, S. R. (2001) Fundamentals of positron emission tomography and applications in preclinical drug development J. Clin. Pharmacol. 41, 482-491
3. Ametamey, S. M., Honer, M., and Schubiger, P. A. (2008) Molecular imaging with PET Chem. Rev. 108, 1501-1516 (Pubitemid 351796395)
4. Mach, R. H. and Schwarz, S. W. (2010) Challenges for developing PET tracers: isotopes, chemistry, and regulatory aspects PET Clinics 5, 131-153
5. Kuhnast, B. and Dolle, F. (2010) The challenge of labeling macromolecules with fluorine-18: three decades of research Curr. Radiopharm. 3, 174-201
6. Schubiger, P. A., Lehmann, L., and Friebe, M. (2006) PET Chemistry, Vol. 62, Springer, New York.
7. Hultsch, C., Berndt, M., Bergmann, R., and Wuest, F. (2007) Radiolabeling of multimeric neurotensin(8-13) analogs with short-lived positron emitter fluorine-18 Appl. Radiat. Isot. 65, 818-826 (Pubitemid 46727067)
8. Fredriksson, A., Johnstrom, P., Stone-Elander, S., Jonasson, P., Nygren, P.-A., Ekberg, K., Johansson, B.-L., and Wahren, J. (2001) Labeling of human C-peptide by conjugation with N-succinimidyl-4-[18F]fluorobenzoate J. Labelled Compd. Radiopharm. 44, 509-519 (Pubitemid 32621692)
9. Schottelius, M., Poethko, T., Herz, M., Reubi, J.-C., Kessler, H., Schwaiger, M., and Wester, H.-J. (2004) First 18F-labeled tracer suitable for routine clinical imaging of sst receptor-expressing tumors using positron emission tomography Clin. Cancer Res. 10, 3593-3606 (Pubitemid 38697592)
10. Guhlke, S., Wester, H.-J., Bruns, C., and Stoecklin, 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. 21, 819-25 (Pubitemid 24263575)
11. Olberg, D. E., Arukwe, J. M., Grace, D., Hjelstuen, O. K., Solbakken, M., Kindberg, G. M., and Cuthbertson, A. (2010) One step radiosynthesis of 6-[18F]fluoronicotinic acid 2,3,5,6-tetrafluorophenyl ester ([18F]F-Py-TFP): a new prosthetic group for efficient labeling of biomolecules with fluorine-18 J. Med. Chem. 53, 1732-1740
12. Wust, F., Hultsch, C., Bergmann, R., Johannsen, B., and Henle, T. (2003) Radiolabeling of isopeptide Ne-(gamma -glutamyl)-L-lysine by conjugation with N-succinimidyl 4-[18F]fluorobenzoate Appl. Radiat. Isot. 59, 43-48
13. De Bruin, B., Kuhnast, B., Hinnen, F., Yaouancq, L., Amessou, M., Johannes, L., Samson, A., Boisgard, R., Tavitian, B., and Dolle, 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 Bioconjugate Chem. 16, 406-420 (Pubitemid 40388217)
14. Prante, O., Einsiedel, J., Haubner, R., Gmeiner, P., Wester, H.-J., Kuwert, T., and Maschauer, S. (2007) 3,4,6-Tri-O-acetyl-2-deoxy-2-[18F] fluoroglucopyranosyl phenylthiosulfonate: a thiol-reactive agent for the chemoselective 18F-glycosylation of peptides Bioconjugate Chem. 18, 254-262 (Pubitemid 46146017)
15. Wangler, B., Quandt, G., Iovkova, L., Schirrmacher, E., Wangler, C., Boening, G., Hacker, M., Schmoeckel, M., Jurkschat, K., Bartenstein, P., and Schirrmacher, R. (2009) Kit-like 18F-labeling of proteins: synthesis of 4-(di-tert-butyl[18F]fluorosilyl)benzenethiol (Si[18F]FA-SH) labeled rat serum albumin for blood pool imaging with PET Bioconjugate Chem. 20, 317-321
16. Glaser, M., Karlsen, H., Solbakken, M., Arukwe, J., Brady, F., Luthra, S. K., and Cuthbertson, A. (2004) 18F-Fluorothiols: a new approach to label peptides chemoselectively as potential tracers for positron emission tomography Bioconjugate Chem. 15, 1447-1453 (Pubitemid 39552036)
17. Mach, R. H., Leudtke, R. R., Unsworth, C. D., Boundy, V. A., Nowak, P. A., Scripko, J. G., Elder, S. T., Jackson, J. R., and Hoffman, P. L. 1993, Fluorine-18 labeled benzamides for studying the dopamine D2 receptor with positron emission tomography J. Med. Chem. 36, 3707-20 (Pubitemid 24004370)
18. Garg, S., Thopate, S. R., Minton, R. C., Black, K. W., Lynch, A. J. H., and Garg, P. K. (2007) 3-Amino-4-(2-((4-[18F]fluorobenzyl)methylamino) methylphenylsulfanyl)benzonitrile, an F-18 fluorobenzyl analogue of DASB: synthesis, in vitro binding, and in vivo biodistribution studies Bioconjugate Chem. 18, 1612-1618 (Pubitemid 47464071)
19. Olberg, D. E., Hjelstuen, O. K., Solbakken, M., Arukwe, J., Karlsen, H., and Cuthbertson, A. (2008) A novel prosthetic group for site-selective labeling of peptides for positron emission tomography Bioconjugate Chem. 19, 1301-1308 (Pubitemid 351874953)
20. Olberg, D. E., Hjelstuen, O. K., Solbakken, M., Arukwe, J. M., Dyrstad, K., and Cuthbertson, A. (2009) Site-specific addition of an 18F-N- methylaminooxy-containing prosthetic group to a vinylsulfone modified peptide J. Labelled Compd. Radiopharm. 52, 571-575
21. Bruus-Jensen, K., Poethko, T., Schottelius, M., Hauser, A., Schwaiger, M., and Wester, H.-J. (2006) Chemoselective hydrazone formation between HYNIC-functionalized peptides and 18F-fluorinated aldehydes Nucl. Med. Biol. 33, 173-183
22. Toyokuni, T., Walsh, J. C., Dominguez, A., Phelps, M. E., Barrio, J. R., Gambhir, S. S., and 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 (Pubitemid 37451774)
23. Berndt, M., Pietzsch, J., and Wuest, F. (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 (Pubitemid 46038147)
24. Namavari, M., Padilla De Jesus, O., Cheng, Z., De, A., Kovacs, E., Levi, J., Zhang, R., Hoerner Joshua, K., Grade, H., Syud Faisal, A., and Gambhir Sanjiv, S. (2008) Direct site-specific radiolabeling of an affibody protein with 4-[18F]fluorobenzaldehyde via oxime chemistry Mol. Imaging Biol. 10, 177-81
25. Poethko, T., Schottelius, M., Thumshirn, G., Hersel, U., Herz, M., Henriksen, G., Kessler, H., Schwaiger, M., and Wester, H.-J. (2004) Two-step methodology for high-yield routine radiohalogenation of peptides: 18F-labeled RGD and ocreotide analogs J. Nucl. Med. 45, 892-902 (Pubitemid 47618571)
26. Namavari, M., Cheng, Z., Zhang, R., De, A., Levi, J., Hoerner, J. K., Yaghoubi, S. S., Syud, F. A., and Gambhir, S. S. (2009) A novel method for direct site-specific radiolabeling of peptides using [18F]FDG Bioconjugate Chem. 20, 432-436
27. Li, X., Link, J. M., Stekhova, S., Yagle, K. J., Smith, C., Krohn, K. A., and Tait, J. F. (2008) Site-specific labeling of annexin V with F-18 for apoptosis imaging Bioconjugate Chem. 19, 1684-1688
28. Hultsch, C., Schottelius, M., Auernheimer, J., Alke, A., and Wester, H.-J. (2009) 18F-Fluoroglucosylation of peptides, exemplified on cyclo(RGDfK) Eur. J. Nucl. Med. Mol. 36, 1469-1474
29. Wuest, F., Hultsch, C., Berndt, M., and Bergmann, R. (2009) Direct labelling of peptides with 2-[18F]fluoro-2-deoxy-D-glucose ([18F]FDG) Bioorg. Med. Chem. Lett. 19, 5426-5428
30. Abdel-Jalil, R. J., Aqarbeh, M., Loeffler, D., Shen, B., Orabi, S. A., Voelter, W., and Machulla, H.-J. (2010) Synthesis and radiolabeling of new N-[(4-[18F]fluorobenzylidene) aminooxy) alkyl]-2-nitroimidazoles as possible hypoxia imaging pharmaceuticals J. Radioanal. Nucl. Chem. 283, 239-243
31. Glaser, M., Morrison, M., Solbakken, M., Arukwe, J., Karlsen, H., Wiggen, U., Champion, S., Kindberg, G. M., and Cuthbertson, A. (2008) Radiosynthesis and biodistribution of cyclic RGD peptides conjugated with novel [18F]fluorinated aldehyde-containing prosthetic groups Bioconjugate Chem. 19, 951-957 (Pubitemid 351614549)
32. Wester, H.-J., Hamacher, K., and Stoecklin, G. (1996) A comparative study of n.c.a. fluorine-18 labeling of proteins via acylation and photochemical conjugation Nucl. Med. Biol. 23, 365-372 (Pubitemid 26164971)
33. Thonon, D., Kech, C., Paris, J., Lemaire, C., and Luxen, A. (2009) New strategy for the preparation of clickable peptides and labeling with 1-(azidomethyl)-4-[18F]-fluorobenzene for PET Bioconjugate Chem. 20, 817-823
34. Marik, J. and Sutcliffe, J. L. (2006) Click for PET: rapid preparation of [18F]fluoropeptides using CuI catalyzed 1,3-dipolar cycloaddition Tetrahedron Lett. 47, 6681-6684 (Pubitemid 44176106)
35. Inkster, J. A. H., Adam, M. J., Storr, T., and Ruth, T. J. (2009) Labeling of an antisense oligonucleotide with [18F]FPy5yne Nucleosides, Nucleotides Nucleic Acids 28, 1131-1143
36. Inkster, J. A. H., Guerin, B., Ruth, T. J., and Adam, M. J. (2008) Radiosynthesis and bioconjugation of [18F]FPy5yne, a prosthetic group for the 18F labeling of bioactive peptides J. Labelled Compd. Radiopharm. 51, 444-452
37. Okarvi, S. M. (2001) Recent progress in fluorine-18 labelled peptide radiopharmaceuticals Eur. J. Nucl. Med. 28, 929-938 (Pubitemid 32663907)
38. Adams, J. P. (2000) Imines, enamines and oximes Perkin 1, 125-139 (Pubitemid 35290363)
39. Singh, Y., Edupuganti, O. P., Villien, M., Defrancq, E., and Dumy, P. (2005) The oxime bond formation as a useful tool for the preparation of oligonucleotide conjugates C. R. Chim. 8, 789-796 (Pubitemid 40667699)
40. Choi, S. R., Golding, G., Zhuang, Z., Zhang, W., Lim, N., Hefti, F., Benedum, T. E., Kilbourn, M. R., Skovronsky, D., and Kung, H. F. (2009) Preclinical properties of 18F-AV-45: a PET agent for Aβ plaques in the brain J. Nucl. Med. 50, 1887-1894
41. Lin, K.-J., Hsu, W.-C., Hsiao, I.-T., Wey, S.-P., Jin, L.-W., Skovronsky, D., Wai, Y.-Y., Chang, H.-P., Lo, C.-W., Yao, C. H., Yen, T.-C., and Kung, M.-P. (2010) Whole-body biodistribution and brain PET imaging with [18F]AV-45, a novel amyloid imaging agent-a pilot study Nucl. Med. Biol. 37, 497-508
42. Poethko, T., Schottelius, M., Thumshirn, G., Herz, M., Haubner, R., Henriksen, G., Kessler, H., Schwaiger, M., and Wester, H.-J. (2004) Chemoselective pre-conjugate radiohalogenation of unprotected mono- and multimeric peptides via oxime formation Radiochim. Acta 92, 317-327
43. Zoppellaro, G., Ivanova, A., Enkelmann, V., Geies, A., and Baumgarten, M. (2003) Synthesis, magnetic properties and theoretical calculations of novel nitronyl nitroxide and imino nitroxide diradicals grafted on terpyridine moiety Polyhedron 22, 2099-2110
44. Zhang, W., Oya, S., Kung, M.-P., Hou, C., Maier, D. L., and Kung, H. F. (2005) F-18 Polyethyleneglycol stilbenes as PET imaging agents targeting Aβ aggregates in the brain Nucl. Med. Biol. 32, 799-809 (Pubitemid 41505313)
45. Mormeneo, D., Casas, J., Llebaria, A., and Delgado, A. (2007) Synthesis and preliminary antifungal evaluation of a library of phytosphingolipid analogues Org. Biomol. Chem. 5, 3769-3777 (Pubitemid 350115418)
46. Wascholowski, V. and Giannis, A. (2006) Sphingolactones: selective and irreversible inhibitors of neutral sphingomyelinase Angew. Chem., Int. Ed. Engl. 45, 827-30 (Pubitemid 43151412)
47. Deroo, S., Defrancq, E., Moucheron, C., Kirsch-De Mesmaeker, A., and Dumy, P. (2003) Synthesis of an oxyamino-containing phenanthroline derivative for the efficient preparation of phenanthroline oligonucleotide oxime conjugates Tetrahedron Lett. 44, 8379-8382 (Pubitemid 37249393)
48. Kung, H. F., Choi, S. R., Qu, W., Zhang, W., and Skovronsky, D. (2010) 18F stilbenes and styrylpyridines for PET imaging of Aβ plaques in alzheimers disease: a miniperspective J. Med. Chem. 53, 933-941
49. Dischino, D. D., Welch, M. J., Kilbourn, M. R., and Raichle, M. E. (1983) Relationship between lipophilicity and brain extraction of carbon-11-labeled radiopharmaceuticals J. Nucl. Med. 24, 1030-1038 (Pubitemid 14206457)