A modular platform for the rapid site-specific radiolabeling of proteins with 18F exemplified by quantitative positron emission tomography of human epidermal growth factor receptor 2

Journal of Medicinal Chemistry

Volumn 52, Issue 19, 2009, Pages 5816-5825

  Gill, Herman S ^a   Tinianow, Jeff N ^a   Ogasawara, Annie ^a   Flores, Judith E ^a   Vanderbilt, Alexander N ^a   Raab, Helga ^a   Scheer, Justin M ^a   Vandlen, Richard ^a   Williams, Simon P ^a   Marik, Jan ^a  

^a GENENTECH INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (1 FLUORO 3,6,9,12,15,18,21 HEPTAOXATRICOS 23 YL) 4 [1 (2,5 PYRROLIDONE 1 YL) 3,6,9,12,15,18 HEXAOXANONADECA 19 YL] 1,2,3 TRIAZOLE; 1 FLUORO 3,6,9,12,15,18 HEXAOXAHENICOS 20 AZIDE; AZIDE; EPIDERMAL GROWTH FACTOR RECEPTOR 2; FLUORINE 18; TANESPIMYCIN; TRASTUZUMAB; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG CONJUGATION; FLUORINATION; GENETIC ENGINEERING; HYDROPHILICITY; ISOTOPE LABELING; MICROWAVE IRRADIATION; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PROTEIN EXPRESSION; PROTEIN MODIFICATION;

EID: 70349649221     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900420c     Document Type: Article

References (43)

1. van Dongen, G. A.; Visser, G. W.; Lub-de Hooge, M. N.; de Vries, E. G.; Perk, L. R. Immuno-PET: a navigator in monoclonal antibody development and applications. Oncologist 2007, 12, 1379-1389.
2. Shively, J. E. 18F labeling for immuno-PET: where speed and contrast meet. J. Nucl. Med. 2007, 48, 170-172.
3. Williams, L. E.; Wu, A. M.; Yazaki, P. J.; Liu, A.; Raubitschek, A. A.; Shively, J. E.; Wong, J. Y. Numerical selection of optimal tumor imaging agents with application to engineered antibodies. Cancer Biother. Radiopharm. 2001, 16, 25-35.
4. Holliger, P.; Hudson, P. J. Engineered antibody fragments and the rise of single domains. Nat. Biotechnol. 2005, 23, 1126-1136.
5. Vaidyanathan, G.; Bigner, D. D.; Zalutsky, M. R. Fluorine-18- labeled monoclonal antibody fragments: a potential approach for combining radioimmunoscintigraphy and positron emission tomography. J. Nucl. Med. 1992, 33, 1535-1541.
6. 18F]fluorobenzoate. Int. J. Radiat. Appl. Instrum. B 1992, 19, 275-281.
7. 18F]fluorobenzoate and its application to the labeling of a monoclonal antibody fragment. Bioconjugate Chem. 1994, 5, 352-356.
8. Wester, H. J.; Hamacher, K.; Stocklin, 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. (Pubitemid 26164971)
9. 18F-labeled T84.66 anticarcinoembryonic antigen diabody. J. Nucl. Med. 2007, 48, 304-310.
10. Grierson, J. R.; Yagle, K. J.; Eary, J. F.; Tait, J. F.; Gibson, D. F.; Lewellen, B.; Link, J. M.; Krohn, K. A. Production of [F-18]- fluoroannexin for imaging apoptosis with PET. Bioconjugate Chem. 2004, 15, 373-379.
11. Page, R. L.; Garg, P. K.; Garg, S.; Archer, G. E.; Bruland, O. S.; Zalutsky, M. R. PET imaging of osteosarcoma in dogs using a fluorine-18-labeled monoclonal antibody Fab fragment. J. Nucl. Med. 1994, 35, 1506-1513.
12. 18F-labeled Mel-14 F(ab′)2 fragment in normal dogs. Nucl. Med. Biol. 1994, 21, 911-919.
13. 18FB). J. Labelled Compd. Radiopharm. 2006, 49, 1213-1221.
14. Olafsen, T.; Cheung, C. W.; Yazaki, P. J.; Li, L.; Sundaresan, G.; Gambhir, S. S.; Sherman, M. A.; Williams, L. E.; Shively, J. E.; Raubitschek, A. A.; Wu, A. M. Covalent disulfide-linked anti- CEA diabody allows site-specific conjugation and radiolabeling for tumor targeting applications. Protein Eng. Des. Sel. 2004, 17, 21-27.
15. Li, X.; Link, J. M.; Stekhova, S.; Yagle, K. J.; Smith, C.; Krohn, K. A.; Tait, J. F. Site-specific labeling of annexin V with F-18 for apoptosis imaging. Bioconjugate Chem. 2008, 19, 1684-1688.
16. Tait, J. F.; Smith, C.; Levashova, Z.; Patel, B.; Blankenberg, F. G.; Vanderheyden, J. L. Improved detection of cell death in vivo with annexin V radiolabeled by site-specific methods. J. Nucl. Med. 2006, 47, 1546-1553.
17. Junutula, J. R.; Bhakta, S.; Raab, H.; Ervin, K. E.; Eigenbrot, C.; Vandlen, R.; Scheller, R. H.; Lowman, H. B. Rapid identification of reactive cysteine residues for site-specific labeling of antibody- Fabs. J. Immunol. Methods 2008, 332, 41-52.
18. Junutula, J. R.; Raab, H.; Clark, S.; Bhakta, S.; Leipold, D. D.; Weir, S.; Chen, Y.; Simpson, M.; Tsai, S. P.; Dennis, M. S.; Lu, Y.; Meng, Y. G.; Ng, C.; Yang, J.; Lee, C. C.; Duenas, E.; Gorrell, J.; Katta, V.; Kim, A.; McDorman, K.; Flagella, K.; Venook, R.; Ross, S.; Spencer, S. D.; Lee Wong, W.; Lowman, H. B.; Vandlen, R.; Sliwkowski, M. X.; Scheller, R. H.; Polakis, P.; Mallet, W. Site-specific conjugation of a cytotoxic drug to an antibody improves the therapeutic index. Nat. Biotechnol. 2008, 26, 925-932.
19. 18F-fluorobenzamido)ethyl] maleimide, and synthesis of RGD peptide-based tracer for PET imaging of alpha v beta 3 integrin expression. J. Nucl. Med. 2006, 47, 1172-1180.
20. 18F]- fluorobenzylidene)aminooxyhexyl]maleimide. Nucl. Med. Biol. 2007, 34, 5-15.
21. 18F-labeling agent. Bioconjugate Chem. 2003, 14, 1253-1259.
22. 18F]SFB). Amino Acids 2009, 36, 283-295.
23. 18F-labeling of peptides and proteins. Bioconjugate Chem. 2008, 19, 1202-1210.
24. 18F]fluoropyridine-based maleimide reagent for the labeling of peptides and proteins. Bioconjugate Chem. 2005, 16, 406-420.
25. 18F]FA-SH) labeled rat serum albumin for blood pool imaging with PET. Bioconjugate Chem. 2009, 20, 317-321.
26. 18F]SiFA-isothiocyanate: a new highly effective radioactive labeling agent for lysine-containing proteins. ChemBioChem 2009, 10, 1321-1324.
27. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew. Chem., Int. Ed. Engl. 2002, 41, 2596-2599.
28. Tornoe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on solid phase: [1, 2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 2002, 67, 3057-3064. (Pubitemid 34457265)
29. 18F]fluoropeptides using Cu(I) catalyzed 1,3-dipolar cycloaddition. Tetrahedron Lett. 2006, 47, 6681-6684.
30. 18F-FDG PET. J. Nucl. Med. 2006, 47, 793-796.
31. Smith-Jones, P. M.; Solit, D. B.; Akhurst, T.; Afroze, F.; Rosen, N.; Larson, S. M. Imaging the pharmacodynamics of HER2 degradation in response to Hsp90 inhibitors. Nat. Biotechnol. 2004, 22, 701-706.
32. 18F]fluoroethylazide for positron emission tomography. Bioconjugate Chem. 2007, 18, 989-993.
33. Lewis, W. G.; Magallon, F. G.; Fokin, V. V.; Finn, M. G. Discovery and characterization of catalysts for azide-alkyne cycloaddition by fluorescence quenching. J. Am. Chem. Soc. 2004, 126, 9152-9153.
34. Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Polytriazoles as copper(I)-stabilizing ligands in catalysis. Org. Lett. 2004, 6, 2853-2855.
35. Rodionov, V. O.; Presolski, S. I.; Diaz, D. D.; Fokin, V. V.; Finn, M. G. Ligand-accelerated Cu-catalyzed azide-alkyne cycloaddition: a mechanistic report. J. Am. Chem. Soc. 2007, 129, 12705-12712. (Pubitemid 350004482)
36. Rodionov, V. O.; Presolski, S. I.; Gardinier, S.; Lim, Y. H.; Finn, M. G. Benzimidazole and related ligands for Cu-catalyzed azidealkyne cycloaddition. J. Am. Chem. Soc. 2007, 129, 12696-12704.
37. 18F labeled nanoparticles for in vivo PET-CT imaging. Bioconjugate Chem. 2009, 20, 397-401.
38. Sereikaite, J.; Jachno, J.; Santockyte, R.; Chmielevski, P.; Bumelis, V. A.; Dienys, G. Protein scission by metal ion-ascorbate system. Protein J. 2006, 25, 369-378. (Pubitemid 44800751)
39. Sen Gupta, S.; Kuzelka, J.; Singh, P.; Lewis, W. G.; Manchester, M.; Finn, M. G. Accelerated bioorthogonal conjugation: a practical method for the ligation of diverse functional molecules to a polyvalent virus scaffold. Bioconjugate Chem. 2005, 16, 1572-1579.
40. Ward, J. F.; Johansen, I.; Aasen, J. Radiosensitization by N-ethyl maleimide;a model chemical system. Int. J. Radiat. Biol. Relat. Stud. Phys. Chem. Med. 1969, 15, 163-170.
41. Hayon, E.; Simic, M. Radiation sensitization reactions of N-ethylmaleimide with model compounds. Radiat. Res. 1972, 50, 464-478.
42. Solit, D. B.; Zheng, F. F.; Drobnjak, M.; Munster, P. N.; Higgins, B.; Verbel, D.; Heller, G.; Tong, W.; Cordon-Cardo, C.; Agus, D. B.; Scher, H. I.; Rosen, N. 17-Allylamino-17-demethoxygeldanamycin induces the degradation of androgen receptor and HER- 2/neu and inhibits the growth of prostate cancer xenografts. Clin. Cancer Res. 2002, 8, 986-993. (Pubitemid 34517631)
43. Wilson, A. A.; Jin, L.; Garcia, A.; DaSilva, J. N.; Houle, S. An admonition when measuring the lipophilicity of radiotracers using counting techniques. Appl. Radiat. Isot. 2001, 54, 203-208.