Dual integrin and gastrin-releasing peptide receptor targeted tumor imaging using 18F-Labeled PEGylated RGD-bombesin heterodimer 18F-FB-PEG 3-Glu-RGD-BBN

Journal of Medicinal Chemistry

Volumn 52, Issue 2, 2009, Pages 425-432

  Liu, Zhaofei ^a,b   Yan, Yongjun ^a   Chin, Frederic T ^a   Wang, Fan ^b   Chen, Xiaoyuan ^a  

^a STANFORD UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ARGINYLGLYCYLASPARTIC ACID; BOMBESIN; FLUORINE 18; GASTRIN RELEASING PEPTIDE RECEPTOR; HETERODIMER; MACROGOL; POLYETHYLENEGLYCOL CYCLO(ARGINYLGLYCYLASPARTYL DEXTRO TYROSYLLYSYL)GLUTAMATE (AMINOCAPROIC ACID GLUTAMINYLTRYPTOPHYLALANYLVALYLGLYCYLHISTIDYLLEUCYLMETHIONINAMIDE) F 18; UNCLASSIFIED DRUG; VITRONECTIN RECEPTOR; ARGINYL-GLYCYL-ASPARTIC ACID; BOMBESIN RECEPTOR; FLUORINE; OLIGOPEPTIDE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; DRUG DESIGN; DRUG DISTRIBUTION; DRUG SYNTHESIS; DRUG TARGETING; DRUG UPTAKE; HUMAN; HUMAN CELL; ISOTOPE LABELING; MOLECULAR IMAGING; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; REACTION ANALYSIS; RECEPTOR AFFINITY; ANIMAL; CHEMISTRY; DIMERIZATION; EXPERIMENTAL NEOPLASM; METABOLISM; SCINTISCANNING;

ANIMALS; BOMBESIN; DIMERIZATION; FLUORINE RADIOISOTOPES; INTEGRIN ALPHAVBETA3; NEOPLASMS, EXPERIMENTAL; OLIGOPEPTIDES; RECEPTORS, BOMBESIN;

EID: 60549098667     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm801285t     Document Type: Article

References (35)

1. Mankoff, D. A.; Link, J. M.; Linden, H. M.; Sundararajan, L.; Krohn, K. A. Tumor receptor imaging. J. Nucl. Med. 2008, 49, 149S-163S.
2. Okarvi, S. M. Peptide-based radiopharmaceuticals: future tools for diagnostic imaging of cancers and other diseases. Med. Res. Rev. 2004, 24 (3), 357-397.
3. Hynes, R. O. Integrins: versatility, modulation, and signaling in cell adhesion. Cell 1992, 69 (1), 11-25.
4. Seftor, R. E.; Seftor, E. A.; Gehlsen, K. R.; Stetler-Stevenson, W. G.; Brown, P. D.; Ruoslahti, E.; Hendrix, M. J. Role of the av/33 integrin in human melanoma cell invasion. Proc. Natl. Acad. Sci. U.S.A 1992, 89 (5), 1557-1561.
5. Brooks, P. C.; Clark, R. A.; Cheresh, D. A. Requirement of vascular integrin alpha v beta 3 for angiogenesis. Science 1994, 264 (5158),569-571.
6. 18F-labeled RGD peptide: initial evaluation for imaging brain tumor angiogenesis. Nucl. Med. Biol. 2004, 31 (2), 179-189.
7. Chen, X.; Sievers, E.; Hou, Y.; Park, R.; Tohme, M.; Bart, R.; Bremner, R.; Bading, J. R.; Conti, P. S. Integrin av/33-targeted imaging of lung cancer. Neoplasia 2005, 7 (3), 271-279.
8. 18F-FRGD2. J. Nucl. Med. 2006, 47 (1), 113-121.
9. 18F-Galacto-RGD PET. J. Nucl. Med. 2008, 49 (2), 255259.
10. 18F]galacto-RGD positron emission tomography for imaging of alphavbeta3 expression on the neovasculature in patients with squa- mous cell carcinoma of the head and neck. Clin. Cancer Res. 2007, 13 (22 Pt 1), 6610-6616.
11. 18F]Galacto-RGD. PLoS Med. 2005, 2 (3), e70.
12. Gugger, M.; Reubi, J. C. Gastrin-releasing peptide receptors in non- neoplastic and neoplastic human breast. Am. J. Pathol. 1999, 155 (6), 2067-2076.
13. Markwalder, R.; Reubi, J. C. Gastrin-releasing peptide receptors in the human prostate: relation to neoplastic transformation. Cancer Res. 1999, 59 (5), 1152-1159.
14. Scheffel, U.; Pomper, M. G. PET imaging of GRP receptor expression in prostate cancer. J. Nucl. Med. 2004, 45 (8), 1277-1278.
15. 18F-labeled bombesin analogs for targeting GRP receptor-expressing prostate cancer. J. Nucl. Med. 2006, 47 (3), 492501.
16. 18F-FDG. J. Nucl. Med. 2007, 48 (8), 1245-1250.
17. Cescato, R.; Maina, T.; Nock, B.; Nikolopoulou, A.; Charalambidis, D.; Piccand, V.; Reubi, J. C. Bombesin receptor antagonists may be preferable to agonists for tumor targeting. J. Nucl. Med. 2008, 49 (2),318-326.
18. Garrison, J. C.; Rold, T. L.; Sieckman, G. L.; Naz, F.; Sublett, S. V.;Figueroa, S. D.; Volkert, W. A.; Hoffman, T. J. Evaluation of the pharmacokinetic effects of various linking group using the 111In- DOTA-X-BBN(7-14)NH2 structural paradigm in a prostate cancer model. Bioconjugate Chem. 2008, 19 (9), 1803-1812.
19. Zhang, H.; Chen, J.; Waldherr, C.; Hinni, K.; Waser, B.; Reubi, J. C.; Maecke, H. R. Synthesis and evaluation of bombesin derivatives on the basis of pan-bombesin peptides labeled with indium-111, lutetium- 177, and yttrium-90 for targeting bombesin receptor-expressing tumors. Cancer Res. 2004, 64 (18), 6707-6715.
20. Van de Wiele, C.; Phonteyne, P.; Pauwels, P.; Goethals, I.; Van den Broecke, R.; Cocquyt, V.; Dierckx, R. A. Gastrin-releasing peptide receptor imaging in human breast carcinoma versus immunohis- tochemistry. J. Nucl. Med. 2008, 49 (2), 260-264.
21. 3 in prostate cancer progression. Neoplasia 2002, 4 (3), 191-194.
22. 18F-labeled BBN- RGD heterodimer for prostate cancer imaging. J. Nucl. Med. 2008,49 (3), 453-461.
23. 18F-labeled PEGylated RGD peptide. Eur. J. Nucl. Med. Mol. Imaging 2004, 31 (8), 1081-1089.
24. 3Eur. J. Nucl. Med. Mol. Imaging 2007, 34 (11), 1823-1831.
25. 18F- labeled PEGylated tetrameric RGD peptide (18F-FPRGD4). J. Nucl. Med. 2007, 48 (9), 1536-1544.
26. Walsh, S.; Shah, A.; Mond, J. Improved pharmacokinetics and reduced antibody reactivity of lysostaphin conjugated to polyethylene glycol. Antimicrob. Agents Chemother. 2003, 47 (2), 554-558.
27. 64Cu-labeled bombesin analogs in a mouse model of human prostate adenocarcinoma. Nucl. Med. Biol. 2006, 33 (3), 371-380.
28. Capello, A.; Krenning, E. P.; Bernard, B. F.; Breeman, W. A.; Erion, J. L.; de Jong, M. Anticancer activity of targeted proapoptotic peptides. J. Nucl. Med. 2006, 47 (1), 122-129.
29. Capello, A.; Krenning, E. P.; Bernard, B. F.; Breeman, W. A.; van Hagen, M. P.; de Jong, M. Increased cell death after therapy with an Arg-Gly-Asp-linked somatostatin analog. J. Nucl. Med. 2004, 45 (10),1716-1720.
30. Bernard, B.; Capello, A.; van Hagen, M.; Breeman, W.; Srinivasan, A.; Schmidt, M.; Erion, J.; van Gameren, A.; Krenning, E.; de Jong, M. Radiolabeled RGD-DTPA-Tyr3-octreotate for receptor-targeted radionuclide therapy. Cancer Biother. Radiopharm. 2004, 19 (2), 173180.
31. Vagner, J.; Xu, L.; Handl, H. L.; Josan, J. S.; Morse, D. L.; Mash, E. A.; Gillies, R. J.; Hruby, V. J. Heterobivalent ligands crosslink multiple cell-surface receptors: the human melanocortin-4 and delta- opioid receptors. Angew. Chem., Int. Ed. 2008, 47 (9), 1685-1688.
32. 125I-labeled RGD peptide are improved by PEGylation. Nucl. Med. Biol. 2004, 31 (1), 11-19.
33. 3 integrin expression. J. Nucl. Med. 2007, 48 (7), 11621171.
34. 3 expression. Eur. J. Nucl. Med. Mol. Imaging 2008, 35 (6), 1100-1108.
35. 3]bombesin in human prostate adenocarcinoma xenografts. J. Nucl. Med. 2004, 45 (8),1390-1397.