Synthesis, radiolabeling and in vitro GRP receptor targeting studies of 99m Tc-Triaza-X-BBN[7-14]NH2 (X = Serylserylserine, Glycylglycylglycine, glycylserylglycine, or beta alanine)

Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry

Volumn 36, Issue 6, 2006, Pages 481-491

  Veerendra, Bhadrasetty ^a   Sieckman, Gary ^b   Hoffman, Timothy ^a,b   Rold, Tammy ^a   Retzloff, Lauren ^a   McCrate, Joseph ^a   Prasanphanich, Adam ^a   Smith, Charles J ^a,b,c  

^a University of Missouri   (United States)

^b VETERANS AFFAIRS MEDICAL CENTER   (United States)

^c UNIVERSITY OF MISSOURI   (United States)

Author keywords

Bombesin; Gastrin releasing peptide; Prostate cancer

Indexed keywords

EID: 33746368099     PISSN: 15533174     EISSN: 15533182     Source Type: Journal    
DOI: 10.1080/15533170600778075     Document Type: Article

References (32)

1. Jurisson, S.; Berning, D.; Jia, W.; Ma, D. Coordination compounds in nuclear medicine. Chem. Rev. 1993, 93, 1137-1156.
2. 99mTc-Labeled small peptides as diagnostic radiopharmaceuticals. Chem. Rev. 1999, 99, 2235-2268.
3. Anderson, C. J.; Welch, M. J. Radiometal-labeled agents (Non-Technetium) for diagnostic imaging. Chem. Rev. 1999, 99, 2219-2234.
4. Volkert, W. A.; Hoffman, T. J. Therapeutic radiopharmaceuticals. Chem. Rev. 1999, 99, 2269-2292.
5. Van de Wiele, C.; Dumont, F.; van Belle, S.; Slegers, G.; Peers, S. H.; Dierckx, R. A. Is there a role for agonist gastrin-releasing peptide receptor radioligands in tumour imaging? Nucl. Med. Commun. 2001, 22, 5-15.
6. Lamberts, S. W.; Bakker, W. H.; Reubi, J. C.; Krenning, E. P. Somatostatin receptor imaging in the localization of endocrine tumours. N. Engl. J. Med. 1990, 323, 1246-1249.
7. 64Cu-labeled bombesin analogue. Bioconjug. Chem. 2003, 14, 756-763.
8. Smith, C. J.; Volkert, W. A.; Hoffman, T. J. Radiolabeled peptide conjugates for targeting of the bombesin receptor superfamily subtypes. Nucl. Med. Biol. 2005, 32 (7), 733-740.
9. Giblin, M. F.; Veerendra, B.; Smith, C. J. Radiometallation of receptor-specific peptides for diagnosis and treatment of human cancer. In vivo. New Anticancer Agents: In Vitro and In Vivo Evaluation 2005, 19, 9-30.
10. Smith, C. J.; Volkert, W. A.; Hoffman, T. J. Gastrin releasing peptide (GRP) receptor targeted radiopharmaceuticals: A concise update. Nucl. Med. Biol. 2003, 30, 861-868.
11. 2]: Syntheses, radiolabeling and in vitro/in vivo GRP receptor targeting studies. Anticancer Res. 2003, 23, 63-70.
12. +. In Technetium, Rhenium, and Other Metals in Chemistry and Nuclear Medicine; Nicolini, M., Mazzi, U., Eds.; SGE Editoriali: Padova, Italy, 1999, pp. 27-34.
13. - in aqueous solution and its reaction with a bifunctional ligand. J. Am. Chem. Soc. 1998, 120, 7987-7988.
14. + and synthesis of tailor-made bifunctional ligand systems. Bioconj. Chem. 2002, 13, 750-756.
15. 99mTc(I)-labeled bombesin analogue for imaging of gastrin releasing peptide receptor-positive tumors. Nucl. Med. Biology 2002, 29, 553-560.
16. 12]. J. Chem. Soc. Chem. Commun. 1996, 1291-1292.
17. 99mTc-labeling and in vivo studies of a bombesin analogue with a novel water-soluble dithiadiphosphine-based bifunctional chelating agent. Bioconj. Chem. 1999, 10, 254-260.
18. 105Rh labeled bombesin analogues: Enhancement of GRP receptor binding affinity utilizing aliphatic carbon chain linkers. J. Labelled Compd. Radiopharm. 1997, 40, 490-493.
19. Baidoo, K. E.; Lin, K. S.; Zhan, Y. G.; Finley, P.; Scheffel, U.; Wagner, H. N., Jr. Design, synthesis, and initial evaluation of high-affinity technetium bombesin analogues. Bioconj. Chem. 1998, 9, 218.
20. 2: An in vitro/in vivo structure-activity relationship study where X = 0-, 3-, 5-, 8-, and 11-carbon tethering moieties. Bioconj. Chem. 2003, 14, 93-102.
21. 2], a new family of GRP-receptor targeting radiopharmaceuticals. In Technetium, Rhenium, and Other Metals in Chemistry and Nuclear Medicine; Nicolini, M., Mazzi, U., Eds.; SGE Editoriali: Padova, Italy, 2002; pp. 339-344.
22. 99mTc-labeled HYNIC-derivatized annexin V for human use. Nucl. Med. Biol. 2003, 30, 771-778.
23. 2: An in vitro/in vivo assessment of the targeting ability of this new radiopharmaceutical for PC-3 human prostate cancer cells. Nucl. Med. Biol. 2003, 30, 101-109.
24. 2 (X = 0, β-Ala, 5-Ava, 8-Aoc, or 11-Aun) analogs as potential radiopharmaceuticals for specific-targeting of gastrin releasing peptide (GRP) receptors expressed on human prostate cancer PC-3 cells. J. Nucl. Med. 2003, 44, 823-831.
25. Pulacchini, S.; Nasser, R.; Sibbons, K. F.; Motevalli, M.; Hawkes, G. E.; Kroemer, R. T.; Bento, E. S.; Watkinson, M. Structure, modeling, and dynamic behaviour of aza- and azaoxa-macrocyclic ligands derived from (R,R)-1,2-diamino-cyclohexane. Org. Biomol. Chem. 2003, 1, 4058-4063.
26. 2 containing a bridging 2-oxa-propane-1,3-diide. Inorg. Chem. 1988, 27, 3796-3804.
27. 2: Novel technetium complexes of 1,4,7-triazacyclononane and hydridotris(pyrazolyl)borate. Inorg. Chem. 1992, 31, 895-899.
28. Cuttitta, F.; Carney, D. N.; Mulshine, J.; Moody, T. W.; Fedorko, J.; Fischler, A.; Minna, J. D. Bombesin-like peptides as autocrine growth factors in human small-cell lung cancer. Nature 1985, 316, 823-826.
29. Mahmoud, S.; Staley, J.; Taylor, J.; Bogden, A.; Moreau, J. P.; Coy, D.; Avis, I.; Cuttitta, F.; Mulshine, J. L.; Moody, T. W. Bombesin analogues inhibit growth of small cell lung cancer in vitro and in vivo. Cancer Res. 1991, 51, 1798-1802.
30. Preston, S. R.; Woodhouse, L. F.; Jones-Blackett Miller, G. V.; Primrose, J. N. High-affinity binding sites for gastrin-releasing peptide on human colorectal cancer tissue but not uninvolved mucosa. Br. J. Cancer 1995, 71, 1097-1089.
31. 2 in ovarian carcinoma induced to express the gastrin releasing peptide receptor by adenoviral vector-mediated gene transfer. J. Nucl. Med. 1997, 38, 1221-1229.
32. Zinn, K. R.; Smith, C. A.; Wu, Q.; Kirkman, R. L.; Mountz, J. M.; Buchsbaum, D. J.; Rogers, B. E. Imaging adenoviral-mediated gene transfer of gastrin releasing peptide receptor (GRPr) using a Tc-99m-labeled bombesin (BBN) analogue. J. Nucl. Med. 1998, 39 (224P), Abstract 994.