Backbone metal-cyclization: A novel approach for simultaneous peptide cyclization and radiolabeling. Application to the combinatorial synthesis of rhenium-cyclic somatostatin analogs

Nuclear Medicine and Biology

Volumn 32, Issue 1, 2005, Pages 39-50

  Fridkin, Gil ^a   Bonasera, Thomas A ^b   Litman, Pninit ^b   Gilon, Chaim ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b Peptor Ltd   (Israel)

Author keywords

Backbone metal cyclization; Radiolabeled somatostatin analogs

Indexed keywords

METAL COMPLEX; PEPTIDE LIBRARY; RADIOISOTOPE; RHENIUM; SOMATOSTATIN DERIVATIVE; SOMATOSTATIN RECEPTOR; SOMATOSTATIN TC 99M; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CHO CELL; CYCLIZATION; DRUG SYNTHESIS; IC 50; ISOTOPE LABELING; NONHUMAN; TUMOR DIAGNOSIS;

BINDING SITES; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG DESIGN; FEASIBILITY STUDIES; HALF-LIFE; HUMANS; ISOTOPE LABELING; METALS; PEPTIDE LIBRARY; PROTEIN BINDING; RADIOISOTOPES; RECEPTORS, SOMATOSTATIN; RHENIUM; SOMATOSTATIN;

EID: 13244299209     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2004.08.007     Document Type: Article

References (31)

1. W.H. Bakker, R. Albert, C. Bruns, W.A. Breeman, L.J. Hofland, and P. Marbach [111In-DTPA-d-Phe1]-octreotide, a potential radiopharmaceutical for imaging of somatostatin receptor-positive tumors: synthesis, radiolabeling and in vitro validation Life Sci. 49 1991 1583 1591
2. A.R. Fritzberg, P.G. Abrams, P.L. Beaumier, S. Kasina, A.C. Morgan, and T.N. Rao Specific and stable labeling of antibodies with technetium-99m with a diamide dithiolate chelating agent Proc. Natl. Acad. Sci. U. S. A. 85 1988 4025 4029
3. S. Liu, D.S. Edwards, R.J. Looby, A.R. Harris, M.J. Poirier, and J.A. Barrett Labeling a hydrazino nicotinamide-modified cyclic IIb/IIIa receptor antagonist with 99mTc using aminocarboxylates as coligands Bioconjug. Chem. 7 1996 63 71
4. R. Albert, P. Smith-Jones, B. Stolz, C. Simeon, H. Knecht, and C. Bruns Direct synthesis of [DOTA-DPhe1]-octreotide and [DOTA-DPhe1,Tyr3]-octreotide (SMT487): two conjugates for systemic delivery of radiotherapeutical nuclides to somatostatin receptor positive tumors in man Bioorg. Med. Chem. Lett. 8 1998 1207 1210
5. S. Froidevaux, and A.N. Eberle Somatostatin analogs and radiopeptides in cancer therapy Biopolymers 66 2002 161 183
6. M.F. Giblin, N. Wang, T.J. Hoffman, S.S. Jurisson, and T.P. Quinn Design and characterization of alpha-melanotropin peptide analogs cyclized through rhenium and technetium metal coordination Proc. Natl. Acad. Sci. U. S. A. 95 1998 12814 12818
7. L. Melendez-Alafort, G. Ferro-Flores, C. Arteaga-Murphy, M. Pedraza-Lopez, M.A. Gonzalez-Zavala, and J.I. Tendilla Labeling peptides with rhenium-188 Int. J. Pharm. 182 1999 165 172
8. C. Gilon, D. Muller, G. Bitan, Y. Salitra, I. Goldwasser, and V. Hornik Cycloscan: backbone cyclic conformationally constraint libraries of peptides R. Ramage R. Epton Peptides 1996: Proceedings of the Twenty-Fourth European Peptide Symposium 1998 Mayflower Scientific Ltd. Kingswinford (UK) 423 424
9. C. Gilon, C. Mang, E. Lohof, A. Friedler, and H. Kessler Synthesis of cyclic peptides M. Goodman C. Toniolo L. Moroder A. Felix Synthesis of peptides and peptidomimetics 2003 Georg Thieme Verlag Stuttgart 422 529
10. M. Afargan, E.T. Janson, G. Gelerman, R. Rosenfeld, O. Ziv, and O. Karpov Novel long-acting somatostatin analog with endocrine selectivity: potent suppression of growth hormone but not of insulin Endocrinology 142 2001 477 486
11. S. Gazal, G. Gellerman, O. Ziv, O. Karpov, P. Litman, and M. Bracha Human somatostatin receptor specificity of backbone-cyclic analogues containing novel sulfur building units J. Med. Chem. 45 2002 1665 1671
12. C. Gilon, M. Huenges, B. Matha, G. Gellerman, V. Hornik, and M. Afargan A backbone-cyclic, receptor 5-selective somatostatin analogue: synthesis, bioactivity, and nuclear magnetic resonance conformational analysis J. Med. Chem. 41 1998 919 929
13. G. Byk, D. Halle, I. Zeltser, G. Bitan, Z. Selinger, and C. Gilon Synthesis and biological activity of NK-1 selective, N-backbone cyclic analogs of the C-terminal hexapeptide of substance P J. Med. Chem. 39 1996 3174 3178
14. M. Altstein, O. Ben-Aziz, S. Daniel, I. Schefler, I. Zeltser, and C. Gilon Backbone cyclic peptide antagonists, derived from the insect pheromone biosynthesis activating neuropeptide, inhibit sex pheromone biosynthesis in moths J. Biol. Chem. 274 1999 17573 17579
15. S.W. Lamberts The role of somatostatin in the regulation of anterior pituitary hormone secretion and the use of its analogs in the treatment of human pituitary tumors Endocr. Rev. 9 1988 417 436
16. T. Reisine, and G.I. Bell Molecular biology of somatostatin receptors Endocr. Rev. 16 1995 427 442
17. W.W. de Herder, and S.W. Lamberts Somatostatin and somatostatin analogues: diagnostic and therapeutic uses Curr. Opin. Oncol. 14 2002 53 57
18. S.W. Lamberts, A.J. van der Lely, W.W. de Herder, and L.J. Hofland Octreotide N. Engl. J. Med. 334 1996 246 254
19. Y. Menda, and D. Kahn Somatostatin receptor imaging of non-small cell lung cancer with 99mTc depreotide Semin. Nucl. Med. 32 2002 92 96
20. O. Nilsson, L. Kolby, B. Wangberg, A. Wigander, H. Billig, and L. William-Olsson Comparative studies on the expression of somatostatin receptor subtypes, outcome of octreotide scintigraphy and response to octreotide treatment in patients with carcinoid tumors Br. J. Cancer 77 1998 632 637
21. D.J. Kwekkeboom, and E.P. Krenning Somatostatin receptor imaging Semin. Nucl. Med. 32 2002 84 91
22. A. Pasternak, Y. Pan, D. Marino, P.E. Sanderson, R. Mosley, and S.P. Rohrer Potent, orally bioavailable somatostatin agonists: good absorption achieved by urea backbone cyclization Bioorg. Med. Chem. Lett. 9 1999 461 469
23. S.M. Okarvi Recent developments in 99Tcm-labelled peptide-based radiopharmaceuticals: an overview Nucl. Med. Commun. 20 1999 1093 1112
24. G. Gellerman, A. Elgavi, Y. Salitra, and M. Kramer Facile synthesis of orthogonally protected amino acid building blocks for combinatorial N-backbone cyclic peptide chemistry J. Pept. Res. 57 2001 277 291
25. R.A. Houghten General method for the rapid solid-phase synthesis of large numbers of peptides: specificity of antigen-antibody interaction at the level of individual amino acids Proc. Natl. Acad. Sci. U. S. A. 82 1985 5131 5135
26. E. Kaiser, R.L. Colescott, C.D. Bossinger, and P.I. Cook Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides Anal. Biochem. 34 1970 595 598
27. H.P. Vanbilloen, G.M. Bormans, M.J. De Roo, and A.M. Verbruggen Complexes of technetium-99m with tetrapeptides, a new class of 99mTc-labelled agents Nucl. Med. Biol. 22 1995 325 338
28. K. Raynor, W.A. Murphy, D.H. Coy, J.E. Taylor, J.P. Moreau, and K. Yasuda Cloned somatostatin receptors: identification of subtype-selective peptides and demonstration of high affinity binding of linear peptides Mol. Pharmacol. 43 1993 838 844
29. T.N. Rao, D. Adhikesavalu, A. Camerman, and A.R. Fritzberg Technetium(V) and Rhenium(V) complexes of 2,3-Bis(mercaptoacetamido)propanoate. Chelate ring stereochemistry and influence on chemical and biological properties J. Am. Chem. Soc. 112 1990 5798 5804
30. 3OMe) Inorg. Chem. 34 1995 1764 1772
31. K. Schwochau Technetium chemistry and radiopharmaceutical applications 2000 Wiley-VCH Weinheim