Synthesis and biological evaluation of a 99mTc-labelled cyclic RGD peptide for imaging the αvβ3 expression;Synthese und biologische evaluierung eines 99mTc-markierten zyklischen RGD-peptides für die nichtinvasive darstellung der αvβ3-expression

NuklearMedizin

Volumn 43, Issue 1, 2004, Pages 26-32

  Haubner, Roland ^a   Bruchertseifer, F ^a   Bock, M ^a   Kessler, H ^a   Schwaiger, M ^a   Wester, H J ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Alpha(v)beta3; Angiogenesis; Integrin; RGD peptides; Stability; Tumor targeting

Indexed keywords

CYANAMIDE; N EPSILON (H ASPARTYLLYSYLCYSTEINYLLYSINE) 5 LYSINE CYCLO(ARGINYLGLYCYLASPARTYL DEXTRO PHENYLALANYLLYSINE) TC 99M; TECHNETIUM 99M; TRACER; UNCLASSIFIED DRUG; VITRONECTIN RECEPTOR;

ANGIOGENESIS; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTRAST ENHANCEMENT; CONTROLLED STUDY; CYCLIZATION; DRUG DISTRIBUTION; DRUG METABOLISM; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; ISOTOPE LABELING; MELANOMA; METASTASIS; MOUSE; NONHUMAN; NUDE MOUSE; OSTEOSARCOMA; PROTEIN SYNTHESIS; RADIOCHEMISTRY; SCINTILLATION CAMERA; TUMOR XENOGRAFT;

EID: 1242330435     PISSN: 00295566     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0038-1623911     Document Type: Article

References (32)

1. Aumailley M, Gurrath M, Muller G et al. Arg-Gly-Asp constrained within cyclic pentapeptides. Strong and selective inhibitors of cell adhesion to vitronectin and laminin fragment P1. FEBS Lett 1991; 291: 50-4.
2. Banerjee S, Pillai MR, Ramamoorthy N. Evolution of Tc-99m in diagnostic radiopharmaceuticals. Semin Nucl Med 2001; 31: 260-77.
3. Bishop GG, McPherson JA, Sanders JM et al. Selective alpha(v)beta(3)-receptor blockade reduces macrophage infiltration and restenosis after balloon angioplasty in the atherosclerotic rabbit. Circulation 2001; 103: 1906-11.
4. Blum JE, Handmaker H, Rinne NA. The utility of a somatostatin-type receptor binding peptide radiopharmaceutical (P829) in the evaluation of solitary pulmonary nodules. Chest 1999; 115: 224-32.
5. Brooks PC, Montgomery AM, Rosenfeld M et al. Integrin alpha v beta 3 antagonists promote tumor regression by inducing apoptosis of angiogenic blood vessels. Cell 1994; 79: 1157-64.
6. Cheresh DA, Spiro RC. Biosynthetic and functional properties of an Arg-Gly-Asp-directed receptor involved in human melanoma cell attachment to vitronectin, fibrinogen, and von Willebrand factor. J Biol Chem 1987; 262: 17703-11.
7. Clezardin P. Recent insights into the role of integrins in cancer metastasis. Cell Mol Life Sci 1998; 54: 541-8.
8. Dechantsreiter MA, Planker E, Matha B et al. N-Methylated cyclic RGD peptides as highly active and selective alpha(V)beta(3) integrin antagonists. J Med Chem 1999; 42: 3033-40.
9. Eliceiri BP, Cheresh DA. Adhesion events in angiogenesis. Curr Opin Cell Biol 2001; 13: 563-8.
10. Fauchere JL, Morris AD, Thurieau C et al. Modulation of the activity and assessment of the receptor selectivity in a series of new RGD-containing peptides. Int J Pept Protein Res 1993; 42: 440-4.
11. Haubner R, Finsinger D, Kessler H. Stereoisomeric Peptide Libraries and Peptidomimetics for Designing Selective Inhibitors of the αvβ3 Integrin for a New Cancer Therapy. Angew Chem Int Ed Engl 1997; 36: 1374-89.
12. Haubner R, Gratias R, Diefenbach B et al. Structural and Functional Aspects of RGD-Containing Cyclic Pentapeptides as Highly Potent and Selective Integrin αVβ3 Antagonists. J Am Chem Soc 1996; 118: 7461-72.
13. 18F-Galacto-RDG: Synthesis, radiolabeling, metabolic stability and radiation dose estimates. Bioconjugate Chem 2004 (in press).
14. Haubner R, Kuhnast B, Wester HJ et al. [F-18]-RGD-Peptides Conjugated with Hydrophilic Tetrapeptides for the Noninvasive Determination of the Alpha(v)beta3 Integrin. J Nucl Med 2002; 43 (Suppl): 89P.
15. Haubner R, Wester HJ, Burkhart F et al. Glycosylated RGD-containing peptides: tracer for tumor targeting and angiogenesis imaging with improved biokinetics. J Nucl Med 2001; 42: 326-36.
16. Haubner R, Wester HJ, Reuning U et al. Radiolabeled alpha(v)beta3 integrin antagonists: a new class of tracers for tumor targeting. J Nucl Med 1999; 40: 1061-71.
17. 18F-labeled RGD-containing glycopeptide and positron emission tomography. Cancer Res 2001; 61: 1781-5.
18. Hoshiga M, Alpers CE, Smith LL et al. Alpha(v)beta3 integrin expression in normal and atherosclerotic artery. Circ Res 1995; 77: 1129-35.
19. Hynes RO. Integrins: versatility, modulation, and signaling in cell adhesion. Cell 1992; 69: 11-25.
20. 111In-pentetreotide scintigraphy. J Nucl Med 2002; 43: 889-95.
21. 18F-Labelled SSTR-Binding SPECT/PET Tracers with Improved Biodistribution. J Labelled Cpd Radiopharm 1999; 42 (Suppl.): S549-S551.
22. Mease RC, Lambert C. Newer methods of labeling diagnostic agents with Tc-99m. Semin Nucl Med 2001; 31: 278-85.
23. Pearson DA, Lister J, McBride WJ et al. Thrombus imaging using technetium-99m-labeled high-potency GPIIb/IIIa receptor antagonists. Chemistry and initial biological studies. J Med Chem 1996; 39: 1372-82.
24. Pfaff M, Tangemann K, Muller B et al. Selective recognition of cyclic RGD peptides of NMR defined conformation by alpha IIb beta 3, alpha V beta 3, and alpha 5 beta 1 integrins. J Biol Chem 1994; 269: 20233-8.
25. Ruoslahti E. RGD and other recognition sequences for integrins. Annu Rev Cell Dev Biol 1996; 12: 697-715.
26. Ruoslahti E, Pierschbacher MD. New perspectives in cell adhesion: RGD and integrins. Science 1987; 238: 491-7.
27. 3-Octreotide by Conjugation with Carbohydrates. Bioconjugate Chem 2002; 13: 1021-30.
28. Sivolapenko GB, Skarlos D, Pectasides D et al. Imaging of metastatic melanoma utilising a technetium-99m labelled RGD-containing synthetic peptide. Eur J Nucl Med 1998; 25: 1383-9.
29. Su ZF, Liu G, Gupta S et al. In vitro and in vivo evaluation of a Technetium-99m-labeled cyclic RGD peptide as a specific marker of alpha(v)beta(3) integrin for tumor imaging. Bioconjug Chem 2002; 13: 561-70.
30. Teitelbaum SL. Osteoclasts, integrins, and osteoporosis. J Bone Miner Metab 2000; 18: 344-9.
31. 18F-labelled, Carbohydrated Analogue of Octreotide. Eur J Nucl Med Mol Imaging 2003; 30: 117-22.
32. Wester HJ, Schottelius M, Scheidhauer K et al. Comparison of radioiodinated TOC, TOCA and Mtr-TOCA: the effect of carbohydration on the pharmacokinetics. Eur J Nucl Med Mol Imaging 2002; 29: 28-38.