Structure-activity relationships of 111In- and 99mTc-labeled quinolin-4-one peptidomimetics as ligands for the vitronectin receptor: Potential tumor imaging agents

Bioconjugate Chemistry

Volumn 17, Issue 5, 2006, Pages 1294-1313

  Harris, Thomas D ^a   Kalogeropoulos, Shirley ^a   Nguyen, Tiffany ^a   Dwyer, Gregory ^a   Edwards, D Scott ^a   Liu, Shuang ^a,b   Bartis, Judit ^a,c   Ellars, Charles ^a,d   Onthank, Dave ^a   Yalamanchili, Padmaja ^a   Heminway, Stuart ^a   Robinson, Simon ^a   Lazewatsky, Joel ^a   Barrett, John ^a  

^a BRISTOL MYERS SQUIBB   (United States)

^b PURDUE UNIVERSITY   (United States)

^c ARQULE INC   (United States)

^d A Subsidiary of Lantheus Holdings   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENDOTHELIAL CELLS;

AS-LIGANDS; BIODISTRIBUTIONS; ENDOTHELIAL-CELLS; INTEGRIN RECEPTORS; PEPTIDOMIMETICS; STRUCTURE-ACTIVITY RELATIONSHIPS; TOTAL SYNTHESIS; TUMOR IMAGING AGENTS; TUMOUR CELLS; VITRONECTIN;

TUMORS;

1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,10 TETRAACETIC ACID; 4 (3,5 DIMETHYLPHENOXY)BUTANOIC ACID; 4 QUINOLONE DERIVATIVE; ALPHA2B BETA3 INTEGRIN; ALPHAVBETA5 INTEGRIN; BUTYRIC ACID DERIVATIVE; CHELATING AGENT; HYDRAZINONICOTINAMIDE DERIVATIVE; INDIUM 111; INTEGRIN; INTEGRIN RECEPTOR; LIGAND; NICOTINAMIDE DERIVATIVE; PEPTIDOMIMETIC AGENT; RADIOPHARMACEUTICAL AGENT; RECEPTOR BLOCKING AGENT; TA 138; TECHNETIUM 99M; UNCLASSIFIED DRUG; VERY LATE ACTIVATION ANTIGEN 5; VITRONECTIN RECEPTOR; VITRONECTIN RECEPTOR ANTAGONIST;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BINDING SITE; BREAST ADENOCARCINOMA; COMPLEX FORMATION; CONJUGATE; DIAGNOSTIC IMAGING; DRUG ACTIVATION; DRUG ADSORPTION; DRUG BIOAVAILABILITY; DRUG CLEARANCE; DRUG DISTRIBUTION; ENDOTHELIUM CELL; GENE OVEREXPRESSION; ISOTOPE LABELING; LIGAND BINDING; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; RECEPTOR AFFINITY; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL; TUMOR DIAGNOSIS; TUMOR GROWTH; TUMOR LOCALIZATION; TUMOR SCINTISCANNING;

EID: 33749005665     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc060063s     Document Type: Article

References (50)

1. van der Flier, A., and Sonnenberg, A. (2001) Function and Interactions of Integrins. Cell Tissue Res. 305, 285-298.
2. Mizeiewski, G. J. (1999) Role of Integrins in Cancer: Survey of Expression Patterns. Proc. Soc. Exp. Biol. Med. 222, 124-138.
3. Hood, J. D., and Cheresh, D. A. (2002) Role of Integrins in Cell Invasion and Migration. Nat. Rev. Cancer 2, 91-100.
4. Tucker, G. C. (2002) Inhibitors of Integrins. Curr. Opin. Pharm. 2, 394-402.
5. 3 on Vascular Cells During Wound Repair. Am. J. Pathol. 148, 1407-1421.
6. 3 Expression on Tumor-Associated Vessels of Human Carcinomas. Int. J. Cancer 71, 320-324.
7. v Integrin Receptors in Wound-Induced Human Angiogenesis in Human Skin/SCID Mice Chimeras. Am. J. Pathol. 151, 975-983.
8. 3. Expert Opin. Ther. Pat. 12, 1009-1021.
9. 3 Antagonists Promote Tumor Regression by Inducing Apoptosis of Angiogenic Blood Vessels. Cell 79, 1157-1164.
10. 3 Blocks Human Breast Cancer Growth and Angiogenesis in Human Skin. J. Clin. Invest. 96, 1815-1822.
11. v Integrin Antagonists: Comparative Anti-Cancer Efficacy with Known Angiogenesis Inhibitors. Anticancer Res. 19, 959-968.
12. 5 Integrin Receptor Antagonist. Cancer Res. 61, 2232-2238.
13. 3 Integrin in Angiogenesis and Restenosis. Drug News Perspect. 14, 143-150.
14. 5 Integrins. Nat. Med. 8, 27-34.
15. Mizejewski, G. J. (1999) Role of Integrins in Cancer: Survey of Expression Patterns. Proc. Soc. Exp. Biol. Med. 222, 124-138.
16. 3 Expression by Bone-Residing Breast Cancer Metastases. Diag. Mol. Pathol. 5, 127-135.
17. 3. Anticancer Res. 19, 1529-1532.
18. 3 Is Modulated by a Focal Adhesion Kinase Pathway. Cancer Res. 59, 1655-1664.
19. Haubner, R., Wester, H.-J., Burkhart, F., Senekowitsch-Schmidtke, R., Weber, W., Goodman, S. L., Kessler, H., and Schwaiger, M. (2001) Glycosylated RGD-Containing Peptides: Tracer for Tumor Targeting and Angiogenesis Imaging with Improved Biokinetics. J. Nucl. Med. 42, 326-336.
20. 18F]Galacto-RGD: Synthesis, Radiolabeling, Metabolic Stability, and Radiation Dose Estimates. Bioconjugate Chem. 15, 61-69.
21. van Hagen, P. M., Breeman, W. A. P., Bernard, H. F., Schaar, M., Mooij, C. M., Srinivasan, A., Schmidt, M. A., Krenning, E. P., and de Jong, M. (2000) Evaluation of a Radiolabeled Cyclic DTPA-RGD Analogue for Tumor Imaging and Radionuclide Therapy. Int. J. Cancer 8, 186-198.
22. 3. J. Nucl. Med. 41, 259P.
23. Janssen, M., Oyen, W. J. G., Massuger, L. F. A. G., Frielink, C., Dijkgraaf, I., Edwards, D. S., Radjopadhye, M., Corstens, F. H. M., and Boerman, O. C. (2002) Comparison of a Monomeric and Dimeric Radiolabeled RGD-Peptide for Tumor Targeting. Cancer Biother. Radiopharm. 17, 641-646.
24. Haubner, R., and Wester, H.-J. (2004) Radiolabeled Tracers for Imaging of Tumor Angiogenesis and Evaluation of Anti-Angiogenic Therapies. Curr. Pharm. Des. 10, 1439-1455.
25. v Integrin Antagonists: Novel Anticancer Agents. Exp. Opin. Invest. Drugs 9, 1271-1279.
26. 3. Exp. Opin. Ther. Pat. 10, 1367-1383.
27. 3 (the Vitronectin Receptor). Drug Discuss. Today 5, 397-408.
28. 3. J. Med. Chem. 43, 27-40.
29. 3 Integrin - Antagonists: Chemical and Structural Requirements for Activity and Selectivity. Mini Rev. Med. Chem. 2, 531-542.
30. Wityak, J. Personal communication.
31. 3 Receptor Antagonists for Tumor Imaging and Radiotherapy. Cancer Biother. Radiopharm. 18, 627-641.
32. 3 - Targeted Nanoparticle and 1.5 T Magnetic Resonance Imaging. Cancer Res. 63, 5838-5843.
33. 3 - Targeted Paramagnetic Nanoparticles. Magn. Reson. Med. 53, 621-627.
34. 3 Integrin In Vivo. Circulation 110, 84-90.
35. Meoli, D. F., Sadeghi, M. M., Krassilnikova, S., Bourke, B. N., Giordano, F. J., Dione, D. P., Su, H., Edwards, D. S., Liu, S., Harris, T. D., Madri, J. A., Zaret, B. L., and Sinusas, A. J. (2004) Noninvasive imaging of myocardial angiogenesis following experimental myocardial infarction. J. Clin. Invest. 113, 1684-1691.
36. Wityak, J., and Tobin, A, E. (1998) Preparation of Novel Integrin Receptor Antagonists. U.S. Patent 6,130,231.
37. 99mTc-Labeled Radiopharmaceuticals. Bioconjugate Chem. 10, 808-814.
38. Badilescu, I. I. (1975) Heterocyclic compounds. III. Cyclization of Ring-Substituted γ-Phenoxybutyric Acids by PPA [Polyphosphoric Acid] to 2,3-Dihydro-1-benzoxepin-5(4H)-ones. Rev. Roum. Chim. 20, 761-774.
39. Abrams, M. J., Juweid, M., TenKate, C. I., Schwartz, D. A., Hauser, M. M., Gaul, F. E., Fuccello, A. J., Rubin, R. H., Strauss, H. W., and Fischman, A. J. (1990) Technetium-99m-human Polyclonal IgG Radiolabeled via the Hydrazinonicotinamide Derivative for Imaging Focal Sites of Infection in Rats. J. Nucl. Med. 31, 2022-2028.
40. Arnold, L. D., Kalantar, T. H., and Vederas, J. C. (1985) Conversion of Serine to Stereochemically Pure β-Substituted α-Amino Acids via β-Lactones. J. Am. Chem. Soc. 107, 7105-7109.
41. Lohse, P. A., and Felber, R. (1998) Incorporation of a Phosphonic Acid Isostere of Aspartic Acid into Peptides Using Fmoc-Solid-Phase Synthesis. Tetrahedron Lett. 39, 2067-2070.
42. 3. J. Med. Chem. 43, 27-40.
43. Trester-Zedlitz, M., Kamada, K., Burley, S. K., Fenyo, D., Chait, B. T., and Muir, T. W. (2003) A Modular Cross-Linking Approach for Exploring Protein Interactions. J. Am. Chem. Soc. 125, 2416-2425.
44. Hubbuch, A., Danho, W., and Zahn, H. (1979) Synthesis of N-Protected Cysteic Acid Derivatives and Their Activated Esters. Liebigs Ann. Chem., 776-783.
45. 1 in Promoting Cellular Attachment and Spreading on Fibronectin. J. Cell Biol. 111, 2795-2800.
46. 3 Receptor Antagonist: Different but Biologically Equivalent. Bioconjugate Chem. 15, 235-241.
47. 177Lu-Labeling of a DOTA-Conjugated Non-peptide Vitronectin Receptor Antagonist. Bioconjugate Chem. 14, 1030-1037.
48. Currie, L. A. (1968) Limits for Qualitative Detection and Quantitative Determination. Anal. Chem. 40, 586-593.
49. 99Tc. Bioconjugate Chem. 8, 146-154.
50. Behr, T. M., Goldenberg, D. M., and Becker, W. (1998) Reducing the Renal Uptake of Radiolabeled Antibody Fragments and Peptides for Diagnosis and Therapy: Present Status, Future Prospects and Limitations. Eur. J. Nucl. Med. 25, 201-212.