Imaging of melanoma using 64Cu- and 86Y-DOTA- ReCCMSH(Arg11), a cyclized peptide analogue of α-MSH

Journal of Medicinal Chemistry

Volumn 48, Issue 8, 2005, Pages 2985-2992

  McQuade, Paul ^a   Miao, Yubin ^c   Yoo, Jeongsoo ^a   Quinn, Thomas P ^c   Welch, Michael J ^a,b   Lewis, Jason S ^a,b  

^a WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b USA   (United States)

^c University of Missouri   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,10 TETRAACETIC ACID CU 64; 1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,10 TETRAACETIC ACID Y 86; ALPHA INTERMEDIN DERIVATIVE; COPPER COMPLEX; CYCLOPEPTIDE; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG; 1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,10 TETRAACETIC ACID (REO ACETYL(CYS(3,4,10),PHE(7),ARG(7))ALPHA MSH(3 13)); 1,4,7,10-TETRAAZACYCLODODECANE 1,4,7,10-TETRAACETIC ACID (REO-ACETYL(CYS(3,4,10),PHE(7),ARG(7))ALPHA-MSH(3-13)); ALPHA INTERMEDIN; COPPER; DRUG DERIVATIVE; MELANOCORTIN 1 RECEPTOR; ORGANOMETALLIC COMPOUND; YTTRIUM;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CANCER SCINTISCANNING; COMPLEX FORMATION; CONTROLLED STUDY; DRUG DISTRIBUTION; DRUG SYNTHESIS; DRUG UPTAKE; FEMALE; ISOTOPE LABELING; MELANOMA; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; RADIOISOTOPE DISTRIBUTION; TUMOR XENOGRAFT; ANIMAL; C57BL MOUSE; CANCER TRANSPLANTATION; CHEMISTRY; EXPERIMENTAL MELANOMA; METABOLISM; SCINTISCANNING; STRUCTURE ACTIVITY RELATION; TISSUE DISTRIBUTION; TUMOR CELL LINE; XENOGRAFT;

ALPHA-MSH; ANIMALS; CELL LINE, TUMOR; COPPER RADIOISOTOPES; FEMALE; ISOTOPE LABELING; MELANOMA, EXPERIMENTAL; MICE; MICE, INBRED C57BL; NEOPLASM TRANSPLANTATION; ORGANOMETALLIC COMPOUNDS; PEPTIDES, CYCLIC; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; RECEPTOR, MELANOCORTIN, TYPE 1; STRUCTURE-ACTIVITY RELATIONSHIP; TISSUE DISTRIBUTION; TRANSPLANTATION, HETEROLOGOUS; YTTRIUM RADIOISOTOPES;

EID: 17444408174     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0490282     Document Type: Article

References (42)

1. Jemal, A.; Tiwari, R. C.; Murray, T.; Ghafoor, A.; Samuels, A.; Ward, E.; Feuer, E. J.; Thun, M. J. Cancer Statistics 2004. CA Cancer J. Clin. 2004, 54, 8-29.
2. Dennis, L. K. Analysis of the melanoma epidemic, both apparent and real: Data from the 1973 through 1994 surveillance, epidemiology, and end results program registry. Arch. Dermatol. 1999, 135, 275-280.
3. Dennis, L. K. Increasing risk of melanoma with increasing age. JAMA 1999, 282, 1037-1038.
4. Eberle, A. N.; Froidevaux, S. Radiolabeled alpha-melanocyte-stimulating hormone analogues for receptor-mediated targeting of melanoma: From tritium to indium. J. Mol. Recognit. 2003, 16, 248-254.
5. 18F-FDG in oncology. J. Nucl. Med. Technol. 2002, 30, 3-9.
6. Herholz, K.; Rudolf, J.; Heiss, W. D. FDG transport and phosphorylation in human gliomas measured with dynamic PET. J. Neurooncol. 1992, 12, 159-165.
7. Som, P.; Atkins, H. L.; Bandoypadhyay, D.; Fowler, J. S.; MacGregor, R. R.; Matsui, K.; Oster, Z. H.; Sacker, D. F.; Shiue, C. Y.; Turner, H.; Wan, C. N.; Wolf, A. P.; Zabinski, S. V. A fluorinated glucose analogue, 2-fluoro-2-deoxy-D-glucose (F-18): Nontoxic tracer for rapid tumor detection. J. Nucl. Med. 1980, 21, 670-675.
8. 18F-fluorodeoxyglucose positron emission tomography in melanoma patients. Cancer 2001, 91, 1530-1542.
9. 15O-water using compartment and noncompartment analysis. J. Nucl. Med. 2001, 42, 248-256.
10. Rossi, C. R.; Foletto, M.; Vecchiato, A.; Alessio, S.; Menin, N.; Lise, M. Management of cutaneous melanoma M0: State of the art and trends. Eur. J. Cancer 1997, 33, 2302-2312.
11. Mountjoy, K. G.; Robbins, L. S.; Mortrud, M. T.; Cone, R. D. The cloning of a family of genes that encode the melanocortin receptors. Science 1992, 257, 1248-1251.
12. Gantz, I.; Konda, Y.; Tashiro, T.; Shimoto, Y.; Miwa, H.; Munzert, G.; Watson, S. J.; DelValle, J.; Yamada, T. Molecular cloning of a novel melanocortin receptor. J. Biol. Chem. 1993, 268, 8246-8250.
13. Gantz, I.; Miwa, H.; Konda, Y.; Shimoto, Y.; Tashiro, T.; Watson, S. J.; DelValle, J.; Yamada, T. Molecular cloning, expression, and gene localization of a fourth melanocortin receptor. J. Biol. Chem. 1993, 268, 15174-15179.
14. Cone, R. D.; Lu, D.; Koppula, S.; Vage, D. I.; Klungland, H.; Boston, B.; Chen, W.; Orth, D. N.; Pouton, C.; Kesterson, R. A. The melanocortin receptors: Agonists, antagonists, and the hormonal control of pigmentation. Recent Prog. Horm. Res. 1996, 51, 287-317; discussion 318.
15. Siegrist, W.; Oestreicher, M.; Stutz, S.; Girard, J.; Eberle, A. N. Radioreceptor assay for alpha-MSH using mouse B16 melanoma cells+. J. Recept. Res. 1988, 8, 323-343.
16. Ghanem, G. E.; Comunale, G.; Libert, A.; Vercammen-Grandjean, A.; Lejeune, F. J. Evidence for alpha-melanocyte-stimulating hormone (alpha-MSH) receptors on human malignant melanoma cells. Int. J. Cancer 1988, 41, 248-255.
17. Siegrist, W.; Solca, F.; Stutz, S.; Giuffre, L.; Carrel, S.; Girard, J.; Eberle, A. N. Characterization of receptors for alpha-melanocyte-stimulating hormone on human melanoma cells. Cancer Res. 1989, 49, 6352-6358.
18. Tatro, J. B.; Wen, Z.; Entwistle, M. L.; Atkins, M. B.; Smith, T. J.; Reichlin, S.; Murphy, J. R. Interaction of an alpha-melanocyte-stimulating hormone-diphtheria toxin fusion protein with melanotropin receptors in human melanoma metastases. Cancer Res. 1992, 52, 2545-2548.
19. Bagutti, C.; Oestreicher, M.; Siegrist, W.; Oberholzer, M.; Eberle, A. N. alpha-MSH receptor autoradiography on mouse and human melanoma tissue sections and biopsies. J. Recept. Signal Transduct. Res. 1995, 15, 427-442.
20. Loir, B.; Perez Sanchez, C.; Ghanem, G.; Lozano, J. A.; Garcia-Borron, J. C.; Jimenez-Cervantes, C. Expression of the MC1 receptor gene in normal and malignant human melanocytes. A semiquantitative RT-PCR study. Cell Mol. Biol. (Noisy-le-grand) 1999, 45, 1083-1092.
21. Jiang, J.; Sharma, S. D.; Fink, J. L.; Hadley, M. E.; Hruby, V. J. Melanotropic peptide receptors: Membrane markers of human melanoma cells. Exp. Dermatol. 1996, 5, 325-333.
22. Cornish, J.; Callon, K. E.; Mountjoy, K. G.; Bava, U.; Lin, J. M.; Myers, D. E.; Naot, D.; Reid, I. R. alpha -melanocyte-stimulating hormone is a novel regulator of bone. Am. J. Physiol. Endocrinol. Metab. 2003, 284, E1181-1190.
23. 7] alpha-MSH. Discovery of a tripeptidyl agonist exhibiting sustained bioactivity. Ann. N. Y. Acad. Sci. 1993, 680, 597-599.
24. Cheng, Z.; Chen, J.; Quinn, T. P.; Jurisson, S. S. Radioiodination of rhenium cyclized alpha-melanocyte-stimulating hormone resulting in enhanced radioactivity localization and retention in melanoma. Cancer Res. 2004, 64, 1411-1418.
25. Giblin, M. F.; Wang, N.; Hoffman, T. J.; Jurisson, S. S.; Quinn, T. P. Design and characterization of alpha-melanotropin peptide analogues cyclized through rhenium and technetium metal coordination. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 12814-12818.
26. 111In-labeled DOTA-conjugated rhenium-cyclized alpha-MSH analogues. J. Med. Chem. 2002, 45, 3048-3056.
27. 64Cu using a biomedical cyclotron. Nucl. Med. Biol. 1997, 24, 35-43.
28. Yoo, J.; Perkins, T. A.; Tang, L.; Rowland, D. J.; Lewis, J. S.; Welch, M. J. Preparation of high specific activity Y-86 using a small biomedical cyclotron. J. Nucl. Med. 2004, 45, 210P.
29. Blower, P. J.; Lewis, J. S.; Zweit, J. Copper radionuclides and radiopharmaceuticals in nuclear medicine. Nucl. Med. Biol. 1996, 23, 957-980.
30. 111In-DOTA-rhenium cyclized alpha-MSH analog: A novel cyclic-peptide analogue with improved tumor-targeting properties. J. Nucl. Med. 2001, 42, 1847-1855.
31. Chen, J.; Cheng, Z.; Hoffman, T. J.; Jurisson, S. S.; Quinn, T. P. Melanoma-targeting properties of (99m)technetium-labeled cyclic alpha-melanocyte-stimulating hormone peptide analogues. Cancer Res. 2000, 60, 5649-5658.
32. Froidevaux, S.; Calame-Christe, M.; Sumanovski, L.; Tanner, H.; Eberle, A. N. DOTA α-melanocyte-stimulating hormone analogues for imaging metastatic melanoma lesions. Ann. N. Y. Acad. Sci. 2003, 994, 378-383.
33. 3-octreotate in a somatostatin receptor-positive, tumor-bearing rat model. Clin. Cancer Res. 1999, 5, 3608-3616.
34. 4-methylthiosemicarbazone) for the prevention of tumor growth at wound sites following laparoscopic surgery: Monitoring therapy response with microPET and magnetic resonance imaging. Cancer Res. 2002, 62, 445-449.
35. Breeman, W. A. P.; Kwekkeboom, D. J.; Kooij, P. P. M.; Bakker, W. H.; Hofland, L. J.; Visser, T. J.; Ensing, G. J.; Lamberts, S. W. J.; Krenning, E. P. Effect of dose and specific activity on tissue distribution of Indium-111-pentetreotide in rats. J. Nucl. Med. 1995, 36, 623-627.
36. 111In for SPECT, PET, and targeted therapeutic applications of somatostatin receptor (hsst2) expressing tumors. Bioconjugate Chem. 2002, 13, 530-541.
37. Froidevaux, S.; Eberle, A. N.; Christe, M.; Sumanovski, L.; Heppeler, A.; Schmitt, J. S.; Eisenwiener, K.; Beglinger, C.; Macke, H. R. Neuroendocrine tumor targeting: Study of novel gallium-labeled somatostatin radiopeptides in a rat pancreatic tumor model. Int. J. Cancer 2002, 98, 930-937.
38. Boswell, C. A.; Sun, X.; Niu, W.; Weisman, G. R.; Wong, E. H.; Rheingold, A. L.; Anderson, C. J. Comparative in vivo stability of copper-64-labeled cross-bridged and conventional tetraazamacrocyclic complexes. J. Med. Chem. 2004, 47, 1465-1474.
39. Sun, X.; Wuest, M.; Weisman, G. R.; Wong, E. H.; Reed, D. P.; Boswell, C. A.; Motekaitis, R.; Martell, A. E.; Welch, M. J.; Anderson, C. J. Radiolabeling and in vivo behavior of copper-64-labeled cross-bridged cyclam ligands. J. Med. Chem. 2002, 45, 469-477.
40. 3-octreotate using a cross-bridged macrocyclic chelator. Clin. Cancer Res. 2004, 10, 8674-8682.
41. 3]-octreotide as carriers for somatostatin receptor-targeted scintigraphy and radionuclide therapy. Int. J. Cancer 1998, 75, 406-411.
42. Knoess, C.; Siegel, S.; Smith, A.; Newport, D.; Richerzhagen, N.; Winkeler, A.; Jacobs, A.; Goble, R. N.; Graf, R.; Wienhard, K.; Heiss, W.-D. Performance evaluation of the microPET-R4 PET scanner for rodents. Eur J. Nucl. Med. Mol. Imaging 2003, 737-747.