Design and evaluation of new Tc-99m-labeled lactam bridge-cyclized alpha-MSH peptides for melanoma imaging

Molecular Pharmaceutics

Volumn 10, Issue 4, 2013, Pages 1400-1408

  Guo, Haixun ^a   Gallazzi, Fabio ^d   Miao, Yubin ^a,b,c  

^a UNIVERSITY OF NEW MEXICO   (United States)

^b UNIVERSITY OF NEW MEXICO   (United States)

^c UNIVERSITY OF NEW MEXICO SCHOOL OF MEDICINE   (United States)

^d University of Missouri   (United States)

Author keywords

99mTc labeled lactam bridge cyclized peptide; alpha melanocyte stimulating hormone; melanoma SPECT imaging

Indexed keywords

ALPHA INTERMEDIN; CHELATING AGENT; INTERMEDIN DERIVATIVE; LACTAM; MELANOCORTIN 1 RECEPTOR; TECHNETIUM 99M;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; BINDING AFFINITY; COMPUTER ASSISTED TOMOGRAPHY; CONTROLLED STUDY; CYCLIZATION; IC 50; IMAGING; KIDNEY CLEARANCE; MELANOMA CELL; METASTATIC MELANOMA; MOUSE; NONHUMAN; PRIORITY JOURNAL; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY;

ALPHA-MSH; ANIMALS; CHELATING AGENTS; DRUG DESIGN; FEMALE; INHIBITORY CONCENTRATION 50; LACTAMS; MELANOMA; MELANOMA, EXPERIMENTAL; MICE; MICE, INBRED C57BL; NEOPLASM TRANSPLANTATION; PEPTIDES; PROTEIN BINDING; TECHNETIUM; TOMOGRAPHY, EMISSION-COMPUTED, SINGLE-PHOTON;

EID: 84875777080     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp3006984     Document Type: Article

References (33)

1. Jemal, A.; Siegel, R.; Xu, J.; Ward, E. Cancer statistics Ca-Cancer J. Clin. 2010, 60, 277-300
2. Giblin, M. F.; Wang, N. N.; Hoffman, T. J.; Jurisson, S. S.; Quinn, T. P. Design and characterization of α-melanotropin peptide analogs cyclized through rhenium and technetium metal coordination Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 12814-12818
3. 99mtechnetium-labeled cyclic alpha-melanocyte-stimulating hormone peptide analogues Cancer Res. 2000, 60, 5649-5658
4. 111In-DOTA-rhenium cyclized alpha-MSH analog: a novel cyclic-peptide analog with improved tumor-targeting properties J. Nucl. Med. 2001, 42, 1847-1855
5. 188Re-labeled alpha-melanocyte stimulating hormone peptide analogs for melanoma therapy Int. J. Cancer 2002, 101, 480-487
6. Froidevaux, S.; Calame-Christe, M.; Tanner, H.; Sumanovski, L.; Eberle, A. N. A novel DOTA-alpha-melanocyte-stimulating hormone analog for metastatic melanoma diagnosis J. Nucl. Med. 2002, 43, 1699-1706
7. 111In-labeled DOTA-conjugated rhenium-cyclized alpha-MSH analogues J. Med. Chem. 2002, 45, 3048-3056
8. Miao, Y.; Whitener, D.; Feng, W.; Owen, N. K.; Chen, J.; Quinn, T. P. Evaluation of the human melanoma targeting properties of radiolabeled alpha-melanocyte stimulating hormone peptide analogues Bioconjugate Chem. 2003, 14, 1177-1184
9. Froidevaux, S.; Calame-Christe, M.; Schuhmacher, J.; Tanner, H.; Saffrich, R.; Henze, M.; Eberle, A. N. A gallium-labeled DOTA-alpha-melanocyte- stimulating hormone analog for PET imaging of melanoma metastases J. Nucl. Med. 2004, 45, 116-123
10. 188Re-labeled alpha-melanocyte-stimulating hormone peptide analog in murine and human melanoma-bearing mouse models J. Nucl. Med. 2005, 46, 121-129
11. Froidevaux, S.; Calame-Christe, M.; Tanner, H.; Eberle, A. N. Melanoma targeting with DOTA-alpha-melanocyte-stimulating hormone analogs: structural parameters affecting tumor uptake and kidney uptake J. Nucl. Med. 2005, 46, 887-895
12. Miao, Y.; Hylarides, M.; Fisher, D. R.; Shelton, T.; Moore, H.; Wester, D. W.; Fritzberg, A. R.; Winkelmann, C. T.; Hoffman, T. J.; Quinn, T. P. Melanoma therapy via peptide-targeted alpha-radiation Clin. Cancer Res. 2005, 11, 5616-5621
13. 86Y-DOTA- ReCCMSH(Arg11), a cyclized peptide analogue of alpha-MSH J. Med. Chem. 2005, 48, 2985-2992
14. 177Lu-labeled α-melanocyte stimulating hormone peptide analogues in a murine melanoma model Nucl. Med. Biol. 2005, 32, 485-493
15. 177Lu labeled alpha-melanocyte stimulating hormone peptide analogues Nucl. Med. Biol. 2006, 33, 723-733
16. 64Cu-labeled rhenium-cyclized alpha-MSH peptide analog using a cross-bridged cyclam chelator J. Nucl. Med. 2007, 48, 64-72
17. 64Cu-labeled alpha-melanocyte-stimulating hormone analog for MicroPET imaging of melanocortin 1 receptor expression Bioconjugate Chem. 2007, 18, 765-772
18. 111In-labeled alpha-melanocyte-stimulating hormone peptides as imaging probes for primary and pulmonary metastatic melanoma detection J. Nucl. Med. 2007, 48, 73-80
19. 177Lu-labeled DOTA conjugated alpha-melanocyte-stimulating hormone peptide in a murine melanoma-bearing mouse model Cancer Biother. Radiopharm. 2007, 22, 333-341
20. 111In-labeled lactam bridge-cyclized alpha-melanocyte stimulating hormone peptide analogues for melanoma imaging Bioconjugate Chem. 2008, 19, 539-547
21. 111In-labeled lactam bridge-cyclized alpha-melanocyte-stimulating hormone peptide Nucl. Med. Biol. 2009, 36, 267-276
22. 111In-labeled lactam bridge-cyclized α-melanocyte stimulating hormone peptide Bioconjugate Chem. 2009, 20, 2162-2168
23. Guo, H.; Yang, J.; Shenoy, N.; Miao, Y. Gallium-67-labeled lactam bridge-cyclized alpha-melanocyte stimulating hormone peptide for primary and metastatic melanoma imaging Bioconjugate Chem. 2009, 20, 2356-2363
24. Guo, H.; Yang, J.; Gallazzi, F.; Miao, Y. Reduction of the ring size of radiolabeled lactam bridge-cyclized alpha-MSH peptide resulting in enhanced melanoma uptake J. Nucl. Med. 2010, 51, 418-426
25. Guo, H.; Yang, J.; Gallazzi, F.; Miao, Y. Effects of the amino acid linkers on melanoma-targeting and pharmacokinetic properties of Indium-111-labeled lactam bridge-cyclized α-MSH peptides J. Nucl. Med. 2011, 52, 608-616
26. +: effect of cyclization on tumor-seeking properties J. Biol. Inorg. Chem. 2008, 13, 449-459
27. 3-labeled pyrazolyl - α-melanocyte-stimulating hormone analog conjugate for melanoma targeting Nucl. Med. Biol. 2008, 35, 91-99
28. Guo, H.; Miao, Y. Cu-64-labeled lactam bridge-cyclized alpha-MSH peptides for PET imaging of melanoma Mol. Pharmaceutics 2012, 9, 2322-2330
29. Guo, H.; Gallazzi, F.; Miao, Y. Ga-67-labeled lactam bridge-cyclized alpha-MSH peptides with enhanced melanoma uptake and reduced renal uptake Bioconjugate Chem. 2012, 23, 1341-1348
30. 188Re at high labeling efficiency and specific radioactivity for tumor pretargeting Appl. Radiat. Isot. 2006, 64, 971-978
31. 99mTc using aminocarboxylates as coligands Bioconjugate Chem. 1996, 7, 63-71
32. 188Re-labeled linear alpha-melanocyte stimulating hormone analogs for specific melanoma targeting Nucl. Med. Biol. 1999, 26, 687-693
33. Giblin, M. F.; Jurisson, S. S.; Quinn, T. P. Synthesis and characterization of rhenium-complexed α-melanotropin analogs Bioconjugate Chem. 1997, 8, 347-353