99mTc-Galacto-RGD2: A novel 99mTc-labeled cyclic RGD peptide dimer useful for tumor imaging

Molecular Pharmaceutics

Volumn 10, Issue 9, 2013, Pages 3304-3314

  Ji, Shundong ^a   Czerwinski, Andrzej ^b   Zhou, Yang ^a   Shao, Guoqiang ^a   Valenzuela, Francisco ^b   Sowiński, Paweł ^c   Chauhan, Satendra ^b   Pennington, Michael ^b   Liu, Shuang ^a  

^a PURDUE UNIVERSITY   (United States)

^b Peptides International Inc   (United States)

^c GDANSK UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

99mTc labeling; Integrin v 3; RGD containing glycopeptide; SPECT; Tumor imaging

Indexed keywords

ALKYNE; ARGINYLGLYCYLASPARTIC ACID; AZIDE; BENZALDEHYDE DERIVATIVE; COPPER; CYCLOPEPTIDE; DIMER; ECHISTATIN; ETHYLAMINE; GALACTOSE; NICOTINIC ACID DERIVATIVE; SUCCINIMIDE DERIVATIVE; SULFONE DERIVATIVE; TECHNETIUM 99M; TRACER; TRIPHENYLPHOSPHINE; VITRONECTIN RECEPTOR;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BINDING AFFINITY; CATALYSIS; CYCLOADDITION; DIPOLE; DRUG DISTRIBUTION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; DRUG TUMOR LEVEL; GLIOMA CELL; IC 50; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; RADIOCHEMISTRY; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY;

ANIMALS; CELL LINE, TUMOR; FEMALE; GLIOMA; GLYCOPEPTIDES; HUMANS; MICE; MICE, NUDE; OLIGOPEPTIDES; ORGANOTECHNETIUM COMPOUNDS; TOMOGRAPHY, EMISSION-COMPUTED, SINGLE-PHOTON;

EID: 84883563450     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp400085d     Document Type: Article

References (60)

1. Folkman, J. Angiogenesis in cancer, vascular, rheumatoid and other disease Nat. Med. 1995, 1, 27-31
2. 3: a new prognostic indicator in breast cancer Clin. Cancer Res. 1998, 4, 2625-2634
3. 3 integrin receptors in breast tumor J. Exp. Clin. Cancer Res. 2001, 20, 585-590
4. 3 subunit with tumor progression Cancer Res. 1990, 50, 6757-6764
5. 3 for angiogenesis Science 1994, 264, 569-571
6. Hwang, R.; Varner, J. V. The role of integrins in tumor angiogenesis Hematol. Oncol. Clin. North Am. 2004, 18, 991-1006
7. 5 integrin expression in glioma periphery Neurosurgery 2001, 49, 380-389
8. Jin, H.; Varner, J. Integrins: roles in cancer development and as treatment targets Br. J. Cancer 2004, 90, 561-565
9. Zitzmann, S.; Ehemann, V.; Schwab, M. Arginine-Glycine-Aspartic acid (RGD)-peptide binds to both tumor and tumor endothelial cells in vivo Cancer Res. 2002, 62, 5139-5143
10. D'Andrea, L. D.; Del Gatto, A.; Pedone, C.; Benedetti, E. Peptide-based molecules in angiogenesis Chem. Biol. Drug Des. 2006, 67, 115-126
11. Meyer, A.; Auremheimer, J.; Modlinger, A.; Kessler, H. Targeting RGD recognizing integrins: drug development, biomaterial research, tumor imaging and targeting Curr. Pharm. Des. 2006, 12, 2723-2747
12. Weber, W. A.; Haubner, R.; Vabuliene, E.; Kuhnast, B.; Webster, H. J.; Schwaiger, M. Tumor angiogenesis targeting using imaging agents Q. J. Nucl. Med. 2001, 45, 179-182
13. Haubner, R.; Wester, H. R. Radiolabeled tracers for imaging of tumor angiogenesis and evaluation of anti-angiogenic therapies Curr. Pharm. Des. 2004, 10, 1439-1455
14. 3-targeted radiotracers for tumor imaging Mol. Pharmaceutics 2006, 3, 472-487
15. Cai, W.; Chen, X. Multimodality imaging of tumor angiogenesis J. Nucl. Med. 2008, 49, 113S-128S
16. 3-targeted radiotracers: maximizing binding affinity via bivalency Bioconjugate Chem. 2009, 20, 2199-2213
17. Ingrid Dijkgraaf, I.; Boerman, O. C. Molecular imaging of angiogenesis with SPECT Eur. J. Nucl. Med. Mol. Imaging 2010, 37 (Suppl 1) S104-S113
18. Tateishi, U.; Oka, T.; Inoue, T. Radiolabeled RGD Peptides as Integrin alpha(v)beta3-targeted PET Tracers Curr. Med. Chem. 2012, 19, 3301-3309
19. 18F-labeled RGD-containing glycopeptide and positron emission tomography Cancer Res. 2001, 61, 1781-1785
20. 3 integrin-binding radiotracer J. Labelled Compd. Radiopharm. 2012, 55, 423-426
21. 18F- Galacto-RGD and can be produced with high specific activity in a cGMP/GRP compliant automated process Nucl. Med. Biol. 2012, 39, 777-784
22. 18F-aryltrifluoroborate conjugates for functional imaging Am. J. Nucl. Med. Mol. Imaging 2013, 3, 44-56
23. 99mTc-labeled RGD peptide as an angiogenesis imaging agent Nucl. Med. Biol. 2013, 40, 262-272
24. 64Cu-labeled tetrameric RGD peptide J. Nucl. Med. 2005, 46, 1707-1718
25. 18F-FPRGD4) J. Nucl. Med. 2007, 48, 1536-1544
26. 3 PET imaging Eur. J. Nucl. Med. Mol. Imaging 2009, 36, 947-957
27. 4 linkers Eur. J. Nucl. Med. Mol. Imaging 2009, 36, 1296-1307
28. 111In-labeled RGD Peptide Nucl. Med. Biol. 2007, 34, 29-35
29. 3 integrin by multimerization of RGD peptides Eur. J. Nucl. Med. Mol. Imaging 2007, 34, 267-273
30. 99mTc-Labeling of a hydrazinonictotinamide-conjugated vitronectin receptor antagonist Bioconjugate Chem. 2001, 12, 624-629
31. 4 linkers Mol. Pharmaceutics 2009, 6, 231-245
32. 99mTc-labeled cyclic Arginine-Glycine-Aspartic (RGD) dimers with triglycine linkers J. Med. Chem. 2008, 51, 7980-7990
33. 3-targeted radiotracer with high tumor uptake and favorable pharmacokinetics Eur. J. Nucl. Med. Mol. Imaging 2009, 36, 1874-1884
34. 4 linkers Bioconjugate Chem. 2009, 20, 750-759
35. 99mTc-labeling of cyclic RGD dimers: effects of technetium chelate on tumor uptake and pharmacokinetics Bioconjugate Chem. 2009, 20, 1559-1568
36. 111In-labeled cyclic RGD peptides: tetrameric not tetravalent Bioconjugate Chem. 2011, 21, 969-978
37. 3 expression Mol. Imaging 2011, 10, 386-97
38. 4 multiplicity on their tumor uptake, excretion kinetics and metabolic stability Theranostics 2011, 1, 322-340
39. 111In-labeled cyclic peptide RGD dimers Amino Acids 2011, 41, 1059-1070
40. 2 in non-human primates Mol. Imaging Biol. 2011, 13, 730-736
41. 99mTc chelates on biological properties Bioconjugate Chem. 2012, 23, 586-595
42. 3 expression Mol. Imaging 2011, 10, 386-397
43. 3 Mol. Imaging 2013, 12, 39-48
44. 2 Theranostics 2012, 2, 577-587
45. 99mTc-3P4- RGD2 scintigraphy Eur. J. Nucl. Med. Mol. Imaging 2011, 38, 2145-52
46. 99mTc-3PRGD2 for integrin receptor imaging of lung cancer: a multicenter study J. Nucl. Med. 2012, 53, 716-22
47. 18F]Galacto-RGD: Synthesis, Metabolic Stability, and Radiation Dose Estimates Bioconjugate Chem. 2004, 15, 61-69
48. Walsh, J. C.; Kolb, H. C. Applications of click chemistry in radiopharmaceutical development Chimia 2010, 64, 29-33
49. 99mTc- labeled radiopharmaceuticals Bioconjugate Chem. 1998, 10, 808-814
50. Shioiri, T.; Yamada, S. Amino acids and peptides. IX. Phosphorus in organic synthesis. IV. Diphenyl phosphorazidate. A new convenient reagent for the peptide synthesis Chem. Pharm. Bull. (Tokyo) 1974, 22, 849-854
51. Shioiri, T.; Yamada, S. (1974) Amino acids and peptides. X. Phosphorus in organic synthesis. V. On the mechanism for the peptide synthesis by diphenyl phosphorazidate Chem. Pharm. Bull. Chem. Pharm. Bull. (Tokyo) 1974, 22, 855-858
52. Efthymiou, T.; Gong, W.; Desaulniers, J. P. Chemical architecture and applications of nucleic acid derivatives containing 1,2,3-triazole functionalities synthesized via click chemistry Molecules 2012, 17, 12665-12703
53. 18F-RGD-K5 determined from whole-body PET/CT in monkeys and humans J. Nucl. Med. 2012, 53, 787-795
54. Mamat, C.; Ramenda, T.; Wuest, F. R. Recent applications of click chemistry for the synthesis of radiotracers for molecular imaging Mini-Rev. Org. Chem. 2009, 6, 21-34
55. Best, M. D. Click chemistry and bioorthogonal reactions: unprecedented selectivity in the labeling of biological molecules Biochemistry 2009, 48, 6571-6584
56. Wängler, C.; Maschauer, S.; Prante, O.; Schafer, M.; Schirrmacher, R.; Bartenstein, P.; Eisenhut, M.; Wängler, B. Multimerization of cRGD peptides by click chemistry: synthetic strategies, chemical limitations, and influence on biological properties ChemBioChem 2010, 11, 2168-2181
57. Galibert, M.; Sancey, L.; Renaudet, O.; Coll, J. L.; Dumy, P.; Boturyn, D. Application of click-click chemistry to the synthesis of new multivalent RGD conjugates Org. Biomol. Chem. 2010, 8, 5133-5138
58. Colombo, M.; Bianchi, A. Click chemistry for the synthesis of RGD-containing integrin ligands Molecules 2010, 15, 178-197
59. Trabocchi, A.; Menchi, G.; Cini, N.; Bianchini, F.; Raspanti, S.; Bottoncetti, A.; Pupi, A.; Calorini, L.; Guarna, A. Click-chemistry-derived triazole ligands of arginine-glycine-aspartate (RGD) integrins with a broad capacity to inhibit adhesion of melanoma cells and both in vitro and in vivo angiogenesis J. Med. Chem. 2010, 53, 7119-7128
60. Kowalczyk, W.; Mascaraque, A.; Sanchez-Navarro, M.; Rojo, J.; Andreu, D. Convergent synthesis of glycodendropeptides by click chemistry approaches Eur. J. Org. Chem. 2012, 4565-4573-4573