A new generation of radiofluorinated pyrimidine-2,4,6-triones as MMP-targeted radiotracers for positron emission tomography

Journal of Medicinal Chemistry

Volumn 55, Issue 1, 2012, Pages 223-232

  Schrigten, Daniela ^a,d   Breyholz, Hans Jörg ^a   Wagner, Stefan ^a   Hermann, Sven ^c   Schober, Otmar ^a   Schäfers, Michael ^c,d   Haufe, Gönter ^b   Kopka, Klaus ^a,d  

^a UNIVERSITY HOSPITAL MÜNSTER   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

^c INST OF REPRO MED OF THE UNIV   (Germany)

^d Interdisciplinary Centre of Clinical Research (IZKF)   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOKINE; GROWTH FACTOR; MATRIX METALLOPROTEINASE; PROTEINASE INHIBITOR; PYRIMIDINE 2,4,6 TRIONE; PYRIMIDINE DERIVATIVE; TRACER; UNCLASSIFIED DRUG;

ARTHRITIS; ARTICLE; ATHEROSCLEROSIS; CYTOKINE RELEASE; DISEASE COURSE; ENZYME ACTIVATION; EXTRACELLULAR MATRIX; HUMAN; IN VITRO STUDY; IN VIVO STUDY; NEOPLASM; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PROTEIN DEGRADATION; STROKE;

ANIMALS; DRUG STABILITY; FLUORINE RADIOISOTOPES; HUMANS; MATRIX METALLOPROTEINASES; MICE; MICE, INBRED BALB C; POLYETHYLENE GLYCOLS; POSITRON-EMISSION TOMOGRAPHY; PYRIMIDINES; RADIOPHARMACEUTICALS; STRUCTURE-ACTIVITY RELATIONSHIP; TISSUE DISTRIBUTION; TRIAZOLES;

EID: 84855834091     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm201142w     Document Type: Article

References (39)

1. Folgueras, A. R.; Pendas, A. M.; Sanchez, L. M.; López- Otín, C. Matrix metalloproteinases in cancer: from new functions to improved inhibition strategies Int. J. Dev. Biol. 2004, 48, 411-424
2. Overall, C. M.; López-Otín, C. Strategies for MMP inhibition in cancer: innovations for the post-trial era Nat. Rev. Cancer 2002, 2, 657-672
3. Wagner, S; Breyholz, H.-J.; Faust, A.; Höltke, C.; Levkau, B.; Schober, O.; Schäfers, M; Kopka, K. Molecular imaging of matrix metalloproteinases in vivo using small molecule inhibitors for SPECT and PET Curr. Med. Chem. 2006, 13, 2819-2838
4. Borkakoti, N. Structural studies of matrix metalloproteinases J. Mol. Med. 2000, 78, 261-268
5. Stamenkovic, I. Extracellular matrix remodelling: the role of matrix metalloproteinases J. Pathol. 2003, 200, 448-464
6. Rhee, J. S.; Coussens, L. M. ECKing MMP function: implications for cancer development Trends Cell Biol. 2002, 12, 209-211
7. Vihinen, P.; Ala-aho, R.; Kahari, V. M. Matrix metalloproteinases as therapeutic targets in cancer Curr. Cancer Drug Targets 2005, 5, 203-220
8. Newby, A. C. Dual role of matrix metalloproteinases (matrixins) in intimal thickening and atherosclerotic plaque rupture Physiol. Rev. 2005, 85, 1-31
9. Tekabe, Y.; Li, Q.; Luma, J.; Weisenberger, D.; Sedlar, M.; Harja, E.; Narula, J.; Johnson, L. L. Noninvasive monitoring the biology of atherosclerotic plaque development with radiolabeled annexin V and matrix metalloproteinase inhibitor in spontaneous atherosclerotic mice J. Nucl. Cardiol. 2010, 17, 1073-1081
10. Razavian, M.; Zhang, J.; Nie, L.; Tavakoli, S.; Razavian, N.; Dobrucki, L. W.; Sinusas, A. J.; Edwards, D. S.; Azure, M.; Sadeghi, M. M. Molecular imaging of matrix metalloproteinase activation to predict murine aneurysm expansion in vivo J. Nucl. Med. 2010, 51, 1107-1115
11. Zhang, J.; Nie, L.; Razavian, M.; Ahmed, M.; Dobrucki, L. W.; Asadi, A.; Edwards, D. S.; Azure, M.; Sinusas, A. J.; Sadeghi, M. M. Molecular imaging of activated matrix metalloproteinases in vascular remodeling Circulation 2008, 118, 1953-1960
12. 11C] methoxyphenyl)sulfonyl]benzylamino}-3-methylbutanamide Nucl. Med. Biol. 2004, 31, 77-85
13. Grams, F.; Brandstetter, H.; DAlo, S.; Geppert, D.; Krell, H. W.; Leinert, H.; Livi, V.; Menta, E.; Oliva, A.; Zimmermann, G. Pyrimidine-2,4,6- triones: a new effective and selective class of matrix metalloproteinase Inhibitors Biol. Chem. 2001, 382, 1277-1285
14. Maquoi, E.; Sounni, N. E.; Devy, L.; Olivier, F.; Frankenne, F.; Krell, H.-W.; Grams, F.; Foidart, J.-M.; Noël, A. Anti-invasive, antitumoral, and antiangiogenic efficacy of a pyrimidine-2,4,6-trione derivative, an orally active and selective matrix metalloproteinase inhibitor Clin. Cancer Res. 2004, 10, 4038-4047
15. Breyholz, H.-J.; Schäfers, M.; Wagner, S.; Höltke, C.; Faust, A.; Rabeneck, H.; Levkau, B.; Schober, O.; Kopka, K. C-5-disubstituted barbiturates as potential molecular probes for noninvasive matrix metalloproteinase imaging J. Med. Chem. 2005, 48, 3400-3409
16. Wagner, S.; Breyholz, H. J.; Law, M. P.; Faust, A.; Höltke, C.; Schröer, S.; Haufe, G.; Levkau, B.; Schober, O.; Schäfers, M.; Kopka, K. Novel fluorinated derivatives of the broad-spectrum MMP inhibitors N -hydroxy-2(R)-{[(4-methoxyphenyl)sulfonyl](benzyl)- and (3-picolyl)-amino}-3- methyl-butanamide as potential tools for the molecular imaging of activated MMPs with PET J. Med. Chem. 2007, 50, 5752-5764
17. Kopka, K.; Breyholz, H.-J.; Wagner, S.; Law, M. P.; Riemann, B.; Schröer, S.; Trub, M.; Guilbert, B.; Levkau, B.; Schober, O.; Schäfers, M. Synthesis and preliminary biological evaluation of new radioiodinated MMP inhibitors for imaging MMP activity in vivo Nucl. Med. Biol. 2004, 31, 257-267
18. Schäfers, M.; Riemann, B.; Kopka, K.; Breyholz, H.-J.; Wagner, S.; Schäfers, K. P.; Law, M. P.; Schober, O.; Levkau, B. Scintigraphic imaging of matrix metalloproteinase activity in the arterial wall in vivo Circulation 2004, 109, 2554-2559
19. Brandstetter, H.; Grams, F.; Glitz, D.; Lang, A.; Huber, R.; Bode, W.; Krell, H. W.; Engh, R. A. The 1.8-Ǻ crystal structure of a matrix metalloproteinase-8 barbiturate inhibitor complex reveals a peviously unobserved mechanism for collagenase substrate recognition J. Biol. Chem. 2001, 276, 17405-17412
20. Tochowicz, A.; Maskos, K.; Huber, R.; Oltenfreiter, R.; Dive, V; Yiotakis, A.; Zanda, M.; Bode, W.; Goettig, P. Crystal structures of MMP-9 complexes with five inhibitors: contribution of the flexible Arg424 side-chain to selectivity J. Mol. Biol. 2007, 371, 989-1006
21. Breyholz, H.-J.; Wagner, S.; Faust, A.; Riemann, B.; Höltke, C.; Hermann, S.; Schober, O.; Schäfers, M.; Kopka, K. Radiofluorinated pyrimidine-2,4,6-triones as molecular probes for noninvasive MMP-targeted imaging ChemMedChem 2010, 5, 777-789
22. 18F- labeled styrylpyridines as PET agents for amyloid plaque imaging Nucl. Med. Biol. 2007, 34, 89-97
23. 18F-FPRGD4) J. Nucl. Med. 2007, 48, 1536-1544
24. 18F-labeled PEGylated RGD peptide Eur. J. Nucl. Med. Mol. Imaging 2004, 31, 1081-1089
25. Faust, A.; Waschkau, B.; Waldeck, J.; Höltke, C.; Breyholz, H.-J.; Wagner, S.; Kopka, K.; Heindel, W.; Schäfers, M.; Bremer, C. Synthesis and evaluation of a novel fluorescent photoprobe for imaging matrix metalloproteinases Bioconjugate Chem. 2008, 19, 1001-1008
26. Hutchings, S.; Liu, W.; Radinov, R. Palladium-catalyzed arylation of diisopropyl malonate applied to the efficient synthesis of the selective MMP inhibitor 5-(4-phenoxyphenyl)-5-[4-(2-pyrimidinyl)-1-piperazinyl]barbituric acid Heterocycles 2006, 67, 763-768
27. Tahtaoui, C.; Parrot, I.; Klotz, P.; Guillier, F.; Galzi, J.-L.; Hilbert, M.; Ilien, B. Fluorescent pirenzepine derivatives as potential bitopic ligands of the human M1 muscarinic receptor J. Med. Chem. 2004, 47, 4300-4315
28. 18F]fluorobenzoate Nucl. Med. Biol. 1992, 19, 275-281
29. Rostovtsev, V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselectoive "ligation" of azides and terminal alkynes Angew. Chem. 2002, 114, 2708-2711
30. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
31. Huang, W.; Meng, Q.; Suzuki, K.; Nagase, H.; Brew, K. Mutational study of the amino-terminal domain and human tissue inhibitor of metalloproteinases 1 (TIMP-1) locates an inhibitory region for matrix metallo proteinases J. Biol. Chem. 1997, 272, 22086-22091
32. Demko, Z. P.; Sharpless, K. B. An intramolecular [2+3] cycloaddition route to fused 5-heterosubstituted tetrazoles Org. Lett. 2001, 3, 4091-4094
33. 18F]fluoroethylazide for positron emission tomography Bioconjugate Chem. 2007, 18, 989-993
34. 18F]fluorobenzoate: a putatively more stable prosthetic group for the fluorine-18 labeling of biomolecules via click chemistry Curr. Radiopharm. 2009, 2, 63-74
35. Ramenda, T.; Kniess, T.; Bergmann, R.; Steinbach, J.; Wuest, F. Radiolabelling of proteins with fluorine-18 via click chemistry Chem. Commun. 2009, 48, 7521-7523
36. Prante, O.; Tietze, R.; Hocke, C.; Löber, S.; Höbner, H.; Kuwert, T.; Gmeiner, P. Synthejkjhmjhvhmnhmsis, radiofluorination and in vitro evaluation of pyrazolo[1,5- a ]pyridine based dopamine D4 receptor ligands: discovery of an inverse agonist radioligand for PET J. Med. Chem. 2008, 51, 1800-1810
37. 18F labeling of bioactive peptides J. Labelled Compd. Radiopharm. 2008, 51, 444-452
38. Prante, O.; Hocke, C.; Löber, S.; Höbner, H.; Gmeiner, P.; Kuwert, T. Tissue distribution of radioiodinated FAUC113: assessment of a pyrazolo[1,5- a ]pyridine-based dopamine D4 receptor radioligand candidate Nuklearmedizin 2006, 45, 41-48
39. Schäfers, K. P.; Reader, A. J.; Kriens, M.; Knoess, C.; Schober, O.; Schäfers, M. Performance evaluation of the 32-module quadHIDAC small-animal PET scanner J. Nucl. Med. 2005, 46, 996-1004