Magnetic resonance molecular imaging of vascular cell adhesion molecule-1 expression in inflammatory lesions using a peptide-vectorized paramagnetic imaging probe

Journal of Medicinal Chemistry

Volumn 52, Issue 15, 2009, Pages 4725-4742

  Burtea, Carmen ^a   Laurent, Sophie ^a   Port, Marc ^b   Lancelot, Eric ^b   Ballet, Sébastien ^b   Rousseaux, Olivier ^b   Toubeau, Gérard ^a   Elst, Luce Vander ^a   Corot, Claire ^b   Muller, Robert N ^a  

^a UNIVERSITY OF MONS   (Belgium)

^b Laboratoire Guerbet   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODY; ARGININE; CONCANAVALIN A; CONTRAST MEDIUM; CYSTEINYLASPARAGINYLASPARAGINYLSERYLLYSYLSERYLHISTIDYLTHREONYLCYSTEINE; GADOLINIUM 1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,10 TETRAACETIC ACID CYSTEINYLASPARAGINYLASPARAGINYLSERYLLYSYLSERYLHISTIDYLTHREONYLCYSTEINE CONJUGATE; GADOLINIUM 1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,10 TETRAACETIC ACID HISTIDYLSERYLCYSTEINYLASPARAGINYLLYSYLASPARAGINYLSERYLCYSTEINYLTHREONINE CONJUGATE; GADOTERIC ACID; LEUCINE; PEPTIDE; THREONINE; UNCLASSIFIED DRUG; VASCULAR CELL ADHESION MOLECULE 1; VASCULAR CELL ADHESION MOLECULE 1 ANTIBODY;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; AORTA WALL; ARTICLE; BINDING AFFINITY; BIOPANNING; BIOTINYLATION; CONTRAST ENHANCEMENT; CONTROLLED STUDY; DRUG EXCRETION; FEMALE; HEPATITIS; HISTOLOGY; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; IN VIVO STUDY; INFLAMMATION; LIVER VEIN; MOLECULAR IMAGING; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING; PHAGE DISPLAY; PROTEIN EXPRESSION; T LYMPHOCYTE;

AMINO ACID SEQUENCE; ANIMALS; ANTIGENS, CD29; APOLIPOPROTEINS E; CELLS, CULTURED; HEPATITIS; HETEROCYCLIC COMPOUNDS; HUMANS; INTEGRIN ALPHA4BETA1; MAGNETIC RESONANCE IMAGING; MICE; MICE, INBRED BALB C; MICE, INBRED C57BL; ORGANOMETALLIC COMPOUNDS; PEPTIDE LIBRARY; VASCULAR CELL ADHESION MOLECULE-1;

EID: 68549122751     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9002654     Document Type: Article

References (49)

1. Ou, R.; Zhang, M.; Huang, L.; Flavell, R. A.; Koni, P. A.; Moskophidis, D. Regulation of immune response and inflammatory reactions against viral infection by VCAM-1. J. Virol. 2008, 82, 2952-2965.
2. Libby, P. Inflammation and cardiovascular disease mechanisms. Am. J. Clin. Nutr. 2006, 83 (Suppl.), 456S-460S.
3. Davis, C.; Fischer, J.; Ley, K.; Sarembock, I. J. The role of inflammation in vascular injury and repair. J. Thromb. Haemostasis 2003, 1, 1699-1709.
4. Libby, P. Inflammation in atherosclerosis. Nature 2002, 420, 868-874.
5. Ley, K.; Huo, Y. VCAM-1 is critical in atherosclerosis. J. Clin. Invest. 2001, 107, 1209-1210.
6. Libby, P.; Aikawa, M.; Schonbeck, U. Cholesterol and atherosclerosis. Biochim. Biophys. Acta 2000, 1529, 299-309.
7. Steinberg, D. Atherogenesis in perspective: Hypercholesterolemia and inflammation as partners in crime. Nat.Med. 2002, 8, 1211-1217.
8. Topper, J. N.; Gimbrone, M. A. Jr. Blood flow and vascular gene expression: fluid shear stress as a modulator of endothelial phenotype. Mol. Med. Today 1999, 5, 40-46.
9. De Caterina, R.; Libby, P.; Peng, H. B.; Thannickal, V. J.; Rajavashisth, T. B.; Gimbrone, M. A. Jr.; Shin, W. S.; Liao, J. K. Nitric oxide decreases cytokine-induced endothelial activation. Nitric oxide selectively reduces endothelial expression of adhesion molecules and proinflammatory cytokines. J. Clin. Invest. 1995, 96, 60-68.
10. de Boer, O. J.; van der Wal, A. C.; Teeling, P.; Becker, A. E. Leucocyte recruitment in rupture prone regions of lipid-rich plaques: a prominent role for neovascularization?. Cardiovasc. Res. 1999, 41, 443-449.
11. 3 integrin expression in atherosclerotic plaques with a mimetic of RGD peptide grafted to Gd-DTPA. Cardiovasc. Res. 2008, 78, 148-157.
12. O'Brien, K. D.; McDonald, T. O.; Chait, A.; Allen, M. D.; Alpers, C. E. Neovascular expression of E-selectin, intercellular adhesion molecule-1, and vascular cell adhesion molecule-1 in human atherosclerosis and their relation to intimal leukocyte content. Circulation 1996, 93, 672-682.
13. Moiseeva, E. P. Adhesion receptors of vascular smooth muscle cells and their functions. Cardiovasc. Res. 2001, 52, 372-386.
14. Bengel, F. M. Atherosclerosis imaging on the molecular level J. Nucl. Cardiol. 2006, 13, 111-118.
15. Naghavi, M.; Libby, P.; Falk, E.; Casscells, S. W.; Litovsky, S.; Rumberger, J.; Badimon, J. J.; Stefanadis, C.; Moreno, P.; Pasterkamp, G.; Fayad, Z.; Stone, P. H.; Waxman, S.; Raggi, P.; Madjid, M.; Zarrabi, A.; Burke, A.; Yuan, C.; Fitzgerald, P. J.; Siscovick, D. S.; de Korte, C. L.; Aikawa, M.; Juhani Airaksinen, K. E.; Assmann, G.; Becker, C. R.; Chesebro, J. H.; Farb, A.; Galis, Z. S.; Jackson, C.; Jang, I. K.; Koenig, W.; Lodder, R. A.; March, K.; Demirovic, J.; Navab, M.; Priori, S. G.; Rekhter, M. D.; Bahr, R.; Grundy, S. M.; Mehran, R.; Colombo, A.; Boerwinkle, E.; Ballantyne, C.; Insull, W.; Schwartz, R. S.; Vogel, R.; Serruys, P. W.; Hansson, G. K.; Faxon, D. P.; Kaul, S.; Drexler, H.; Greenland, P.; Muller, J. E.; Virmani, R.; Ridker, P. M.; Zipes, D. P.; Shah, P. K.; Willerson, J. T. From vulnerable plaque to vulnerable patient: a call for new definitions and risk assessment strategies. Circulation 2003, 108, 1664-1672.
16. Jaffer, F. A.; Libby, P.; Weissleder, R. Molecular and cellular imaging of atherosclerosis. Emerging applications. J. Am. Coll. Cardiol. 2006, 47, 1328-1338.
17. Burtea, C.; Laurent, S.; Vander Elst, L.; Muller, R. N. Contrast Agents. Magnetic Resonance. In Handbook of Experimental Pharmacology; Semmler, W., Schwaiger, M., Eds.; Springer-Verlag: Berlin and Heidelberg, Germany, 2008; Vol. 185, Part 1, pp 135-165.
18. 123Iodine-labeled anti-VCAM-1 antibody scintigraphy in the assessment of experimental colitis. Eur. J. Gastroenterol. Hepatol. 2001, 13, 31-38.
19. Tsurkas, A.; Shinde-Patil, V. R.; Kelly, K. A.; Patel, P.; Wolley, A.; Allport, J. R.; Weissleder, R. In vivo imaging of activated endothelium using an anti-VCAM-1 magnetooptical probe. Bioconjugate Chem. 2005, 16, 576-581.
20. Kelly, K. A.; Allport, J. R.; Tsurkas, A.; Shinde-Patil, V. R.; Josephson, L.; Weissleder, R. Detection of vascular adhesion molecule-1 expression using a novel multimodal nanoparticle. Circ. Res. 2005, 96, 327-336.
21. Hamilton, A. J.; Huang, S. L.; Warnick, D.; Rabbat, M.; Kane, B.; Nagaraj, A.; Klegerman, M.; McPherson, D. D. Intravascular ultrasound molecular imaging of atheroma components in vivo. J. Am. Coll. Cardiol. 2004, 43, 453-460.
22. Laurent, S.; Forge, D.; Port, M.; Roch, A.; Robic, C.; Vander Elst, L.; Muller, R. N. Magnetic iron oxide nanoparticles: synthesis, stabilization, vectorization, physicochemical characterizations, and biological applications. Chem. Rev. 2008, 108, 2064-2110.
23. McAteer, M. A.; Sibson, N. R.; von Zur Muhlen, C.; Schneider, J. E.; Lowe, A. S.; Warrick, N.; Channon, K. M.; Anthony, D. C.; Choudhury, R. P. In vivo magnetic resonance imaging of acute brain inflammation using microparticles of iron oxide. Nat. Med. 2007, 13, 1253-1258.
24. McAteer, M. A.; Schneider, J. E.; Ali, Z. A.; Warrick, N.; Bursill, C. A.; von zur Muhlen, C.; Greaves, D. R.; Neubauer, S.; Channon, K. M.; Choudhury, R. P. Magnetic resonance imaging of endothelial adhesion molecules in mouse atherosclerosis using dual-targeted microparticles of iron oxide. Arterioscler., Thromb., Vasc. Biol. 2008, 28, 77-83.
25. von Zur Muhlen, C.; Sibson, N. R.; Peter, K.; Campbell, S. J.; Wilainam, P.; Grau, G. E.; Bode, C.; Choudhury, R. P.; Anthony, D. C. A contrast agent recognizing activated platelets reveals murine cerebral malaria pathology undetectable by conventional MRI. J. Clin. Invest. 2008, 118, 1198-207.
26. von zur Muhlen, C.; von Elverfeldt, D.; Moeller, J. A.; Choudhury, R. P.; Paul, D.; Hagemeyer, C. E.; Olschewski, M.; Becker, A.; Neudorfer, I.; Bassler, N.; Schwarz, M.; Bode, C.; Peter, K. Magnetic resonance imaging contrast agent targeted toward activated platelets allows in vivo detection of thrombosis and monitoring of thrombolysis. Circulation 2008, 118, 258-267.
27. Neuwelt, E. A.; Várallyay, C. G.; Manninger, S.; Solymosi, D.; Haluska, M.; Hunt, M. A.; Nesbit, G.; Stevens, A.; Jerosch-Herold, M.; Jacobs, P. M.; Hoffman, J. M. The potential of ferumoxytol nanoparticle magnetic resonance imaging, perfusion, and angiography in central nervous system malignancy: a pilot study. Neurosurgery 2007, 60, 601-611.
28. Toso, C.; Vallee, J. P.; Morel, P.; Ris, F.; Demuylder-Mischler, S.; Lepetit-Coiffe, M.; Marangon, N.; Saudek, F.; James Shapiro, A. M.; Bosco, D.; Berney, T. Clinical magnetic resonance imaging of pancreatic islet grafts after iron nanoparticle labeling. Am. J. Transplant. 2008, 8, 701-706.
29. Cunningham, C. H.; Arai, T.; Yang, P. C.; McConnell, M. V.; Pauly, J. M.; Conolly, S. M. Positive contrast magnetic resonance imaging of cells labeled with magnetic nanoparticles. Magn. Reson. Med. 2005, 53, 999-1005.
30. Dahnke, H.; Liu, W.; Herzka, D.; Frank, J. A.; Schaeffter, T. Susceptibility gradient mapping (SGM): A new postprocessing method for positive contrast generation applied to superparamagnetic iron oxide particle (SPIO)-labeled cells. Magn. Reson. Med. 2008, 60, 595-603.
31. Boutry, S.; Burtea, C.; Laurent, S.; Toubeau, G.; Vander Elst, L.; Muller, R. N. Magnetic resonance imaging of inflammation with a specific selectin-targeted contrast agent. Magn. Reson. Med. 2005, 53, 800-807.
32. Sibson, N. R.; Blamire, A. M.; Bernades-Silva, M.; Laurent, S.; Boutry, S.; Muller, R. N.; Styles, P.; Anthony, D. C. MRI detection of early endothelial activation in brain inflammation. Magn. Reson. Med. 2004, 51, 248-252.
33. Ladner, R. C.; Sato, A. K.; Gorzelany, J.; de Souza, M. Phage display-derived peptides as therapeutic alternatives to antibodies. Drug Discovery Today 2004, 9, 525-529.
34. Byrne, M. F.; Corcoran, P. A.; Atherton, J. C.; Sheehan, K. M.; Murray, F. E.; Fitzgerald, D. J.; Murphy, J. F. Stimulation of adhesion molecule expression by Helicobacter pylori and increased neutrophil adhesion to human umbilical vein endothelial cells. FEBS Lett. 2002, 532, 411-414.
35. William, C.; Schindler, R.; Frei, U.; Eckardt, K.-U. Increases in oxygen tension stimulate expression of ICAM-1 and VCAM-1 on human endothelial cells. Am. J. Physiol.: Heart Circ. Physiol. 1999, 276, 2044-2052.
36. Bremerich, J.; Colet, J. M.; Giovenzana, G. B.; Aime, S.; Scheffler, K.; Laurent, S.; Bongartz, G.; Muller, R. N. Slow clearance gadolinium-based extracellular and intravascular contrast media for three-dimensional MR angiography. J. Magn. Reson. Imaging 2001, 13, 588-593.
37. Vander Elst, L.; Raynal, I.; Port, M.; Tisnes, P.; Muller, R. N. In vitro relaxometric and luminescence characterization of P792 (Gadomelitol, Vistarem), an efficient and rapid clearance blood pool MRI contrast agent. Eur. J. Inorg. Chem. 2005, 6, 1142-1148.
38. Laurent, S.; Vander Elst, L.; Muller, R. N. Comparative study of the physicochemical properties of six clinical low molecular weight gadolinium contrast agents. Contrast Media Mol. Imaging 2006, 1, 128-137.
39. 1 and ligand binding analysis. Biophys. J. 2002, 82, 447-457.
40. 4 subunit in the upper face of the β-propeller model. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 7198-7203.
41. 4 subunit of the integrin VLA-4: distinct effects on adhesion to CS1/fibronectin, VCAM-1, and invasion. J. Cell Biol. 1993, 123, 245-253.
42. Morikawa, H.; Hachiya, K.; Mizuhara, H.; Nishiguchi, S.; Shiomi, S.; Kuroki, T.; Kaneda, K. Sublobular veins as the main site of lymphocyte adhesion/transmigration and adhesion molecule expression in the porto-sinusoidal-hepatic venous system during concanavalin A-induced hepatitis in mice. Hepatology 2000, 31, 83-94.
43. Wolf, D.; Hallmann, R.; Sass, G.; Sixt, M.; Kusters, S.; Fregien, B.; Trautwein, C.; Tiegs, G. TNF-α-induced expression of adhesion molecules in the liver is under the control of TNFR1 - relevance for concanavalin A-induced hepatitis 1. J. Immunol. 2001, 166, 1300-1307.
44. Jaruga, B.; Hong, F.; Kim, W.-H.; Gao, B. IFN-γ/STAT1 acts as a proinflammatory signal in T cell-mediated hepatitis via induction of multiple chemokines and adhesion molecules: a critical role of IRF-1. Am. J. Physiol.: Gastrointest. Liver Physiol. 2004, 287, G1044-G1052.
45. Iiyama, K.; Hajra, L.; Li, M.; Iiyama, H.; DiChiara, M.; Medoff, B. D.; Cybulsky, M.I. Patterns of vascular cell adhesion molecule-1 and intercellular adhesion molecule-1 expression in rabbit and mouse atherosclerotic lesions and at sites predisposed to lesion formation. Circ. Res. 1999, 85, 199-207.
46. Broisat, A.; Riou, L. M.; Ardisson, V.; Boturyn, D.; Dumy, P.; Fagret, D.; Ghezzi, C. Molecular imaging of vascular cell adhesion molecule-1 expression in experimental atherosclerotic plaques with radiolabelled B2702-p. Eur. J. Nucl. Med. Mol. Imaging 2007, 34, 830-840.
47. Aime, S.; Botta, M.; Fedeli, F.; Gianolio, E.; Terreno, E.; Anelli, P. High-relaxivity contrast agents for magnetic resonance imaging based on multisite interactions between a beta-cyclodextrin oligomer and suitably functionalized Gd-III chelates. Chem. - Eur. J. 2001, 7, 5262-5269.
48. Vander Elst, L.; Port, M.; Raynal, I.; Simonot, C.; Muller, R. N. Physicochemical characterization of P760, a new macromolecular contrast agent with high relaxivity. Eur. J. Inorg. Chem. 2003, 13, 2495-2501.
49. Port, M.; Rousseaux, O.; Muller, R. N.; Burtea, C. Compounds for the Diagnosis of Apoptosis. European Patent WO 2008/125420 (A2), 2008.