[en] GdIII-containing metallostar contrast agents are gaining increased attention, since their architecture allows for a slower tumbling rate which in turn results in larger relaxivities. So far these metallostars find possible applications as blood pool contrast agents. In this work, the first example of a tissue selective metallostar contrast agent is described. This RGD-peptide decorated RuII(GdIII)3 metallostar is synthesized as an avß3-integrin specific contrast agent, with possible applications in the detection of atherosclerotic plaques and tumor angiogenesis. The contrast agent showed a relaxivity of 9.65 s-1mM-1, which represents an increase of 170% compared to a low molecular weight analogue, due to a decreased tumbling rate (tR = 470 ps). The presence of the MLCT band (absorption 375-500 nm, emission 525-850 nm) of the central RuII(Ph-Phen)3-based complex, grants the metallostar attractive luminescent properties. The 3MLCT emission is characterized by a quantum yield of 4.69 % and a lifetime of 804 ns, which makes it an interesting candidate for time-gated luminescence imaging. The potential application as a selective MRI contrast agent for avß3-integrin expressing tissues is shown by an in vitro relaxometric analysis as well as an in vitro T1-weighted MR image.
Research center :
CMMI - Centre de Recherche en Microscopie et Imagerie Médicale
Disciplines :
Radiology, nuclear medicine & imaging Chemistry
Author, co-author :
Verwilst, Peter
Eliseeva, Svetlana
Vander Elst, Luce ; Université de Mons > Faculté de Médecine et de Pharmacie > Chimie générale, organique et biomédicale
Burtea, Carmen ; Université de Mons > Faculté de Médecine et de Pharmacie > Chimie générale, organique et biomédicale
Laurent, Sophie ; Université de Mons > Faculté de Médecine et de Pharmacie > FMP - Service du Doyen ; Université de Mons > Faculté de Médecine et de Pharmacie > Chimie générale, organique et biomédicale
Petoud, Stéphane
Muller, Robert ; Université de Mons > Faculté de Médecine et de Pharmacie > Chimie générale, organique et biomédicale
Parac-Vogt, T.N.
De Borggraeve, W.M.
Language :
English
Title :
A Tripodal Ruthenium-Gadolinium Metallostar as a Potential a(v)ß(3) Integrin Specific Bimodal Imaging Contrast Agent
Publication date :
04 June 2012
Journal title :
Inorganic Chemistry
ISSN :
0020-1669
Publisher :
American Chemical Society, United States - District of Columbia
Volume :
51
Issue :
11
Pages :
6405-6411
Peer reviewed :
Peer Reviewed verified by ORBi
Research unit :
M108 - Chimie générale, organique et biomédicale
Research institute :
R550 - Institut des Sciences et Technologies de la Santé R100 - Institut des Biosciences
Constable, E. C.; Eich, O.; Fenske, D.; Housecroft, C. E.; Johnston, L. A. Chem.-Eur. J. 2000, 6, 4364-4370
Jacques, V.; Desreux, J. In Contrast Agents I; Krause, W., Ed.; Springer: Berlin/Heidelberg: 2002; Vol. 221, pp 123-164.
Costa, J.; Ruloff, R.; Burai, L.; Helm, L.; Merbach, A. E. J. Am. Chem. Soc. 2005, 127, 5147-5157
Livramento, J. B.; Sour, A.; Borel, A.; Merbach, A. E.; Tóth, é. Chem.-Eur. J. 2006, 12, 989-1003
Livramento, J. B.; Weidensteiner, C.; Prata, M. I. M.; Allegrini, P. R.; Geraldes, C. F. G. C.; Helm, L.; Kneuer, R.; Merbach, A. E.; Santos, A. C.; Schmidt, P.; Tóth, é. Contrast Media Mol. Imaging 2006, 1, 30-39
Parac-Vogt, T. N.; Elst, L. V.; Kimpe, K.; Laurent, S.; Burtea, C.; Chen, F.; Van Deun, R.; Ni, Y. C.; Muller, R. N.; Binnemans, K. Contrast Media Mol. Imaging 2006, 1, 267-278
Paris, J.; Gameiro, C.; Humblet, V.; Mohapatra, P. K.; Jacques, V.; Desreux, J. F. Inorg. Chem. 2006, 45, 5092-5102
Dehaen, G.; Verwilst, P.; Eliseeva, S. V.; Laurent, S.; Vander Elst, L.; Muller, R. N.; De Borggraeve, W. M.; Binnemans, K.; Parac-Vogt, T. N. Inorg. Chem. 2011, 50, 10005-10014
Dehaen, G.; Eliseeva, S. V.; Kimpe, K.; Laurent, S.; Vander Elst, L.; Muller, R. N.; Dehaen, W.; Binnemans, K.; Parac-Vogt, T. N. Chem.-Eur. J. 2012, 18, 293-302
Kalyanasundaram, K. Coord. Chem. Rev. 1982, 46, 159-244
Juris, A.; Balzani, V.; Barigelletti, F.; Campagna, S.; Belser, P.; von Zelewsky, A. Coord. Chem. Rev. 1988, 84, 85-277
Aime, S.; Barge, A.; Cabella, C.; Crich, S. G.; Gianolio, E. Curr. Pharm. Biotechnol. 2004, 5, 509-518
Beeby, A.; Botchway, S. W.; Clarkson, I. M.; Faulkner, S.; Parker, A. W.; Parker, D.; Williams, J. A. J. Photochem. Photobiol., B 2000, 57, 83-89
Charbonnière, L. J.; Ziessel, R.; Montalti, M.; Prodi, L.; Zaccheroni, N.; Boehme, C.; Wipff, G. J. Am. Chem. Soc. 2002, 124, 7779-7788
Koullourou, T.; Natrajan, L. S.; Bhavsar, H.; Pope, S. J.; Feng, J.; Narvainen, J.; Shaw, R.; Scales, E.; Kauppinen, R.; Kenwright, A. M.; Faulkner, S. J. Am. Chem. Soc. 2008, 130, 2178-2179
Bonnet, C. S.; Tóth, é. C. R. Chim. 2010, 13, 700-714
Louie, A. Chem. Rev. 2010, 110, 3146-3195
Tallec, G.; Fries, P. H.; Imbert, D.; Mazzanti, M. Inorg. Chem. 2011, 50, 7943-7945
Bonnet, C. S.; Buron, F.; Caillé, F.; Shade, C. M.; Drahoš, B.; Pellegatti, L.; Zhang, J.; Villette, S.; Helm, L.; Pichon, C.; Suzenet, F.; Petoud, S.; Tóth, é. Chem.-Eur. J. 2012, 18, 1419-1431
Burtea, C.; Laurent, S.; Murariu, O.; Rattat, D.; Toubeau, G.; Verbruggen, A.; Vansthertem, D.; Elst, L. V.; Muller, R. N. Cardiovasc. Res. 2008, 78, 148-157
Park, J. A.; Lee, J. J.; Jung, J. C.; Yu, D. Y.; Oh, C.; Ha, S.; Kim, T. J.; Chang, Y. M. ChemBioChem 2008, 9, 2811-2813
Verwilst, P.; Eliseeva, S. V.; Carron, S.; Vander Elst, L.; Burtea, C.; Dehaen, G.; Laurent, S.; Binnemans, K.; Muller, R. N.; Parac-Vogt, T. N.; De Borggraeve, W. M. Eur. J. Inorg. Chem. 2011, 2011, 3577-3585
Hoshiga, M.; Alpers, C. E.; Smith, L. L.; Giachelli, C. M.; Schwartz, S. M. Circ. Res. 1995, 77, 1129-1135
Neeman, M.; Gilad, A. A.; Dafni, H.; Cohen, B. J. Magn. Reson. Imag. 2007, 25, 1-12
Hirayama, T.; Taki, M.; Kodan, A.; Kato, H.; Yamamoto, Y. Chem. Commun. 2009, 3196-3198
Pokorski, J. K.; Miller Jenkins, L. M.; Feng, H.; Durell, S. R.; Bai, Y.; Appella, D. H. Org. Lett. 2007, 9, 2381-2383
Onishi, H.; Sekine, K. Talanta 1972, 19, 473-478
Dijkgraaf, I.; Rijnders, A. Y.; Soede, A.; Dechesne, A. C.; van Esse, G. W.; Brouwer, A. J.; Corstens, F. H. M.; Boerman, O. C.; Rijkers, D. T. S.; Liskamp, R. M. J. Org. Biomol. Chem. 2007, 5, 935-944
Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599
Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064
Muller, R. N.; Raduchel, B.; Laurent, S.; Platzek, J.; Pierart, C.; Mareski, P.; Vander Elst, L. Eur. J. Inorg. Chem. 1999, 1949-1955
Laurent, S.; Houze, L. V.; Guerit, N.; Muller, R. N. Helv. Chim. Acta 2000, 83, 394-406
Botteman, F.; Nicolle, G. M.; Vander Elst, L.; Laurent, S.; Merbach, A. E.; Muller, R. N. Eur. J. Inorg. Chem. 2002, 2686-2693
Micskei, K.; Powell, D. H.; Helm, L.; Brucher, E.; Merbach, A. E. Magn. Reson. Chem. 1993, 31, 1011-1020
Laurent, S.; Vander Elst, L.; Muller, R. N. Contrast Media Mol. Imaging 2006, 1, 128-137
Vander Elst, L.; Maton, F.; Laurent, S.; Seghi, F.; Chapelle, F.; Muller, R. N. Magn. Reson. Med. 1997, 38, 604-614
Tei, L.; Barge, A.; Crich, S. G.; Pagliarin, R.; Negri, V.; Ramella, D.; Cravotto, G.; Aime, S. Chem.-Eur. J. 2010, 16, 8080-8087
Caravan, P.; Ellison, J. J.; McMurry, T. J.; Lauffer, R. B. Chem. Rev. 1999, 99, 2293-2352
Solomon, I. Phys. Rev. 1955, 99, 559
Bloembergen, N. J. Chem. Phys. 1957, 27, 572-573
Freed, J. H. J. Chem. Phys. 1978, 68, 4034-4037
Vander Elst, L.; Sessoye, A.; Laurent, S.; Muller, R. N. Helv. Chim. Acta 2005, 88, 574-587
Dwek, R. A. In Nuclear Magnetic Resonance in Biochemistry, Applications to Enzyme Systems; Clarendon Press: Oxford, 1973; pp 174-283.
Huang, S.; Endo, R. I.; Nemerow, G. R. J. Virol. 1995, 69, 2257-2263
