Lanthanide(III) complexes of DOTA-glycoconjugates: A potential new class of lectin-mediated medical imaging agents

Chemistry - A European Journal

Volumn 10, Issue 22, 2004, Pages 5804-5816

  André, João P ^a   Geraldes, Carlos F G C ^b   Martins, José A ^a   Merbach, André E ^c   Prata, Maria I M ^d   Santos, Ana C ^d   De Lima, João J P ^d   Tóth, Éva ^c  

^a UNIVERSITY OF MINHO   (Portugal)

^b UNIVERSITY OF COIMBRA   (Portugal)

^c EPFL   (Switzerland)

^d UNIVERSITY OF COIMBRA   (Portugal)

Author keywords

Glycoconjugates; Lanthanides; Lectins; Macrocycles; Magnetic resonance imaging

Indexed keywords

COMPLEXATION; GLUCOSE; ISOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SUGAR (SUCROSE);

AMIDE BONDS; CHELATING MOIETY; LECTINS; STRUCTURAL ISOMERS;

RARE EARTH ELEMENTS;

1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,10 TETRAACETIC ACID; AMIDE; CHELATING AGENT; CYCLOALKANE DERIVATIVE; DENDRIMER; EUROPIUM; GADOTERIC ACID; GALACTOSE; GLUCOSE; GLYCOCONJUGATE; HETEROCYCLIC COMPOUND; LACTOSE; LANTHANIDE; LECTIN; SAMARIUM;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; ISOMER; MOLECULAR RECOGNITION; PROTON NUCLEAR MAGNETIC RESONANCE; SCINTISCANNING;

CARBOHYDRATES; GALACTOSE; GLUCOSE; HETEROCYCLIC COMPOUNDS, 1-RING; LACTOSE; LANTHANOID SERIES ELEMENTS; LECTINS; LIGANDS; MAGNETIC RESONANCE IMAGING; MOLECULAR STRUCTURE; RADIONUCLIDE IMAGING; SOLUTIONS;

EID: 9244230554     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400187     Document Type: Article

References (59)

1. A. Heppeler, S. Froidevaux, A. N. Eberle, H. R. Maecke, Curr. Med. Chem. 2000, 7, 971-994.
2. C. J. Anderson, M. J. Welch, Chem. Rev. 1999, 99, 2219-2234.
3. W. A. Volkert, T. J. Hoffman, Chem. Rev. 1999, 99, 2269-2292.
4. S. M. Qaim, Radiochim. Acta 2001, 89, 297-302.
5. R. P. Junghans, D. Dobbs, M. W. Brechbiel, S. Mirzadeh, A. A. Raubitschek, O. A. Gansow, T. A. Walmann, Cancer Res. 1993, 53, 5683-5689.
6. S. W. J. Lamberts, A. J. Van der Lely, W. W. de Herder, L. Hofland, New Engl. J. Med. 1996, 334, 246-254.
7. P. Caravan, J. J. Ellison, T. J. McMurry, R. B. Lauffer, Chem. Rev. 1999, 99, 2293-2352.
8. É. Tóth, L. Helm, A. E. Merbach, Top. Curr. Chem. 2002, 221, 61-101.
9. S. Aime, C. Cabella, S. Colombatto, S. G. Crich, E. Gianolio, F. Maggioni, J. Magn. Res. Imag. 2002, 16, 394-406.
10. F. Cavagna, M. Daprà, F. Maggioni, C. De Haën, E. Felder, Magn. Reson. Med. 1991, 22, 329-333.
11. H. S. -Willich, M. Brehm, C. L. J. Ewers, G. Michl, A. M. -Fahrnow, O. Petrov, J. Platzek, B. Raduchel, D. Sülzle, Inorg. Chem. 1999, 38, 1134-1144.
12. S. M. Rocklage, W. P. Cacheris, S. C. Quay, F. E. Hahn, K. N. Raymond, Inorg. Chem. 1989, 28, 477-485.
13. M. I. Papisov, A. Bogdanov, B. Schaffer, N. Nossif, T. Shen, R. Weissleder, T. J. Brady, J. Magn. Magn. Mater. 1993, 122, 383-386.
14. G. W. Kabalka, M. A. Davis, T. H. Moss, E. Buonocore, K. Hubner, E. Holmberg, K. Maruyama, L. Huang, Magn. Res. Med. 1991, 19. 406-415.
15. J. P. Andŕ, É. Tóth, H. Fischer, A. Seelig, H. R. Mäcke, A. E. Merbach, Chem. Eur. J. 1999, 5, 2977-2983.
16. T. K. Dam, C. F. Brewer, Chem. Rev. 2002, 102, 387-429.
17. H. Lis, N. Sharon, Chem. Rev. 1998, 98, 637-674.
18. a) M. Mammen, S.-K. Choi, G. M. Whitesides, Angew. Chem. 1998, 110, 2908-2953; Angew. Chem. Int. Ed. 1998, 37, 2754-2794;
19. a) M. Mammen, S.-K. Choi, G. M. Whitesides, Angew. Chem. 1998, 110, 2908-2953; Angew. Chem. Int. Ed. 1998, 37, 2754-2794;
20. b) J. J. Lundquist, E. J. Toone, Chem. Rev. 2002, 102, 555-578.
21. I. Vrasidas, S. André, P. Valentini, C. Bock, M. Lensch, H. Kaltner, R. M. J. Liskamp, H.-J. Gabius, R. J. Pieters, Org. Biomol. Chem. 2003, 1, 803-810.
22. P. H. Weigel, J. H. N. Yik, Biochim. Biophys. Acta (General Subjects) 2002, 7572, 341-363.
23. N. Yamazaki, S. Kojima, N. V. Bovin, S. André, S. Gabius, H.-J. Gabius, Adv. Drug Delivery Rev. 2000, 43, 225-244.
24. G. Gregoriadis, Lancet 1981, 2, 241-246.
25. K. A. Deal, M. E. Criste, M. J. Welsh, Nucl. Med. Biol. 1998, 25, 379-385.
26. S. Ishibashi, R. E. Hammer, J. Herz, J. Biol. Chem. 1994, 269, 27803-27806.
27. Y. Koyama, M. Ishikawa, A. Yeda, R. Sudo, S. Kojima, A. Sugunaka, Polym. J. 1993, 25, 355-361.
28. D. R. Vera, R. Stadalnik, K. Krohn, J. Nucl. Med. 1985, 26, 1157-1167.
29. M. M. Alauddin, A. Y. Louie, A. Shahinian, T. J. Meade, P. S. Conti, Nucl. Med. Biol. 2003, 30, 261-265.
30. S. D. Colquhoum, C. A. Conelly, D. R. Vera, J. Nucl. Med. 2001, 42, 110-116.
31. K. Miki, K. Kubota, Y. Inoue, D. R. Vera, M. Makuuchi, J. Nucl. Med. 2001, 42, 733-737.
32. N. Shuke, H. O. Kizaki, S. Kino, J. Sato, Y. Ishikawa, C. L. Zhao, S. Kineya, N. Watabane, K. Yokoama, T. Aburano, J. Nucl. Med. 2003, 44, 475-482.
33. B. K. Schaffer, C. Linker, M. Papisov, E. Tsai, N. Nossiff, T. Shibata, A. Bogdanov, T. J. Brady, R. Weissleder, Magn. Reson. Imaging 1993, 11, 411-417.
34. P. Reimer, R. Weissleder, A. S. Lee, S. Buettner, J. Wittenberg, T. J. Brady. Radiology 1991, 178, 769-774.
35. P. Reimer, R. Weissleder, T. J. Brady, Radiology 1992, 182, 1161-1167.
36. B. Gallez, V. Lacour, R. Demeure, R. Debuyst, F. Dejehet, J. L. Dekeyser, P. Dumont, Magn. Reson. Imaging 1994, 12, 61-69.
37. D. R. Vera, M. H. Buonocore, E. R. Wisner, R. W Katzberg, R. C. Stadalnik, Acad. Radial. 1995, 2, 497-506.
38. A. Bianchi, L. Calabi, F. Corana, S. Fontana, P. Losi, A. Maiocchi, L. Paleari, B. Valtancoli, Coord. Chem. Rev. 2000, 204, 309-393.
39. a) W. B. Turnbull, J. F. Stoddart, Rev. Mol. Biotech. 2002, 90, 231-255;
40. b) D. Zanini, R. Roy, J. Org. Chem. 1996, 61, 7348-7354.
41. C. F. G. C. Geraldes, A. D. Sherry, M. P. M. Marques, M. C. Alpoim, S. Cortes, J. Chem. Sac. Perkin Trans. 2 1991, 137-146.
42. J. A. Peters, E. Zitha-Bovens, D. Corsi, C. F. G. C. Geraldes, "Structure and Dynamics of Gadolinium-Based Contrast Agents" in The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging (Eds.: É. Tóth, A. E. Merbach), Wiley, Chichester, 2001, p. 315-381.
43. S. Aime, M. Botta, G. Ermondi, Inorg. Chem. 1992, 31, 4291-4299.
44. S. Aime, M. Botta, M. Fasano, M. P. M. Marques, C. F. G. C. Geraldes, D. Pubanz, A. E. Merbach, Inorg. Chem. 1997, 36, 2059-2068.
45. S. Aime, M. Botta, E. Garino, S. G. Crich, G. Giovenzana, R. Pagliarin, G. Palmisano, M. Sisti, Chem. Eur. J. 2000, 6, 2609-2617.
46. É. Tóth, L. Helm, A. E. Merbach, "Relaxivity of Gadolinium(III) Complexes: Theory and Mechanism" in The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging (Eds.: É. Tóth, A. E. Merbach) Wiley, Chichester, 2001, p. 45-119.
47. D. H. Powell, O. M. Ni Dhubhghaill, D. Pubanz, L. Helm, Y. S. Lebedev, W. Schlaepfer, A. E. Merbach, J. Am. Chem. Soc. 1996, 118, 9333-9346.
48. A. D. Sherry, R. D. Brown III, C. F. G. C. Geraldes, S. H. Koenig, K.-T. Kuan, M. Spiller. Inorg. Chem. 1989, 28, 620-622.
49. 3+ Chelates" in The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging (Eds. : É. Tóth, A. E. Merbach), Wiley, Chichester, 2001, p. 383-415.
50. S. Rast, A. Borel, L. Helm, E. Belorizky, P. H. Fries, A. E. Merbach, J. Am. Chem. Soc. 2001, 123, 2637-2644;
51. b) S. Rast, P. H. Fries, E. Belorizky, A. Borel, L. Helm, A. E. Merbach, J. Chem. Phys. 2001, 115, 7554-7563.
52. Unpublished results.
53. A. D. Nunn, K. E. Liner, M. F. Tweedle, Q. J. Nucl. Med. 1997, 41, 155.
54. V. Jacques, J. F. Desreux, in New Classes of MRI Contrast Agents in Topics in Current Chemistry, Vol. 221: Contrast Agents I. Magnetic Resonance Imaging (Ed. W. Krause) Springer, Berlin, 2002, p. 123-164.
55. a) A. D. McLachlan, Proc. R. Soc. London, Proc. R. Soc. London Ser. A 1964, 280, 271;
56. b) D. H. Powell, A. E. Merbach, G. Gonzalez, E. Brücher, K. Micskei, M. F. Ottaviani. K. Köhler, A. von Zelewsky, O. Y. Grinberg, Y. S. Lebedev, Helv. Chim. Acta 1993, 76, 2129-2146.
57. a) Y. C. Lee, R. R. Townsend, M. R. Hardy, J. Lönngren, J. Arnarp, M. Haraldsson, H. Lönn, J. Biol. Chem. 1983, 258, 199-202;
58. b) R. T. Lee, Y. C. Lee, Biochem. Biophys. Res. Commun. 1988, 155, 1444-1451;
59. c) E. A. L. Biessen, H. Broxterman, J. H. Van Boom, T. J. Van Berkel, J. Med. Chem. 1995, 38, 1846-1852.