Lanthanide (III) complexes that contain a self-immolative arm: Potential enzyme responsive contrast agents for magnetic resonance imaging

Chemistry - A European Journal

Volumn 18, Issue 5, 2012, Pages 1408-1418

  Chauvin, Thomas ^a   Torres, Susana ^b   Rosseto, Renato ^b   Kotek, Jan ^c   Badet, Bernard ^b   Durand, Philippe ^b   Tóth, Éva ^a  

^a CENTRE DE BIOPHYSIQUE MOLÉCULAIRE   (France)

^b INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

^c CHARLES UNIVERSITY   (Czech Republic)

Author keywords

Enzymatic detection; Lanthanides; MRI contrast agents; PARACEST; Water exchange

Indexed keywords

AMINE DERIVATIVES; CASCADE REACTIONS; CONTRAST AGENT; ENZYMATIC ACTIVITIES; ENZYMATIC CLEAVAGE; ENZYMATIC DETECTION; ENZYMATIC REACTION; ENZYME SUBSTRATES; EXCHANGE RATES; LANTHANIDE COMPLEX; MODEL COMPOUND; MRI CONTRAST AGENTS; NUCLEAR MAGNETIC RELAXATION DISPERSION; PARACEST; PH VALUE; PHYSIOLOGICAL PH; PROTON-EXCHANGE; PROTONATED; RELAXIVITY; SATURATION POWER; SATURATION TIME; SPECIFIC DETECTION; STRUCTURAL CHANGE; SUGAR UNITS; VARIABLE TEMPERATURE; VARIOUS PH; WATER EXCHANGE; WATER MOLECULE;

ENZYMES; GADOLINIUM; MAGNETIC RESONANCE IMAGING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC COMPOUNDS; PROTONS; RARE EARTH ELEMENTS; SPHERES; SUBSTRATES; SUGARS; YTTERBIUM;

PH EFFECTS;

CONTRAST MEDIUM; GADOLINIUM; LANTHANIDE; ORGANOMETALLIC COMPOUND; WATER; YTTERBIUM;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE IMAGING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

CONTRAST MEDIA; GADOLINIUM; LANTHANOID SERIES ELEMENTS; MAGNETIC RESONANCE IMAGING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; WATER; YTTERBIUM;

EID: 84857179526     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201101779     Document Type: Article

References (78)

1. Acc. Chem. Res. 2009, 42, issue 7, special issue on molecular imaging.
2. A. E. Merbach, É. Tóth, The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging, Wiley, New York, 2001, p. 471.
3. K. M. Ward, A. H. Aletras, R. S. Balaban, J. Magn. Reson. 2000, 143, 79-87.
4. S. Viswanathan, Z. Kovacs, K. N. Green, S. J. Ratnakar, A. D. Sherry, Chem. Rev. 2010, 110, 2960-3018.
5. C. M. Watson, P. A. Trainor, T. Radziewic, G. J. Pelka, S. X. Zhou, M. Parameswaran, G. A. Quinlan, M. Gordon, K. Sturm, P. P. L. Tam, Methods Mol. Biol. 2008, 461, 149-164.
6. a) C.-H. Tung, Q. Zeng, K. Shah, D.-E. Kim, D. Schellingerhout, R. Weissleder, Cancer Res. 2004, 64, 1579-1583;
7. b) V. Josserand, I. Texier-Nogues, P. Huber, M. Favrot, J. L. Coll, Gene. Ther. 2007, 14, 1587-1593;
8. c) G.-J. Zhang, T.-B. Chen, B. Connolly, S.-A. Lin, R. Hargreaves, A. Vanko, B. Bednar, D. J. MacNeil, C. Sur, D. L. Williams, Assay Drug Dev. Technol. 2009, 7, 391-399.
9. a) M. M. Alauddin, A. Y. Louie, A. Shahinian, T. J. Meade, P. S. Conti, J. Nucl. Med. 2002, 43, 138P-139P;
10. b) R. A. Moats, S. E. Fraser, T. J. Meade, Angew. Chem. 1997, 109, 749-752;
11. Angew. Chem. Int. Ed. Engl. 1997, 36, 726-728;
12. c) L. M. Urbanczyk-Pearson, F. J. Femia, J. Smith, G. Parigi, J. A. Duimstra, A. L. Eckermann, C. Luchinat, T. J. Meade, Inorg. Chem. 2008, 47, 56-68;
13. d) L. M. Urbanczyk-Pearson, T. J. Meade, Nat. Protoc. 2008, 3, 341-350;
14. e) M. M. Alauddin, A. Y. Louie, A. Shahinian, T. J. Meade, Nucl. Med. Biol. 2003, 30, 261-265.
15. J. H. Kang, J.-K. Chung, J. Nucl. Med. 2008, 49, 164S-179S.
16. Y.-T. Chang, C.-M. Cheng, Y.-Z. Su, W.-T. Lee, J.-S. Hsu, G.-C. Liu, T.-L. Cheng, Y.-M. Wang, Bioconjugate Chem. 2007, 18, 1716-1727.
17. K. Hanaoka, K. Kikuchi, T. Terai, T. Komatsu, T. Nagano, Chem. Eur. J. 2008, 14, 987-995.
18. J. A. Duimstra, F. J. Femia, T. J. Meade, J. Am. Chem. Soc. 2005, 127, 12847-12855.
19. a) P. L. Carl, P. K. Chakravarty, J. A. Katzenellenbogen, J. Med. Chem. 1981, 24, 479-480;
20. b) J.-L. Guerquin-Kern, A. Volk, E. Chenu, R. Lougerstay-Madec, C. Monneret, J.-C. Florent, D. Carrez, A. Croisy, NMR Biomed. 2000, 13, 306-310;
21. c) R. Madec-Lougerstay, J.-C. Florent, C. Monneret, J. Chem. Soc. Perkin Trans. 1 1999, 1369-1375;
22. d) F. M. H. de Groot, W. J. Loos, R. Koekkoek, L. W. A. vanBerkom, G. F. Busscher, A. E. Seelen, C. Albrecht, P. deBruijn, H. W. Scheeren, J. Org. Chem. 2001, 66, 8815-8830.
23. T. Chauvin, P. Durand, M. Bernier, H. Meudal, B.-T. Doan, F. Noury, B. Badet, J.-C. Beloeil, É. Tóth, Angew. Chem. 2008, 120, 4442-4444;
24. Angew. Chem. Int. Ed. 2008, 47, 4370-4372.
25. J. M. Z. Gladych, D. Hartley in Comprehensive Organic Chemistry: the synthesis and reactions of organic compounds, Vol. 2 (Eds.: D. Barton, W. D. Ollis), Pergamon Press, New York, 1979, pp. 61-130.
26. B. Yoo, M. D. Pagel, Tetrahedron Lett. 2006, 47, 7327-7330.
27. a) I. I. Creaser, R. J. Geue, J. M. Harrowfield, A. J. Herlt, A. M. Sargeson, M. R. Snow, J. Springborg, J. Am. Chem. Soc. 1982, 104, 6016-6025;
28. b) M. P. Suh, W. Shin, D. Kim, S. Kim, Inorg. Chem. 1984, 23, 618-620;
29. c) M. P. Suh, D. Kim, Inorg. Chem. 1985, 24, 3712-3714;
30. d) M. P. Suh, W. Shin, H. Kim, C. H. Koo, Inorg. Chem. 1987, 26, 1846-1852;
31. e) M. P. Suh, S.-G. Kangl, Inorg. Chem. 1988, 27, 2544-2546;
32. f) T. Kojima, T. Usui, T. Tanase, M. Yashiro, S. Yoshikawa, R. Kuroda, S. Yano, M. Hidai, Inorg. Chem. 1990, 29, 446-450;
33. g) T. Kojima, R. Kuroda, S. Yano, M. Hidaif, Inorg. Chem. 1991, 30, 3580-3582;
34. h) L. Fabbrizzi, A. M. M. Lanfredi, P. Pallavicini, A. Perotti, A. Taglietti, F. Ugozzoli, J. Chem. Soc. Dalton Trans. 1991, 3263-3269;
35. i) T. Kojima, T. Usui, A. Shimada, M. Yashiro, T. Tanase, R. Yoshioka, R. Kuroda, S. Yano, M. Hidai, M. Kato, K. Kobayashi, T. Sakurai, S. Yoshikawa, Inorg. Chem. 1991, 30, 4535;
36. j) M. P. Suh, B. Y. Shim, T.-S. Yoon, Inorg. Chem. 1994, 33, 5509-5514;
37. k) P. V. Bernhardt, P. C. Sharpe, Inorg. Chem. 2000, 39, 2020-2025;
38. l) P. Bernhardt, J. C. Hetherington, J. Chem. Soc. Dalton Trans. 1996, 4325-4330.
39. a) M. D. Fletcher, M. M. Campbell, Chem. Rev. 1998, 98, 763-795;
40. b) W. J. N. Meester, J. H. van Maarseveen, H. E. Schoemaker, H. Hiemstra, F. P. J. T. Rutjes, Eur. J. Org. Chem. 2003, 2519.
41. M. Suchý, R. H. E. Hudson, Eur. J. Org. Chem. 2008, 4847-4865.
42. a) P. Surdy, P. Rubini, N. Buzás, B. Henry, L. Pellerito, T. Gajda, Inorg. Chem. 1999, 38, 346-352;
43. b) F. Gharib, M. H. Fekri, J. Solution Chem. 2003, 32, 855-863.
44. C. M. Loudon, M. R. Almond, J. N. Jacob, J. Am. Chem. Soc. 1981, 103, 4508.
45. F. Moriya, K. Maklno, N. Suzukl, S. Rokushlka, H. Hatano, J. Phys. Chem. 1980, 84, 3085-3090.
46. a) L. R. Gahan, T. W. Hambley, A. M. Sargeson, M. R. Snow, Inorg. Chem. 1982, 21, 2699-2706;
47. b) M. P. Suh, W. Shin, S.-G. Kang, M. S. Lah, T.-M. Chung, Inorg. Chem. 1989, 28, 1602-1605.
48. R. W. Alder, T. M. G. Carniero, R. W. Mowlam, A. G. Orpen, P. A. Petillo, D. J. Vachon, G. R. Weisman, J. M. White, J. Chem. Soc. Perkin Trans. 2 1999, 589-599.
49. a) Y. Mo, Nat. Chem. 2010, 2, 666-671;
50. b) O. Takahashi, K. Yamasaki, Y. Kohno, K. Ueda, H. Suezawa, M. Nishio, Carbohydr. Res. 2009, 344, 1225-1229;
51. c) S. Chandrasekhar, ARKIVOC 2005, 37-66.
52. a) M. K. Kesharwani, W. Thiel, B. Ganguly, J. Phys. Chem. A 2010, 114, 10684-10693;
53. b) B. Ganguly, B. Fuchs, J. Org. Chem. 1997, 62, 8892-8901.
54. a) W. De, W. J. Horrocks, D. R. Sudnick, J. Am. Chem. Soc. 1979, 101, 334-340;
55. b) R. M. Supkowski, W. De, W. J. Horrocks, Inorg. Chim. Acta 2002, 340, 44-48;
56. c) A. Beeby, I. M. Clarkson, R. S. Dickins, S. Faulkner, D. Parker, L. Royle, A. S. deSousa, J. A. G. Williams, M. Woods, J. Chem. Soc. Perkin Trans. 2 1999, 493-502.
57. N. Graeppi, D. H. Powell, G. Laurenczy, L. Zékény, A. E. Merbach, Inorg. Chim. Acta 1995, 235, 311-326.
58. a) P. H. Fries, E. Belorizky, J. Chem. Phys. 2005, 123, 124510;
59. b) P. Miéville, H. Jaccard, F. Reviriego, R. Tripier, L. Helm, Dalton Trans. 2011, 40, 4260-4267.
60. D. H. Powell, O. M. N. Dhubhghaill, D. Pubanz, L. Helm, Y. S. Lebedev, W. Schlaepfer, A. E. Merbach, J. Am. Chem. Soc. 1996, 118, 9333-9346.
61. B. Yoo, M. D. Pagel, J. Am. Chem. Soc. 2006, 128, 14032-14033.
62. a) S. Forsén, R. A. Hoffman, J. Chem. Phys. 1963, 39, 2892-2901;
63. b) S. Forsén, R. A. Hoffman, J. Chem. Phys. 1964, 40, 1189-1196.
64. M. T. McMahon, A. A. Gilad, J. Zhou, P. Z. Sun, J. W. M. Bulte, P. C. M. vanZijl, Magn. Reson. Med. 2006, 55, 836-847.
65. S. Zhang, P. Winter, K. Wu, A. D. Sherry, J. Am. Chem. Soc. 2001, 123, 1517-1518.
66. W. T. Dixon, J. Ren, A. J. M. Lubag, J. Ratnakar, E. Vinogradov, I. Hancu, R. E. Lenkinski, A. D. Sherry, Magn. Reson. Med. 2010, 63, 625-632.
67. S. Zhang, L. Michaudet, S. Burgess, A. D. Sherry, Angew. Chem. 2002, 114, 1999-2001;
68. Angew. Chem. Int. Ed. 2002, 41, 1919-1921.
69. E. Liepinsh, G. Otting, Magn. Reson. Med. 1996, 35, 30-42.
70. G. Liu, Y. Li, M. D. Pagel, Magn. Reson. Med. 2007, 58, 1249-1256.
71. B. Yoo, M. S. Raam, R. M. Rosenblum, M. D. Pagel, Contrast Media Mol. Imaging 2007, 2, 189-198.
72. S. Aime, A. Barge, D. D. Castelli, F. Fedeli, A. Mortillaro, F. U. Nielsen, E. Terreno, Magn. Reson. Med. 2002, 47, 639-648.
73. R. L. Vold, J. S. Waugh, M. P. Klein, D. E. Phelps, J. Chem. Phys. 1968, 48, 3831.
74. S. Meiboom, D. Gill, Rev. Sci. Instrum. 1958, 29, 688-691.
75. A. D. Hugi, L. Helm, A. E. Merbach, Helv. Chim. Acta 1985, 68, 508-521.
76. D. S. Raiford, C. L. Fisk, E. D. Becker, Anal. Chem. 1979, 51, 2050-2051.
77. H. M. Irving, M. G. Miles, L. Pettit, Anal. Chim. Acta 1967, 38, 475-488.
78. L. Zékány, I. Nagypál in Computation Methods for Determination of Formation Constants (Ed.: D. J. Leggett), Plenum, New York, 1985, p. 291.