Discovery of powerful uranyl ligands from efficient synthesis and screening

Chemistry - A European Journal

Volumn 11, Issue 12, 2005, Pages 3689-3697

  Sawicki, Marcin ^a   Siaugue, Jean Michel ^a   Jacopin, Christophe ^b   Moulin, Christophe ^b   Bailly, Théodorine ^c   Burgada, Ramon ^c   Meunier, Stéphane ^a   Baret, Paul ^d   Pierre, Jean Louis ^d   Taran, Frédéric ^a  

^a CEA   (France)

^b CEA SACLAY   (France)

^c CNRS/LCSB/UMR 7033   (France)

^d UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

Actinides; Chelates; Michael addition; Tripodal ligands; Uranium

Indexed keywords

AMINES; CHELATION; COMPLEXATION; DERIVATIVES; SCREENING; SYNTHESIS (CHEMICAL); URANIUM COMPOUNDS;

CHELATES; CHELATING MOIETIES; COMPLEXATION PROPERTIES; LIGANDS;

ORGANIC COMPOUNDS;

LIGAND; NAPHTHALENE DERIVATIVE; ORGANOMETALLIC COMPOUND; SULFOCHLOROPHENOL S; SULFONE; URANIUM;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; PH; SYNTHESIS;

HYDROGEN-ION CONCENTRATION; LIGANDS; MOLECULAR STRUCTURE; NAPHTHALENES; ORGANOMETALLIC COMPOUNDS; SULFONES; URANIUM;

EID: 20644461510     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200401056     Document Type: Article

References (67)

1. a) A. E. V. Gorden, J. Xu, K. N. Raymond, P. Durbin, Chem. Rev. 2003, 103, 4207-4282;
2. b) O. Anderson, Chem. Rev. 1999, 99, 2683-2710;
3. c) D. M. Taylor, G. N. Stradling, M. H. Henge-Napoli, Radiat. Prot. Dosim. 2000, 87, 11-17;
4. d) R. Wood, C. Sharp, P. Gourmelon, B. Le Guen, G. N. Stradling, D. M. Taylor, M. H. Henge-Napoli, Radiat. Prot. Dosim. 2000, 87, 51-57;
5. e) P. W. Durbin, B. Kullgren, K. N. Raymond, Radiat. Prot. Dosim. 1998, 79, 433-443;
6. f) G. N. Strandling, J. Alloys Comp. 1998, 271-273, 72-77.
7. a) C. Madic, Radiat. Prot. Dosim. 1989, 26, 15-22;
8. b) L. A. Dietz, Bull. Soc. Pharm. Lille Bull Atomic Scientists 1991, 47, 47;
9. c) A. Max, T. Mason, ATW-Int. Z. Kernenergie 1996, 41, 79-84.
10. Q. Lu, J. H. Callahan, G. E. Collins, Chem. Commun. 2000, 1913-1914.
11. a) S. Shinkai, H. Koreishi, K. Ueda, T. Arimura, O. Manabe, J. Am. Chem. Soc. 1987, 109, 6371-6376;
12. b) J. Vincent, J. F. Desreux, Inorg. Chem. 1996, 35, 7205-7210;
13. c) J. L. Sessler, D. Seidel, A. E. Vivian, V. Lynch, B. L. Scott, D. W. Keogh, Angew. Chem. 2001, 113, 611-614;
14. Angew. Chem. Int. Ed. 2001, 40, 591-594;
15. d) I. Tabushi, Y. Kobuke, K. Ando, M. Kishimoto, E. Ohara, J. Am. Chem. Soc. 1980, 102, 5948-5949;
16. e) T. N. Lambert, L. Dasaradhi, V. J. Huber, A. S. Gopalan, J. Org. Chem. 1999, 64, 6097-6101.
17. a) M. H. Battacharyya, B. Breitenstein, H. Métivier, B. A. Muggenburg, G. N. Stradling, V. Volf, Radiat. Prot. Dosim. 1992, 41, 27-36;
18. b) G. N. Stradling, M. H. Henge-Napoli, F. Paquet, J. L. Poney, P. Fritsch, D. M. Taylor, Radiat. Prot. Dosim. 2000, 87, 29-40;
19. c) F. Paquet, B. Ramounet, M. H. Henge-Napoli, H. Métivier, P. Gourmelon, Radiat. Prot. Dosim. 1998, 79, 467-470;
20. d) M. Archimbaud, M. H. Henge-Napoli, D. Lilienbaum, M. Desloges, C. Montagne, Radiat. Prot. Dosim. 1994, 53, 327-330;
21. e) J. L. Domingo, A. Ortega, J. M. Llobet, J. L. Paternain, J. Corbela, Res. Commun. Chem. Pathol. Pharmacol. 1989, 64, 161-164;
22. f) G. N. Strandling, S. A. Gray, J. C. Moody, M. Ellender, Hum. Exp. Toxicol. 1991, 10, 195-198.
23. R. W. Leggett, Health Phys. 1989, 57, 365-383.
24. M. P. Finkel, Proc. Soc. Exp. Biol. Med. 1953, 83, 494-498.
25. a) J. Xu, K. N. Raymond, Inorg. Chem. 1999, 38, 308-315;
26. b) P. W. Durbin, B. Kullgren, J. Xu, K. N. Raymond, Radiat. Prot. Dosim. 1994, 53, 305-309;
27. c) P. W. Durbin, B. Kullgren, J. Xu, K. N. Raymond, Radiat. Prot. Dosim. 1998, 79, 433-443.
28. a) P. W. Durbin, B. Kullgren, J. Xu, K. N. Raymond, Health Phys. 1997, 72, 865-879;
29. b) P. W. Durbin, B. Kullgren, S. N. Ebbe, J. Xu, K. N. Raymond, Health Phys. 2000, 78, 511-521.
30. a) M. C. Pirrung, K. Park, L. N. Tumey, J. Comb. Chem. 2002, 4. 329-344;
31. b) T. Opatz, R. M. Liskamp. J. Comb. Chem. 2002, 4, 275-284;
32. c) A. J. Brouwer, H. J. van der Linden, R. M. J. Liskamp, J. Org. Chem. 2000, 65, 1750-1757;
33. d) C. Gennari, H. P. Nestler, U. Piarulli, B. Salom, Liebigs Ann. 1997, 637-647;
34. e) I. Chataigner, C. Gennari, S. Ongeri, U. Piarulli, S. Ceccarelli, Chem. Eur. J. 2001, 7, 2628-2634;
35. f) C. Gennari, U. Piarulli, Chem. Rev. 2003, 103, 3071-3100.
36. a) I. Tabushi, Y. Kobuke, K. Ando, M. Kishimoto, E. Ohara, J. Am. Chem. Soc. 1980, 102, 5948-5949;
37. S. Shinkai, H. Koreishi, K. Ueda, T. Arimura, O. Manube, J. Am. Chem. Soc. 1987, 109, 6371-6376.
38. I. Tabushi, Y. Kobuke, A. Yoshizawa, J. Am. Chem. Soc. 1984, 106, 2481-2482 and references therein.
39. O. Braun, C. Contino, M. H. Hengé-Napoli, E. Ansoborlo, B. Pucci, Analusis 1999, 27, 65-68.
40. a) Z. Cizek, J. Dolezal, Anal. Chim. Acta 1979, 109, 381;
41. b) V. M. Ivanov, N. V. Ermakova, J. Anal. Chem. 2002, 57, 110-117;
42. c) Z. Cizek, Anal. Chim. Acta 1979, 109, 381-391.
43. A.-M. Albrecht-Gary, S. Blanc, F. Biaso, F. Thomas, P. Baret, G. Gellon, J-L. Pierre, G. Serratrice, Eur. J. Inorg. Chem. 2003, 2596-2605.
44. See Supporting Information for details.
45. V. M. S. Gil: N. C. Oliveira, J. Chem. Educ. 1990, 67, 473-478.
46. P. Gans. A. Sabatini, A. Vacca, Anal. Chim. Acta 1999, 89, 45-49.
47. L. Alderighi, P. Gans, A. Ienco, D. Peters, A. Sabatini, A. Vacca, Coord. Chem. Rev. 1999, 184, 311-318.
48. For compounds 1D-G, 2F-H, 3F-G, 4B-F, 4H, 5B and 5E: a) R. Burgada, T. Bailly, M. Lecouvey, V. Larue, Y. Leroux, Eur. J. Org. Chem. 2001, 349-352;
49. b) T. Bailly, R. Burgada, T. Prangé, M. Lecouvey, Tetrahedron Lett. 2003, 44, 189-192;
50. c) R. Burgada, T. Bailly, M. Lecouvey, C. R. Chim. 2004, 7, 35-39;
51. d) M. Kanaan, R. Burgada, Phosphorus Sulfur Relat. Elem. 1988, 37, 217-229;
52. e) T. Bailly, R. Burgada, Phosphorus, Phosphorus Sulfur Silicon Relat. Elem. 1994, 86, 217-228;
53. f) T. Bailly, R. Burgada. Phosphorus, Phosphorus Sulfur Silicon Relat. Elem. 1995, 101, 131-140;
54. g) T. Bailly, R. Burgada, C. R. Acad. Sci. Paris IIc. 1998, 241-245.
55. For compounds 3A-E, 3H and 4A: a) P. Baret, V. Beaujolais, C. Béguin, D. Gaude, J-L. Pierre, G. Serratrice, Eur. J. Inorg. Chem. 1998, 613-619;
56. b) G. Serratrice, H. Boukhalfa, C. Béguin, P. Baret, C. Caris, J-L. Pierre, Inorg. Chem. 1997, 36, 3898-3910;
57. c) M. Streater, P. D. Taylor, R. C. Hider, J. Porter, J. Med. Chem. 1990, 33, 1749-1755.
58. S. Meunier, J. M. Siaugue, M. Sawicki, F. Calbour, S. Dezard, F. Taran, C. Mioskowski, J. Comb. Chem. 2003, 5, 201-204.
59. a) M. H. Henge-Napoli, M. Archimbaud, E. Ansoborlo, H. Metivier, P. Gourmelon, Int. J. Radiat. Biol. 1995, 68, 389-393;
60. b) B. Ramounet-Le Gall, G. Grillon, G. Rateau, R. Burgada, T. Bailly, P. Fritsch, Radiat. Prot. Dosim. 2003, 105, 535-538.
61. F. Thomas, C. Béguin, J. L. Pierre, G. Serratrice, Inorg. Chim. Acta 1999, 291, 148-157.
62. a) J. T. Bell, R. E. Biggers, J. Mol. Spectrosc. 1968, 25, 312;
63. b) E. Rabinowitsch, R. L. Belford, Spectroscopy and Photophysics of Uranyl Compounds, Pergamon Press, 1964, Oxford.
64. C. Moulin, P. Decambox, V. Moulin, J. G. Decaillon, Anal. Chem. 1995, 67, 348.
65. 2+ by A7B6 in these conditions.
66. a) J. E. Bollinger, Q. M. Roundhill, Inorg. Chem. 1994, 33, 6421-6424;
67. b) C. Jacopin, M. Sawicki, G. Plancque, D. Doizi, F. Taran, E. Ansoborlo, B. Amekraz, C. Moulin, Inorg. Chem. 2003, 42, 5015-5022.