Mn2+ Complexes with 12-Membered pyridine based macrocycles bearing carboxylate or phosphonate pendant arm: Crystallographic, thermodynamic, kinetic, redox, and 1H/17O relaxation studies

Inorganic Chemistry

Volumn 50, Issue 24, 2011, Pages 12785-12801

  Drahoš, Bohuslav ^a,b   Kotek, Jan ^a   Ciśarǒvá, Ivana ^a   Hermann, Petr ^a   Helm, Lothar ^c   Lukeš, Ivan ^a   Tóth, Éva ^b  

^a CHARLES UNIVERSITY   (Czech Republic)

^b CENTRE DE BIOPHYSIQUE MOLÉCULAIRE   (France)

^c EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID; CHELATING AGENT; CONTRAST MEDIUM; COORDINATION COMPOUND; FUSED HETEROCYCLIC RINGS; MANGANESE; PHOSPHONIC ACID DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE IMAGING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; PH; POTENTIOMETRY; SYNTHESIS; TEMPERATURE; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

CARBOXYLIC ACIDS; CHELATING AGENTS; CONTRAST MEDIA; COORDINATION COMPLEXES; CRYSTALLOGRAPHY, X-RAY; HETEROCYCLIC COMPOUNDS, 2-RING; HYDROGEN-ION CONCENTRATION; KINETICS; MAGNETIC RESONANCE IMAGING; MAGNETIC RESONANCE SPECTROSCOPY; MANGANESE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHOSPHONIC ACIDS; POTENTIOMETRY; PYRIDINES; TEMPERATURE; THERMODYNAMICS;

EID: 84055221918     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic201935r     Document Type: Article

References (69)

1. Schwert, D. D.; Davies, J. A.; Richardson, N. Non-gadolinium based MRI contrast agents. In Contrast agents I: magnetic resonance imaging; Krause, W., Ed.; Springer: Berlin, Germany, 2002; pp 165-200.
2. Kubicìěk, V.; Totìh, Eì. Adv. Inorg. Chem. 2009, 61, 63-129.
3. Caravan, P.; Ellison, J. J.; McMurry, T. J.; Lauffer, R. B. Chem. Rev. 1999, 99, 2293-2352.
4. Toìth, Eì., Merbach, A. E. The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging; John Wiley & Sons: Chichester, U.K., 2001.
5. Hermann, P.; Kotek, J.; Kubicìěk, V.; Lukeš I. Dalton Trans. 2008, 3027-3047.
6. Sherry, A. D.; Caravan, P.; Lenkinski, R. E. J. Magn. Reson. Imag. 2009, 30, 1240-1248.
7. Bannister, J. V.; Bannister, W. H.; Rotilio, G. Crit. Rev. Biochem. 1976, 22, 111-180.
8. Wedler, F. C.; Denman, R. B. Curr. Top. Cell Regul. 1984, 24, 153-169.
9. Aschner, M.; Erikson, K. M.; Dorman, D. C. Crit. Rev. Toxicol. 2005, 35, 1-32.
10. NMR Biomed. 2004, 17, 527-634. The issue No. 8 is dedicated to the Manganese Enhanced Magnetic Resonance Imaging (MEMRI).
11. Bock, N. A.; Silva, A. C. Future Neurol. 2007, 2, 297-305.
12. Cersosimo, M. G.; Koller, W. C. NeuroToxicology 2006, 27, 340-346.
13. Gallez, B.; Baudelet, C.; Geurts, M. Magn. Reson. Imag. 1998, 16, 1211-1215.
14. Drahoš B.; Kubicìěk, V.; Bonnet, C. S.; Hermann, P.; Lukeš I.; Toìth, Eì. Dalton Trans. 2011, 40, 1945-1951.
15. Rocklage, S. M.; Cacheris, W. P.; Quay, S. C.; Hahn, F. E.; Raymond, K. N. Inorg. Chem. 1989, 28, 477-485.
16. Koenig, S. H.; Baglin, C.; Brown, R. D.; Brewer, C. F. Magn. Reson. Med. 1984, 1, 496-501.
17. Troughton, J. S.; Greenfield, M. T.; Greenwood, J. M.; Dumas, S.; Wiethoff, A. J.; Wang, J.; Spiller, M.; McMurry, T. J.; Caravan, P. Inorg. Chem. 2004, 43, 6313-6323.
18. Aime, S.; Anelli, P. L.; Botta, M.; Brocchetta, M.; Canton, S.; Fedeli, F.; Gianolio, E.; Terreno, E. J. Biol. Inorg. Chem. 2002, 7, 58-67.
19. Maigut, J.; Meier, R.; Zahl, A.; van Eldik, R. Inorg. Chem. 2008, 47, 5702-5719.
20. Bertin, A.; Steibel, J.; Michou-Gallani, A.-I.; Gallani, J.-L.; Felder-Flesch, D. Bioconjugate Chem. 2009, 20, 760-767.
21. Geraldes, C. F. G. C.; Sherry, A. D.; Brown, R. D.; Koenig, S. H. Magn. Reson. Med. 1986, 3, 242-250.
22. Balogh, E.; He, Z.; Hsieh, W.; Liu, S.; Toìth, Eì. Inorg. Chem. 2007, 46, 238-250.
23. Bianchi, A.; Calabi, L.; Giorgi, C.; Losi, P.; Mariani, P.; Palano, D.; Paoli, P.; Rossi, P.; Valtancoli, B. J. Chem. Soc., Dalton Trans. 2001, 917-922.
24. Wang, S.; Westmoreland, T. D. Inorg. Chem. 2009, 48, 719-728.
25. Tei, L.; Gugliotta, G.; Fekete, M.; Kaìlmaìn, F. K.; Botta, M. Dalton Trans. 2011, 40, 2025-2032.
26. (a) Newton, J. E.; Jackels, F. C. J. Coord. Chem. 1988, 19, 265-277.
27. (b) Jackels, S. C.; Durham, M. M.; Newton, J. E.; Henninger, T. C. Inorg. Chem. 1992, 31, 234-239.
28. Drahoš, B.; Kotek, J.; Hermann, P.; Lukeš, I.; Toìth, Eì. Inorg. Chem. 2010, 49, 3224-3238.
29. Drahoš, B.; Pniok, M.; Kotek, J.; Hermann, P.; Lukeš, I.; Toìth, E. Dalton Trans. 2011, 40, 10131-10146.
30. Perrin, D. D. Purification of Laboratory Chemicals; Pergamon Press: Oxford, U.K., 1988.
31. Gali, H.; Prabhu, K. R.; Karra, S. R.; Katti, K. V. J. Org. Chem. 2000, 65, 676-680.
32. Bieber, L. W.; de Arauìjo, M. C. F. Molecules 2002, 7, 902-906.
33. Aime, S.; Botta, M.; Frullano, L.; Geninatti Crich, S.; Giovenzana, G.; Pagliarin, R.; Palmisano, G.; Sirtori, F. R.; Sisti, M. J. Med. Chem. 2000, 43, 4017-4024.
34. Siaugue, J. M.; Segat-Dioury, F.; Sylvestre, I.; Favre-Reìguillon, A.; Foos, J.; Madic, C.; Guy, A. Tetrahedron 2001, 57, 4713-4718.
35. Baker, W.; Buggle, K. M.; McOmie, J. F. W.; Watkins, D. A. M. J. Chem. Soc. 1958, 3594-3603.
36. Dioury, F.; Ferroud, C.; Guya, A.; Port, M. Tetrahedron 2009, 65, 7573-7579.
37. (a) Otwinovski, Z.; Minor, W. HKL Denzo and Scalepack Program Package; Nonius BV: Delft, The Netherlands, 1997
38. (b) Otwinovski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326.
39. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435-435.
40. Sheldrick, G. M. SHELXL97, A Computer Program for Refinement of Crystal Structures; University of Göttingen, Göttingen, Germany, 1997.
41. Kyìvala, M.; Lukeš, I. Proceedings of the International Conference on Chemometrics '95, Pardubice, Czech Republic, 1995; p 63.
42. Kyìvala, M.; Lubal, P.; Lukeš, I. IX. Spanish-Italian and Mediterranean Congress on Thermodynamics of Metal Complexes (SIMEC 98), Girona, Spain, 1998. The full version of the OPIUM program is available (free of charge) on http://web.natur.cuni.cz/~kyvala/opium.html.
43. (a) Martell, A. E.; Smith, R. M. Critical Stability Constants; Plenum Press: New York, 1974-1989; Vols. 1-6.
44. (b) NIST Standard Reference Database 46 (Critically Selected Stability Constants of Metal Complexes), Version 7.0, 2003.
45. (c) Baes, C. F., Jr.; Mesmer, R. E. The Hydrolysis of Cations; Wiley: New York, 1976.
46. (a) Taìborskyì, P.; Lubal, P.; Havel, J.; Kotek, J.; Rudovskyì, J.; Hermann, P.; Lukeš, I. Collect. Czech. Chem. Commun. 2005, 70, 1909-1942.
47. (b) Försterovaì, M.; Svobodovaì, I.; Lubal, P.; Taìborskyì, P.; Kotek, J.; Hermann, P.; Lukeš, I. Dalton Trans. 2007, 535-549.
48. Raiford, D. S.; Fisk, C. L.; Becker, E. D. Anal. Chem. 1979, 51, 2050-2051.
49. Vold, R. L.; Waugh, J. S.; Klein, M. P.; Phelps, D. E. J. Chem. Phys. 1968, 48, 3831-3832.
50. Meiboom, S.; Gill, D. Rev. Sci. Instrum. 1958, 29, 688-691.
51. Hugi, A. D.; Helm, L.; Merbach, A. E. Helv. Chim. Acta 1985, 68, 508-521.
52. Cusanelli, A.; Nicula-Dadci, L.; Frey, U.; Merbach, A. E. Inorg. Chem. 1997, 36, 2211-2217.
53. Ducommun, Y.; Earl, W. L.; Merbach, A. E. Inorg. Chem. 1979, 18, 2754-2759.
54. Siaugue, J. M.; Segat-Dioury, F.; Sylvestre, I.; Favre-Reìguillon, A.; Foos, J.; Madic, C.; Guy, A. Tetrahedron 2001, 57, 4713-4718.
55. Lukeš I.; Kotek, J.; Vojt-sìěk, P.; Hermann, P. Coord. Chem. Rev. 2001, 216-217, 287-312.
56. Costa, J.; Delgado, R. Inorg. Chem. 1993, 32, 5257-5265.
57. Kim, W. D.; Hrncir, D. C.; Kiefer, G. E.; Sherry, A. D. Inorg. Chem. 1995, 34, 2225-2232.
58. Delgado, R.; Quintino, S.; Teixeira, M.; Zhang, A. J. Chem. Soc., Dalton Trans. 1997, 55-63.
59. Geraldes, C. F. G. C.; Sherry, A. D.; Cacheris, W. P. Inorg. Chem. 1989, 28, 3336-3341.
60. Geraldes, C. F. G. C.; Sherry, A. D.; Marques, M. P. M.; Alpoim, M. C.; Cortes, S. J. Chem. Soc., Perkin Trans. 2 1991, 137-146.
61. Rohovec, J.; Kyvìala, M.; Vojt-sìěk, P.; Hermann, P.; Lukeš I. Eur. J. Inorg. Chem. 2000, 195-203.
62. Huskens, J.; Sherry, A. D. J. Am. Chem. Soc. 1996, 118, 4396-4404.
63. Sarka, L.; Burai, L.; Brücher, E. Chem.-Eur. J. 2000, 6, 719-724.
64. Ducommun, Y.; Newmann, K. E.; Merbach, A. E. Inorg. Chem. 1980, 19, 3696-3703.
65. Dees, A.; Zahl, A.; Puchta, R.; van Eikema Hommes, N. J. R.; Heinemann, F. W.; Ivanovicì-Burmazovicì, I. Inorg. Chem. 2007, 46, 2459-2470.
66. Zetter, M. S.; Grant, M.; Wood, E. J.; Dodgen, H. W.; Hunt, J. P. Inorg. Chem. 1972, 11, 2701-2706.
67. Helm, L.; Merbach, A. E. Chem. Rev. 2005, 105, 1923-1959.
68. Maigut, J.; Meier, R.; Zahl, A.; van Eldik, R. J. Am. Chem. Soc. 2008, 130, 14556-14569.
69. Fukuda, Y.; Hirota, M.; Kon-no, M.; Nakao, A.; Umezawa, K. Inorg. Chim. Acta 2002, 339, 322-326.