Mn2+ complexes of 1-oxa-4,7-diazacyclononane based ligands with acetic, phosphonic and phosphinic acid pendant arms: Stability and relaxation studies

Dalton Transactions

Volumn 40, Issue 39, 2011, Pages 10131-10146

  Drahoŝ, Bohuslav ^a,b   Pniok, Miroslav ^a   Havlíĉková, Jana ^a   Kotek, Jan ^a   Císar̂ová, Ivana ^a   Hermann, Petr ^a   Lukeŝ, Ivan ^a   Tóth, Éva ^b  

^a CHARLES UNIVERSITY   (Czech Republic)

^b CENTRE DE BIOPHYSIQUE MOLÉCULAIRE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACID MOIETY; AIR OXIDATION; COORDINATED WATER; COORDINATION NUMBER; HYDRATION EQUILIBRIA; MACRO-CYCLIC LIGANDS; MACROCYCLICS; NITROGEN ATOM; NMR MEASUREMENTS; NMR TITRATION; PENDANT ARMS; PHOSPHINIC ACID; PHOSPHONIC; POTENTIOMETRIC DATA; POTENTIOMETRY; PROTONATION CONSTANTS; PROTONATION SEQUENCES; RELAXATION PROPERTY; RELAXATION STUDIES; ROTATIONAL DYNAMICS; STABILITY CONSTANTS; TRANSMETALLATION; VARIABLE TEMPERATURE; WATER EXCHANGE;

COMPLEXATION; CRYSTAL STRUCTURE; MANGANESE; MANGANESE COMPOUNDS; METAL IONS; POTENTIOMETERS (ELECTRIC MEASURING INSTRUMENTS); PROTONATION; THERMODYNAMIC STABILITY;

LIGANDS;

ACETIC ACID; COORDINATION COMPOUND; LIGAND; MANGANESE; MANGANESE(II) 1 OXA 4,7 DIAZACYCLONONANE; MANGANESE(II)-1-OXA-4,7-DIAZACYCLONONANE; ORGANOMETALLIC COMPOUND; PHOSPHINIC ACID DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CHEMISTRY; CONFORMATION; KINETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

ACETIC ACID; COORDINATION COMPLEXES; CRYSTALLOGRAPHY, X-RAY; KINETICS; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MANGANESE; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; PHOSPHINIC ACIDS; PHOSPHONIC ACIDS;

EID: 80053374650     PISSN: 14779226     EISSN: 14779234     Source Type: Journal    
DOI: 10.1039/c1dt10543d     Document Type: Article

References (96)

1. E. Terreno D. D. Castelli A. Viale S. Aime Chem. Rev. 2010 110 3019 3042
2. Future Med. Chem., Ed. E. Tóth and S. Pétoud, 2010, 2, pp. 305-531
3. S. Aime D. D. Castelli S. G. Crich E. Gianolio E. Terreno Acc. Chem. Res. 2009 42 822 831
4. MRI in Practice, C. Westbrook and C. Roth, Buckwell Publishing Ltd, Oxford, 2005
5. MRI Basic Principles and Applications, M. A. Brown and R. C. Semelka, John Wiley & Sons, New Jersey, 2010
6. É. Tóth and A. E. Merbach, The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging, John Wiley & Sons, Chichester, 2001
7. P. Caravan J. J. Ellison T. J. McMurry R. B. Lauffer Chem. Rev. 1999 99 2293 2352
8. P. Hermann J. Kotek V. Kubíek I. Luke Dalton Trans. 2008 3027 3047
9. A. D. Sherry P. Caravan R. E. Lenkinski J. Magn. Reson. Imaging 2009 30 1240 1248
10. J. Eisinger R. G. Shulman W. E. Blumberg Nature 1961 192 963 964
11. P. C. Lauterbur Nature 1973 242 190 191
12. Y. S. Kang J. C. Gore I. M. Armitage Magn. Reson. Med. 1984 1 396 409
13. D. W. Christianson Prog. Biophys. Mol. Biol. 1997 67 217 252
14. A. S. Mildvan M. Cohn Biochemistry 1963 338 910 919
15. J. Eisinger F. Fawaz-Estrup R. G. Shulman J. Chem. Phys. 1965 42 43 53
16. S. Aime S. Canton S. G. Crich E. Terreno Magn. Reson. Chem. 2002 40 41 48
17. M. Aschner K. M. Erikson D. C. Dorman Crit. Rev. Toxicol. 2005 35 1 32
18. N. A. Bock A. C. Silva Future Neurol. 2007 2 297 305
19. NMR Biomed., Ed. A. P. Koretsky and A. C. Silva, 2004, 17, pp. 527-634
20. G. L. Wolf, K. R. Burnett, E. J. Goldstein and P. M. Joseph, Magnetic Resonance Annual 1985, H. Kressel, Ed., Raven, New York, 1985, 231-266
21. B. Gallez C. Baudelet M. Geurts Magn. Reson. Imaging 1998 16 1211 1215
22. M. G. Cersosimo W. C. Koller NeuroToxicology 2006 27 340 346
23. S. M. Rocklage W. P. Cacheris S. C. Quay F. E. Hahn K. N. Raymond Inorg. Chem. 1989 28 477 485
24. U. Kettritz J. F. Schlund K. Wilbur L. B. Eisenberg R. C. Semelka Magn. Reson. Imaging 1996 14 1185 1190
25. T. Murakami R. L. Baron M. S. Peterson J. H., III. Oliver P. L. Davis B. S. Confer M. P. Federle Radiology 1996 200 69 77
26. S. H. Koenig C. Baglin R. D., III. Brown C. F. Brewer Magn. Reson. Med. 1984 1 496 501
27. S. Aime P. L. Anelli M. Botta M. Brocchetta S. Canton F. Fedeli E. Gianolio E. Terreno JBIC, J. Biol. Inorg. Chem. 2002 7 58 67
28. J. S. Troughton M. T. Greenfield J. M. Greenwood S. Dumas A. J. Wiethoff J. Wang M. Spiller T. J. McMurry P. Caravan Inorg. Chem. 2004 43 6313 6323
29. J. Maigut R. Meier A. Zahl R. van Eldik Inorg. Chem. 2008 47 5702 5719
30. A. Bertin J. Steibel A. I. Michou-Gallani J. L. Gallani D. Felder-Flesch Bioconjugate Chem. 2009 20 760 767
31. H. A. Tang Y. Sheng R. D. Yang Inorg. Chem. Commun. 2003 6 1213 1216
32. D. W. Zhang Z. Y. Yang S. P. Zhang R. D. Yang Transit. Met. Chem. 2006 31 333 336
33. Y. Huang X. Zhang Q. Zhang X. Dai J. Wu Magn. Reson. Imaging 2011 29 554 560
34. C. F. G. C. Geraldes A. D. Sherry R. D., III. Brown S. H. Koenig Magn. Reson. Med. 1986 3 242 250
35. E. Balogh Z. He W. Hsieh S. Liu É. Tóth Inorg. Chem. 2007 46 238 250
36. M. Tan Z. Ye E.-K. Jeong X. Wu D. L. Parker D.-R. Lu Bioconjugate Chem. 2011 22 931 937
37. A. Bianchi L. Calabi C. Giorgi P. Losi P. Mariani D. Palano P. Paoli P. Rossi B. Valtancoli J. Chem. Soc., Dalton Trans. 2001 917 922
38. S. Wang T. D. Westmoreland Inorg. Chem. 2009 48 719 728
39. M. Tan X. Wu E.-K. Jeong Q. Chen D. L. Parker Z.-R. Lu Mol. Pharmaceutics 2010 7 936 943
40. L. Tei G. Gugliotta M. Fekete F. K. Kálmán M. Botta Dalton Trans. 2011 40 2025 2032
41. J. E. Newton F. C. Jackels J. Coord. Chem. 1988 19 265 277
42. S. C. Jackels M. M. Durham J. E. Newton T. C. Henninger Inorg. Chem. 1992 31 234 239
43. B. Draho J. Kotek P. Hermann I. Luke É. Tóth Inorg. Chem. 2010 49 3224 3238
44. B. Draho V. Kubíek C. S. Bonnet P. Hermann I. Luke É. Tóth Dalton Trans. 2011 40 1945 1951
45. A. Neves W. Walz K. Wieghardt B. Nuber J. Weissl Inorg. Chem. 1988 27 2484 2489
46. M. F. Cabral J. Costa R. Delgado J. J. R. Frausto de Silva M. F. Vilhena Polyhedron 1990 9 2847 2857
47. W. Clegg P. B. Iveson J. C. Lockhart J. Chem. Soc., Dalton Trans. 1992 3291 3298
48. Purification of Laboratory Chemicals, D. D. Perrin, Pergamon Press, Oxford, 1988
49. G. R. Newkome S. Pappalardo V. K. Gupta F. R. Fronczek J. Org. Chem. 1983 48 4848 4851
50. A. Bencini L. Fabbrizzi A. Poggi Inorg. Chem. 1981 20 2544 2549
51. M. Ouchi Y. Inoue T. Kanzaki T. Hakushi J. Org. Chem. 1984 49 1408 1412
52. J. E. Richman T. J. Atkins J. Am. Chem. Soc. 1974 26 2268 2270
53. V. J. Thöm M. S. Shaikjee R. D. Hancock Inorg. Chem. 1986 25 2992 3000
54. J. Notni P. Hermann J. Havlíková J. Kotek V. Kubíek J. Plutnar N. Loktionova P. J. Riss F. Rösch I. Luke Chem. Eur. J. 2010 16 7174 7185
55. V. Kubíek J. Havlíková J. Kotek G. Tircsó P. Hermann É. Tóth I. Luke Inorg. Chem. 2010 49 10960 10969
56. M. Kývala and I. Luke, International Conference Chemometrics '95, Pardubice, Czech Republic, 1995, p. 63
57. M. Kývala, P. Lubal and I. Luke, 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
58. A. E. Martell and R. M. Smith, Critical Stability Constants, Vols. 1-6, Plenum Press, New York, 1974-1989
59. NIST Standard Reference Database 46 (Critically Selected Stability Constants of Metal Complexes), Version 7.0, 2003
60. C. F. Baes, Jr., and R. E. Mesmer, The Hydrolysis of Cations, Wiley, New York, 1976
61. M. Försterová I. Svobodová P. Lubal P. Táborský J. Kotek P. Hermann I. Luke Dalton Trans. 2007 535 549
62. V. Kubíek J. Kotek P. Hermann I. Luke Eur. J. Inorg. Chem. 2007 333 344
63. D. S. Raiford C. L. Fisk E. D. Becker Anal. Chem. 1979 51 2050 2051
64. R. L. Vold J. S. Waugh M. P. Klein D. E. Phelps J. Chem. Phys. 1968 48 3831 3832
65. S. Meiboom D. Gill Rev. Sci. Instrum. 1958 29 688 691
66. A. D. Hugi L. Helm A. E. Merbach Helv. Chim. Acta 1985 68 508 521
67. Z. Otwinowski and W. Minor, HKL Denzo and Scalepack Program Package by Nonius BV, Delft, 1997
68. Z. Otwinowski W. Minor Methods Enzymol. 1997 276 307 326
69. A. Altomare G. Cascarano C. Giacovazzo A. Guagliardi M. C. Burla G. Polidori M. Camalli J. Appl. Cryst. 1994 27 435 435
70. G. M. Sheldrick, SHELXL97. Program for Crystal Structure Refinement from Diffraction Data, University of Göttingen, Göttingen 1997
71. P. Coppens,(1970). Crystallographic Computing, eds, F. R. Ahmed, S. R. Hall, &, C. P. Huber, pp. 255-270, Copenhagen, Munksgaard
72. I. Lázár R. Király Z. Takács J. Coord. Chem. 2000 51 293 304
73. V. Jacques and J. Desreux, Synthesis of MRI Contrast Agents II: Macrocyclic Ligands, in The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging, É. Tóth, and, A. E. Merbach, ed., John Wiley&Sons, Chichester, 2001
74. J. Rohovec P. Vojtíek P. Hermann J. Ludvík I. Luke J. Chem. Soc., Dalton Trans. 2000 141 148
75. K. Senanayake A. L. Thompson J. A. K. Howard M. Botta D. Parker Dalton Trans. 2006 5423 5428
76. P. Vojtíek J. Rohovec Collect. Czech. Chem. Commun. 2006 71 264 278
77. P. Vojtíek J. Rohovec J. Klimentová Eur. J. Inorg. Chem. 2008 3948 3956
78. I. Luke J. Kotek P. Vojtíek P. Hermann Coord. Chem. Rev. 2001 216-217 287 312
79. J. Rohovec I. Luke P. Vojtíek I. Císaová P. Hermann J. Chem. Soc., Dalton Trans. 1996 2685 2691
80. M. Luká M. Kývala P. Hermann I. Luke D. Sanna G. Micera J. Chem. Soc., Dalton Trans. 2001 2850 2857
81. Z. Kotková G. A. Pereira K. Djanashvili J. Kotek J. Rudovský P. Hermann L. V. Elst R. N. Muller C. F. G. C. Geraldes I. Luke J. A. Peters Eur. J. Inorg. Chem. 2009 119 136
82. R. Yang L. J. Zompa Inorg. Chem. 1976 15 1499 1502
83. M. J. Van der Merve J. C. A. Boeyens R. D. Hancock Inorg. Chem. 1985 24 1208 1213
84. C. F. G. C. Geraldes A. D. Sherry W. P. Cacheris Inorg. Chem. 1989 28 3336 3341
85. K. Bazakas I. Luke J. Chem. Soc., Dalton Trans. 1995 1133 1137
86. J. Huskens A. D. Sherry J. Am. Chem. Soc. 1996 118 4396 4404
87. Z. Kovacs A. D. Sherry Tetrahedron Lett. 1995 36 9269 9272
88. M. I. Kabachnik T. Ya. Medved Yu. M. Polikarpov M. P. Pasechnik Izv. Akad. Nauk. SSSR, Ser. Khim. 1984 835 843
89. Y. Ducommun K. E. Newmann A. E. Merbach Inorg. Chem. 1980 19 3696 3703
90. I. Bertini F. Briganti Z. Xia C. J. Luchinat J. Magn. Reson., Ser. A 1993 101 198 201
91. S. Aime M. Botta E. Terreno P. L. Anelli F. Uggeri Magn. Reson. Med. 1993 30 583 591
92. F. Avecilla J. A. Peters C. F. G. C. Geraldes Eur. J. Inorg. Chem. 2003 23 4179 4186
93. M. S. Zetter M. Grant E. J. Wood H. W. Dodgen J. P. Hunt Inorg. Chem. 1972 11 2701 2706
94. L. Helm A. E. Merbach Chem. Rev. 2005 105 1923 1959
95. S. Aime M. Botta J. I. Bruce V. Mainero D. Parker E. Terreno Chem. Commun. 2001 115 116
96. J. I. Bruce R. S. Dickins L. J. Govenlock T. Gunnlaugsson S. Lopinski M. P. Lowe D. Parker R. D. Peacock J. J. B. Perry S. Aime M. Botta J. Am. Chem. Soc. 2000 122 9674 9684