Computational NMR spectroscopy of transition-metal/nitroimidazole complexes: Theoretical investigation of potential radiosensitizers

Helvetica Chimica Acta

Volumn 88, Issue 10, 2005, Pages 2705-2721

  Ramalho, Teodorico C ^a   Bühl, Michael ^b   Figueroa Villar, José Daniel ^a   Bicca De Alencastro, Ricardo ^c  

^a MILITARY INSTITUTE OF ENGINEERING   (Brazil)

^b MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^c FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; CONTINUUM MECHANICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

CONTINUUM MODELS; SPIN-ORBIT (SO) COUPLING; TRANSITION METAL COMPLEXES;

ORGANOMETALLICS;

1,2 DIMETHYL 5 NITRO 1H IMIDAZOLE; IMIDAZOLE DERIVATIVE; NITROIMIDAZOLE DERIVATIVE; PLUTONIUM; RADIOSENSITIZING AGENT; RHENIUM COMPLEX; RUTHENIUM COMPLEX; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ACCELERATION; ARTICLE; GEOMETRY; NUCLEAR MAGNETIC RESONANCE IMAGING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PREDICTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RADIOSENSITIZATION; REPRODUCIBILITY; SOLVATION; THEORETICAL STUDY;

EID: 27644533266     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200590210     Document Type: Article

References (105)

1. R. Benn, A. Rufinska, Angew. Chem., Int. Ed. 1986, 25, 861.
2. P. S. Pregosin, 'Transitional Metal Nuclear Magnetic Resonance', Elsevier Amsterdam, 1991.
3. W. von Philipsborn, Chem. Soc. Rev. 1999, 28, 95.
4. 'Calculation of NMR and EPR Parameters. Theory and Applications', Eds. M. Kaupp, M. Bühl, V. G. Malkin, Wiley-VCH, Weinheim, 2004.
5. T. Helgaker, M. Jszunski, K. Ruud, Chem. Rev. 1999, 99, 293.
6. M. Bühl, F. T. Mauschick, F. Terstegen, B. Wrackmeyer, Angew. Chem., Int. Ed. 2002, 41, 2312.
7. J. M. Brown, B. G. Wouters, Cancer Res. 1999, 59, 1391.
8. H. Horis, H. Nagasawa, in 'Advances in Environmental Science and Technology, Vol. 28: Environmental Oxidants', John Wiley & Sons, New York, 1994.
9. H. Hori, C. Z. Jin, M. Kiyono, S. Kasai, M. Shimamura, S. Inayama, Bioorg. Med. Chem. 1997, 5, 591.
10. J. D. Chapman, L. R. Coia, C. C. Stobe, E. L. Engelhart, M. C. Fenning, R. F. Schneider, Br. J. Cancer 1996, 74, S204.
11. B. P. Espósito, R. Najjar, Coord. Chem. Rev. 2002, 232, 137.
12. A. Nunn, K. Linder, H. W. Strauss, Eur. J. Nucl. Med. 1995, 22, 265.
13. I. Ségalas, A. L. Beauchamp, Can. J. Chem. 1992, 70, 943.
14. N. Farrell, Transition Metal Complexes as Drugs and Chemotherapeutic Agents', Kluwer Academic, Dordrecht, 1989, Chapt. 8, p. 183.
15. H. Kusuoka, K. Hashimoto, K. Fukuchi, T. Nishimura, J. Nucl. Med. 1994, 35, 1371.
16. R. B. Lauffer, Chem. Rev. 1987, 87, 901.
17. C. J. Anderson, M. J. Welch, Chem. Rev. 1999, 99, 2219.
18. C. L. McCoy, D. J. O. McIntyre, S. P. Robinson, E. O. Aboagye, J. R. Griffiths, Br. J. Cancer 1996, 74, S226.
19. R. C. Urtasun, J. D. Chapman, J. A. Raleigh, A. J. Franko, C. J. Koch, Int. J. Rad. Oncol. 1986, 12, 1263.
20. H. Ali, J. E. van Lier, Chem. Rev. 1999, 99, 2379.
21. T. C. Ramalho, M. A. La-Scalea, R. B. de Alencastro, J. D. Figueroa-Villar, Biophys. Chem. 2004, 110, 267.
22. T. C. Ramalho, E. F. F. Cunha, R. B. de Alencastro, J. Theor. Comput. Chem. 2004, 3, 1.
23. T. C. Ramalho, E. F. F. Cunha, R. B. de Alencastro, J. Phys.: Condens. Mater. 2004, 16, 6159.
24. T. C. Ramalho, M. Bühl, Magn. Reson. Chem. 2005, 43, 139.
25. T. C. Ramalho, J. D. Figueroa-Villar, T. L. C. Martins, Magn. Reson. Chem. 2003, 41, 983.
26. K. Coutinho, S. Canuto, Adv. Quantum Chem. 1997, 28, 89.
27. K. Coutinho, S. Canuto, J. Chem. Phys. 2000, 113, 9132.
28. K. Coutinho, S. Canuto, M C. Zerner, J. Chem. Phys. 2000, 112, 9874.
29. K. Coutinho, S. Canuto, J. Mol. Struct. THEOCHEM 2003, 632, 235.
30. M. Bühl, in 'Calculation of NMR and EPR Parameters. Theory and Applications', Eds. M. Kaupp, M. Bühl, V. G. Malkin, Wiley-VCH, Weinheim, 2004, p. 421.
31. M. Bühl, S. Gaemers, C. J. Elsevier, Chem.-Eur. J. 2000, 6, 3272.
32. T. Ziegler, Chem. Rev. 1991, 91, 651.
33. W. Koch, M. C. Holthausen, 'A Chemist's Guide to Density Functional Theory', Wiley-VCH, Weinheim, 2000.
34. K. W. Zilm, J. C. Duchamp, in 'Nuclear Magnetic Shieldings and Molecular Structure', Ed. J. A. Tossel, NATO ASI Series C386, Kluwer, Dordrecht, 1993, pp. 315.
35. G. Schreckenbach, S. K. Wolff, T. Ziegler, J. Phys. Chem. A 2000, 104, 8244.
36. D. B. Chesnut, in 'Reviews in Computational Chemistry', Eds. K. B. Libkowitz, D. B. Boyd, VCH, New York, 1996, Vol. 8, p. 245.
37. D. B. Chesnut, in 'Annual Reports on NMR Spectroscopy', Ed. G. A. Webb, Academic Press, New York, 1994, Vol. 29, p. 71.
38. J. Autschbach in 'Calculation of NMR and ESR Parameters. Theory and Applications' Eds. M. Kaupp, M. Bühl, V. G. Malkin, Wiley-VCH, Weinheim, 2004, p. 227;
39. J. Autschbach, T. Ziegler, in 'Calculation of NMR and ESR Parameters. Theory and Applications' Eds. M. Kaupp, M. Bühl, V. G. Malkin, Wiley-VCH, Weinheim, 2004, p. 249;
40. J. Autschbach, Structure Bonding 2004, 112, 1.
41. M. Bühl, M. Kaupp, V. G. Malkin, O. L. Malkina, J. Comput. Chem. 1999, 20, 91.
42. a) A. D. Becke, Phys. Rev. A. 1988, 38, 3098;
43. b) J. P. Perdew, Phys. Rev. B 1986, 33, 8822;
44. c) J. P. Perdew, Phys. Rev. B 1986, 34, 7406.
45. P. Fuentealba, H. Preuss, H. Stoll, L. v. Szentpaly, Chem. Phys. Lett. 1989, 89, 418.
46. M. Kaupp, P. v. R. Schleyer, H. Stoll, H. Preuss, J. Chem. Phys. 1991, 94, 1360.
47. F. D. Rochon, R. Melanson, N. Farrell, Acta Crystallogr., Sect. C 1993, 49, 1703.
48. C. Anderson, A. L. Beauchamp, Can. J. Chem. 1995, 73, 471.
49. N. Galvan-Tejada, S. Bernes, S. E. Castillo-Blum, H. Nöth, R. Vicente, N. Barba-Behrens, J. Inorg. Biochem. 2002, 91, 339.
50. T. M. Dyson, E. C. Morrison, D. A. Tochter, L. D. Dale, D. I. Edwards, Inorg. Chim. Acta 1990, 169, 127.
51. J. R. Bales, C. J. Coulson, D. W. Gilmour, M. A. Mazid, S. Neidle, R. Kuroda, B. J. Peart, C. A. Ramsden, P. J. Sadler, J. Chem. Soc., Chem. Commun. 1985, 432.
52. R. Ditchfield, Mol. Phys. 1974, 27, 789;
53. K. Wolinski, J. F. Hinton, P. Pulay, J. Am. Chem. Soc. 1990, 112, 8251;
54. J. R. Cheeseman, G. W. Trucks, T. A. Keith, M. J. Frisch, J. Chem. Phys. 1996, 104, 5497.
55. A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
56. W. Kutzelnigg, U. Fleischer, M. Schindler, 'NMR Basic Principles and Progress', Springer-Verlag, Berlin, 1990, Vol. 23, p. 165.
57. S. Huzinaga, M. Klobukowski, J. Mol. Struct. 1988, 167, 1.
58. T. M. Cances, B. Mennucci, J. Tomasi, J. Chem. Phys. 1997, 107, 3032.
59. V. Barone, M. Cossi, J. Tomasi, J. Comput. Chem. 1998, 19, 404.
60. M. Cossi, V. Barone, B. Mennucci, J. Tomasi, Chem. Phys. Lett. 1998, 286, 253.
61. M. Cossi, G. Scalmani, N. Rega, V. Barone, J. Chem. Phys 2002, 117, 43.
62. M. Orozco, F. J. Luque, Chem. Rev. 2000, 100, 4187.
63. M. Cossi, O. Crescenzi, J. Chem. Phys. 2003, 118, 8863.
64. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Cui Q. K. Morokuma, P. Salvador, J. J. Dannenberg, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian Inc., Pittsburgh PA, 2003.
65. E. J. Baerends, D. E. Ellis, P. Ros, Chem. Phys. 1973, 2, 41.
66. G. te Velde, E. J. Baerends, J. Comput. Phys. 1992, 99, 84.
67. E. J. Baerends, P. M. Boerrigter, L. Cavallo, L. Deng, R. M. Dickson, D. E. Ellis, L. Fan, T. H. Fischer, C. Fonseca Guerra, S. J. A. van Gisbergen, J. A. Groeneveld, O. V. Gritsenko, F. E. Harris, P. van den Hoek, H. Jacobsen, G. van Kessel, F. Koostra, E. van Lenthe, P. V. Osinga, P. H. T. Philipsen, D. Post, C. C. Pye, W. Ravenek, P. Ros, P. R. T. Schipper, G. Schreckenbach, J. G. Snijders, M. Sola, D. Swerhone, G. te Velde, P. Vernooijs, L. Versluis, O. Visser, E. van Wezenbeek, G. Wiesenekker, S. K. Wolff, T. K. Woo, T. Ziegler, ADF 1999, Theoretical Chemistry, Vrije Universiteit, Amsterdam, The Netherlands, 1999.
68. S. K. Wolff, T. Ziegler, E. van Lenthe, E. J. Baerends, J. Chem. Phys. 1999, 110, 7689.
69. E. van Lenthe, R. van Leeuwen, E. J. Baerends, J. G. Snijders, Int. J. Quantum Chem. 1996, 57, 281.
70. R. R. Ernst, G. Bodenhausen, 'Principles of Nuclear Magnetic Resonance in One and Two Dimensions', Clarendon Press, Oxford, UK, 1987;
71. G. E. Martin, A. S. Zektzer, 'Two-Dimensional NMR Methods for Establishing Molecular Connectivity', Wiley-VCH, New York, 1988.
72. B. C. Chen, W. von Philipsborn, K. Nagarajan, Helv. Chim. Acta 1983, 66, 1537.
73. F. M. Macdonald, P. J. Sadler, Magn. Reson. Chem. 1991, 29, S52.
74. T. G. Appleton, J. R. Hall, S. F. Ralph, Inorg. Chem. 1985, 24, 4685.
75. R. W. Dykstra, A. M. Harrison, J. Magn. Reson. 1982, 46, 338;
76. C. Brevard, P. Granger, Inorg. Chem. 1983, 22, 532.
77. M. Bühl, Chem. Phys. Lett. 1997, 267, 251.
78. S. Gaemers, J. van Slageren, C. M. O'Connor, J. G. Vos, R. Hage, C. J. Elsevier, Organometallics 1999, 18, 5238.
79. M. A. O. Volland, P. Hofmann, Helv. Chim. Acta 2001, 84, 3456.
80. M. Bühl, M. Hakansson, A. H. Mahmoudkhani, L. Öhrström, Organometallics 2000, 19, 5589.
81. P. W. N. M. Van Leeuwen, C. Claver, 'Rhodium Catalyzed Hydroformylation', Kluwer Academic, Dordrecht, 2000;
82. R. S. Dickson, 'Homogeneous Catalysis with Compounds of Rhodium and Iridium (Catalysis by Metal Complexes)', Vol. 8, Reidel, Dordrecht, 1985.
83. P. Tsiveriotis, N. Hadjiliadis, Coord. Chem. Rev. 1999, 192, 171.
84. S. J. Lippard, J. M. Berg, 'Principles of Bioinorganic Chemistry', University Science Books, Mill Valley, CA, 1994.
85. G. J. Martin, M. L. Martin, J.-P. Gouesnard, 'NMR Basic Principles and Progress', Vol. 18, Eds. P. Diehl, E. Fluck, R. Kosfeld, Springer-Verlag, Berlin, 1981.
86. M. Witanowski, L. Stefaniak, G. A. Webb, Ann. Rep. NMR Spectrosc. 1992, 25, 1.
87. T. M. Gilbert, T. Ziegler, J. Phys. Chem. A 1999, 103, 7535.
88. E. B. Boyar, S. D. Robinson, J. Chem. Soc., Dalton Trans. 1985, 629.
89. D. Magieram, W. Baumann, I. S. Podkorytov, J. Omelanczuk, H. Duddek, Eur. J. Inorg. Chem. 2002, 3253.
90. G. G. Christoph, J. Halpern, G. P. Khare, Y. B. Koh, C. Romanoswski, Inorg. Chem. 1981, 20, 3029.
91. M. Bühl, Chem.-Eur. J. 1999, 5, 3515.
92. C. Anderson, A. L. Beauchamp, Inorg. Chem. 1995, 34, 6065;
93. I. R. Baird, S. J. Rettig, BvR. James, K. A. Skov, Can. J. Chem. 1998, 76, 1379.
94. C. Anderson, A. L. Beauchamp, Inorg. Chim. Acta 1995, 233, 33.
95. M. Bühl, P. Imhof, M. Repisky, ChemPhysChem 2004, 5, 410.
96. S. Grigoleit, M. Bühl, Chem.-Eur. J. 2004, 10, 5541.
97. R. Cammi, B. Mennucci, J. Tomasi, J. Chem. Phys. 1999, 110, 7627.
98. K. V. Mikkelsen, K. Ruud, T. Helgaker, J. Comput. Chem. 1999, 20, 1281.
99. M. Kaupp, V. G. Malkin, O. L. Malkina, D. R. Salahub, Chem. Phys. Lett. 1995, 235, 382.
100. M. Kaupp, V. G. Malkin, O. L. Malkina, D. R. Salahub, J. Am. Chem. Soc. 1995, 117, 1851.
101. M. Kaupp, O. L. Malkina, V. G. Malkin, P. Pyykkö, Eur. J. Chem. 1998, 4, 118.
102. G. Schreckenbach, S. K. Wolff, T. Ziegler, J. Phys. Chem. A 2000, 104, 8244.
103. J. Autschbach, C. D. Igna, T. Ziegler, J. Am. Chem. Soc. 2003, 125, 1028.
104. A. Bagno, M. Bonchio, Magn. Reson. Chem. 2004, 42, S79.
105. L. Orian, A. Bisello, S. Santi, Chem.-Eur. J. 2004, 10, 4029.