Probing NMR parameters, structure and dynamics of 5-nitroimidazole derivatives. Density functional study of prototypical radiosensitizers

Magnetic Resonance in Chemistry

Volumn 43, Issue 2, 2005, Pages 139-146

  Ramalho, Teodorico C ^a   Bühl, Michael ^b  

^a MILITARY INSTITUTE OF ENGINEERING   (Brazil)

^b MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

15N NMR; Molecular dynamics simulations; NMR; Radiosensitizers; Solvent effects; Spin spin coupling constants

Indexed keywords

CHEMICAL SHIFT; CONTINUUM MECHANICS; DENSITY FUNCTIONAL THEORY; MOLECULES; SOLVENTS; SPIN DYNAMICS;

15N NMR; DYNAMICS SIMULATION; MOLECULAR DYNAMIC SIMULATION; NITROIMIDAZOLES; NMR STRUCTURES; PARAMETER DYNAMICS; POLARIZABLE CONTINUUM MODEL; RADIOSENSITIZERS; SOLVENT EFFECTS; SPIN-SPIN COUPLING CONSTANTS;

MOLECULAR DYNAMICS;

4 NITROIMIDAZOLE; METRONIDAZOLE; NIMORAZOLE; RADIOSENSITIZING AGENT; SECNIDAZOLE; SOLVENT; TINIDAZOLE; 4-NITROIMIDAZOLE; NITROIMIDAZOLE DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; CALCULATION; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; GEOMETRY; MATHEMATICAL COMPUTING; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; POLARIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SOLVATION; CHEMISTRY; CONFORMATION; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NITROIMIDAZOLES; RADIATION-SENSITIZING AGENTS;

EID: 15244360338     PISSN: 07491581     EISSN: None     Source Type: Journal    
DOI: 10.1002/mrc.1514     Document Type: Article

References (74)

1. Brown JM. J. Natl. Cancer Inst. 1991; 83: 178.
2. Hatherill JR. Eat to Beat Cancer. A Research Scientist Explains How to Avoid up to 90% of All Cancers. Renaissance Books, 1998.
3. Kasai S, Nagasawa H, Yamashita M. Biorg. Med. Chem. 2001; 9: 453.
4. Teicher BA. Cancer Metastasis Rev. 1994; 13: 139.
5. Tomida A, Tsuruo T. Anti-Cancer Drug. Des. 1999; 14: 169.
6. Brown JM, Wouters BG. Cancer Res. 1999; 59: 1391.
7. Horis H, Nagasawa H. In Advances in Environmental Science and Technology. Vol. 28: Environmental Oxidants. Wiley: New York, 1994, p 62.
8. Viodé C, Bettache N. Biochem. Pharmacol. 1999; 57: 549.
9. Hori H, Jin CZ, Kiyono M, Kasai S, Shimamur M, Inayama S. Biorg. Med. Chem. 1997; 5: 591.
10. Chapman JD, Coia LR, Stobe CC, Engelhart EL, Fenning MC, Schneider RF. Br. J. Cancer 1996; 74: S204.
11. Ames AR, Ryan MD, Kovaic P. Life Sci. 1987; 41: 1895.
12. Ramalho TC, La-Scalea MA, Alencastro RB, Figueroa-Villar JD. Biophys. Chem. 2004; 110: 267.
13. Ramalho TC, Cunha EFF, Alencastro RB. J. Theor. Comput. Chem. 2004; 3: 1.
14. Ramalho TC, Cunha EFF, Alencastro RB. J. Phys.: Condens. Matter 2004; 16: 6159.
15. Anderson CJ, Welch MJ. Chem. Rev. 1999; 99: 2219.
16. McCoy CL, McIntyre DJO, Robinson SP, Aboagye EO, Griffiths JR. Br. Cancer 1996; 74: S226.
17. Zilm KW, Duchamp JC. In Nuclear Magnetic Shieldings and Molecular Structure, Tossel JA (ed). NATO ASI Series C386. Kluwer: Dordrecht, 1993, p 315.
18. Kaupp M, Bühl M, Malkin VG (eds). Calculation of NMR and ESR Parameters. Theory and Applications. Wiley-VCH: Weinheim, 2004.
19. (a) Bühl M, Kaupp M, Malkina OL, Malkin VG. J. Comput. Chem. 1999; 20: 91;
20. (b) Bühl M. Theor. Chem. Acc. 2002; 107: 336.
21. Orozco M, Luque FJ, Chem. Rev. 2000; 100: 4187.
22. Stilinger FH, Rahman A. J. Chem. Phys. 1974; 74: 3336.
23. Jorgensen WL, Chandrasekhar J, Madura JD, Impey RW, Klein ML. J. Chem. Phys. 1983; 79: 926.
24. Munronrana ML, Sklenar V. J. Am. Chem. Soc. 2003; 125: 3649.
25. Grant DM, Harris RK (eds). Encyclopedia of Nuclear Magnetic Resonance, vols 1-8. Wiley: Chichester, 1996.
26. Torrent M, Mansour D, Morokuma K. J. Phys. Chem. A 2001; 105: 4546.
27. Helgaker T, Jszunski M, Ruud K. Chem. Rev. 1999; 99: 293.
28. Helgaker T, Pecul M. In Calculation of NMR and ESR Parameters. Theory and Applications, Kaupp M, Bühl M, Malkin VG (eds). Wiley-VCH: Weinheim, 2004; 101.
29. (a) Ernst RR, Bodenhausen G. Principles of Nuclear Magnetic Resonance in One and Two Dimensions, Clarendon Press: Oxford, 1987;
30. (b) Martin GE, Zektzer AS. Two-Dimensional NMR Methods for Establishing Molecular Connectivity. Wiley-VCH: New York, 1988.
31. (a) Becke AD. Phys. Rev. A 1988; 38: 3098;
32. (b) Perdew JP. Phys. Rev B 1986; 33: 8822;
33. (c) Perdew JP. Phys. Rev. B 1986; 34: 7406.
34. Cances TM, Mennucci B, Tomasi J. J. Chem. Phys. 1997; 107: 3032.
35. Barone V, Cossi M, Tomasi J. J. Comput. Chem. 1998; 19: 404.
36. Cossi M, Barone V, Mennucci B, Tomasi J. Chem. Phys. Lett. 1998; 286: 253.
37. Cossi M, Scalmani G, Rega N, Barone V. J. Chem. Phys. 2002; 117: 43.
38. Calva-Tejada N, Bernes S, Castillo-Blum SE, Nöth H, Vicente R, Barba-Behren N. J. Inorg. Biochem. 2002; 91: 339.
39. Car R, Parrinello M. Phys. Rev. Lett. 1985; 55: 4487.
40. Dauber-Osgutorpe P, Roberts VA, Osgutorpe DG. Proteins 1988; 4: 31.
41. Allen MP, Tildesley DJ. Computer Simulation of Liquids. Oxford University Press: Oxford, 1987.
42. Hutter J, Alavi A. Deutsch, Bernasconi M, Goedecker S, Marx D, Tuckerman M, Parrinello M. CPMD Version 3.1a. Max-Planck-Institut für Festkörperforshung: Stuttgart and IBM Research Laboratory: Zürich, 1995-99.
43. Troullier, Martins JL. Phys. Rev. B 1991; 43: 1993.
44. Kleinman L, Bylander DM. Phys. Rev. Lett. 1982; 48: 1425.
45. (a) Ditchfield R. Mol. Phys. 1974; 27: 789;
46. (b) Wolinski K, Hinton JF, Pulay P. J. Am. Chem. Soc. 1990; 112: 8251;
47. (c) Cheeseman JR, Trucks GW, Keith TA, Frisch MJ. J. Chem. Phys. 1996; 104: 5497.
48. (a) Becke AD. J. Chem. Phys. 1993; 98: 5648;
49. (b) Lee C, Yang W, Parr RG. Phys. Rev. B 1998; 37: 785.
50. Kutzelnigg W, Fleischer U, Schindler M. In NMR Basic Principles and Progress, vol. 23 Springer: Berlin, 1990; 165.
51. Barone V. In Recent Advances in Density Functional Methods, Part I, Chong DP (ed). World Scientific: Singapore, 1996, p 287.
52. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA Jr, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Salvador P, Dannenberg JJ, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA. Gaussian 03. Gaussian: Pittsburgh, PA, 2003.
53. Chen BC, von Philipsborn W. Helv. Chim. Acta 1983; 66: 1537.
54. Mckillop A, Wright DE, Podmore LML, Chambers RK. Tetrahedron 1983; 22: 3797.
55. Silvestri R, Artico M, Marceddu ST, DeMontis F, LaColla P. Bioorg. Med. Chem. Lett. 2000; 10: 253.
56. Cossi M, Crescenzi O. Theor. Chem. Acc. 2004; 111: 162.
57. Pivnenko NS, Drushlyak TG, Kutulya LA, Vashchenko VV. Doroshenko AO, Goodby JW. Magn. Reson. Chem. 2002; 40: 566.
58. Ramalho TC, Martins TLC, Figueroa-Villar JD. Magn. Reson. Chem. 2003; 41: 981.
59. Parrinello M, Sebastiani D. J. Phys. Chem. A 2001; 105: 1951.
60. Cossi M, Crescenzi O. J. Chem. Phys. 2003; 19: 8863.
61. Cremer D, Olsson L, Reichel F, Kraka E. Isr. J. Chem. 1993; 33: 369.
62. Mennucci B, Martínez JM, Tomasi J. J. Phys. Chem. A 2001; 105: 7287.
63. Cossi M, Scalmani G, Rega N, Barone V. J. Chem. Phys. 2002; 117: 43.
64. Cossi M, Crescenzi O. Theor. Chem. Acc. 2004; 111: 162.
65. Malkin VG, Malkina OL, Steinebrunner G, Huber H. Chem. Eur. J. 1996; 2: 452.
66. (a) Bühl M, Parrinello M. Chem. Eur. J. 2001; 7: 4487;
67. (b) Bühl M, Mauschick FT, Terstegen F, Wrackmeyer B. Angew. Chem. Int. Ed. 2002; 4: 2312;
68. (c) Bühl M, Mauschick FT. Phys. Chem. Chem. Phys. 2002; 4: 5508;
69. (d) Bühl M, Schurhammer R, Imhof P, J. Am. Chem. Soc. 2004; 126: 3310.
70. Schwegler E, Galli G, Gygi F. Phys. Rev. Lett. 2000; 84: 2429.
71. Bühl M, Steinke T, Schleyer PvR, Boese R. Angew. Chem. Int. Ed. Engl. 1991; 30: 1160.
72. Cossi M, Crescenzi O. J. Chem. Phys. 2003; 118: 8863.
73. Barfield M, Chakrabarty B. Chem. Rev. 1969; 69: 757.
74. Barfield M. Magn. Reson. Chem. 2003; 41: 344.