Theoretical evaluation of adiabatic and vertical electron affinity of some radiosensitizers in solution using FEP, ab initio and DFT methods

Biophysical Chemistry

Volumn 110, Issue 3, 2004, Pages 267-279

  Ramalho, Teodorico C ^a   De Alencastro, Ricardo Bicca ^b   La Scalea, Mauro Aquiles ^c   Figueroa Villar, José Daniel ^a  

^a MILITARY INSTITUTE OF ENGINEERING   (Brazil)

^b Lab 609   (Brazil)

^c UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Electron affinity; HF and DFT calculations; Radiosensitizers

Indexed keywords

CARBON TETRACHLORIDE; NITROFURAN DERIVATIVE; NITROIMIDAZOLE DERIVATIVE; RADIOSENSITIZING AGENT; SOLVENT; WATER;

AB INITIO CALCULATION; ARTICLE; BINDING AFFINITY; DENSITY FUNCTIONAL THEORY; ELECTRON; ENERGY; FINITE ELEMENT ANALYSIS; POLARIZATION; PRIORITY JOURNAL; THEORY; THERMODYNAMICS;

EID: 84962418134     PISSN: 03014622     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bpc.2004.03.002     Document Type: Article

References (71)

1. Kasai S., Nagasawa H., Yamashita M. New antimetastatic hypoxic cell radiosensitizers: design, synthesis, and biological activities of 2-nitroimidazole-acetamide, TX-1877, and its analogues. Bioorg. Med. Chem. 9:2001;453-464
2. Teicher B.A. Hypoxia and drug-resistance. Cancer Metastasis Rev. 13:1994;139-168
3. Tomida A., Tsuruo T. Drug resistance mediated by cellular stress response to the microenvironment of solid tumors. Anti-Cancer Drug Des. 14:1999;169-175
4. Brown J.M., Wouters B.G. Apoptosis p53 and tumor cell sensitivity to anticancer agents. Cancer Res. 59:1999;1391-1399
5. Horis H., Nagasawa H., Terada H. Advances in Environmental Science and Technology: Oxidants in the Environment. 1994;Wiley, New York
6. Viodé C., Bettache N. Enzymatic reduction studies of nitroheterocycles. Biochem. Pharmacol. 57:1999;549-557
7. Chen M., Moir D., Benoit F.M., et al. Purification and identification of several sulphonated azo dyes using reversed-phase preparative high-performance liquid chromatography. J. Chromatogr., A. 825:1998;37-44
8. Bu Y., Liu Y., Deng C. Correlation study of Franck-Condon barriers associated with electron self-exchange reactions with ionization potentials and electron affinities and experimental Born-Oppenheimer potentials. J. Mol. Struct., THEOCHEM. 422:1998;219-228
9. 3-. Chem. Phys. Lett. 343:2001;99-104
10. La-Scalea M.A., Serrano S.H.P., Gutz I.G.R. Voltammetric behaviour of metronidazole at mercury of metronidazole at mercury electrodes. J. Braz. Chem. Soc. 10:1999;127-135
11. Brett A.M.O., Serrano S.H.P., Gutz I., La-Scalea M.A., Cruz M.L. Voltammetric behavior of nitroimidazoles at a DNA-biosensor. Electronal. 9:1997;1132-1137
12. La-Scalea M.A., Brett A.M.O., Serrano S.H.P. DNA-modified electrodes: a new alternative for electroanalysis. Quím. Nova. 22:1999;417-424
13. Ortiz J.V. Electron-binding energies of anionic alkali-metal atoms from partial 4th-order electron propagator theory calcultions. J. Chem. Phys. 89:1988;6348-6352
14. von Niessen W., Schirmer J., Cederbaum L.S. Computational methods for the one-particle Green-function. Comput. Phys. Rep. 1:1984;57-125
15. Ahmed A.A., Julliard M., Chanon F., Chanon M., Gracian F., Pfister-Guillouzo G. Photoelectron spectroscopy of quinoline derivatives. Correlation of experimental ionization potentials with calculated molecular energies. Spectrochim. Acta, Part A: Mol. Biomol. Spectrosc. 53:1997;335-343
16. Hori H., Jin C.Z., Kiyono M., Kasai S., Shimamura M., Inayama S. Design, synthesis, and biological activity of anti-angiogenic hypoxic cell radiosensitizer haloacetylcarbamoyl-2-nitroimidazoles. Bioorg. Med. Chem. 5:1997;591-599
17. Chapamn J.D., Coia L.R., Stobe C.C., Engelhart E.L., Fenning M.C., Schneider R.F. Prediction of tumour hypoxia and radioresistance with nuclear medicine markers. Br. J. Cancer. 74:1996;S204-S208
18. Ames J.R., Ryan M.D., Kovaic P. Mode of action of antiprotozoan agents - electron-transfer and oxy radicals. Life Sci. 41:1987;1895-1902
19. Halliwell B., Gutterridge J.M.C. Free Radicals in Bilogy and Medicine. 1985;Oxford Univ. Press, New York
20. Bett A.M.O., Serrano S.H.P., La-Scalea M.A. Mechanism of interaction of in situ produced nitroimidazole reduction derivatives with DNA using electrochemical DNA biosensor. Methods Enzymol. 300:1999;314-321
21. Adams G.E., Flockhart I.R., Smithen C.E., Straford I.J., Wardman P., Watts M.E. Effects of structure and hyperthermia on radiosensitizing and differential citotoxic properties of hypoxic cell sensitizers. Radiat. Res. 67:1976;550-551
22. Reynolds C.A., King P.M., Richards W.G. Accurate redox potentials from theoretical calculations - methyl-substituted benzoquinones. J. Chem. Soc., Chem. Commun. 21:1988;1434-1436
23. Lister S.G., Reynolds C.A., Richards W.G. Energetics of reactions involving radical species in solution: calculation of relative electrode potentials for nitroimidazoles using density functional and continuum methods. Int. J. Quant. Chem. 59:1997;135-145
24. Jarger R., Kast S.M. Quantification and visualization of molecular-surface flexibility. J. Mol. Graph. Model. 13:2001;89-97
25. PC Spartan Pro 1.0.1, Wavefunction, 18401 Von Karman Avenue, Suite 370, Irvine, CA 92612 USA.
26. Biosym/MSI Insight II, version 95.0. 1995;Biosym/MSI, San Diego
27. 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, Q. Cui, 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, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, and J.A. Pople, Gaussian, Pittsburgh PA, 2001.
28. Hohenberg P., Kohn W. Inhomogeneous electron gas. Phys. Rev., B. 136:1964;B864-B869
29. Stewart J.J.P. Optimization of parameters for semiempirical methods. J. Comput. Chem. 10:1989;209-264
30. Becke A.D. Density-functional exchange energy approximation with correct asymptotic-behavior. Phys. Rev., A. 38:1988;3098-3100
31. Kohn W., Sham L.J. Self-consistent equations including exchange and correlation effects. Phys. Rev. 140:1965;A1133-A1140
32. Motta-Neto D.J., Zerner M.C., Bicca de Alencastro R. On the implications of the structure of 3′-azido-3′ deoxythymidine and related-compounds to antiviral activity. Int. J. Quantum Chem., Quantum Chem. Symp. 44:1992;743-757
33. Miertus S., Scrocco E., Tomasi J. Electrostatic interaction of a solute with a continuum - a direct utilization of ab initio molecular potentials for the prevision of solvent effects. Chem. Phys. 55:1981;117-129
34. Colominas C., Luque F.J., Teixido J. Cavitation contribution to the free energy of solvation. Comparison of different formalisms in the context of MST calculations. Chem. Phys. 240:1999;253-264
35. Dauber-Osgutorpe P., Roberts V.A., Osgutorpe D.G. Structure and energetics of ligand-binding to proteins - Escherichia coli dihydrofolate reductase trimethoprim, a drug-receptor system. Proteins. 4:1988;31-47
36. Colominas C., Luque F.J., Orzco M. Monte Carlo MST: new strategy for representation of solvent configurational space in solution. J. Comput. Chem. 20:1999;665-678
37. Bracuti A.J. Crystal structure of 4, 5-dinitroimidazole (45DNI). J. Chem. Crystallogr. 28:1998;367-371
38. Breneman C.M., Wiberg K.B. Determining atom-centered monopoles from molecular electrostatic potentials - the need for high sampling density in formamide conformational-analysis. J. Comput. Chem. 11:1990;361-373
39. Singh U.C., Kollman P.A. An approach to computing electrostatic charges for molecules. J. Comput. Chem. 5:1984;129-145
40. Goldman P., Koch R.L., Yeung T.C. Comparing the reduction of nitroimidazoles in bacteria and mammalian-tissues and relating it biological-activity. Biochem. Pharmacol. 35:1986;43-51
41. Warshel A., King G. Polarization constraints in molecular-dynamics simulation of aqueous-solutions - the surface constraint all atom solvent (SCAAS) model. Chem. Phys. Lett. 121:1985;124-129
42. King G., Warshel A. A surface constrained all-atom solvent model for effective simulations of polar solutions. J. Chem. Phys. 91:1989;3647-3661
43. Straatsma T.P., Berendsen H.J.C. Free-energy of ionic hydration-analysis of a thermodynamic integration technique to evaluate free-energy differences by molecular dynamics simulations. J. Chem. Phys. 89:1988;5876-5886
44. Aqvist J. Ion water interaction potentials derives form free-energy perturbation simulations. J. Phys. Chem. 94:1990;8021-8024
45. Tomasi J., Perisco M. Molecular-interactions in solution - an overview of methods based on continuous distributions of the solvent. Chem. Rev. 94:1994;2027-2094
46. Bachs M., Orzco M., Luque F.J. Optimization of solute cavities an van-der-Waals parameters in ab-initio MST-SCRF calculations of neutral molecules. J. Comput. Chem. 15:1994;446-454
47. 4. J. Comput. Chem. 17:1996;806-820
48. Orozco M., Luque F.J. Optimization of the cavity size for ab-initio MST-SCRF calculations of monovalent ions. Chem. Phys. 182:1994;237-248
49. Mezei M. The finite-difference thermodynamic integration, tested on calculating the hydration free-energy difference between acetone and dimethylamine in water. J. Chem. Phys. 86:1987;7084-7088
50. Guimarães C.R.W., Bicca de Alencastro R. Thermodynamic analysis of thrombin inhibition by benzamidine and p-methylbenzamidine via free-energy perturbations: inspection of intraperturbed-group contributions using the finite difference thermodynamic integration (FDTI) algorithm. J. Phys. Chem., B. 106:2002;466-476
51. Kollman P. Free-energy calculations - application to chemical and biochemical phenomena. Chem. Rev. 93:1993;2395-2417
52. Press W.H., Flanney B.P., Teukolsky S.A., Vetterling W.T. Numerical Recipes. The Art of Scientific Computing. 1986;Cambridge Univ. Press, CV Cambridge, UK
53. Johnson B.G., Gill P.M., Pople J.A. The performance of a family of density functional methods. J. Chem. Phys. 98:1993;5612-5626
54. Wardman P., Clarke E.D. One-electron reduction potentials of substituted nitroimidazoles measured by pulse-radiolysis. J. Chem. Soc., Faraday Trans. 76:1976;1377-1390
55. Knox R.J., Knight R.C., Edwards D.I. Interaction of nitroimidazole with DNA in vitro - structure-activity-relationships. Br. J. Cancer. 44:1981;741-745
56. Chen G.X., Ong P.P., Ting L. DFT approach for electron affinity of negative atomic ions. Chem. Phys. Lett. 290:1998;211-215
57. Reynolds C.A., Richards W.G. Theoretical calculation of electrode-potentials - electron-withdrawing compounds. Int. J. Quant. Chem. 41:1992;293-310
58. Reynolds C.A. Theoretical electrode-potentials and conformational energies of benzoquinones and naphthoquinones in aqueous-solution. J. Am. Chem. Soc. 112:1990;7545-7551
59. Fischer C.F., Lagowski J.B., Vosko S.H. Ground states of CA- and SC- from two theoretical points-of-view. Phys. Rev. Lett. 59:1987;2263-2266
60. Wymore T., Gao X., Wong T.C. Molecular dynamics simulation of a solvated dodecylphospocholine micelle. Biophys. J. 76:1999;A57
61. Tomasi J., Mennucci B., Cances E. The IEF version of the PCM solvation method: an overview of a new method addressed to study molecular solutes at the QM ab initio level. J. Mol. Struct., THEOCHEM. 464:1999;211-226
62. Cammi R., Cosssi M., Mennucci B., Tomasi J. Theoretical Aspects of Biochemical Reactivity. 1997;Khuwer Academic Publishing, France
63. Cances E., Mennucci B., Tomasi J. A new integral equation formalism for the polarizable continuum model: theoretical background and applications to isotropic and anisotropic dielectrics. J. Chem. Phys. 107:1997;3032-3041
64. Adams G.E., Clarke E.D., Flockhart I.R., Jacob R.S., Sehmi D.S., Startfor I.J., Wardman P., Watts M.E. Structure-activity relationships in the development of hypoxic cell radiosensitizers: I. Sensitization efficiency. Int. J. Radiat. Biol. 35:1979;133-150
65. Adams G.E., Clarke E.D., Flockhart I.R., Jacob R.S., Sehmi D.S., Startfor I.J., Wardman P., Watts M.E. Structure-activity relationships in the development of hypoxic cell radiosensitizers: II. Cytotoxicity and therapeutic ratio. Int. J. Radiat. Biol. 35:1979;151-160
66. Pires J.R., Saito C., Gomes S.L., Giesbrecht A.M., Amaral A.T. Investigation of 5-nitrofuran derivatives: synthesis, antibacterial activity, and quantitative structure-activity relationships. J. Med. Chem. 44:2001;3673-3681
67. Chauviere G., Bouteille B., Enanga B., Albuquerque C., Croft S.L., Dumas M., Perie J. Synthesis and biological activity of nitro heterocycles analogous to megazol, a trypanocidal lead. J. Med. Chem. 46:2003;427-440
68. Benakli K., Terme T., Maldonado J. A convenient synthesis of highly conjugated 5-nitroimidazoles. Heterocycles. 57:2002;1689-1695
69. Wardman P., Clarke E.D., Jacobs R.S., Minchinton A., Stratford M.R.L., Watts M.E., Woodcock M., Moazzam M., Parrick J., Wallace R.G., Smithen C.E. Brady L.W. Radiation Sensitizers: Their Use in the Clinical Management of Cancer. 1980;83-90 Masson, New York, NY
70. Clarke E.D., Wardman P. Oxygen inhibition of nitroreductase-electron- transfer from nitro radical-anions to oxygen. Biochem. Biophys. Res. Commun. 69:1976;942-949
71. Rienstra-Kiracofe J.C., Tschumper G.S., Schaefer H.F. III Atomic and molecular electron affinities: photoelectron experiments and theoretical computations. Chem. Rev. 102:2002;231-282