Guanine-derived radicals: Dielectric constant-dependent stability and UV/Vis spectral properties: A DFT study

Radiation Research

Volumn 169, Issue 3, 2008, Pages 364-372

  Naumov, Sergej ^a   Von Sonntag, Clemens ^a,b  

^a LEIBNIZ INSTITUTE OF SURFACE ENGINEERING IOM   (Germany)

^b MAX PLANCK INSTITUTE FOR CHEMICAL ENERGY CONVERSION   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYGUANOSINE; FREE RADICAL; GUANINE; GUANOSINE; NUCLEOSIDE; DNA; WATER;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIELECTRIC CONSTANT; DNA DAMAGE; IONIZING RADIATION; PRIORITY JOURNAL; PROTON TRANSPORT; ULTRAVIOLET RADIATION; CHEMICAL MODEL; CHEMISTRY; COMPUTER SIMULATION; ELECTRIC CONDUCTIVITY; KINETICS; METHODOLOGY; PULSE RADIOLYSIS; RADIATION DOSE; RADIATION EXPOSURE; RADIATION RESPONSE; SOLUTION AND SOLUBILITY; ULTRAVIOLET SPECTROPHOTOMETRY;

COMPUTER SIMULATION; DNA; DOSE-RESPONSE RELATIONSHIP, RADIATION; ELECTRIC CONDUCTIVITY; FREE RADICALS; GUANINE; KINETICS; MODELS, CHEMICAL; MODELS, MOLECULAR; PULSE RADIOLYSIS; RADIATION DOSAGE; SOLUTIONS; SPECTROPHOTOMETRY, ULTRAVIOLET; ULTRAVIOLET RAYS; WATER;

EID: 41649102444     PISSN: 00337587     EISSN: None     Source Type: Journal    
DOI: 10.1667/RR1082.1     Document Type: Article

References (40)

1. C. von Sonntag, Free-Radical-Induced DNA Damage and Its Repair. A Chemical Perspective. Springer-Verlag, Berlin, Heidelberg, 2006.
2. C. von Sonntag, Free-radical-induced DNA damage as approached by quantum mechanics and Monte Carlo calculations: an overview from the standpoint of an experimentalist. Adv. Quantum Chem. 52, 5-20 (2007).
3. X. Li and M. D. Sevilla, DFT treatment of radiation produced radicals in DNA model systems. Adv. Quantum Chem. 52, 59-87 (2007).
4. F. Turecek, Computational studies of radicals relevant to nucleic acid damage. Adv. Quantum Chem. 52, 89-120 (2007).
5. E. Cauet and J. Liévin, Radical cations of the nucleic acid bases and radiation damage to DNA: Ab initio study. Adv. Quantum Chem. 52, 121-147 (2007).
6. R. B. Martin, Nuucleoside sites for transition metal ion binding. Acc. Chem. Res. 18, 32-38 (1985).
7. Q. Luo, Q. S. Li, Y. Xie and H. F. Schaefer, Radicals derived from guanine: structures and energetics. Collect. Czech. Chem. Commun. 70, 826-836 (2005).
8. R. L. Willson, P. Wardman and K-D. Asmus, Interaction of dGMP radical with cysteamine and promethazine as possible model of DNA repair. Nature (London) 252, 323-324 (1974).
9. K-D. Asmus, D. J. Deeble, A. Garner, K. M. Idriss Ali and G. Scholes, Chemical aspects of radiosensitization. Reaction of sensitizers with radicals produced in the radiolysis of aqueous solutions of nucleic acid components. Br. J. Cancer 37 (Suppl. III), 46-49 (1978).
10. L. P. Candeias and S. Steenken, Structure and acid-base properties of one-electron-oxidized deoxyguanosine, guanosine, and 1-methylguanosine. J. Am. Chem. Soc. 111, 1094-1099 (1989).
11. A. Adhikary, A. Kumar, D. Becker and M. D. Sevilla, The guanine cation radical: investigation of deprotonation states by ESR and DFT. J. Phys. Chem. B 110, 24171-24180 (2006).
12. E. O. Hole and E. Sagstuen, Free radical formation in crystals of 2′-deoxyguanosine 5′-monophosphate irradiated at 15 K: An ESR study. Radiat. Res. 109, 190-205 (1987).
13. E. O. Hole, E. Sagstuen, W. H. Nelson and D. M. Close, Free radical formation in single crystals of 2′-deoxyguanosine 5′-monophosphate; and guanine hydrobromide monohydrate after X-irradiation at 10 and 65 K: An ESR, ENDOR and FSE study. Free Radic. Res. Commun. 6, 87-90 (1989).
14. E. O. Hole, W. H. Nelson, E. Sagstuen, and D. M. Close, Free radical formation in single crystals of 2′-deoxyguanisine 5′-monophosphate tetrahydrate disodium salt: An EPR/ENDOR study. Radiat. Res. 129, 119-138 (1992).
15. E. O. Hole, E. Sagstuen, W. H. Nelson and D. M. Close, The structure of the guanine cation: ESR/ENDOR of cyclic guanosine monophosphate single crystals after X irradiation at 10 K. Radiat. Res. 129, 1-10 (1992).
16. D. M. Close, E. Sagstuen and W. H. Nelson, ESR study on the guanine cation. J. Chem. Phys. 82, 4386-4388 (1985).
17. W. H. Nelson, E. O. Hole, E. Sagstuen and D. M. Close, ESR/ENDOR study of guanine•HCI•2H2O X-irradiated at 20K. Int. J. Radiat. Biol. 54, 963-986 (1988).
18. L. Jaquet, J. M. Kelly and A. Kirsch-De Mesmaeker, Photoadduct between tris(1,4,5,8-tetraazaphenanthrene)ruthenium(II) and guanosine monophosphate - a model for a new covalent binding of metal complexes to DNA. J. Chem. Soc. Chem. Commun., 913-914 (1995).
19. C. Chatgilialoglu, C. Caminal, A. Altieri, G. C. Vougiokalakis, Q. G. Mulazzani, T. Gimisis and M. Guerra, Tautomerism in the guanyl radical. J. Am. Chem. Soc. 128, 13796-13805 (2006).
20. C. Chatgilialoglu, C. Carminal, M. Guerra and Q. G. Mulazzani, Tautomers of one-electron-oxidized guanosine. Angew. Chem. Int. Ed. 44, 6030-6032 (2005).
21. S. Naumov and C. von Sonntag, UV-visible absorption spectra of alkyl-, vinyl-, aryl- and thiylperoxyl radicals and some related radicals in aqueous solution: a quantum-chemical study. J. Phys. Org. Chem. 18, 586-594 (2005).
22. S. V. Jovanovic and M. G. Simic, One-electron redox potentials of purines and pyrimidines. J. Phys. Chem. 90, 974-978 (1986).
23. M. Faraggi and M. H. Klapper, One electron oxidation of guanine and 2′-deoxyguanosine by the azide radical in alkaline solutions. J. Chim. Phys. 91, 1062-1069 (1994).
24. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zaktzewski, J. A. Montgomery, Jr., R. E. Stratmann and J. A. Pople, Gaussian 98, Revision A.11. Gaussian Inc., Pittsburgh, PA, 1998.
25. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin and J. A. Pople, Gaussian 03, Version 6.0. Gaussian Inc., Pittsburgh, PA, 2003.
26. A. D. Becke, Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98, 5648-5652 (1993).
27. A. D. Becke, Density-functional thermochemistry. IV. A new dynamical correlation functional and implications for exact-exchange mixing. J. Chem. Phys. 104, 1040-1046 (1996).
28. C. Lee, W. Yang and R. G. Parr, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 37, 785-789 (1988).
29. E. Cancès, B. Mennucci and J. Tomasi, A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics. J. Chem. Phys 107, 3032-3041 (1997).
30. B. Mennucci and J. Tomasi, Continuum solvation models: A new approach to the problem of solute's charge distribution and cavity boundaries. J. Chem. Phys. 106, 5151-5158 (1997).
31. M. Cossi, V. Barone, B. Mennucci and J. Tomasi, Ab initio study of ionic solutions by a polarizable continuum dielectric model. Chem. Phys. Lett. 286, 253-260 (1998).
32. M. Cossi, G. Scalmani, N. Rega and V. Barone, New developments in the polarizable continuum model for quantum mechanical and classical calculations on molecules in solution. J. Chem. Phys. 117, 43-54 (2002).
33. V. Barone and M. Cossi, Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model. J. Phys. Chem. A 102, 1995-2001 (1998).
34. M. Cossi, N. Rega, G. Scalmani and V. Barone, Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model. J. Comput. Chem. 24, 669-681 (2003).
35. M. Cossi, V. Barone, R. Cammi and J. Tomasi, Ab initio study of solvated molecules: a new implementation of polarizable continuum. Chem. Phys. Lett. 255, 327-335 (1996).
36. R. Bauernschmitt and R. Ahlrichs, Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory. Chem. Phys. Lett. 256, 454-464 (1996).
37. S. D. Wetmore, R. J. Boyd and L. A. Eriksson, Comparison of experimental and calculated hyperfine coupling constants. Which radicals are formed in irradiated guanine? J. Phys. Chem. B 102, 9332-9343 (1998).
38. C. J. Mundy, M. E. Colvin and A. A. Quong, Irradiated guanine: a Car-Parinello molecular dynamics study of dehydrogenation in the presence of an OH radical. J. Phys. Chem. A 106, 10063-10071 (2002).
39. S. V. Jovanovic and M. G. Simic, The DNA guanyl radical: kinetics and mechanisms of generation and repair. Biochim. Biophys. Acta 1008, 39-44 (1989).
40. A. Adhikary, A. Y. S. Malkhasian, S. Collins, J. Koppen, D. Becker and M. D. Sevilla, UVA-visible photo-exitation of guanine radical cations produces sugar radicals in DNA and model structures. Nucleic Acids Res. 33, 5553-5564 (2005).