Complex formation between a DNA duplex and lipid-like spermine derivatives: Hydrophobic protection of DNA from one-electron oxidation

Bioconjugate Chemistry

Volumn 16, Issue 4, 2005, Pages 820-826

  Cao, Huachuan ^a   Schuster, Gary B ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROPHOBICITY; KETONES; POSITIVE IONS;

COMPLEX FORMATIONS; DNA DUPLEXES; GUANINE; HYDROPHOBICS; IRRADIATED SAMPLES; NUCLEOBASE RADICALS; ONE-ELECTRON OXIDATION; OXIDATIVE REACTION; RADICAL CATIONS; SPERMINE DERIVATIVES;

DNA;

ANTHRAQUINONE DERIVATIVE; CATION; DNA; DOUBLE STRANDED DNA; GUANINE; LIPID; NUCLEIC ACID BASE; OXYGEN; PIPERIDINE; SPERMINE DERIVATIVE; WATER;

ARTICLE; COMPLEX FORMATION; COVALENT BOND; DNA BINDING; HYDROPHOBICITY; IRRADIATION; OXIDATION; PHOTOACTIVATION;

EID: 22644437586     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc0500185     Document Type: Article

References (37)

1. Schuster, G. B., and Landman, U. (2004) The Mechanism of Long-Distance Radical Cation Transport in Duplex DNA: Ion-Gated Hopping of Polaron-Like Distortions. Top. Curr. Chem. 236, 139-162.
2. Jortner, J., Bixon, M., Voityuk, A. A., and Rosch, N. (2002) Superexchange Mediated Charge Hopping in DNA. J. Phys. Chem. A 106, 7599-7606.
3. Berlin, Y. A., Burin, A. L., and Ratner, M. A. (2002) Elementary steps for charge transport in DNA: thermal activation vs tunneling. Chem. Phys. 275, 61-74.
4. Lewis, F. D., Liu, J., Zuo, X., Hayes, R. T., and Wasielewski, M. R. (2003) Dynamics and Energetics of Single-Step Hole Transport in DNA Hairpins. J. Am. Chem. Soc. 125, 4850-4861.
5. Liu, C.-S., Hernandez, R., and Schuster, G. B. (2004) The Mechanism of Radical Cation Transport in DNA. J. Am. Chem. Soc. 126, 2877-2884.
6. O'Neill, M. A., and Barton, J. K. (2004) DNA Charge Transport: Conformationally Gated Hopping through Stacked Domains. J. Am. Chem. Soc. 126, 11471-11483.
7. Kasai, H., Yamaizumi, Z., Berger, M., and Cadet, J. (1992) Photosensitized Formation of 7,8-Dihydro-8-oxo-2′-deoxyguanosine (8-Hydroxy-2′-deoxyguanosine) in DNA by Riboflavin: A Non Singlet Oxygen Mediated Reaction. J. Am. Chem. Soc. 114, 9692-9694.
8. Ly, D., Kan, Y., Armitage, B., and Schuster, G. B. (1996) Cleavage of DNA by Irradiation of Substituted Anthraquinones: Intercalation Promotes Electron Transfer and Efficient Reaction at GG Steps. J. Am. Chem. Soc. 118, 8747-8748.
9. Cullis, P. M., Malone, M. E., and Merson-Davies, L. A. (1996) Guanine Radical Cations Are Precursors of 7,8-Dihydro-8-oxo-2′-deoxyguanosine But Are Not Precursors of Immediate Strand Breaks in DNA. J. Am. Chem. Soc. 118, 2775-2781.
10. Hickerson, R. P., Prat, F., Muller, J. G., Foote, C. S., and Burrows, C. J. (1999) Sequence and Stacking Dependence of 8-Oxoguanine Oxidation: Comparison of One-Electron vs Singlet Oxygen Mechansms. J. Am. Chem. Soc. 121, 9423-9428.
11. Remy, J. S., Sirlin, C., Vierling, P., and Behr, J. P. (1994) Gene-Transfer with a Series of Lipophilic DNA-Binding Molecules. Bioconjugate Chem. 5, 647-654.
12. Dauty, E., Remy, J.-S., Blessing, T., and Behr, J.-P. (2001) Dimerizable Cationic Detergents with a Low cmc Condense Plasmid DNA into Nanometric Particles and Transfect Cells in Culture. J. Am. Chem. Soc. 123, 9227-9234.
13. Gershon, H., Ghirlando, R., Guttman, S. B., and Minsky, A. (1993) Mode of formation and structural features of DNA-cationic liposome complexes used for transfection. Biochemistry 32, 7143-7151.
14. Radler, J. O., Koltover, I., Salditt, T., and Safinya, C. R. (1997) Structure of DNA-Cationic Liposome Complexes: DNA Intercalation in Multilamellar Membranes in Distinct Interhelical Packing Regimes. Science 275, 810-814.
15. Korolev, N., Lyubartsev, A. P., Laaksonen, A., and Nordenskiold, L. (2002) On the Competition between Water, Sodium Ions, and Spermine in Binding to DNA: A Molecular Dynamics Simulation Study. Biophys. J. 82, 2860-2875.
16. Remy, J.-P., Sirlin, C., Verling, P., and Behr, J.-P. (1994) Gene Transfer with DNA Binding Molecules. Bioconjugate Chem. 5, 647-654.
17. Dias, R. S., Lindman, B., and Miguel, M. G. (2002) DNA interaction with cationic vesicles. J. Phys. Chem. B 106, 12600-12607.
18. Gray, D. M., Hung, S.-H., and Johnson, K. H. (1995) Absorption and Circular Dichroism Spectroscopy of Nucleic Acid Duplexes and Triplexes. Methods Enzymol. 246, 19-36.
19. Olmsted, J., III., and Kearns, D. R. (1977) Mechanism of Ethidium Bromide Fluorescence Enhancement on Binding to Nucleic Acids. Biochemistry 16, 3647-3654.
20. Lepecq, J. B., and Paoletti, C. A (1967) Fluorescent Complex between Ethidium Bromide and Nucleic Acids - Physical-Chemical Characterization. J. Mol. Biol. 27, 87.
21. Long-Range Charge Transfer in DNA I; Schuster, G. B., Ed. (2004) Springer: Heidelberg, Germany, Vol. 236.
22. Long-Range Charge Transfer in DNA II; Schuster, G. B., Ed. (2004) Springer; Heidleberg, Germany, Vol. 237.
23. Bhagwat, M., and Gerlt, J. A. (1996) 3′- and 5′-Strand Cleavage Reactions Catalyzed by the Fpg Protein from Escherichia coli Occur via Successive β-and δ-Elimination Mechanisms, Respectively. Biochemistry 35, 659-665.
24. Armitage, B. A., Yu, C., Devadoss, C., and Schuster, G. B. (1994) Cationic Anthraquinone Derivatives as Catalytic DNA Photonucleases: Mechanisms for DNA Damage and Quinone Recycling. J. Am. Chem. Soc. 116, 9847-9859.
25. Hosford, M. E., Muller, J. G., and Burrows, C. J. (2004) Spermine Participates in Oxidative Damage of Guanosine and 8-Oxoguanosine Leading to Deoxyribosoylurea Formation. J. Am. Chem. Soc. 126, 9540-9541.
26. Sies, H. (1993) Singlet oxygen induced DNA damage. Mutat. Res. 275, 367-75.
27. Schuster, G. B. (2000) Long-Range Charge Transfer in DNA: Transient Structural Distortions Control the Distance Dependence. Acc. Chem. Res. 33, 253-260.
28. Liu, C.-S., and Schuster, G. B. (2003) Base Sequence Effects in Radical Cation Migration in Duplex DNA: Support for the Polaron-Like Hopping Model. J. Am. Chem. Soc. 125, 6098-6102.
29. Henderson, P. T., Jones, D., Hampikian, G., Kan, Y., and Schuster, G. B. (1999) Long-Distance Charge Transport in Duplex DNA: The Phonon-Assisted Polaron-Like Hopping Mechanism. Proc. Natl. Acad. Sci. U.S.A. 96, 8353-8358.
30. Misiaszek, M., Crean, C., Joffe, A., Geacintov, N. E., and Shafirovich, V. (2004) Oxidative DNA Damage Associated with Combination of Guanine and Superoxide Radicals and Repair Mechanisms via Radical Trapping. J. Biol. Chem. 279, 32106-32115.
31. Shui, X. Q., McFail-Isom, L., Hu, G. G., and Williams, L. D. (1998) The B-DNA dodecamer at high resolution reveals a spine of water on sodium. Biochemistry 37, 8341-8355.
32. Tari, L. W., and Secco, A. S. (1995) Base-Pair Opening and Spermine Binding - B-DNA Features Displayed in the Crystal-Structure of a Gal Operon Fragment - Implications for Protein-DNA Recognition. Nucleic Acids Res. 23, 2065-2073.
33. Egli, M., Tereshko, V., Teplova, M., Minasov, G., Joachimiak, A., Sanishvili, R., Weeks, C. M., Miller, R., Maier, M. A., An, H. Y., and Cook, P. D. (1998) Manoharan, M. X-ray crystallographic analysis of the hydration of A- and B-form DNA at atomic resolution. Biopolymers 48, 234-252.
34. Schmid, N., and Behr, J. P. (1991) Location of Spermine and Other Polyamines on DNA as Revealed by Photoaffinity Cleavage with Polyaminobenzenediazonium Salts. Biochemistry 30, 4357-4361.
35. Feuerstein, B. G., Pattabiraman, N., and Marton, L. J. (1990) Molecular Mechanics of the Interactions of Spermine with DNA - DNA Bending as a Result of Ligand-Binding. Nucleic Acids Res. 18, 1271-1282.
36. Feuerstein, B. G., Pattabiraman, N., and Marton, L. J. (1986) Spermine DNA Interactions - a Theoretical-Study. Proc. Natl Acad. Sci. U.S.A. 83, 5948-5952.
37. Zakrzewska, K., and Pullman, B. (1986) Spermine Nucleic-Acid Interactions - a Theoretical-Study. Biopolymers 25, 375-392.