Molecular mechanism of GG-specific photooxidation of DNA

Journal of Medical and Dental Sciences

Volumn 45, Issue 3, 1998, Pages 161-169

  Kino, Katsuhito ^a   Sugiyama, Hiroshi ^a  

^a TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

Author keywords

8 oxo G; Aging; Cancer; Mutation; Oxidative DNA damage; Repair

Indexed keywords

2 AMINOIMIDAZOLE; 2-AMINOIMIDAZOLE; 8 HYDROXYGUANINE; 8-HYDROXYGUANINE; DRUG DERIVATIVE; GUANINE; IMIDAZOLE DERIVATIVE;

ANIMAL; CATTLE; DNA ADDUCT; DNA DAMAGE; HUMAN; METABOLISM; OXIDATIVE STRESS; PHOTOCHEMICAL SMOG; POINT MUTATION; REVIEW;

ANIMALS; CATTLE; DNA ADDUCTS; DNA DAMAGE; GUANINE; HUMANS; IMIDAZOLES; OXIDANTS, PHOTOCHEMICAL; OXIDATIVE STRESS; POINT MUTATION;

EID: 0032149102     PISSN: 13428810     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (53)

1. Irani K, Xia Y, Zweier JL, et al. Mitogenic signaling mediated by oxidants in Ras-transformed fibroblasts. Science 1997; 275: 1649-52.
2. 2 for platelet-derived growth factor signal transduction. Science 1996 ; 270: 296-9.
3. Ohba M, Shibanuma M, Kuroki T, et al. Production of hydrogen peroxide by transforming growth factor-b1 and its involvement in induction of egr-1 in mouse osteoblast cells. J Cell Biol 1994; 126: 1079-8.
4. 2-terminal kinases. J Biol Chem 1996; 271: 15703-7.
5. Los M, Schenk H, Hexel K, et al. IL-2 gene expression and NF-κ B. activation through CD28 requires reactive oxygen production by 5-lipoxygenase. EMBO J 1995; 14: 3731-40.
6. Schmidt KN, Amstad P, Cerutti P, Baeuerle PA: Identification of hydrogen peroxide as the relevant messenger in the activation pathway of transcription factor NF-κB. Adv Exp Med Biol 1996; 387: 63-8.
7. Friedberg EC, Walker GC, Siede W. DNA Repair and Mutagenesis, Washington D.C.: ASM Press ; 1995.
8. Ames BN, Shigenaga MK, Hagen TM. Oxidants, antioxidants and the degenerative diseases of aging. Proc Natl Acad Sci USA 1993; 90: 7915-22.
9. Shigenaga MK, Park JW, Cundy KC, et al. In vitro oxidative damage: Measurement of 8-hydroxy-2'-deoxyguanosine in DNA and urine by high-performance liquid chromatography with electrochemical detection. Method Enzymol 1990; 186: 521-30.
10. Kasai H, Nishimura S. Formation of 8-hydroxydeoxyguanosine in DNA by oxygen radicals and its biological significance. In Oxidative Stress:Oxidants and Antioxidants. Edited by Sies H. London: Academic Press; 1991: 99-116.
11. Grollman AP, Moriya M: Mutagenesis by 8-oxoguanine: An enemy within. Trends Genet. 1993; 9: 246-9.
12. Michaels ML, Cruz C, Gtollman AP, et al. Evidence that MutY and MutM combine to prevent mutations by an oxidatively damaged form of guanine in DNA. Proc Natl Acad Sci USA 1992; 89: 7022-5.
13. Michaels ML, Tchou J, Grollman AP, et al. A repair system for 8-oxo-7,8-dihydrodeoxyguanine. Biochemistry 1992; 31: 10964-8.
14. Michaels ML, Miller JH. The GO system protects organisms from the mutagenic effect of the spontaneous lesion 8-hydroxyguanine(7,8-dihydro-8-oxoguanine). J Bacteriol 1992; 174: 6321-5.
15. Maki H, Sekiguchi M: MutT protein specifically hydrolyzes a potent mutagenic substrate for DNA synthesis. Nature 1992; 355: 273-5.
16. Tajiri T, Maki H, Sekiguchi M. Functional cooperation of MutT, MutM and MutY proteins in preventing mutations caused by spontaneous oxidation of guanine nucleotide in Escherichia coli. Mutat Res DNA Repair 1995; 336: 257-67.
17. Lu R, Nash HM, Verdine GL A mammalian DNA repair enzyme that excises oxidatively damaged guanine maps to a locus frequently lost in lung cancer. Current Biol 1997; 7: 397-407.
18. Saito I, Takayama M, Kawanishi S. Photoactivatable DNA-cleaving amino acids: Highly sequence-selective DNA photocleavage by novel L-lysine derivatives. J Am Chem Soc 1995; 117: 5590-1.
19. Saito I, Takayama M, Sugiyama H, Nakatani K, Tsuchida A, Yamamoto M. Photoinduced DNA cleavage via electron transfer: Demonstration that guanine residues located 5' to guanine are the most electron-donating sites. J Am Chem Soc 1995; 117: 6406-7.
20. Matsugo S, Kawanishi S, Yamamoto K, Sugiyama H, Matsuura T, Saito I. Bis(hydroperoxy)naphthaldiimide as a "Photo-Fenton reagent": Sequence-specific photocleavage of DNA. Angew Chem Int Ed Engl. 1991; 30: 1351-3.
21. Ito K, Inoue S, Yamamoto K, et al. 8-Hydroxydeoxyguanosine formation at the 5' site of 5'-GG-3' sequences in double-stranded DNA by UV radiation with riboflavin. J Biol Chem 1993; 268: 13221-7.
22. Takayama M. Design of novel photochemical DNA-cleaving molecules and the DNA cleavage mechanism. Ph D thesis, Kyoto University, 1995.
23. Breslin DT, Schuster GB. Anthraquinone photonucleases: Mechanisms for GG-selective and nonselective cleavage of double-stranded DNA. J Am Chem Soc 1996; 118: 2311-9.
24. Ly D, Kan Y, Armitage, B, Schuster, GB. Cleavage of DNA by irradiation of substituted anthraquinones: Intercalation promotes electron transfer and efficient reaction at GG steps. J Am Chem Soc 1996; 117: 8747-8.
25. Hall DB, Holmlin RE, Barton JK. Oxidative DNA damage through long-range electron transfer. Nature 1996; 382: 731-5.
26. +using the flash-quench technique. J Am Chem Soc 1997; 119: 2921-5.
27. Muller JC, Hickerson RP, Perez RJ, et al. DNA damage from sulfite autooxidation catalyzed by a Nickel(II) peptide. J Am Chem Soc 1997; 119: 1501-6.
28. 2. J Am Chem Soc 1998; 120: 248-57.
29. Melvin T, Plumb MA, Botchway SW, et al. 193 nm Light induces single strand breakage of DNA predominantly at guanine. Photochem Photobiol 1995; 61: 584-91.
30. Armitage B, Yu C, Devadoss C, et al. Cationic anthraquinone derivatives as catalytic DNA photonucleases: Mechanisms for DNA damage and quinone recycling. J Am Chem Soc 1994; 116: 9847-59.
31. Orlov VM, Smirnov AN, Varshavsky YM. Ionization potentials and electron-donor ability of nucleic acid bases and their analogues. Tetrahedron Lett 1976; 48: 4377-8.
32. Jovanovic SV, Simic MG. One-electron redox potentials of purines and pyrimidines. J Phy Chem 1986; 90: 974-8.
33. Koopmans, TA. Über die Zuordnung von wellenfulktionen und eigenwerten zu den einzelnen eleclronen eines atoms. Physica 1933, 1: 104-113.
34. Colson AO, Besler B, Colse DM, et al. Ab initio molecular orbital calculations of DNA bases and their radical ions in various protonation states: Evidence for proton transfer in GC base pair radical. J. Phys. Chem. 1992; 96: 661-8.
35. Sugiyama H, Saito I. Theoretical studies of GG-specific photocleavage of DNA via electron transfer: Significant lowering of ionization potential and 5'-localization of HOMO of stacked GG bases in B-form DNA. J Am Chem Soc 1997; 118: 7063-8.
36. Aida M, Nagata C. An ab initio molecular orbital study on the stacking interaction between nucleic acid bases: Dependence on the sequence and relation to the conformation. Int J Quantum Chem 1986, 29: 1253-61.
37. Aida M. An ab initio molecular orbital study on the sequence-dependency of DNA conformation: An evaluation of intra- and inter-strand stacking interaction energy. J Theor Biol 1988; 130: 327-35.
38. Arkin MR, Stemp, EDA, Pulver, SC, Barton, JK. Long-range oxidation of guanine by Ru(III) in duplex DNA. Chemistry & Biology 1997; 4: 389-400.
39. Gasper, SM, Schuster, GB. Intramolecular photoinduced electron transfer to anthraquinones linked to duplex DNA: The effect of gaps and traps on long-range radical cation migration. J Am Chem Soc 1997; 119: 12762-71.
40. Hall DB, Barton JK. Sensitivity of DNA-mediated electron transfer to the intervening π-stack: A probe for the integrity of the DNA base stack. J Am Chem Soc 1997; 119: 5045-6.
41. Armitage B, Ly D, Koch T, et al. Peptide nucleic acid-DNA duplexes: Long range hole migration from an internally linked anthraquinone. Proc Natl Acad Sci USA 1997; 94: 12320-5.
42. Kasai H, Yamaizumi Z, Berger M, Cadet J. 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 1992; 114: 9692-1.
43. Cullis PM, Malone ME, Merson-Davies LA. Guanine radical cation are precursors of 7,8-dihydro-8-oxo-2'-deoxyguanosine but are not precursors of immediate strand breaks in DNA. J Am Chem Soc 1996; 118: 2775-81.
44. Cadet J, Berger M, Buchko GW, et al. 2,2-Diamino-4-[(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)amino]- 5-(2H)-o xazolone: A novel and predominant radical oxidation product of 3', 5'-di-O-acetyl-2'-deoxyguanosine. J Am Chem Soc 1994; 116: 7403-4.
45. Adam W, Saha-Möller CR, Schönberger A. Photooxidation of 8-oxo-7,8-dihydro-2'-deoxyguanosine by thermally generated triplet-excited ketones from 3-(hydroxymethyl)-3,4,4-trimethyl-1,2-dioxetane and composition with type I and type II photosensitizes. J Am Chem Soc 1996; 118: 9233-8.
46. McBride TJ, Schneider JE, Froyd RA, et al. Mutations induced by methylene blue plus light in single-stranded M13mp2. Proc Natl Acad Sci USA 1992; 89: 6866-70.
47. Ono T, Negishi K, Hayatsu H. Spectra of superoxide-induced mutations in the lacl gene of a wild-type and a mutM strain of Escherichia coli K-12. Mutat Res 1995; 326: 175-83.
48. Negishi K, Hao W. Spectrum of mutations in single-stranded DNA phage M13mp2 exposed to sunlight: Predominance of G-to-C transversion. Carcinogenesis 1992; 13: 1615-8.
49. Zhang QM, Kasai Y, Nakahara T, et al. Isolation and characterization of a novel mutator strain of Escherichia coli that generates G:C-C:G transversions, personal comunication.
50. Sargentini N, Smith KG. DNA sequence analysis of γ-radiation (anionic)-induced and spontaneous lacl mutations in Escherichia coli K-12. Mutat Res 1994; 309: 147-63.
51. Akasaka S, Yamamoto K. Hydrogen peroxide induces G:C to T:A and G:C to C:G transversions in the supF gene of Escherichia coli. Mol Gen Genet 1994; 243: 500-5.
52. Garrigue AL, Munoz AT, Antonia SJ, Gesmonde J, Vellucci VF, Reiss M. Missense mutations of the transforming growth factor β type II receptor in human head and neck squamous carcinoma cells. Cancer Res 1995; 55: 3982-7.
53. Yanson IK, Teplitsky AB, Sukhodub LF. Experimental studies of molecular interactions between nitrogen bases of nucleic acids. Biopolymers 1979; 18: 1149-70.