Radiation-induced formation of purine 5′,8-cyclonucleosides in isolated and cellular DNA: High stereospecificity and modulating effect of oxygen

Organic and Biomolecular Chemistry

Volumn 8, Issue 14, 2010, Pages 3211-3219

  Belmadoui, Nourreddine ^a   Boussicault, Fabien ^b   Guerra, Maurizio ^b   Ravanat, Jean Luc ^a   Chatgilialoglu, Chryssostomos ^b   Cadet, Jean ^a  

^a UNIV GRENOBLE ALPES   (France)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYADENOSINE; DEOXYRIBONUCLEOSIDES; DIASTEREOMERS; HPLC-MS ANALYSIS; HPLC-MS/MS; INHIBITORY EFFECT; INTRAMOLECULAR ADDITIONS; MODULATING EFFECT; ORDERS OF MAGNITUDE; RADIATION-INDUCED; STEREOSPECIFICITY;

DNA; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXYGEN;

GENES;

DNA; HYDROXYL RADICAL; OXYGEN; PURINE NUCLEOSIDE; WATER;

ANIMAL; ARTICLE; CATTLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; CYCLIZATION; DNA DAMAGE; DNA REPAIR; DRUG EFFECT; ENZYME SPECIFICITY; GAMMA RADIATION; GENETICS; HUMAN; METABOLISM; MONOCYTE; RADIATION EXPOSURE; STEREOISOMERISM; BOVINAE; DRUG EFFECTS; RADIATION RESPONSE;

ANIMALS; CATTLE; CYCLIZATION; DNA; DNA DAMAGE; DNA REPAIR; GAMMA RAYS; HUMANS; HYDROXYL RADICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MONOCYTES; OXYGEN; PURINE NUCLEOSIDES; STEREOISOMERISM; SUBSTRATE SPECIFICITY; WATER;

EID: 77954580095     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c004531d     Document Type: Article

References (65)

1. C. J. Burrows J. G. Muller Chem. Rev. 1998 98 1109 1151
2. J. Cadet T. Douki D. Gasparutto J.-L. Ravanat Mutat. Res., Fundam. Mol. Mech. Mutagen. 2003 531 5 23
3. J. Cadet, T. Douki and J.-L. Ravanat, in The Chemical Biology of DNA Damage, ed., N. E. Geacintov,, and, S. S. Broyde,, Wiley-VCH Verlag, Veinheim, 2010, 53-80
4. H. C. Box H. G Freund E. E. Budzinski J. C. Wallace A. E. MacCubbin Radiat. Res. 1995 141 91 94
5. T. Douki J. Rivière J. Cadet Chem. Res. Toxicol. 2002 15 445 454
6. I. S. Hong K. N. Carter K. Sato M. M. Greenberg J. Am. Chem. Soc. 2007 129 4089 4098
7. P. Jaruga M. Dizdaroglu DNA Repair 2008 7 1413 1425
8. Y. Wang Chem. Res. Toxicol. 2008 21 276 281
9. Z. Keck Naturforsch. 1968 23b 1034 1043
10. N. Mariaggi J. Cadet R. Téoule Tetrahedron 1976 32 2385 2387
11. J. A. Raleigh W. Kremers R. Whitehouse Radiat. Res. 1976 65 414 422
12. M. Dizdaroglu Biochem. J. 1986 238 247 254
13. P. Jaruga Y. Xian B. C. Nelson M. Dizdaroglu Biochem. Biophys. Res. Commun. 2009 386 656 666
14. F. Boussicault P. Kaloudis C. Caminal Q. G. Mulazzani C. Chatgilialoglu J. Am. Chem. Soc. 2008 130 8377 8385
15. P. J. Brooks D. S. Wise; D. A. Berry; J. V. Kosmoski; M. J. Smerdon R. L. Somers H. Mackie A. Y. Spoonde E. J. Ackerman K. Coleman R. E. Tarone J. H. Robbins J. Biol. Chem. 2000 275 22355 22362
16. I. Kuraoka C. Bender A. Romieu J. Cadet R. D. Wood T. Lindahl Proc. Natl. Acad. Sci. U. S. A. 2000 97 3832 3837
17. P. J. Brooks Neuroscience 2007 145 1407 1417
18. P. J. Brooks DNA Repair 2008 7 1168 1179
19. I. Kuraoka P. Robins C. Masutani F. Hanaoka D. Gapsarutto J. Cadet R. D. Woods T. Lindahl J. Biol. Chem. 2001 276 49283 49288
20. G. Kirkali N. C. de Souza-Pinto P. Jaruga V. A. Bohr M. Dizdaroglu, M. DNA Repair 2009 8 274 278
21. M. Dizdaroglu P. Jaruga H. Rodriguez Free Radical Biol. Med. 2001 30 774 784
22. P. Jaruga M. Birincioglu H. Rodriguez M. Dizdaroglu Biochemistry 2002 41 3703 3711
23. A. Romieu D. Gasparutto J. Cadet Chem. Res. Toxicol. 1999 12 412 421
24. A. D. Becke Phys. Rev. A: At., Mol., Opt. Phys. 1988 38 3098 3100
25. A. D. Becke J. Chem. Phys. 1996 104 1040 1046
26. Y. Zhao B. J. Lynch D. G. Truhlar J. Phys. Chem. A 2004 108 2715 2719
27. 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, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, 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, C. Gonzalez and J. A. Pople, Gaussian 03, Revision D.2, Gaussian, Inc., Wallingford CT, 2004
28. J. Tomasi B. Menucci E. Cances THEOCHEM 1999 464 211 226
29. J. W. T. Spink and R. J. Woods, in An Introduction to Radiation Chemistry, Wiley, New York, 3rd edn, 1990, p. 100
30. G. V. Buxton C. L. Greenstock, C. L. W. P. Helman A. B. Ross J. Phys. Chem. Ref. Data 1988 17 513 886
31. Ross, W. G. Mallard, W. P. Helman, G. V. Buxton, R. E. Huie and P. Neta, NDRL-NIST Solution Kinetic Database - Ver. 3, Notre Dame Radiation Laboratory, Notre Dame, IN and NIST Standard Reference Data, Gaithersburg, MD, 1998
32. B. H. T. Bielski D. E. Cabelli R. L. Arudi J. Phys. Chem. Ref. Data 1985 14 1041 1100
33. R. Battino T. R. Rettich T. Tominaga J. Phys. Chem. Ref. Data 1983 12 163 178
34. R. Zander Z. Naturforsch. 1976 31C 339 352
35. R. Zander Adv. Exp. Med. Biol. 1976 75 463 467
36. J.-L. Ravanat B. Duretz A. Guiller T. Douki J. Cadet J. Chromatogr., B: Biomed. Sci. Appl. 1998 715 349 356
37. S. Frelon T. Douki J.-L. Ravanat J.-P. Pouget C. Tornabene J. Cadet Chem. Res. Toxicol. 2000 13 1002 1010
38. C. Chatgilialoglu M. Guerra Q. G. Mulazzani J. Am. Chem. Soc. 2003 125 3839 3848
39. C. Chatgilialoglu R. Bazzanini L. B. Jimenez M. A. Miranda Chem. Res. Toxicol. 2007 20 1820 1824
40. M. Guerra R. Amorati G. F. Peduli J. Org. Chem. 2004 69 5460 5467
41. S. W. Benson, in Thermochemical Kinetics, Wiley, New York, 2nd edn, 1976
42. T. Douki J.-L. Ravanat J.-P. Pouget I. Testard J. Cadet Int. J. Radiat. Biol. 2006 82 119 127
43. P. Jaruga J. Theruvathu M. Dizdaroglu P. J. Brooks P. Nucleic Acids Res. 2004 32 e87
44. J.-L. Ravanat T. Douki P. Duez E. Gremaud K. Herbert T. Hofer J. Lasserre C. Saint-Pierre A. Favier J. Cadet Carcinogenesis 2002 23 1911 1918
45. P. Regulus S. Spessotto M. Gateau J. Cadet A. Favier J.-L. Ravanat Rapid Commun. Mass Spectrom. 2004 18 2223 2228
46. J. M. Falcone H. C. Box Biochim. Biophys. Acta, Protein Struct. Mol. Enzymol. 1997 1337 267 275
47. K. S. Lim A. Jenner B. Halliwell Nat. Protoc. 2006 1 1995 2002
48. H. Hong H. Cao Y. Wang Nucleic Acids Res. 2007 35 7118 7127
49. J. Cadet T. Douki J.-L. Ravanat Acc. Chem. Res. 2008 41 1075 1083
50. P. C. Dedon Chem. Res. Toxicol. 2008 21 206 219
51. C. Chatgiglialoglu, in Radical and Radical Ion Reactivity in Nucleic Acid Chemistry, ed., M. M. Greenberg,, Wiley, New Jersey, 2009, pp. 99-133
52. D. Sy C. Savoye M. Begusova V. Michalik M. Charlier M. Spotheim-Maurizot Int. J. Radiat. Biol. 1997 72 147 155
53. W. K. Pogozelski T. D. Tullius Chem. Rev. 1998 98 1089 1108
54. C. von Sonntag, in Free-Radical-Induced DNA Damage and Its Repair: A Chemical Perspective, Springer-Verlag, Berlin, 2006
55. A. Manetto D. Georganakis T. Gimisis L. Leondiadis P. Mayer T. Carell C. Chatgilialoglu J. Org. Chem. 2007 72 3659 3666
56. M. Russo L. B. Jimenez Q. G. Mulazzani M. D'Angelantonio M. Guerra M. A Miranda C. Chatgilialoglu Chem.-Eur. J. 2006 12 7684 7693
57. M.-L. Dirksen W. F. Blakely E. Holwitt M. Dizdaroglu Int. J. Radiat. Biol. 1988 54 195 204
58. P. Jaruga M. Birincioglu H. Rodriguez M. Dizdaroglu Biochemistry 2002 41 3703 3711
59. R. A. Egler E. Fernandes K. Rothermund S. Sereika N. de Souza-Pinto P. Jaruga M. Dizdaroglu E. V. Prochownick Oncogene 2005 24 8038 8050
60. M. D'Errico E. Parlanti M. Teson B. M. Bernardes de Jesus P. Degan A. Calcagnile P. Jaruga M. BjØrås M. Crescenzi A. M. Pedrini J.-M. Egly G. Zambruno M. Stefanini M. Dizdaroglu E. Dogliotti EMBO J. 2006 25 4305 4315
61. M. D'Errico E. Parlanti M. Teson P. Degan T. Lemma A. Calcagnile I. Iavarone P. Jaruga M. Ropolo A. M. Pedrini D. Orioli G. Frosina G. Zambruno M. Dizdaroglu M. Stefanini E. Dogliotti Oncogene 2007 26 4336 4343
62. K. Randerath E. randerath G.-D. Zhou D. Li Mutat. Res., Fundam. Mol. Mech. Mutagen. 1999 424 183 194
63. K. Randerath G.-D. Zhou R. L. Somers J. H. Robbins P. J. Brooks J. Biol. Chem. 2001 276 36051 36057
64. J. Cadet H. Poulsen Free Radic. Biol. Med. 2010 48 1457 1459
65. J. Cadet T. Douki J.-L. Ravanat Free Radic. Biol. Med. 2010 49 9 21