5′,8-Cyclopurine-2′-deoxynucleosides: Molecular structure and charge distribution - DFT study in gaseous and aqueous phase

Journal of Molecular Structure: THEOCHEM

Volumn 915, Issue 1-3, 2009, Pages 73-78

  Karwowski, Boleslaw T ^a  

^a MEDICAL UNIVERSITY OF LODZ   (Poland)

Author keywords

Charge distribution; DFT; Dipole moment; Molecular structure; Tandem base lesion

Indexed keywords

EID: 70350133384     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2009.08.020     Document Type: Article

References (58)

1. Watson D.J., and Crick F.H.C. Nature 171 (1953) 737
2. Saenger W. Principles of Nucleic Acid Structure (1984), Springer-Verlag, New York Inc.
3. Bugg C.B., and Ealick S.E. Crystallographic and Modeling Methods in Molecular Design (1990), Springer, New York
4. Kennard O., and Hunter W.N. Angew. Chem. Int. Ed. Engl. 30 (1991) 1254
5. Wijmenga S.S., and van Buuren N.N.M. Prog. Nucl. Magn. Reson. Spectrosc. 32 (1998) 287
6. Bloomfield V.A., Crothers D.M., and Tinco Jr. I. Nucleic Acids Structures, Properties and Function (2000), University Science Books, Sausalito, CA
7. Hecht S.M. Bioorganic Chemistry: Nucleic Acids (1994), Oxford University Press, Oxford
8. Cadet J., Douki T., and Ravanat J.-L. Redox-Genome Interactions in Health and Disease (2003), Marcel Dekker, Inc., New York
9. Cadet J., Douki T., Gasparutto D., and Ravanat J.-L. Mutat. Res. 531 (2003) 5
10. Miaskiewicz K., Miller J.H., and Fuciarelli A.F. Nucleic Acids Res. 23 (1995) 515
11. Chatgilialoglu C., Guerra M., and Mulazzani Q.G.J. J. Am. Chem. Soc. 125 (2003) 3839
12. Flyunt R., Bazzanini R., Chatgilialoglu C., and Mulazzani Q.G.J. J. Am. Chem. Soc. 122 (2000) 4225
13. Chatgilialoglu C., Bazzanini R., Jimenez L.B., and Miranda M.A. Chem. Res. Toxicol. 20 (2007) 1820
14. Boussicault F., Kaloudis P., Caminal C., Quinto G., Mulazzani G.G., and Chatgilialoglu C. J. Am. Chem. Soc. 130 (2008) 8377
15. bo Zhang R., and Eriksson L.A. Chem. Phys. Lett. 417 (2006) 303
16. Dizdaroglu M., Jaruga P., and Rodriguez H. Free Radical Biol. Med. 30 (2001) 774
17. Jaruga P., Birincioglu M., Rodriguez H., and Dizdaroglu M. Biochemistry 41 (2002) 3703
18. Schroder E.E., Budzinski J.C., Wallace J.D., Zimbrick J.D., and Box H.C. Int. J. Radiat. Biol. 68 (1995) 509
19. Dirksen M.-L., Brakely W.F., Holwitt E., and Dizdaroglu M. Int. J. Radiat. Biol. 54 (1998) 195
20. Brooks B.J. Neuroscience 145 (2007) 1407
21. Kuraoka I., Robins P., Masutani C., Hanaoka F., Gasparutto D., Cadet J., Wood R.D., and Lindahl T. J. Biol. Chem. 276 (2001) 49283
22. Cadet J., Douki T., Gasparutto D., and Ravanat J.-L. Radiat. Phys. Chem. 72 (2005) 293
23. Altieri F., Grillo C., Maceroni M., and Chicharelli S. Antioxid. Redox Signal. 10 (2008) 891
24. Gasparutto D., Bourdat A.G., D'Ham C., Durate V., and Cadet J. Biochimie 82 (2000) 19
25. Romieu A., Gasparutto D., Molko D., and Cadet J. J. Org. Chem. 63 (1998) 5245
26. Romieu A., Gasparutto D., and Cadet J. Chem. Res. Toxicol. 12 (1999) 412
27. Matsuda A., Muneyama K., Nishida T., Sato T., and Ueda T. Nucleic Acids Res. 12 (1979) 3349
28. Karwowski B., Gaillard J., Grand A., and Cadet J. Org. Biomol. Chem. 6 (2008) 3408
29. Karwowski B. Tetrahedron Asymmetry 19 (2008) 2390
30. Ababneh M.A., Large C.C., and Georghiou S.J. J. Appl. Sci. Res. 11 (2007) 1288
31. Hehre W.J., Radom L., Schleyer P., and Pople R.J.A. Ab Initio Molecular Orbital Theory (1986), Wiley, New York
32. Krishnan R., Schlegel H.B., and Pople J.A. J. Chem. Phys. 72 (1980) 4654
33. Nguyen L.T., Le T.N., and Nguyen M.T. J. Chem. Soc. Faraday Trans. 94 (1998) 3541
34. Miertus S., and Tomasi J. Chem. Phys. 65 (1982) 239
35. Gaussian 03, Revision D.01, 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, 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, J.A. Pople, Gaussian, Inc., Pittsburgh PA, 2003.
36. Chu C.K., and Backer D.C. Nucleosides and Nucleotides as Antitumor and Antiviral Agents (1993), Plenum Press, New York
37. Evangelista F.A., and Schaefer III H.F. J. Phys. Chem. A 108 (2004) 10258
38. Klipartic E.J., Pitzer K.S., and Spitzer R. J. Am. Chem. Soc. 69 (1947) 2483
39. Altona C., and Sundaralingam M. J. Am. Chem. Soc. 15 (1972) 8205
40. Shishkin O.V., Pelmenschikov A., Hovorun D.M., and Leszczynski J. J. Mol. Struct. 526 (2000) 329
41. Freier S.M., and Altmann K.-H. Nucleic Acids. Res. 25 (1997) 4429
42. Sarmah P., and Deka R.C. Mol. Simul. 34 (2008) 879
43. Ghosh A., Joy A., Shuster G.B., Douki T., and Cadet J. Org. Biomol. Chem. 6 (2008) 916
44. Barnett R.N., Cleveland C.L., Landman U., Boone E., Kanvah S., and Schuster G.B. J. Phys. Chem. A 107 (2003) 3525
45. Takada T., Kawai K., Fujitsuka M., and Majima T. Proc. Natl. Acad. Sci. USA 101 (2004) 14002
46. Kawai K., Takada T., Tojo S., and Majima T. J. Am. Chem. Soc. 125 (2003) 6842
47. Kawai K., Takada T., Tojo S., and Majima T. J. Am. Chem. Soc. 126 (2004) 1125
48. Takada T., Kawai K., Fujitsuka M., and Majima T. J. Am. Chem. Soc. 128 (2006) 11012
49. Giese B. Curr. Opin. Chem. Biol. 6 (2002) 612
50. Gise B. Acc. Chem. Res. 33 (2002) 631
51. Rihardson A.N., Gu J., Wang S., Xie Y., and Schaefer III H.F. J. Am. Chem. Soc. 126 (2004) 4404-4411
52. Rienstra-Kiracofe J.C., Tschumper G.S., and Scheafer III H.F. Chem. Rev. 102 (2002) 231
53. Dolgounitcheva O., Zakrzewski V.G., and Ortiz J.V. J. Phys. Chem. 105 (2001) 8782
54. Defrancois C., Abdoul-Carime H., Khelifa N., Scherman J.-P., Brenner V., and Millie P. J. Phys. Chem. 102 (1995) 4952
55. Davis B.D., et al. Pure Appl. Chem. 55 (1983) 1273
56. Follmann H., Küntz I., and Zacharias W. Eur. J. Biochem. 58 (1975) 31
57. Pettegrew J.W., Miles D.W., and Eyring H. Proc. Natl. Acad. Sci. USA 74 (1977) 1785
58. Oyler N.A., and Adamowicz L. J. Phys. Chem. 97 (1993) 11122