NMR structure of duplex DNA containing the α-OH-PdG · dA base pair: A mutagenic intermediate of acrolein

Biopolymers

Volumn 93, Issue 4, 2010, Pages 391-401

  Zaliznyak, Tanya ^a   Lukin, Mark ^a   El khateeb, Mahmoud ^a   Bonala, Rahda ^a   Johnson, Francis ^a   de los Santos, Carlos ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

Acrolein adducts; Damaged DNA structure; DNA lesions; NMR structure

Indexed keywords

ANTI ORIENTATION; BASE PAIRS; CIGARETTE SMOKES; DNA DUPLEXES; DNA LESIONS; DNA STRUCTURE; DUPLEX DNA; HYDROGEN BOND INTERACTION; MAIN COMPONENT; METABOLIC PRODUCTS; MOLECULAR DYNAMICS SIMULATIONS; NMR DATA; NMR STRUCTURES; PROTON SIGNALS; PROTONATED; RIGHT-HANDED HELIX; SOLUTION STRUCTURES; THREE-DIMENSIONAL STRUCTURE; WATSON-CRICK BASE PAIRS;

ALDEHYDES; DNA; GENES; HERBICIDES; HYDROGEN BONDS; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; RESONANCE;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ACROLEIN; ALPHA HYDROXYPROPANODEOXYGUANOSINE; DEOXYGUANOSINE DERIVATIVE; DOUBLE STRANDED DNA; UNCLASSIFIED DRUG;

ARTICLE; BASE PAIRING; CHEMICAL STRUCTURE; DNA CONFORMATION; DNA FLANKING REGION; DNA REPLICATION; DNA STRUCTURE; ENANTIOMER; HYDROGEN BOND; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEIC ACID BASE SUBSTITUTION; PROTON TRANSPORT;

ACROLEIN; DEOXYADENOSINES; DEOXYGUANOSINE; DNA; DNA DAMAGE; MODELS, MOLECULAR; MOLECULAR DYNAMICS SIMULATION; MUTAGENS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; NUCLEIC ACID CONFORMATION; OLIGONUCLEOTIDES;

EID: 77949892043     PISSN: 00063525     EISSN: 10970282     Source Type: Journal    
DOI: 10.1002/bip.21366     Document Type: Article

References (40)

1. Izard, C.; Libermann, C. Mutat Res 1978, 47, 115-138.
2. Roemer, E.; Stabbert, R.; Rustemeier, K.; Veltel, D. J.; Meisgen, T. J.; Reininghaus, W.; Carchman, R. A.; Gaworski, C. L.; Podraza, K. F. Toxicology 2004, 195, 31-52.
3. Zhang, S.; Villalta, P. W.; Wang, M.; Hecht, S. S. Chem Res Toxicol 2007, 20, 565-571.
4. Esterbauer, H.; Schaur, R. J.; Zoller, H. Free Radical Biol Med 1991, 11, 81-128.
5. Wu, H.-Y.; Lin, Y.-L. Anal Chem 1995, 76, 1603-1612.
6. Chung, F. L.; Nath, R. G.; Nagao, M.; Nishikawa, A.; Zhou, G. D.; Randerath, K. Mutat Res 1999, 242, 71-81.
7. Lee, Y.; Sayre, L. M. J Biol Chem 1998, 273, 19490-19494.
8. Alarcon, R. A. Cancer Treat Rep 1976, 60, 327-335.
9. McDiarmid, M. A.; Iype, P. T.; Kolodner, K.; Jacobson-Kram, D.; Strickland, P. T. Mutat Res 1991, 248, 93-99.
10. Galliani, G.; Pantarotto, C. Tetrahedron Lett 1983, 24, 4491-4492.
11. Chung, F. L.; Young, R.; Hecht, S. S. Cancer Res 1984, 44, 990-995.
12. Uchida, K.; Kanematsu, M.; Sakai, K.; Matsuda, T.; Hattori, N.; Mizuno, Y.; Suzuki, D.; Miyata, T.; Noguchi, N.; Niki, E.; Osawa, T. Proc Natl Acad Sci USA 1998, 95, 4882-4887.
13. Marnett, L. J.; Hurd, H. K.; Hollstein, M. C.; Levin, D. E.; Esterbauer, H.; Ames, B. N. Mutat Res 1985, 148, 25-34.
14. Curren, R. D.; Yang, L. L.; Conklin, P. M.; Grafstrom, R. C.; Harris, C. C. Mutat Res 1988, 209, 17-22.
15. Smith, R. A.; Cohen, S. M.; Lawson, T. A. Carcinogenesis 1990, 11, 497-498.
16. Kawanishi, M.; Matsuda, T.; Nakayama, A.; Takebe, H.; Matsui, S.; Yagi, T. Mutat Res 1998, 417, 63-75.
17. Khullar, S.; Varaprasad, C. V.; Johnson, F. J. Med Chem 1999, 42, 947-950.
18. Nechev, L. V.; Harris, C. M.; Harris, T. M. Chem Res Toxicol 2000, 13, 421-429.
19. Huang, Y.; Torres M. C.; Iden, C. R.; Johnson F. Bioorg Chem 2003, 31, 136-148.
20. Yang, I.-Y.; Hossain, M.; Miller, H.; Khullar, S.; Johnson, F.; Grollman, A.; Moriya, M. J Biol Chem 2001, 276, 9071-9076.
21. Vander Veen, L. A.; Hashim, M. F.; Nechev, L. V.; Harris, T. M.; Harris, C. M.; Marnett, L. J. J Biol Chem 2001, 276, 9066-9070.
22. Yang, I.-Y.; Johnson, F.; Grollman, A. P.; Moriya, M. Chem Res Toxicol 2002, 15, 160-164.
23. Yang, I.-Y.; Chan, G.; Miller, H.; Huang, Y.; Torres, M. C.; Johnson, F.; Moriya, M. Biochemistry 2002, 41, 13826-13832.
24. de los Santos, C.; Zaliznyak, T.; Johnson, F. J Biol Chem 2001, 276, 9077-9082.
25. Zaliznyak, T.; Bonala, R.; Attaluri S.; Johnson, F.; de los Santos, C. Nucleic Acids Res 2009, 37, 2153-2163.
26. Minetti, C. A. S. A.; Remeta, D. P.; Johnson, F.; Iden, C. R.; Breslauer, K. J. Biopolymers 2010, 93, 370-382.
27. States, D. J.; Habekorn, R. A.; Ruben, D. J. J Mag Res 1982, 48, 286-292.
28. Plateau P.; Gueron M. J. Am Chem Soc 1982, 104, 7310-7311.
29. Brünger, A. XPLOR Version 3.1 A system for X-Ray Crystallography and NMR; Yale University Press: New Haven, CT, 1993.
30. Brooks, B. R.; Buccoleri, R. E.; Olafson, B. D.; States, D. J.; Swaminathan, S.; Karplus, M. J Comput Chem 1983, 4, 187-217.
31. Friedman, R. A.; Honig, B. Biopolymers 1992, 32, 145-159.
32. Yip, P.; Case, D. A. J Magn Reson 1989, 83, 643-648.
33. Lavery, R.; Sklenar, H. J Biomol Struct Dyn 1988, 6, 655-667.
34. Pettersen, E. F.; Goddard, T. D.; Huang, C. C.; Couch, G. S.; Greenblatt, D. M.; Meng, E. C.; Ferrin, T. E. J Comput Chem 2004, 25, 1605-1612.
35. van de Ven, F. J. M.; Hilbers, C. W. J Biochem 1988, 178, 1-38.
36. de los Santos, C. In Comprehensive Natural Products Chemistry, Barton D.; Nakanishi, K.; Meth-Cohn, O., Eds., Vol. 7; Elsevier Science Ltd.: Oxford, 1999; Chapter 3.
37. Sanchez, A. M.; Minko, I. G.; Kurtz, A. J.; Kanuri, M.; Moriya, M.; Lloyd, R. S. Chem Res Toxicol 2003, 16, 1019-1028.
38. Nair, D. T.; Johnson, R. E.; Prakash, L.; Prakash, S.; Aggarwal, A. K. Structure 2008, 16, 239-245.
39. Nair, D. T.; Johnson, R. E.; Prakash, S.; Prakash, L.; Aggarwal, A. K. Nature 2004, 430, 377-380.
40. Prakash, S.; Johnson, R. E.; Prakash, L. Annu Rev Biochem 2005, 74, 317-53.