Reaction of acrolein with 2′-deoxyadenosine and 9-ethyladenine - Formation of cyclic adducts

Bioorganic Chemistry

Volumn 34, Issue 1, 2006, Pages 39-48

  Pawłowicz, Agnieszka J ^a   Munter, Tony ^a   Klika, Karel D ^b   Kronberg, Leif ^a  

^a ÅBO AKADEMI UNIVERSITY   (Finland)

^b UNIVERSITY OF TURKU   (Finland)

Author keywords

2 Deoxyadenosine adducts; 9 Ethyladenine; Acrolein; Bicyclic adduct; Stereochemistry; Structural assignment

Indexed keywords

9 ETHYLADENINE; ACROLEIN; ADENINE DERIVATIVE; DEOXYADENOSINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; DIASTEREOISOMER; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; ULTRAVIOLET RADIATION;

ACROLEIN; ADENINE; DEOXYADENOSINES; DNA ADDUCTS; HYDROGEN-ION CONCENTRATION; MODELS, CHEMICAL; SPECTRUM ANALYSIS; STEREOISOMERISM;

EID: 31744440590     PISSN: 00452068     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bioorg.2005.10.006     Document Type: Article

References (28)

1. R.G. Nath, J.E. Ocando, J.B. Guttenplan, and F.-L. Chung Cancer Res. 58 1998 581 584
2. International Agency for Research on Cancer. Evaluation of the Carcinogenic Risk of Chemicals to Humans. IARC Monograph 19 (1979) 479-494.
3. International Agency for Research on Cancer. Evaluation of the Carcinogenic Risk of Chemicals to Humans. IARC Monograph 36 (1985) 133-177.
4. K. Uchida, M. Kanematsu, Y. Morimitsu, T. Osawa, N. Noguchi, and E. Niki J. Biol. Chem. 273 1998 16058 16066
5. F.-L. Chung, R.G. Nath, M. Nagao, A. Nishikawa, G.D. Zhou, and K. Randerath Mutat. Res. 424 1999 71 81
6. J. Pan, and F.-L. Chung Chem. Res. Toxicol. 15 2002 367 372
7. L.J. Marnett, H.K. Hurd, M.C. Hollstein, D.E. Levin, H. Esterbauer, and B.N. Ames Mutat. Res. 148 1985 25 31
8. R.D. Curren, L.L. Yang, P.M. Conklin, R.C. Grafstrom, and C.C. Harris Mutat. Res. 209 1988 17 22
9. R.A. Smith, S.M. Cohen, and T.A. Lawson Carcinogenesis 11 1990 497 498
10. F.-L. Chung, R. Young, and S.S. Hecht Cancer Res. 44 1984 990 995
11. F.-L. Chung, K.R. Roy, and S.S. Hecht J. Org. Chem. 53 1988 14 17
12. E.R. Marinelli, F. Johnson, C.R. Iden, and P.-L. Yu Chem. Res. Toxicol. 3 1990 49 58
13. R.A. Smith, D.S. Williamson, R.L. Cerny, and S.M. Cohen Cancer Res. 50 1990 3005 3012
14. P. Virta, A. Koch, M.U. Roslund, P. Mattjus, E. Kleinpeter, L. Kronberg, R. Sjöholm, and K.D. Klika Org. Biomol. Chem. 3 2005 2924 2929
15. M.U. Roslund, P. Virta, and K.D. Klika Org. Lett. 6 2004 2673 2676
16. J. Mäki, K.D. Klika, R. Sjöholm, and L. Kronberg J. Chem. Soc. Perkin Trans. 1 2001 1216 1219
17. J. Mäki, P. Tähtinen, L. Kronberg, and K.D. Klika J. Phys. Org. Chem. 18 2005 240 249
18. S. Berger, S. Braun, H.O. Kalinowski, in: NMR Spectroscopy of the Non-Metallic Elements, Wiley, Chichester, 1997, English Edition, Ch. 4.
19. J. Arpalahti, and K.D. Klika Eur. J. Inorg. Chem. 1999 1199 1201
20. K.D. Klika, and J. Arpalahti J. Chem. Soc. Chem. Commun. 2004 666 667
21. See for example: R. Laatikainen, M. Niemitz, U. Weber, J. Sundelin, T. Hassinen, J. Vepsäläinen, J. Magn. Reson. Ser. A 120 (1996) 1-10.
22. See also: Peak Research NMR Software, Perch Solutions Ltd., Kuopio, Finland, 2003. Available from: 〈 http://www.perchsolutions.com〉.
23. A. Rosling, K. Klika, F. Fülöp, R. Sillanpää, and J. Mattinen Heterocycles 51 1999 2575 2588
24. A. Rosling, K. Klika, F. Fülöp, R. Sillanpää, and J. Mattinen Acta Chem. Scand. 53 1999 103 113
25. A. Rosling, M. Hotokka, K. Klika, F. Fülöp, R. Sillanpää, and J. Mattinen Acta Chem. Scand. 53 1999 213 221
26. P. Tähtinen, A. Bagno, K.D. Klika, and K. Pihlaja J. Am. Chem. Soc. 125 2003 4609 4618
27. J.B. Macon, and R. Wolfenden Biochemistry 7 1968 3453 3458
28. T. Fujii, and T. Itaya Heterocycles 48 1998 359 390