A practical approach for the chemical synthesis of 2′-deoxyguanosine-C8 adducts with mutagenic/carcinogenic amino- or nitro-arenes

Tetrahedron Letters

Volumn 44, Issue 32, 2003, Pages 5969-5973

  Takamura Enya, Takeji ^a   Ishikawa, Satoko ^b   Mochizuki, Masataka ^b   Wakabayashi, Keiji ^a  

^a NATIONAL CANCER CENTER RESEARCH INSTITUTE   (Japan)

^b KEIO UNIVERSITY   (Japan)

Author keywords

Arylamination reaction; DG C8 adducts

Indexed keywords

AROMATIC NITRO COMPOUND; CARCINOGEN; DEOXYGUANOSINE; MUTAGENIC AGENT; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

AMINATION; ARTICLE; CHEMICAL REACTION; DEPROTECTION REACTION; SYNTHESIS;

EID: 0037629746     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01484-9     Document Type: Article

References (27)

1. Paputa-Peck M.C., Marano R.S., Schuetzle D., Riley T.L., Hampton C.V., Prater T.J., Skewes L.M., Jensen T.E., Ruele P.H., Bosch L.C., Duncan W.P. Anal. Chem. 55:1983;1946-1954.
2. Schuetzle D. Environ. Health Perspect. 47:1983;65-80.
3. Djozan Dj., Faraj-Zadeh M.A. Chromatographia. 41:1995;568-572.
4. Rivera L., Cutro M.J.C., Galceran M.T., Puignou L. J. Chromatogr. A. 731:1996;85-94.
5. Reistad R., Rossland O.J., Latva-Kala K.J., Rasmussen T., Viske R., Becher G., Alexander J. Food Chem. Toxicol. 35:1997;945-955.
6. Less M., Schmidt T.C., von Löu E., Strok G. J. Chromatogr. A. 810:1998;173-182.
7. Purohit V., Basu K. Chem. Res. Toxicol. 13:2000;673-692.
8. Tokiwa H., Ohnishi Y. CRC Crit. Rev. Toxicol. 17:1986;23-60 IARC Monographs on the Evaluation of Carcinogenic Risk to Humans; International Agency for Research on Cancer (IARC), Lyon, 1989; Vol. 46.
9. Beland F.A., Marques M.M. DNA Adducts: Identification and Biological Significance. 125:1984;229-244 IARC, Lyon.
10. Fu P.P. Drug Metabolism Rev. 22:1990;209-268 Food Borne Carcinogens, Heterocyclic Amines; Nagao, M.; Sugimura, T., Ed.; John Wiley & Sons Ltd: Chichester, UK, 2000.
11. Fu P.P. Drug Metabolism Rev. 22:1990;209-268 Food Borne Carcinogens, Heterocyclic Amines; Nagao, M.; Sugimura, T., Ed.; John Wiley & Sons Ltd: Chichester, UK, 2000.
12. Brown K., Guenther E.A., Dingley K.H., Cosman M., Harvey C.A., Shields S.J., Turteltaub K.W. Nucleic Acids Res. 29:2001;1951-1959.
13. Hartwig J.F. Synlett. 4:1997;329-340.
14. Lakshman M.K., Hilmer J.H., Martin J.Q., Keeler J.C., Dinh Y.Q.V., Ngassa F.N., Russon L.M. J. Am. Chem. Soc. 123:2001;7779-7787. and references cited therein.
15. Wang Z., Rizzo C.J. Org. Lett. 3:2001;565-568.
16. Gillet L.C., Scharer O.D. Org. Lett. 4:2002;4205-4208.
17. Meier C., Gräsl S. Synlett. 2002;802-804.
18. Enya T., Suzuki H., Watanabe T., Hirayama T., Hisamatsu Y. Environ. Sci. Technol. 31:1997;2772-2776.
19. Saneyoshi M. Chem. Pharm. Bull. 16:1968;1616-1619.
20. Soli E.D., Manoso A.S., Patterson M.C., DeShong P., Favor D.A., Hirschmann R., Smith A.B. III. J. Org. Chem. 64:1999;3171-3177.
21. 6: 675.2931).
22. Wolfe J.P., Tomori H., Sadighi J.P., Yin J., Buchwald S.L. J. Org. Chem. 65:2000;1158-1174.
23. Lakshman M.K., Keeler J.C., Hilmer J.H., Martin J.Q. J. Am. Chem. Soc. 121:1999;6090-6091.
24. Laksman M.K., Hilmer J.H., Martin J.Q., Keeler J.C., Dinh Y.Q.V., Ngassa F.N., Russon L.M. J. Am. Chem. Soc. 123:2001;7779-7787.
25. 2: 1103.5287).
26. 3, and materials were extracted with dichloromethane. The organic layer was combined, dried and evaporated, and the residue was chromatographed on silica gel using hexane-ethylacetate as an eluent.
27. +).