Selective N1-alkylation of 2′-deoxyguanosine with a quinolinyl quinone methide

Chemical Research in Toxicology

Volumn 20, Issue 8, 2007, Pages 1069-1074

  Zhou, Qibing ^a   Xu, Ting ^a   Mangrum, John B ^a  

^a VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; DEOXYGUANOSINE; FLUORIDE; GUANINE; N,N DIMETHYLFORMAMIDE; PHOSPHATE BUFFERED SALINE; QUINOLINYL QUINONE METHIDE; QUINONE DERIVATIVE; SODIUM CHLORIDE; UNCLASSIFIED DRUG;

ADDUCTION; ALKYLATION; AQUEOUS SOLUTION; ARTICLE; DESILYLATION; ELIMINATION REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; PH;

ACETATES; ALKYLATION; BUFFERS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEOXYGUANOSINE; DIMETHYLFORMAMIDE; DNA ADDUCTS; FLUORIDES; HYDROGEN-ION CONCENTRATION; INDOLEQUINONES; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; SILICON; SOLVENTS;

EID: 34548492719     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx700162d     Document Type: Article

References (32)

1. Gates, K. S. (1999) Covalent Modification of DNA by Natural Products. In Comprehensive Natural Products Chemistry (Barton, D., Nakanishi, K., Meth-Cohn, O., and Kool, E. T., Eds.) Vol. 7, pp 491-552, Elsevier, New York.
2. Thompson, D. C., Thompson, J. A., Sugumaran, M., and Moldeus, P. (1992) Biological and toxical consequences of quinone methide formation. Chem.-Biol. Interact. 86, 129-162.
3. Moore, H. W., and Czerniak, R. (1981) Naturally occurring quinones as potential bioreductive alkylating agents. Med. Res. Rev. 1, 249-280.
4. Grünanger, P. (1979) Chinomethide. In Methoden der Organisch Chemie (Muller, E., and Bayer, O., Eds.) Vol. VII/3b, pp 395-521, Houben-Weyl, Stuttgart, Germany.
5. Wagner, H. U., and Gompper, R. (1974) Quinone methides. In The Chemistry of Quinonoid Compound (Patai, S., Ed.) Vol. 1, pp 1145-1178, John Wiley & Sons, New York.
6. Turner, A. B. (1964) Quinone methides. Chem. Soc. Rev. 18, 347-360.
7. Dowers, T. S., Qin, Z.-H., Thatcher, G. R. J., and Bolton, J. L. (2006) Bioactivation of selective estrogen receptor modulators (SERMs). Chem. Res. Toxicol. 19, 1125-1137.
8. Bolton, J. L., Pisha, E., Zhang, F., and Qiu, S. (1998) Role of quinoids in estrogen carcinogenesis. Chem. Res. Toxicol. 11, 1113-1127.
9. Iverson, S. L., Hu, L. Q., Vukomanovic, V., and Bolton, J. L. (1995) The influence of the p-alkyl substituent on the isomerization of o-quinones to p-quinone methides: Potential bioactivation mechanism for catechols. Chem. Res. Toxicol. 8, 537-544.
10. Bolton, J. L., Acay, N. M., and Vukomanovic, V. (1994) Evidence that 3-allyl-o-quinone spontaneously rearrange to their more electrophilic quinone methides: Potential bioactivation mechanism for the hepatocarcinogen safrole. Chem. Res. Toxicol. 7, 443-450.
11. 2+-induced oxidation of a diterpenone catechol and concurrent damage on DNA. Chem. Res. Toxicol. 18, 382-388.
12. Zuniga, M. A., Wehunt, M. P., and Zhou, Q. (2006) DNA oxidative damage by catechol analogs of terpene quinone methides in the presence of Cu(II) and/or NADH. Chem. Res. Toxicol. 19, 828-836.
13. Zhou, Q., and Rokita, S. E. (2003) A general strategy for target-promoted alkylation in biological systems. Proc. Natl. Acad. Sci. U.S.A. 26, 15452-15457.
14. Wang, P., Liu, R., Wu, X., Ma, H., Cao, X., Zhou, P., Zhang, J., Weng, X., Zhang, X.-L., Qi, J., Zhou, X., and Weng, L. (2003) A potent, water-soluble and photoinducible DNA cross-linking agent. J. Am. Chem. Soc. 125, 1116-1117.
15. Richter, S. N., Maggi, S., Mels, S. C., Palumbo, M., and Freccero, M. (2004) Binol quinone methides as bisalkylating and DNA cross-linking agents. J. Am. Chem. Soc. 126, 13973-13979.
16. Lewis, M. A., Yoerg, D. G., Bolton, J. L., and Thompson, J. A. (1996) Alkylation of 2′-deoxynucleosides and DNA by quinone methides derived from 2,6-di-tert-butyl-4-methylphenol. Chem. Res. Toxicol. 9, 1368-1374.
17. Pande, P., Shearer, J., Yang, J., Greenberg, W. A., and Rokita, S. E. (1999) Alkylation of nucleic acids by a model quinone methide. J. Am. Chem. Soc. 121, 6773-6779.
18. Veldhuyzen, W. F., Shallop, A. J., Jones, R. A., and Rokita, S. E. (2001) Thermodynamic versus kinetic products of DNA alkylation as modeled by reaction of deoxyadenosine. J. Am. Chem. Soc. 123, 11126-11132.
19. Veldhuyzen, W. F., Lam, Y.-F., and Rokita, S. E. (2001) 2′-Deoxyguanosine reacts with a model quinone methide at multiple sites. Chem. Res. Toxicol. 14, 1345-1351.
20. Weinert, E. E., Frankenfield, K. N., and Rokita, S. E. (2005) Time-dependent evolution of adducts formed between deoxylnucleotides and a model quinone methide. Chem. Res. Toxicol. 18, 1364-1370.
21. Freccero, M., Gandolfi, R., and Sarzi-Amade, M. (2003) Selectivity of purine alkylation by a quinone methide. Kinetic or thermodynamic control? J. Org. Chem. 68, 6411-6423.
22. Weinert, E. E., Dondi, R., Colloredo-Melz, S., Frankenfield, K. N., Mitchell, C. H., Freccero, M., and Rokita, S. E. (2006) Substituents on quinone methides strongly modulate formation and stability of their nucleophilic adducts. J. Am. Chem. Soc. 128, 11940-11947.
23. Dai, J., and Zhou, Q. (2007) A Convenient Synthesis of an N-(1-Alkoxyl-9-fluorenyl)serine Acridine Conjugate. Synth. Commun. 37, 129-135.
24. Li, W., Nelson, D. P., Jensen, M. S., Hoerrner, R. S., Cai, D., Larsen, R. D., and Reider, P. J. (2002) An improved protocol for the preparation of 3-pyridyl- and some arylboronic acids. J. Org. Chem. 67, 5394-5397.
25. Hadfield, A., Schweitzer, H., Trova, M. P., and Green, K. (1994) Practical, large-scale synthesis of 2,2-dimethyl-5-hydroxy-4-oxobenzo-1,3- dioxin. Synth. Commun. 24, 1025-1028.
26. Zhou, Q., and Turnbull, K. D. (2001) Quinone Methide Phosphodiester Alkylation under Aqueous Conditions. J. Org. Chem. 66, 7072-7077.
27. Toteva, M. M., Moran, M., Amyes, T. L., and Richard, J. P. (2003) Substituent effects on carbocation stability: The pKR for p-quinone methide. J. Am. Chem. Soc. 125, 8814-8819.
28. Jobe, D. J., and Westaway, K. C. (1993) Fourier transform infrared spectroscopy studies of cyanide ion solutions of dimethylformamide and aqueous dimethylformamide. Can. J. Chem. 71, 1353-1361.
29. Shah, D. J., and Tlwarl, K. K. (1981) Effect of salt on the distribution of acetic acid between water and organic solvent. J. Chem. Eng. Data 26, 372-378.
30. Wu, Y. G., Masaaki, T., Toshiyuki, T., Atsushi, Y., Tomomi, K., and Chung, N. H. (2001) An extended Johnson-Furter equation to salting-out phase separation of aqueous solution of water-miscible organic solvents. Fluid Phase Equilib. 192, 1-12.
31. Winstein, S., Appel, B., Baker, R., and Diaz, A. (1965) Ion pairs in solvolysis and exchange. Spec. Publ. - Chem. Soc. 19, 109-130.
32. Hefter, G. (2005) Ion salvation in aqueous-organic mixture. Pure Appl. Chem. 77, 605-617.