Methyltransferase-directed DNA strand scission

Journal of the American Chemical Society

Volumn 127, Issue 41, 2005, Pages 14136-14137

  Comstock, Lindsay R ^a   Rajski, Scott R ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; DNA METHYLTRANSFERASE;

ARTICLE; DNA ALKYLATION; DNA DAMAGE; DNA METHYLATION; DNA STRAND; OXIDATION REDUCTION REACTION; REACTION ANALYSIS;

ANIMALS; DNA; DNA DAMAGE; DNA, SINGLE-STRANDED; METHYLATION; METHYLTRANSFERASES; MOLECULAR STRUCTURE;

EID: 26844534670     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja054128y     Document Type: Article

References (16)

1. Comslock, L. R.; Rajski, S. R. J. Org. Chem. 2004, 69, 1425.
2. Comstock, L. R.; Rajski, S. R. Nucleic Acids Res. 2005, 33, 1644.
3. Elegantly reviewed in: (a) Sigman, D. S.; Mazumber, A.; Perrin, D. M. Chem. Rev. 1993, 93, 2295.
4. (b) Pogozelski, W. K.; Tullius, T. D. Chem. Rev. 1998, 98, 1089.
5. (a) Gallagher, J.; Chen, C. B.; Pan, C. Q.; Perrin, D. M.; Cho, Y. M.; Sigman, D. S. Bioconjugate Chem. 1996, 7, 413.
6. (b) Martelli, A.; Constant, J. F.; Demeunynck, M.; Lhomme, J.; Dumy, P. Tetrahedron 2002, 58, 4291.
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9. Average yields of MTase-promoted DNA alkylation with 1 are 14% (M.TaqI) and 30% (M.Hhal) based on phosphorimaging. We propose a theoretical yield of 50% in each case; the altered sterics of methylation sites modified with 1 are likely to render each MTase capable of only one alkylation per duplex as opposed to the usual two (one methylation for each strand).
10. Restituyo, J. A.; Comstock, L. R.; Petersen, S. G.; Stringfellow, T.; Rajski, S. R. Org. Lett. 2003, 5, 4357.
11. See Supporting Information.
12. Average yields of 7, 8, and 9 (Scheme 1) are 61, 52, and 55%, respectively. Average yields of conjugates 10, 11, and 12 are 69, 78, and 76%, respectively. These represent the percent conversion of alkylated DNA strands to those bearing the pendant phenanthroline moieties represented in Scheme 1.
13. Phosphorimaging and data processing with ImageQuant revealed the yields for the three major scission products to be 12% (A), 13% (G), and 15% (T). Values are relative to all scission products observed.
14. The scission yields for the three major scission products are 15% (C), 16% (G), and 13% (G). These data were obtained in a fashion identical to those related to M.TaqI.
15. (a) Nur, I.; Szyf, M.; Razin, A.; Glaser, G.; Rottem, S.; Razin, S. J. Bateriol. 1985, 164,. 19.
16. (b) Renbaum, P.; Razin, A. FEBS Lett. 1992, 313, 243.