Selenium-Mediated Dehalogenation of Halogenated Nucleosides and its Relevance to the DNA Repair Pathway

Angewandte Chemie - International Edition

Volumn 54, Issue 32, 2015, Pages 9298-9302

  Mondal, Santanu ^a   Manna, Debasish ^a   Mugesh, Govindasamy ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

dehalogenation; DNA repair; halogen bonds; nucleosides; selenium

Indexed keywords

CELL PROLIFERATION; DEHALOGENATION; DNA; HALOGENATION; NUCLEIC ACIDS; SELENIUM;

DNA REPAIR; DNA REPAIR PATHWAYS; HALOGEN BONDS; LIVING TISSUES; MODIFIED NUCLEOSIDES; NUCLEOSIDES; PROLIFERATING CELLS; URACIL-DNA GLYCOSYLASE;

BIOMOLECULES;

DNA; NUCLEOSIDE; SELENIUM; URACIL DNA GLYCOSIDASE;

CHEMISTRY; CONFORMATION; DNA REPAIR; HALOGENATION; METABOLISM; STATIC ELECTRICITY; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; DNA; DNA REPAIR; HALOGENATION; MOLECULAR CONFORMATION; NUCLEOSIDES; SELENIUM; STATIC ELECTRICITY; URACIL-DNA GLYCOSIDASE;

EID: 84938196630     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201503598     Document Type: Article

References (35)

1. H. G. Gratzner, Science 1982, 218, 474-475
2. C. Zhao, W. Deng, F. H. Gage, Cell 2008, 132, 645-660
3. C.-R. Wang, Q.-B. Lu, J. Am. Chem. Soc. 2010, 132, 14710-14713.
4. M. T. Hakala, J. Biol. Chem. 1959, 234, 3072-3076
5. J. M. Robertson, W. D. Ensminger, S. Walker, T. S. Lawrence, Clin. Invest. 1997, 37, 331-335
6. S. Kummar, L. Anderson, K. Hill, E. Majerova, D. Allen, Y. Horneffer, S. P. Ivy, L. Rubinstein, P. Harris, J. H. Doroshow, J. M. Collins, Clin. Cancer Res. 2013, 19, 1852-1857
7. Y. Chen, Z. Ran, W. Jianmei, J. Bo, Z. Dayong, S. Miaoli, L. Fenju, Cancer Biother. Radiopharm. 2014, 29, 395-402.
8. K. Wild, T. Bohner, G. Folkers, G. E. Schulz, Protein Sci. 1997, 6, 2097-2106.
9. W. J. Hume, R. Saffhill, Chem.-Biol. Interact. 1986, 60, 227-232
10. G. P. Cook, M. M. Greenberg, J. Am. Chem. Soc. 1996, 118, 10025-10030.
11. Y. Wataya, D. V. Santi, Biochem. Biophys. Res. Commun. 1975, 67, 818-823
12. C. Garrett, Y. Wataya, D. V. Santi, Biochemistry 1979, 18, 2798-2804.
13. Y. Wataya, K. Negishi, H. Hayatsu, Biochemistry 1973, 12, 3992-3998
14. T. Chikuma, K. Negishi, H. Hayatsy, Chem. Pharm. Bull. 1978, 26, 1746-1752.
15. A. C. Bianco, D. Salvatore, B. Gereben, M. J. Berry, P. R. Larsen, Endocr. Rev. 2002, 23, 38-89
16. J. Köhrle, Methods Enzymol. 2002, 347, 125-167.
17. S. R. Thomas, P. M. McTamney, J. M. Adler, N. LaRonde-LeBlanc, S. E. Rokita, J. Biol. Chem. 2009, 284, 19659-19667.
18. D. Manna, G. Mugesh, Angew. Chem. Int. Ed. 2010, 49, 9246-9249
19. Angew. Chem. 2010, 122, 9432-9435
20. D. Manna, G. Mugesh, J. Am. Chem. Soc. 2011, 133, 9980-9983
21. D. Manna, G. Mugesh, J. Am. Chem. Soc. 2012, 134, 4269-4279
22. D. Manna, S. Mondal, G. Mugesh, Chem. Eur. J. 2015, 21, 2409-2416.
23. R. M. Starzyk, S. W. Koontz, P. Schimmel, Nature 1982, 298, 136-140.
24. CCDC 1042446 (IU), 1060822 (IUd), 1060823 (IdUd), 1042448 (17), 1042447 (18), 1042449 (19) contain the supplementary crystallographic data for this paper. These data are provided free of charge by The Cambridge Crystallographic Data Centre.
25. A. J. Parker, J. Stewart, K. J. Donald, C. A. Parish, J. Am. Chem. Soc. 2012, 134, 5165-5172.
26. P. Metrangolo, F. Meyer, T. Pilati, G. Resnati, G. Terraneo, Angew. Chem. Int. Ed. 2008, 47, 6114-6127
27. Angew. Chem. 2008, 120, 6206-6220
28. P. Metrangolo, G. Resnati, Nat. Chem. 2012, 4, 437-438.
29. Gaussian 09, Revision A.1, M. J. Frisch et al. Gaussian, Inc., Wallingford CT, 2009. The full references are given in the Supporting Information.
30. An overview of σ-hole bonding, an important and widely occurring noncovalent interaction:, P. Politzer, J. S. Murray, in Practical Aspects of Computational Chemistry Methods, Concepts, and Applications (Eds.:, J. Leszczynski, M. K. Shukla,), Springer, Heidelberg, 2009, Chap. 6.
31. A. J. F. Griffiths, S. R. Wessler, S. B. Carroll, J. Doebley, Introduction to Genetic Analysis, 10 th ed., W. H. Freeman, New York, 2011.
32. J. P. Henderson, J. Byun, J. Takeshita, J. W. Heinecke, J. Biol. Chem. 2003, 278, 23522-23528
33. J. P. Henderson, J. Byun, M. V. Williams, M. L. McCormick, W. C. Parks, L. A. Ridnour, J. W. Heinecke, Proc. Natl. Acad. Sci. USA 2001, 98, 1631-1636
34. S. J. Weiss, S. T. Test, C. M. Eckmann, D. Roos, S. Regiani, Science 1986, 234, 200-203
35. J. Takeshita, J. Byun, T. Q. Nhan, D. K. Pritchard, S. Pennathur, S. M. Schwartz, A. Chait, J. W. Heinecke, J. Biol. Chem. 2006, 281, 3096-3104.