DNA interstrand cross-link formation using furan as a masked reactive aldehyde

Current Protocols in Nucleic Acid Chemistry

Volumn , Issue SUPPL.54, 2013, Pages

  Carrette, Lieselot L G ^a   Gyssels, Ellen ^a   Madder, Annemieke ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

Cross linking; Furan; Nucleoside; Oligonucleotide

Indexed keywords

ALDEHYDE; FURAN; FURAN DERIVATIVE; NUCLEOSIDE; OLIGODEOXYNUCLEOTIDE; OLIGONUCLEOTIDE; PHOSPHORAMIDOUS ACID;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DNA CROSS LINKING; DNA STRAND; OXIDATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 84890815812     PISSN: 19349270     EISSN: 19349289     Source Type: Journal    
DOI: 10.1002/0471142700.nc0512s54     Document Type: Article

References (15)

1. Bakhiya, N. and Appel, K.E. 2010. Toxicity and carcinogenity of furan in human diet. Arch. Toxicol. 84:563-578.
2. Grillari, J., Katinger H., and Voglauer, R. 2007. Contributions of DNA interstrand cross-links to aging of cells and organisms. Nucleic Acids Res. 35:7566-7576.
3. Guainazzi, A. and Scharer, O.D. 2010. Using synthetic DNA interstrand crosslinks to elucidate repair pathways and identify new therapeutic targets for cancer chemotherapy. Cell. Mol. Life Sci. 67:3683-3697.
4. Halila, S., Velasco, T., De Clercq, P., and Madder, A. 2005. Fine-tuning furan toxicity: Fast and quantitativeDNAinterchain crosslink formation upon selective oxidation of a furan containing oligonucleotide. Chem. Commun. 7:936-938.
5. Jawalekar, A.M., Op de Beeck, M., van Delft, F.L., and Madder, A. 2011. Synthesis and incorporation of a furan-modified adenosine building block for DNA interstrand crosslinking. Chem. Commun. 47:2796-2798.
6. Kirschenheuter, G.P., Zhai, Y.S., and Pieken, W.A. 1994. An improved synthesis of 2'-azido-2'- deoxyuridine. Tetrahedron Lett. 35:8517-8520.
7. Lin, F.L., Hoyt, H.M., van Halbeek, H., Bergman, R.G., and Bertozzi, C.R. 2005. Mechanistic investigation of the Staudinger ligation. J. Am. Chem. Soc. 127:2686-2695.
8. McGee, D.P.C., Vaughn Settle, A., Vargeese, C., and Zhai, Y.S. 1996. 2'-Amino-2'-deoxyuridine via an intramolecular cyclization of a trichloroacetimidate. J. Org. Chem. 61:781-785.
9. Noll, D.M., McGregor Mason, T., and Miller, P.S. 2006 Formation and repair of interstrand crosslinks in DNA. Chem. Rev. 106:277-301.
10. Op de Beeck, M. and Madder, A. 2011. Unprecedented C-selective interstrand cross-linking through in situ oxidation of furan-modified oligodeoxynucleotides. J. Am. Chem. Soc. 133:796-807.
11. Op de Beeck, M. and Madder, A. 2012. Sequence specific DNA cross-linking triggered by visible light. J. Am. Chem. Soc. 134:10737-10740.
12. Peterson, L.A. 2006. Electrophilic intermediates produced by bioactivation of furan. Drug Metab. Rev. 38:615-626.
13. Singh, I., Vyle, J.S., and Heaney, F. 2009 Fast, copper-free click chemistry: A convenient solidphase approach to oligonucleotide conjugation. Chem. Comm. 22:3276-3278.
14. Stevens, K. and Madder, A. 2009. Furan-modified oligonucleotides for fast, high-yielding and siteselective DNA inter-strand cross-linking with non-modified complements. Nucleic Acid. Res. 37:1555-1565.
15. Stevens, K., Claeys, D.D., Catak, S., Figaroli, S., Hocek, M., Tromp, J.M., Schurch, S., Van Speybroeck, V., and Madder, A. 2011. Furanoxidation- triggered inducible DNA crosslinking: Acyclic versus cyclic furan-containing building blocks-on the benefit of restoring the cyclic sugar backbone. Chem. Eur. J. 17:6940-6953.