Rapid and efficient DNA strand cross-linking by click chemistry

ChemBioChem

Volumn 9, Issue 8, 2008, Pages 1280-1285

  Kočalka, Petr ^a   El Sagheer, Afaf H ^a   Brown, Tom ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

Click chemistry; Cross linking; CuAAC reaction; DNA

Indexed keywords

DOUBLE STRANDED DNA; ALKYNE; AZIDE; CROSS LINKING REAGENT; DEOXYURIDINE; DNA; OLIGONUCLEOTIDE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DNA CROSS LINKING; DNA DENATURATION; DNA STRAND; DNA STRUCTURE; NANOTECHNOLOGY; NUCLEOTIDE METABOLISM; PRIORITY JOURNAL; THERMOSTABILITY; CAPILLARY ELECTROPHORESIS; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; SYNTHESIS; TIME;

ALKYNES; AZIDES; CIRCULAR DICHROISM; CROSS-LINKING REAGENTS; DEOXYURIDINE; DNA; ELECTROPHORESIS, CAPILLARY; MOLECULAR STRUCTURE; OLIGONUCLEOTIDES; TIME FACTORS;

EID: 49249097455     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200800006     Document Type: Article

References (43)

1. R. Huisgen, Proc. Chem. Soc. London 1961, 357.
2. R. Huisgen, Angew. Chem. 1963, 75, 604-637
3. R. Huisgen, Angew. Chem. Int. Ed. Engl. 1963, 2, 565-632.
4. R. Huisgen, 1,3-Dipolar Cycloadditional Chemistry, Wiley, New York, 1984.
5. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075
6. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
7. C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064.
8. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708-2711
9. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
10. H. C. Kolb, K. B. Sharpless, Drug Discovery Today 2003, 8, 1128-1137.
11. V. D. Bock, H. Hiemstra, J. H. van Maarseveen, Eur. J. Org. Chem. 2006, 51-68.
12. T. S. Seo, X. P. Bai, D. H. Kim, Q. L. Meng, S. D. Shi, H. Ruparelt, Z. M. Li, N. J. Turro, J. Y. Ju, Proc. Natl. Acad. Sci. USA 2005, 102, 5926-5931.
13. N. K. Devaraj, G. P. Miller, W. Ebina, B. Kakaradov, J. P. Collman, E. T. Kool, C. E. D. Chidsey, J. Am. Chem. Soc. 2005, 127, 8600-8601.
14. D. I. Rozkiewicz, J. Gierlich, G. A. Burley, K. Gutsmiedl, T. Carell, B. J. Ravoo, D. N. Reinhoudt, ChemBioChem 2007, 8, 1997-2002.
15. M. Humenik, Y. W. Huang, Y. R. Wang, M. Sprinzl, ChemBioChem 2007, 8, 1103-1106.
16. F. Seela, V. R. Sirivolu, Helv. Chim. Acta 2007, 90, 535-552.
17. F. Seela, V. R. Sirivolu, Chem. Biodiversity 2006, 3, 509-514.
18. I. Géci, V. V. Filichev, E. B. Pedersen, Chem. Eur. J. 2007, 13, 6379-6386.
19. R. L. Weller, S. R. Rajski, Org. Lett. 2005, 7, 2141-2144.
20. P. Kočalka, N. K. Andersen, F. Jensen, P. Nielsen, ChemBioChem 2007, 8, 2106-2116.
21. T. S. Seo, Z. M. Li, H. Ruparel, J. Y. Ju, J. Org. Chem. 2003, 68, 609-612.
22. J. Gierlich, G. A. Burley, P. M. E. Gramlich, D. M. Hammond, T. Carell, Org. Lett. 2006, 8, 3639-3642.
23. G. A. Burley, J. Gierlich, M. R. Mofid, H. Nir, S. Tal, Y. Eichen, T. Carell, J. Am. Chem. Soc. 2006, 128, 1398-1399.
24. C. Bouillon, A. Meyer, S. Vidal, A. Jochum, Y. Chevolot, J. P. Cloarec, J. P. Praly, J. J. Vasseur, F. Morvan, J. Org. Chem. 2006, 71, 4700-4702.
25. R. Kumar, A. El-Sagheer, J. Tumpane, P. Lincoln, L. M. Wilhelmsson, T. Brown, J. Am. Chem. Soc. 2007, 129, 6859-6864.
26. A. H. El-Sagheer, R. Kumar, S. Findlow, J. M. Werner, A. N. Lane, T. Brown, ChemBioChem 2008, 9, 50-52.
27. K. Gogoi, M. V. Mane, S. S. Kunte, V. A. Kumar, Nucleic Acids Res. 2007, 35, e139.
28. C. J. Wilds, A. M. Noronha, S. Robidoux, P. S. Miller, J. Am. Chem. Soc. 2004, 126, 9257-9265.
29. D. M. Noll, A. M. Noronha, P. S. Miller, J. Am. Chem. Soc. 2001, 123, 3405-3411.
30. A. M. Noronha, C. J. Wilds, P. S. Miller, Biochemistry 2002, 41, 8605-8612.
31. A. M. Noronha, D. M. Noll, C. J. Wilds, P. S. Miller, Biochemistry 2002, 41, 760-771.
32. A. M. Noronha, D. M. Noll, P. S. Miller, Nucleosides Nucleotides Nucleic Acids 2001, 20, 1303-1307.
33. E. A. Harwood, S. T. Sigurdsson, N. B. F. Edfeldt, B. R. Reid, P. B. Hopkins, J. Am. Chem. Soc. 1999, 121, 5081-5082.
34. T. Bando, A. Narita, I. Saito, H. Sugiyama, J. Am. Chem. Soc. 2003, 125, 3471-3485.
35. C. Dohno, S.-n. Uno, K. Nakatani, J. Am. Chem. Soc. 2007, 129, 11898-11899.
36. E. T. Kool, Annu. Rev. Biophys. Biomol. Struct. 1996, 25, 1-28.
37. D. A. Di Giusto, S. M. Knox, Y. Lai, G. D. Tyrelle, M. T. Aung, G. C. King, ChemBioChem 2006, 7, 535-544.
38. J. Tumpane, P. Sandin, R. Kumar, V. E. C. Powers, E. P. Lundberg, N. Gale, P. Baglioni, J.-M. Lehn, B. Albinsson, P. Lincoln, L. M. Wilhelmsson, T. Brown, B. Nordén, Chem. Phys. Lett. 2007, 440, 125-129.
39. D. Graham, J. A. Parkinson, T. Brown, J. Chem. Soc. Perkin Trans. 1 1998, 1131-1138.
40. C. Grandjean, A. Boutonnier, C. Guerreiro, J.-M. Fournier, L. A. Mulard, J. Org. Chem. 2005, 70, 7123-7132.
41. The water-soluble ligand is described in the Supporting Information to T. R. Chan, R. Hilgraf, K. B. Sharpless, V. V. Fokin, Org. Lett. 2004, 6, 2853-2855.
42. G. J. Langley, J. M. Herniman, N. L. Davies, T. Brown, Rapid Commun. Mass Spectrom. 1999, 13, 1717-1723.
43. F. W. Hobbs, J. Org. Chem. 1989, 54, 3420-3422.