Efficient RNA-targeting by the introduction of aromatic stacking in the duplex major groove via 5-(1-phenyl-1,2,3-triazol-4-yl)-2′-deoxyuridines

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 13, 2010, Pages 4702-4710

  Andersen, Nicolai Krog ^a   Chandak, Navneet ^b   Brulíková, Lucie ^a,d   Kumar, Pawan ^b   Jensen, Michael Dalager ^a   Jensen, Frank ^c   Sharma, Pawan K ^b   Nielsen, Poul ^a  

^a UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

^b KURUKSHETRA UNIVERSITY   (India)

^c AARHUS UNIVERSITY   (Denmark)

^d PALACKÝ UNIVERSITY   (Czech Republic)

Author keywords

Stacking; Click chemistry; Oligonucleotides; RNA targeting

Indexed keywords

5 (1 PHENYL 1,2,3 TRIAZOL 4 YL) 2' DEOXYURIDINE DERIVATIVE; DEOXYURIDINE DERIVATIVE; DOUBLE STRANDED DNA; OLIGONUCLEOTIDE; PHENOL; PHENYLTRIAZOLE DERIVATIVE; PYRIMIDINE NUCLEOSIDE; RNA; SULFONAMIDE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; COPPER ASSISTED AZIDE ALKYNE CYCLOADDITION; CYCLOADDITION; HYDROPHILICITY; MOLECULAR MODEL; THERMOSTABILITY;

ALKYNES; AZIDES; CATALYSIS; CIRCULAR DICHROISM; COPPER; DEOXYURIDINE; DNA; MODELS, MOLECULAR; NUCLEIC ACID HYBRIDIZATION; RNA;

EID: 77954218023     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.05.019     Document Type: Article

References (26)

1. H. Yan Science 306 2004 2048
2. J. Wengel Org. Biomol. Chem. 2 2004 277
3. J. Kurreck Eur. J. Biochem. 270 2003 1628
4. I. Luyten, and P. Herdewijn Eur. J. Med. Chem. 33 1998 515
5. K.-Y. Lin, R.J. Jones, and M. Matteucci J. Am. Chem. Soc. 117 1995 3873
6. R.W. Wagner, M.D. Matteucci, J.G. Lewis, A.J. Gutierrez, C.M. Moulds, and B.C. Froehler Science 260 1993 1510
7. A.J. Gutierrez, M.D. Matteucci, D. Grant, S. Matsumura, R.W. Wagner, and B.C. Froehler Biochemistry 36 1997 743
8. A.J. Gutierrez, T.J. Terhorst, M.D. Matteucci, and B.C. Froehler J. Am. Chem. Soc. 116 1994 5540
9. R.W. Sinkeldam, N.J. Greco, and Y. Tor ChemBioChem 9 2008 706
10. H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem., Int. Ed. 40 2001 2004
11. H.C. Kolb, and K.B. Sharpless Drug Discovery Today 8 2003 1128
12. C.W. Tornøe, C. Christensen, and M. Meldal J. Org. Chem. 67 2002 3057
13. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless Angew. Chem., Int. Ed. 41 2002 2596
14. P. Koalka, N.K. Andersen, F. Jensen, and P. Nielsen ChemBioChem 8 2007 2106
15. G.A. Burley, J. Gierlich, M.R. Mofid, H. Nir, S. Tal, Y. Eichen, and T. Carell J. Am. Chem. Soc. 128 2006 1398
16. J. Gierlich, G.A. Burley, P.M.E. Gramlich, D.M. Hammond, and T. Carell Org. Lett. 8 2006 3639
17. S.B. Buck, J. Bradford, K.R. Gee, B.J. Agnew, S.T. Clarke, and A. Salic BioTechniques 44 2008 927
18. J. Andersen, U. Madsen, F. Björkling, and X. Liang Synlett 2005 2209
19. Q. Cai, W. Zhu, H. Zhang, Y. Zhang, and D. Ma Synthesis 2005 496
20. B.L. Wilkinson, L.F. Bornaghi, T.A. Houston, A. Innocenti, D. Wullo, C.T. Supuran, and S.A. Poulsen J. Med. Chem. 50 2007 1651
21. macromodel, Version 9.1, Schrödinger, LLC, New York, NY, 2005.
22. G. Chang, W.C. Guida, and W.C. Still J. Am. Chem. Soc. 111 1989 4379
23. S.J. Weiner, P.A. Kollman, D.A. Case, U.C. Singh, C. Ghio, G. Alagona, S. Profeta, and P. Weiner J. Am. Chem. Soc. 106 1984 765
24. S.J. Weiner, P.A. Kollman, D.T. Nguyen, and D.A. Case J. Comput. Chem. 7 1986 230
25. W.C. Still, A. Tempcyk, R.C. Hawley, and T. Hendrickson J. Am. Chem. Soc. 112 1990 6127
26. gaussian-03. Gaussian Inc., 340 Quinnipiac St., Bldg 40, Wallingford, CT 06492, USA.