2′-aminoethoxy-2-amino-3-methylpyridine in triplex-forming oligonucleotides: High affinity, selectivity and resistance to enzymatic degradation

Chemistry - A European Journal

Volumn 17, Issue 52, 2011, Pages 14851-14856

  Lou, Chenguang ^a   Shelbourne, Montserrat ^a   Fox, Keith R ^a   Brown, Tom ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

DNA structures; nuclease resistance; nucleosides; oligonucleotides

Indexed keywords

BASE PAIRS; C-NUCLEOSIDES; DNA STRUCTURE; ENZYMATIC DEGRADATION; FOOTPRINTING; HIGH AFFINITY; KNOCK OUTS; NUCLEOSIDES; PHOSPHORAMIDITES; SINGLE-STRANDED DNA; TRIPLEX-FORMING OLIGONUCLEOTIDES;

BIOMOLECULES; GENE EXPRESSION; MONOMERS;

OLIGONUCLEOTIDES;

2' AMINOETHOXY 2 AMINO 3 METHYLPYRIDINE; 2'-AMINOETHOXY-2-AMINO-3-METHYLPYRIDINE; DNA; OLIGONUCLEOTIDE; PYRIDINE DERIVATIVE; TRIPLEX DNA;

ARTICLE; BASE PAIRING; CHEMISTRY; DRUG EFFECT; ENZYME ACTIVATION; METABOLISM; MOLECULAR GENETICS; NUCLEOTIDE SEQUENCE; SYNTHESIS;

BASE PAIRING; BASE SEQUENCE; DNA; ENZYME ACTIVATION; MOLECULAR SEQUENCE DATA; OLIGONUCLEOTIDES; PYRIDINES;

EID: 83755163564     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102287     Document Type: Article

References (25)

1. M. D. Frankkamenetskii, S. M. Mirkin, Annu. Rev. Biochem. 1995, 64, 65-95.
2. T. Le Doan, L. Perrouault, D. Praseuth, N. Habhoub, J. L. Decout, N. T. Thuong, J. Lhomme, C. Helene, Nucleic Acids Res. 1987, 15, 7749-7760.
3. H. E. Moser, P. B. Dervan, Science 1987, 238, 645-650.
4. P. A. Beal, P. B. Dervan, Science 1991, 251, 1360-1363.
5. D. M. Gowers, K. R. Fox, Nucleic Acids Res. 1999, 27, 1569-1577.
6. M. Duca, P. Vekhoff, K. Oussedik, L. Halby, P. B. Arimondo, Nucleic Acids Res. 2008, 36, 5123-5138.
7. K. R. Fox, Curr. Med. Chem. 2000, 7, 17-37.
8. D. A. Rusling, V. J. Broughton-Head, T. Brown, K. R. Fox, Curr. Chem. Biol. 2008, 2, 1-10.
9. P. J. Bates, C. A. Laughton, T. C. Jenkins, D. C. Capaldi, P. D. Roselt, C. B. Reese, S. Neidle, Nucleic Acids Res. 1996, 24, 4176-4184.
10. S. Hildbrand, A. Blaser, S. P. Parel, C. J. Leumann, J. Am. Chem. Soc. 1997, 119, 5499-5511.
11. S. Hildbrand, C. Leumann, Angew. Chem. 1996, 108, 2100-2102
12. Angew. Chem. Int. Ed. Engl. 1996, 35, 1968-1970.
13. C. Lou, Q. Xiao, R. R. Tailor, N. Ben Gaied, N. Gale, M. E. Light, K. R. Fox, T. Brown, Med. Chem. Commun. 2011, 2, 550-558.
14. C. G. Lou, Q. A. Xiao, L. Brennan, M. E. Light, N. Vergara-Irigaray, E. M. Atkinson, L. M. Holden-Dye, K. R. Fox, T. Brown, Bioorg. Med. Chem. 2010, 18, 6389-6397.
15. B. Cuenoud, F. Casset, D. Husken, F. Natt, R. M. Wolf, K. H. Altmann, P. Martin, H. E. Moser, Angew. Chem. 1998, 110, 1350-1353
16. Angew. Chem. Int. Ed. 1998, 37, 1288-1291.
17. A. Majumdar, N. Puri, N. McCollum, S. Richards, B. Cuenoud, P. Miller, M. M. Seidman, in Therapeutic Oligonucleotides 2003, pp. 141-153.
18. D. Guianvarc'h, R. Benhida, J. L. Fourrey, R. Maurisse, J. S. Sun, Chem. Commun. 2001, 1814-1815.
19. D. A. Rusling, V. E. C. Powers, R. T. Ranasinghe, Y. Wang, S. D. Osborne, T. Brown, K. R. Fox, Nucleic Acids Res. 2005, 33, 3025-3032.
20. M. J. J. Blommers, F. Natt, W. Jahnke, B. Cuenoud, Biochemistry 1998, 37, 17714-17725.
21. M. Vonpierre, Helv. Chim. Acta 1995, 78, 486-504.
22. N. Puri, A. Majumdar, B. Cuenoud, F. Natt, P. Martin, A. Boyd, P. S. Miller, M. M. Seidman, Biochemistry 2002, 41, 7716-7724.
23. S. Buchini, C. J. Leumann, Angew. Chem. 2004, 116, 4015-4018
24. Angew. Chem. Int. Ed. 2004, 43, 3925-3928.
25. Y. Wang, D. A. Rusling, V. E. C. Powers, O. Lack, S. D. Osborne, K. R. Fox, T. Brown, Biochemistry 2005, 44, 5884-5892.