Peptide nucleic acid containing a meta-substituted phenylpyrrolocytosine exhibits a fluorescence response and increased binding affinity toward RNA

Organic Letters

Volumn 11, Issue 21, 2009, Pages 4878-4881

  Wojciechowski, Filip ^a   Hudson, Robert H E ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTISENSE OLIGONUCLEOTIDE; CYTOSINE; DNA; DRUG DERIVATIVE; FLUORESCENT DYE; PEPTIDE NUCLEIC ACID; RNA;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; STEREOISOMERISM; SYNTHESIS;

CYTOSINE; DNA; FLUORESCENT DYES; MOLECULAR STRUCTURE; OLIGONUCLEOTIDES, ANTISENSE; PEPTIDE NUCLEIC ACIDS; RNA; STEREOISOMERISM;

EID: 70350666648     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9019474     Document Type: Article

References (26)

1. (a) Wilson, J. N.; Kool, E. T. Org. Biomol Chem. 2006, 4, 4265-4274.
2. (b) Okamoto, A.; Saito, Y.; Saito, I. Photochem. Photobiol C 2005, 6, 108-122.
3. (c) Rist, M. J.; Marino, J. P. Curr. Org. Chem 2002, 6, 775-793.
4. (a) Uhlmann, E.; Peyman, A. Chem. Rev. 1990, 90, 543-584.
5. (b) Peptide Nucleic Acids, Morpholinos and Related Antisense Biomolecules; Janson, C. G., During, M. J., Eds.; Landes Biosciences: Georgetown, TX, 2006; Chapters 1-5, 9-12, and 14-18.
6. Nielsen, P. E; Egholm, M.; Berg, R. H.; Buchardt, O. Science 1991, 254, 1497-1500.
7. Wojciechowski, F.; Hudson, R. H. Curr. Top. Med. Chem. 2007, 7, 667-679.
8. Lin, K.-Y.; Jones, R. J.; Matteucci, M. D. J. Am. Chem. Soc. 1995, 117, 3873-3874.
9. (a) Hudson, R. H. E; Dambenieks, A. K.; Viirre, R. D. Synlett 2004, 13, 2400-2402.
10. (b) Hudson, R. H. E.; Ghorbani-Choghamarani, A. Synlett 2007, 6, 870-873.
11. (a) Lin, K.-Y.; Matteucci, M. D. J. Am. Chem. Soc. 1998, 120, 8531-8532.
12. (b) Wilds, C. J.; Maier, M. A.; Tereshko, V.;
13. (c) Manoharan, M.; Egli, M. Angew. Chem., Int. Ed. 2002, 41, 115-117.
14. (d) Wilds, C. J; Maier, M. A.; Manoharan, M.; Egli, M. HeIu. Chim. Acta 2003, 86, 966-978.
15. (e) Ausin, C.; Ortega, J.-A.; Robles, J.; Grandas, A.; Pedroso, E. Org. Lett. 2002, 4, 4073-4075.
16. (t) Rajeev, K. G.; Maier, M. A.; Lesnik, E. A.; Manoharan, M. Org. Lett. 2002, 4, 4395-4398.
17. (g) Chenna, V.; Rapireddy, S.; Sahu, B.; Ausin, C.; Pedroso, E.; Ly, D. H. ChemBioChem 2008, 9, 2388-2391.
18. (a) Flanagan, W. M.; Wolf, J. J.; Olson, P.; Grant, D.; Lin, K.-Y; Wagner, R. W; Matteucci, M. D. Proc Natl. Acad. Sci. U.S.A. 1999, 96, 3513-3518.
19. (b) Maier, M. A.; Leeds, J. M.; Balow, G.; Springer, R. H.; Bharadwaj, R.; Manoharan, M. Biochemistry 2002, 41, 1323-1327.
20. (c) Nakagawa, O.; Ono, S.; Li, Z.; Tsujimoto, A.; Sasaki, S. Angew. Chem., Int. Ed. 2007, 46, 1-5.
21. (d) Barhate, N.; Cekan, P.; Massey, A. P.; Sigurdsson, S. Th. Angew. Chem., Int. Ed. 2007, 46, 2655-2658.
22. (a) Wojciechowski, F.; Hudson, R. H. E. J. Am. Chem. Soc. 2008, 130, 12574-12575.
23. (b) Wojciechowski, F.; Hudson, R. H. E. Nucleic Acids Sym. Ser (Oxford) 2008, 52, 401-402.
24. Ortega, J.-A.; Blas, J. R.; Orozco, M.; Grandas, A.; Pedroso, E.; Robles, J. Org. Lett. 2007, 9, 4503-4506.
25. Wojciechowski, F.; Hudson, R. H. E. J. Org. Chem. 2008, 73, 3807-3816.
26. Hardman, S. J. O.; Botchway, S. W.; Thompson, K. C. Photochem. Photobiol. 2008, 84, 1473-1479.