Abasic-site-containing oligodeoxynucleotides as aptamers for riboflavin

Angewandte Chemie - International Edition

Volumn 45, Issue 10, 2006, Pages 1563-1568

  Sankaran, N B ^a,b   Nishizawa, Seiichi ^a,b   Seino, Takehiro ^a,b   Yoshimoto, Keitaro ^c   Teramae, Norio ^a,b  

^a TOHOKU UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

Abasic sites; Aptamers; Flavins; Fluorescence probes; Nucleic acids

Indexed keywords

ABASIC SITES; APTAMERS; FLAVINS; FLUORESCENCE PROBES; OLIGODEOXYNUCLEOTIDES; RIBOFLAVIN;

DNA; MOLECULAR DYNAMICS; NUCLEIC ACIDS; OPTIMIZATION;

PROTEINS;

APTAMER; OLIGODEOXYRIBONUCLEOTIDE; RIBOFLAVIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TITRIMETRY; TRANSITION TEMPERATURE;

APTAMERS, NUCLEOTIDE; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; NUCLEIC ACID CONFORMATION; OLIGODEOXYRIBONUCLEOTIDES; RIBOFLAVIN; TITRIMETRY; TRANSITION TEMPERATURE;

EID: 33744938018     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200502979     Document Type: Article

References (33)

1. T. Hermann, D. J. Patel, Science 2000, 287, 820.
2. A. D. Ellington, J. W. Szostak, Nature 1990, 346, 818.
3. K. Harada, A. D. Frankel, EMBO J. 1995, 14, 5798.
4. M. Famulok, J. Am. Chem. Soc. 1994, 116, 1698.
5. a) S. D. Jhaveri, R. Kirby, R. Conrad, E. J. Maglott, M. Bowser, R. T. Kennedy, G. Glick, A. D. Ellington, J. Am. Chem. Soc. 2000, 122, 2469;
6. b) S. Jhaveri, M. Rajendran, A. D. Ellington, Nat. Biotechnol. 2000, 18, 1293;
7. c) E. J. Merino, K. M. Weeks, J. Am. Chem. Soc. 2003, 125, 12 370.
8. P. Burgstaller, M. Famulok, Angew. Chem. 1994, 106, 1163;
9. Angew. Chem. Int. Ed. Engl. 1994, 55, 1084.
10. C. T. Lauhon, J. W. Szostak, J. Am. Chem. Soc. 1995, 117, 1246.
11. M. Roychowdhury-Saha, S. M. Lato, E. D. Shank, D. H. Burke, Biochemistry 2002, 41, 2492.
12. R. D. Jenison, S. C. Gill, A. Pardi, B. Polisky, Science 1994, 263, 1425.
13. M. N. Stojanovic, P. de Prada, D. W. Landry, J. Am. Chem. Soc. 2001, 123, 4928.
14. T. Lindahl, B. Nyberg, Biochemistry 1972, 11, 3610.
15. H. E. Krokan, R. Standal, G. Slupphaug, Biochem. J. 1997, 325, 1.
16. T. Lindahl, Nature 1993, 362, 709.
17. J. H. J. Hoeijmakers, Nature 2001, 411, 366.
18. E. C. Friedberg, Nature 2003, 421, 436.
19. K. Yoshimoto, S. Nishizawa, M. Minagawa, N. Teramae, J. Am. Chem. Soc. 2003, 125, 8982.
20. K. Yoshimoto, C.-Y. Xu, S. Nishizawa, T. Haga, H. Satake, N. Teramae, Chem. Commun. 2003, 2960.
21. S. Nishizawa, K. Yoshimoto, T. Seino, C.-Y. Xu, M. Minagawa, H. Satake, A. Tong, N. Teramae, Talanta 2004, 65, 175.
22. The importance of flavins in various biological processes has been highlighted; see, for example: a) Flavins and Flavoproteins (Eds.: S. K. Chapman, R. N. Perham, N. S. Scrutton), Rudolf Weber Agency for Scientific Publications, Berlin, 2002;
23. b) Chemistry and Biochemistry of Flavoenzymes, Vol. 1 (Ed.: F. Müller), CRC, Boca Raton, 1991.
24. P. Fan, A. K. Suri, R. Fiala, D. Live, D. J. Patel, J. Mol. Biol. 1996, 258, 480.
25. M. Piotto, V. Saudek, V. Sklenar, J. Biomol. NMR 1992, 2, 661.
26. P. K. Bhattacharya, J. Cha, J. K. Barton, Nucleic Acids Res. 2002, 30, 4740.
27. I. Haq, J. Ladbury, J. Mol. Recognit. 2000, 13, 188.
28. [6] whereby aptamers for FMN or FAD were isolated by in vitro selection. While the RNA aptamers (FMN-2 and 35FMN-2) based on the internal-loop structure were not able to distinguish between these flavin derivatives, FAD-1 or 27FAD-1 containing the stem-loop structure as the binding motif showed moderate selectivity for 7,8-dimethylalloxazine over FMN and FAD: the dissociation constants of 27FAD-1 with 7,8-dimethylalloxazine, FMN, and FAD were reported to be 35, 280, and 273 μM, respectively.
29. F. Leng, J. B. Chaires, M. J. Waring, Nucleic Acids Res. 2003, 31, 6191.
30. B. König, H.-T. Gallmeier, R. Reichenbach-Klinke, Chem. Commun. 2001, 2390.
31. J. A. Tillotson, M. M. Bashor, Anal. Biochem. 1980, 107, 214.
32. J. Becvar, G. Palmer, J. Biol. Chem. 1982, 257, 5607.
33. I. Caelen, A. Kalman, L. Wahlström, Anal. Chem. 2004, 76, 137.