Benzoquinazoline derivatives as substitutes for thymine in nucleic acid complexes. Use of fluorescence emission of benzo[g]quinazoline-2,4-(1H, 3H)- dione in probing duplex and triplex formation

Biochemistry

Volumn 37, Issue 39, 1998, Pages 13765-13775

  Godde, Frédéric ^a   Toulmé, Jean Jacques ^a   Moreau, Serge ^a  

^a INSERM   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DOUBLE STRANDED DNA; QUINAZOLINE DERIVATIVE; THYMINE;

ARTICLE; DRUG DNA INTERACTION; FLUORESCENCE; MOLECULAR INTERACTION; PRIORITY JOURNAL; TRIPLE HELIX;

DEOXYRIBONUCLEOSIDES; DNA; HEAT; NUCLEIC ACID CONFORMATION; NUCLEIC ACID DENATURATION; NUCLEIC ACID HETERODUPLEXES; OLIGONUCLEOTIDES; PURINE NUCLEOTIDES; PYRIMIDINE NUCLEOTIDES; QUINAZOLINES; SPECTROMETRY, FLUORESCENCE; THYMINE;

EID: 0032578563     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi9811967     Document Type: Article

References (43)

1. Toulmé, J. J. (1992) in Antisense RNA and DNA (Murray, J. A. H., Ed.) pp 175-194, Wiley, New York.
2. Chastain, M., and Tinoco, I., Jr. (1991) Prog. Nucleic Acid Res. Mol. Biol. 41, 131-147.
3. Gait, M. J., and Karn, J. (1993) Trends Biochem. Sci. 18, 255-259.
4. Hehl, A., Vassella, E., Braun, R., and Roditi, I. (1994) Proc. Natl. Acad. Sci. U.S.A. 91, 370-374.
5. Lima, W. F., Monia, B. P., Ecker, D. J., and Freier, S. M. (1992) Biochemistry 31, 12055-12061.
6. Toulmé, J. J., Le Tinévez, R., and Brossalina, E. (1996) Biochimie 78, 663-673.
7. Brossalina, E., and Toulmé, J. J. (1993) J. Am. Chem. Soc. 115, 796-797.
8. Pascolo, E., and Toulmé, J.-J. (1996) J. Biol. Chem. 271, 24187-24192.
9. Felsenfeld, G., and Miles, H. T. (1967) Annu. Rev. Biochem. 36, 407-449.
10. Thuong, N. T., and Hélène, C. (1993) Angew. Chem., Int. Ed. 32, 666-690.
11. Sun, J. S., De Bizemont, T., Duval-Valentin, G., Montenay-Garestier, T., and Hélène, C. (1991) C. R. Acad. Sci. 313, 585-590.
12. Scaria, P. V., and Shafer, R. H. (1996) Biochemistry 35, 10985-10994.
13. Roberts, R. W., and Crothers, D. M. (1992) Science 258, 1463-1366.
14. Escudé, C., Francois, J. C., Sun, J. S., Ott, G., Sprinzl, M., Garestier, T., and Helene, C. (1993) Nucleic Acids Res. 21, 5547-5553.
15. Han, H., and Dervan, P. B. (1993) Proc. Natl. Acad. Sci. U.S.A. 90, 3806-3810.
16. Wang, S. H., and Kool, E. T. (1994) Nucleic Acids Res. 22, 2326-2333.
17. Wang, S., and Kool, E. T. (1995) Nucleic Acids Res. 23, 1157-1164.
18. Froehler, B. C., Jones, R. J., Cao, X. D., and Terhorst, T. J. (1993) Tetrahedron Lett. 34, 1003-1006.
19. Michel, J., Toulmé, J. J., Vercauteren, J., and Moreau, S. (1996) Nucleic Acids Res. 24, 1127-1135.
20. Michel, J., Gueguen, G., Vercauteren, J., and Moreau, S. (1997) Tetrahedron 53, 8457-8478.
21. Colocci, N., and Dervan, P. B. (1994) J. Am. Chem. Soc. 116, 785-786.
22. Newcomb, L. F., and Gellman, S. H. (1994) J. Am. Chem. Soc. 116, 4993-4994.
23. Guckian, K. M., Schweitzer, B. A., Ren, R. X. F., Sheils, C. J., Paris, P. L., Tahmassebi, D. C., and Kool, E. T. (1996) J. Am. Chem. Soc. 118, 8182-8183.
24. Curd, F. H. S., Landquist, J. K., and Rose, F. L. (1948) J. Chem. Soc., 1759-1766.
25. Rosowsky, A., and Modest, E. J. (1966) J. Org. Chem. 31, 2607-2613.
26. Freskos, J. N. (1989) Nucleosides Nucleotides 8, 549-555.
27. Beaucage, S. L., and Iyer, R. P. (1992) Tetrahedron 48, 2223-2311.
28. Bax, A., and Subramanian, S. (1986) J. Magn. Reson. 67, 565-569.
29. Bax, A., and Summers, M. F. (1986) J. Am. Chem. Soc. 108, 2093-2094.
30. Wang, S., Friedman, A. E., and Kool, E. T. (1995) Biochemistry 34, 9774-9784.
31. Giovannangeli, C., Montenay-Garestier, T., Rougée, M., Chassignol, M., Thuong, N. T., and Hélène, C. (1991) J. Am. Chem. Soc. 113, 7775-7777.
32. Kool, E. T. (1996) Annu. Rev. Biophys. Biomol. Struct. 25, 1-28.
33. Best, G. C., and Dervan, P. B. (1995) J. Am. Chem. Soc. 117, 1187-1193.
34. Wilson, W. D., Hopkins, H. P., Mizan, S., Hamilton, D. D., and Zon, G. (1994) J. Am. Chem. Soc. 116, 3607-3608.
35. Rajagopal, P., and Feigon, J. (1989) Nature 339, 637-640.
36. Bhattacharya, B. K., Chari, M. V., Durland, R. H., and Revankar, G. R. (1995) Nucleosides Nucleotides 14, 45-63.
37. Gambino, J., Yang, T. F., and Wright, G. E. (1994) Tetrahedron 50, 11363-11368.
38. Jungmann, O., and Pfleiderer, W. (1997) Nucleosides Nucleotides 16, 863-868.
39. Parmentier, G., Schmitt, G., Dolle, F., and Luu, B. (1994) Tetrahedron 50, 5361-5368.
40. Hunter, C. A., and Lu, X. J. (1997) J. Mol. Biol. 265, 603-619.
41. Xu, D. G., Evans, K. O., and Nordlund, T. M. (1994) Biochemistry 33, 9592-9599.
42. Hawkins, M. E., Pfleiderer, W., Balis, F. M., Porter, D., and Knutson, J. R. (1997) Anal. Biochem. 244, 86-95.
43. Kandimalla, E. R., Venkataraman, G., Sasisekharan, V., and Agrawal, S. (1997) J. Biomol. Struct. Dyn. 14, 715-726.