Hybrid Oligonucleotides Containing Stilbene Units. Excimer Fluorescence and Photodimerization

Journal of the American Chemical Society

Volumn 117, Issue 34, 1995, Pages 8785-8792

  Lewis, Frederick D ^a   Wu, Taifeng ^a   Burch, Eric L ^a   Bassani, Dario M ^a   Yang, Jye Shane ^a   Letsinger, Robert L ^a   Schneider, Siegfried ^b   Jäger, Wighard ^b  

^a NORTHWESTERN UNIVERSITY   (United States)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGONUCLEOTIDE; STYRENE DERIVATIVE;

ARTICLE; DIMERIZATION; DRUG SYNTHESIS; FLUORESCENCE; PHOTOCHEMISTRY;

EID: 0029085205     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00139a011     Document Type: Article

References (48)

1. Mahler, H. R.; Cordes, E. H. Biological Chemistry, 2nd ed.; Harper & Row: New York, 1971; pp 224–227.
2. Saenger, W. Principles of Nucleic Acid Structure; Springer-Verlag: New York, 1984.
3. Picirilli, J. A.; Kanch, T.; Moroney, S. E.; Benner, S. A. Nature 1990, 343, 33–37.
4. Bergstrom, D. E.; Zhang, P.; Toma, P. H.; Andrews, P. C.; Nichols, R. J. Am. Chem. Soc. 1995, 117, 1201—1209.
5. Schweitzer, B. A.; Kool, E. T. J. Am. Chem. Soc. 1995, 117, 1863–1872.
6. Durand, M.; Chevrie, K.; Chassignol, M.; Thuong, N. T.; Naurizot, J. D. Nucleic Acids Res. 1990, 21, 6353–6359.
7. Kessler, D. I.; Pettitt, B. M.; Cheng, Y.-K.; Smith, S. R.; Jayaraman, K.; Vu, H. M.; Hogan, M. E. Nucleic Acids Res. 1993, 24, 4810–4815.
8. Salunkhe, M.; Wu, T.; Letsinger, R. L. J. Am. Chem. Soc. 1992, 114, 8768–8772.
9. Letsinger, R. L.; Wu, T. J. Am. Chem. Soc. 1994, 116, 811–812.
10. Saltiel, J.; Sun, Y.-P. In Photochromism, Molecules and Systems; Dürr, H., Bouais-Laurent, H., Eds.; Elsevier: Amsterdam, 1990; pp 64–164.
11. Waldeck, D. H. Chem. Rev. 1991, 91, 415–436.
12. Lewis, F. D.; Johnson, D. E. J. Photochem. 1977, 421–423.
13. Lewis, F. D. Adv. Photochem. 1986, 13, 165–235.
14. Peters, K. S.; Freilich, S. C.; Lee, J. J. Phys. Chem. 1993, 97, 5482–5485.
15. Shechter, H.; Link, W. J.; Tiers, C. V. D. J. Am. Chem. Soc. 1963, 85, 1601–1605.
16. Altomare, A.; Carlini, C.; Ciardelli, F.; Solaro, R.; Houben, J. L.; Rosato, N. Polymer 1983, 24, 95–100.
17. Song, X.; Geiger, C.; Leinhos, U.; Perlstein, J.; Whitten, D. G. J. Am. Chem. Soc. 1994, 116, 10340–10341.
18. Anger, I.; Sandros, K.; Sundahl, M.; Wennerstrom, O. J. Phys. Chem, 1993, 97, 1920–1923.
19. Letsinger, R. L.; Wu, T. J. Am. Chem. Soc. 1995, 117, 7323–7328.
20. Letsinger, R. L.; Chaturvedi, S. K.; Farooqui, F.; Salunkhe, M. J. Am. Chem. Soc. 1993, 115, 7535–7536.
21. van Houte, L. P. A.; Van Grondelle, R.; Retel, J.; Westra, J. G.; Zinger, D.; Sutherland, J. C.; Kim, S. K.; Geacintov, N. E. Photochem. Photobiol. 1989, 49, 387–394.
22. Margulis, L.; Pluzhnikov, P.; Mao, B.; Kuzmin, V. A.; Chang, Y. J.; Scott, T. W.; Geacintov, N. E. Chem. Phys. Lett. 1991, 187, 597–603.
23. O’Connor, D.; Shafirovich, V. Y.; Geacintov, N. E. J. Phys. Chem. 1994, 98, 9831–9839.
24. Shafirovich, V. Y. P. L. P.; Kuzmin, V. A.; Thorgeirsson, T. E. S. K. D.; Geacintov, N. E. J. Am. Chem. Soc. 1994, 116, 63–72.
25. Telser, J.; Cruickshank, K. A.; Morrison, L. E.; Netzel, T. L. J. Am. Chem. Soc. 1989, 111, 6966–6976.
26. Telser, J.; Cruickshank, K. A.; Morrison, L. E.; Netzel, T. L.; Chan, C. J. Am. Chem. Soc. 1989, 111, 7226–7232.
27. Yang, J.-S. Unpublished results.
28. Armitage, B.; Yu, C.; Devadoss, C.; Schuster, G. B. J. Am. Chem. Soc. 1994, 116, 9847–9859.
29. Sevilla, M. D.; Besler, B.; Colson, A. J. Phys. Chem. 1995, 99, 1060–1063.
30. Birks, J. B. Photophysics of Aromatic Molecules; Wiley-Inter-science: London, 1970.
31. Hayashi, T.; Malaga, N.; Sakata, Y.; Misumi, S.; Morita, M.; Tanaka, J. J. Am. Chem. Soc. 1976, 98(19), 5910–5913.
32. Atherton, S. J.; Harriman, A. J. Am. Chem. Soc. 1993, 115, 1816–1822.
33. Ito, Y.; Miyata, S.; Nakatsuka, M.; Sqegusa, T.; Takamoto, M.; Wada, Y. J. Chem. Soc., Chem. Commun. 1982, 375–376.
34. Venkatesan, K.; Ramamurthy, V. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH Publishers: New York, 1991; pp 133—184.
35. Jenkins, Y.; Barton, J. K. J. Am. Chem. Soc. 1992, 114, 8736–8738.
36. Kierzek, R.; Turner, D. H.; Bevilacqua, P. C. J. Am. Chem. Soc. 1993, 115, 4985–4992.
37. Cardullo, R. A.; Agrawal, S.; Flores, C.; Zamecnik, P. D.; Wolf, D. E. Proc. Natl. Acad. Sci, U.S.A. 1988, 85, 8790–8794.
38. Clegg, R. M.; Murchie, A. I. H.; Zechel, A.; Lilley, D. M. Proc. Natl. Acad. Sci, U.S.A. 1988, 90, 2994–2998.
39. Morrison, L. E.; Stols, L. M. Biochemistry 1993, 32, 3095—3104.
40. Perkins, T. A.; Goodman, J. L.; Kool, E. T. J. Chem. Soc., Chem. Commun. 1993, 215–216.
41. Telser, J.; Cruickshank, K. A.; Morrison, L. E.; Netzel, T. L.; Chan, C. J. Am. Chem. Soc. 1989, 111, 7226–7232.
42. Ferentz, A. E.; Verdine, G. L. J. Am. Chem. Soc. 1991, 113, 4000–4002.
43. Shi, Y.-B.; Lipson, S. E.; Chi, D. Y.; Spielmann, H. P.; Monforte, J. A.; Hearst, J. E. In Bioorganic Photochemistry; Morrison, H., Ed.; Wiley-Interscience: New York, 1990; pp 341–378.
44. Bahn, P.; Miller, P. S. Bioconjugate Chem. 1990, 1, 82–88.
45. Parseuth, D.; Doan, T. L.; Chassignol, M.; Decout, J.-L.; Habhoub, N.; Lhomme, J.; Thuong, N. T.; Helene, C. Biochemistry 1988, 27, 3031—3038.
46. Lewis, F. D.; Reddy, G. D.; Schneider, S.; Gahr, M. J. Am. Chem. Soc. 1991, 113, 3498–3506.
47. Li, R.; Lim, E. C. J. Chem. Phys. 1972, 57, 605–612.
48. Heller, H. G.; Langan, J. R. J. Chem. Soc., Perkin Trans. 2 1981, 341–343.