Deactivation behavior and excited-state properties of (coumarin-4- yl)methyl derivatives. 1. Photocleavage of (7-methoxycoumarin-4-yl)methyl- caged acids with fluorescence enhancement

Journal of Organic Chemistry

Volumn 64, Issue 25, 1999, Pages 9109-9117

  Schade, Björn ^a   Hagen, Volker ^a   Schmidt, Reinhard ^b   Herbrich, Ralph ^b   Krause, Eberhard ^a   Eckardt, Torsten ^a   Bendig, Jürgen ^c  

^a LEIBNIZ INSTITUT FÜR MOLEKULARE PHARMAKOLOGIE   (Germany)

^b GOETHE UNIVERSITY   (Germany)

^c HUMBOLDT UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

COUMARIN DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; FLUORESCENCE; HYDROPHILICITY; PHOTOCHEMISTRY; PHOTODEGRADATION; PHOTOLYSIS; REACTION ANALYSIS;

EID: 0032783950     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9910233     Document Type: Article

References (38)

1. (a) Corrie, J. E. T.; Trentham, D. R. In Bioorganic Photochemistry; Morrison, H., Ed.; Wiley: New York, 1993; Vol. 2, pp 243-305.
2. (b) Adams, S. R.; Tsien, R. Y. Annu. Rev. Physiol. 1993, 55, 755-784.
3. (c) McCray, J. A.; Trentham, D. R.; Annu. Rev. Biophys. Biophys. Chem. 1989, 18, 239-270.
4. (a) Hagen, V.; Dzeja. C.; Bendig, J.; Baeger, I.; Kaupp, U. B. J. Photochem. Photobiol. B: Biol. 1997, 42, 71-78.
5. (b) Hagen, V.; Dzeja, C.; Frings, S.; Bendig, J.; Krause, E.; Kaupp, U. B. Biochemistry 1996, 35, 7762-7771.
6. For reviews see: (a) Pillai, V. N. R. Org. Photochem. 1987, 9, 225-323. (b) Pillai, V. N. R. Synthesis 1980, 1-26.
7. For reviews see: (a) Pillai, V. N. R. Org. Photochem. 1987, 9, 225-323. (b) Pillai, V. N. R. Synthesis 1980, 1-26.
8. (a) Furuta, T.; Torigai, H.; Sugimoto, M.; Iwamura, M. J. Org. Chem. 1995, 60, 3953-3956.
9. (b) Bendig, J.; Helm, S.; Hagen, V. J. Fluoresc. 1897, 7, 357-361.
10. (c) Furuta, T.; Iwamura, M. Caged Compounds. In Methods of Enzymology; Marriott, G., Ed.; Academic Press: San Diego, CA, 1998; Vol. 291, pp 50-63.
11. (a) Itoh, Y.; Gouki, M.; Goshima, T.; Hachimori, A.; Kojima, M.; Karatsu, T. J. Photochem. Photobiol. A 1998, 117, 91.
12. (b) Pincock, J. A. Acc. Chem. Res. 1997, 30, 43.
13. (c) Arnold, B.; Donald, L.; Jurgens, A.; Pincock, J. A. Can. J. Chem. 1985, 63, 3140.
14. Hilborn, J. W.; MacKnight, E.; Pincock, J. A.; Wedge, P. J. J. Am. Chem. Soc. 1994, 116, 3337.
15. Givens, R. S.; Matuszewski, B. J. Am. Chem. Soc. 1984, 106, 6860-6861.
16. Seixas de Melo, J. S.; Becker, R. S.; Macanita, A. L. J. Phys. Chem. 1994, 98, 6054-6058.
17. Sehgal, J. M.; Seshadri, T. R. J. Sci. Ind. Res. 1953, 12B, 346.
18. Wilcox, M.; Viola, R. W.; Johnson, K. W.; Billington, A. P.; Carpenter, B. K.; McCray, J. A.; Guzikowski, A. P.; Hess, G. P. J. Org. Chem. 1990, 55, 1585-1589.
19. Ito, K.; Sawanobori, J. Synth. Commun. 1982, 12 (9), 665-671.
20. First described by: Givens, R. S.; Matuszewski, B. See ref 7.
21. Givens, R. S.; Matuszewski, B.; Athey, P. S.; Stoner, M. R. J. Am. Chem. Soc. 1990, 112, 6016-6021.
22. Furuta, T.; Torigai, H.; Osawa, T.; Iwamura, M. J. Chem. Soc., Perkin Trans 1 1993, 3139-3142.
23. (a) Engels, J. Bioorg. Chem. 1979, 8, 9-16.
24. (b) Nerbonne, J. M.; Richard, S.; Nargeot, J.; Lester, H. A. Nature 1984, 310, 74-76.
25. Hagen, V.; Bendig, J.; Frings, S.; Wiesner, B.; Schade, B.; Helms, S.; Lorenz, D.; Kaupp, U. B. J. Photochem. Photobiol B: Biol., in press.
26. Dippy, J. F. J. J. Chem. Soc. 1938, 9, 1222-1227.
27. Vandenbelt, J. M.; Henrich, C.; Vanden Berg, S. G. Anal. Chem. 1954, 26, 726.
28. Willi, A. V.; Stocker, J. F. Helv. Chim. Acta 1955, 38, 1279.
29. Wideqvist, B. Ark. Kemi 1951, 2, 383-386.
30. Marziano, N. C.; Sampoli, M.; Gonizzi, M. J. Phys. Chem. 1986, 90 (18), 4347-4353.
31. Galkin, V. I.; Sayakhov, R. D.; Garifzyanov, A. R.; Cherkasov, R. A.; Pudovik, A. N. Dokl. Chem. (Engl. Transl.) 1991, 378, 114-116.
32. Furuta, T.; Whang, S. S.-H.; Dantzker, J. L.; Dore, T. M.; Bybee, W. J.; Callaway, E. M.; Denk, W.; Tsien, R. Y. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 1193-1200 and references cited herein.
33. Seidel, C. A. M.; Schulz, A.; Sauer, M. H. M. J. Phys. Chem. 1996, 100, 5541-5553.
34. Ito, K.; Maruyama, J. Chem. Pharm. Bull. 1983, 31 (9), 3014-3023.
35. Kuhn, H. J.; Braslawsky, S. E.; Schmidt, R. Pure Appl. Chem. 1989, 61, 187-210.
36. Demas, J. N.; Crosby, G. A. J. Phys. Chem. 1971, 75, 991; EPA Newsl. 1986, 28, 21.
37. Demas, J. N.; Crosby, G. A. J. Phys. Chem. 1971, 75, 991; EPA Newsl. 1986, 28, 21.
38. Grewer, C.; Brauer, H.-D. J. Phys. Chem. 1993, 97, 5001-5006.