Reactivities of Carboxyalkyl-Substituted 1,4,5,8-Naphthalene Diimides in Aqueous Solution

Journal of the American Chemical Society

Volumn 126, Issue 13, 2004, Pages 4293-4300

  Abraham, Bindu ^a   McMasters, Sun ^a   Mullan, Mellisa A ^a   Kelly, Lisa A ^a  

^a UNIVERSITY OF MARYLAND BALTIMORE COUNTY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; ELECTRON TRANSITIONS; LASER PULSES; PHOTOLYSIS; REDOX REACTIONS; SYNTHESIS (CHEMICAL);

ELECTRON DONORS; LASER FLASH PHOTOLYSIS;

AROMATIC HYDROCARBONS;

1,4,5,8 NAPHTHALENE DIIMIDE DERIVATIVE; ACETIC ACID; ALANINE; ALKYL GROUP; BENZYLVIOLOGEN; CARBOXYL GROUP; FERRICYANIDE; GLYCINE; N,N' BIS[2 (N PYRIDINIUM)ETHYL] 1,4,5,8 NAPHTHALENE DIIMIDE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CALCULATION; CHEMICAL MODIFICATION; ELECTRON TRANSPORT; MOLECULAR INTERACTION; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY; SOLUBILITY; SUBSTITUTION REACTION; THERMODYNAMICS;

ANIMALS; ANTINEOPLASTIC AGENTS; DNA; IMIDES; NAPHTHALENES; OXIDATION-REDUCTION; SPECTROMETRY, FLUORESCENCE; WATER;

EID: 1842502870     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0389265     Document Type: Article

References (36)

1. Brana, M. F.; Sanz, A. M.; Castellano, J. M.; Roldan, M. C.; Roldan, C. Eur. J. Med. Chem. 1981, 16, 207-212.
2. Brana, M. F.; J. M., C.; Perron, D.; Maher, C.; Conlon, D.; Bousquet, P. F.; George, J.; Qian, X.; Robinson, S. P. J. Med. Chem. 1997, 40, 449-454.
3. Brana, M. F.; Castellano, J. M.; Moran, M.; Perez de Vega, M. J.; Perron, D.; Conlon, D.; Bousquet, P. F.; Romerdahl, C. A.; Robinson, S. P. Anti-Cancer Drug Des. 1996, 297-309.
4. Bailly, C.; Carrasco, C.; Joubert, A.; Bal, C.; Wattez, N.; Hildebrand, M.-P.; Lansiaux, A.; Colson, P.; Houssier, C.; Cacho, M.; Ramos, A.; Brana, M. F. Biochemistry 2003, 42, 4136-4150.
5. Brana, M. F.; Dominguez, G.; Saez, B.; Romerdahl, C.; Robinson, S.; Barlozzari, T. Eur. J. Med. Chem. 2002, 37, 541-551.
6. Liu, Z.; Hecker, K.; Rill, R. L. J. Biomol. Struct. Dyn. 1996, 14, 331-338.
7. Guelev, V.; Sorey, S.; Hoffman, D. W.; Iverson, B. L. J. Am. Chem. Soc. 2002, 124, 2864-2865.
8. Lokey, R. S.; Kwok, Y.; Guelev, V.; Pursell, C. J.; Hurley, L. H.; Iverson, B. L. J. Am. Chem. Soc. 1997, 119, 7202-7210.
9. Takenaka, S.; Yokoyama, M.; Kondo, H. Chem. Commun. 1997, 115-116.
10. Bevers, S.; Schutte, S.; McLaughlin, L. W. J. Am. Chem. Soc. 2000, 122, 5905-5915.
11. Okamoto, A.; Nakamura, T.; Yoshida, K.; Nakatani, K.; Saito, I. Org. Lett. 2000, 2, 3249-3251.
12. Steullet, V.; Dixon, D. W. Bioorg. Med. Chem. Lett. 1999, 9, 2935-2940.
13. Nunez, M. E.; Noyes, K. T.; Gianolio, D. A.; McLaughlin, L. W.; Barton, J. K. Biochemistry 2000, 39, 6190-61999.
14. Matsugo, S.; Kawanishi, S.; Yamamoto, K.; Sugiyama, H.; Matsuura, T.; Saito, I. Angew. Chem., Int. Ed. Engl. 1991, 30, 1351-1353.
15. Aveline, B. A.; Matsugo, S.; Redmond, R. W. J. Am. Chem. Soc. 1997, 119, 11785-11795.
16. Yamamoto, T.; Meaeda, Y.; Matsugo, S.; Kitano, H. Photochem. Photobiol. 1997, 66, 65-71.
17. Rogers, J. E.; Kelly, L. A. J. Am. Chem. Soc. 1999, 121, 3854-3861.
18. Rogers, J. E.; Weiss, S. J.; Kelly, L. A. J. Am. Chem. Soc. 2000, 122, 427-436.
19. Sawyer, D. T.; Sobkowiak, A.; Roberts, J. L. In Electrochemistry for Chemists, 2nd ed.; Wiley-Interscience: New York, 1995; p 27.
20. Wardman, P. J. Phys. Chem. Ref. Data 1989, 18, 1637-1723.
21. Rodrigues, M. A.; Brochsztain, S.; Barros, T.; Baptisma, M. S.; Politi, M. J. Photochem. Photobiol. 1999. 70, 35-39.
22. Brochsztain, S.; Politi, M., J. Langmuir 1999, 15, 4486-4494.
23. Viehbech, A.; Goldberg, M. J.; Kovac, C. A. J. Electrochem. Soc. 1990, 137, 1460-1466.
24. Demas, J. N. Excited-State Lifetime Measurements; Academic Press Inc.: New York, 1983.
25. Workentin, M. S.; Parker, V. D.; Morkin, T. L.; Wayner, D. D. M. J. Phys. Chem. A 1998, 102, 6503-6512.
26. DeFelippis, M. R.; Murthy, C. P.; Broitman, F.; Weinraub, D.; Faraggi, M.; Klapper, M. H. J. Phys. Chem. 1991, 95, 3416-3419.
27. Tsukhara, K.; Wilkins, R. G. J. Am. Chem. Soc. 1985, 107, 2632-2635.
28. Farrington, J.; Ebert, M.; Land, E. J. J. Chem. Soc., Faraday, Trans. 1 1978, 74, 665-672.
29. Watanabe, T.; Honda, K. J. Phys. Chem. 1982, 86, 2617-2619.
30. Griesbeck, A. G.; Henz, A.; Kramer, W.; Lex, J.; Nerowski, F.; Oelgemoller, M. Helv. Chim. Acta 1997, 80, 912-933.
31. Gomer, H.; Oelgemoller, M.; Griesbeck, A. G. J. Phys. Chem. A 2002, 106, 1458-1464.
32. Griesbeck, A. G.; Kramer, W.; Heinrich, T.; Lex, J. Photochem. Photobiol. Sci. 2002, 1, 237-239.
33. Griesbeck, A. G.; Schieffer, S. Photochem. Photobiol. Sci. 2003, 2, 113-117.
34. Takahashi, Y.; Miyashi, T.; Yoon, U. C.; Oh, S. W.; Mancheno, M.; Su, Z. ; Falvey, D.; Mariano, P. S. J. Am. Chem. Soc. 1999, 121, 3926-3932.
35. Melhuish, W. H. J. Phys. Chem. 1961, 65, 229-235.
36. -1.