Synthesis and investigation of the DNA-binding and DNA-photodamaging properties of indolo[2,3-b]quinolizinium bromide

European Journal of Organic Chemistry

Volumn , Issue 6, 2001, Pages 1157-1161

  Ihmels, Heiko ^a   Faulhaber, Katja ^a   Wissel, Kathrin ^a   Bringmann, Gerhard ^a   Messer, Kim ^a   Viola, Giampietro ^b   Vedaldi, Daniela ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b UNIVERSITY OF PADOVA   (Italy)

Author keywords

Bioorganic chemistry; DNA cleavage; DNA recognition; Dyes; Heterocycles; Photochemistry

Indexed keywords

BROMINE DERIVATIVE; CYTOSINE; GUANINE; INDOLE DERIVATIVE; INDOLO[2,3 B]QUINOLIZINIUM BROMIDE; QUINOLIZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BASE PAIRING; CATTLE; CIRCULAR DICHROISM; DNA CLEAVAGE; DNA DAMAGE; DRUG DNA BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORESCENCE; NONHUMAN; THYMUS; TITRIMETRY; ULTRAVIOLET RADIATION;

EID: 0035082441     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200103)2001:6<1157::AID-EJOC1157>3.0.CO;2-Z     Document Type: Article

References (31)

1. Ethidium bromide: J.-B. LePecq, C. Paoletti, J. Mol. Biol. 1967, 27, 87-106.
2. Proflavine: L. S. Lermann, J. Mol. Biol. 1961, 3, 18-30.
3. Diazaperopyrenium: A. Slama-Schwok, J. Jazwinski, A. Béré, T. Montenay-Garestier, M. Rougée, C. Hélène, J.-M. Lehn, Biochemistry 1989, 28, 3227-3234.
4. Methylene blue: E. Tuite, J. M. Kelly, J. Photochem. Photobiol. B: Biol. 1993, 21, 103-124.
5. Pyridinium-substituted naphthaleneimides: J. E. Rogers, S. J. Weiss, L. A. Kelly, J. Am. Chem. Soc. 2000, 122, 427-436.
6. B. Armitage, Chem. Rev. 1998, 98, 1171-1200.
7. I. E. Kochevar, D. D. Dunn, in Bioorganic Photochemistry (Ed.: H. Morrison), John Wiley and Sons, New York, 1990, pp. 273-315.
8. W. D. Wilson, in Nucleic Acids in Chemistry and Biology (Eds.: G. M. Blackburn, M. J. Gait), IRL Press, Oxford, U.K., 2nd Ed., 1996, pp. 329-374.
9. S. J. Wagner, A. Skripchenko, D. Robinette, J. W. Foley, L. Cincotta, Photochem. Photobiol. 1998, 67, 343-349.
10. B. Lambrecht, H. Mohr, J. Knüver-Kopf, H Schmitt, Vox Sang. 1993, 60, 207-213.
11. S. P. Gupta, Chem. Rev. 1994, 94, 1507-1551.
12. W. D. Wilson, A. N. Gough, J. J. Doyle, M. W. Davidson, J. Med. Chem. 1976, 19, 1261-1263.
13. T.-K. Liu, E. Bathory, E. J. LaVoie, A. R. Srinivasan, W. K. Olson, R. R. Sauers, L. F. Liu, D. S. Pilch, Biochemistry 2000 39, 7107-7116.
14. A. Molina, J. J. Vaquero, J. L. Garcia-Navio, J. Alvarez-Builla, B. de Pascal-Teresa, F. Gado, M. M. Rodrigo, J. Org. Chem. 1999, 64, 3907-3915.
15. H. Ihmels, B. Engels, K. Faulhaber, C. Lennartz, Chem. Eur J. 2000, 6, 2854-2864.
16. K. Bonjean, M. C. De Pauw-Gillet, M. P. Defresne, P. Colson, C. Houssier, L. Dasonneville, C. Bailly, R. Greimers, C. Wright, J. Quetin-Leclercq, M. Tits, L. Ancenot, Biochemistry 1998, 37, 5136-5146.
17. J. Kebrle, A. Rossi, K. Hoffmann, Helv. Chim. Acta 1959, 42, 907-918.
18. Part of this work has been presented as a poster at the 4th Electronic Conference on Synthetic Organic Chemistry, 01.09.-31.09.2000 (http://www.unibas.ch/mdpi/ecsoc-4.htm).
19. C. K. Bradsher, J. C. Parham, J. Org. Chem. 1963, 28, 83-85.
20. R. Lui, P. Zhang, T. Gan, J. M. Cook, J. Org. Chem. 1997, 62, 7447-7456.
21. Cyclizatipn in the presence of bromide ions led to nucleophilic substitution at the 2-position. For similar examples, see: M. Hasegawa, K. Yamada, Y. Naeahama, M. Somei, Heterocycles 1999, 51, 2815-2821.
22. W.-K. Gries, E. Günther, S. Hünig, Liebigs Ann. 1991, 1021-1028.
23. P. Suppan. N. Ghoneim, Solvatochromism, The Royal Society of Chemistry, London, 1997.
24. C. R. Cantor, P. R. Schimmel, Biophysical Chemistry Part 2: Techniques for the Study of Biological Structure and Function, Freeman, New York, 1980, 444-454.
25. S. Steenken, S. Jovanovic, J. Am. Chem. Soc. 1997, 119, 617-618.
26. J. D. McGhee, P. H. von Hippel, J. Mol. Biol. 1974, 86, 469-489.
27. P. Fosse, C. Paoletti, J. M. Saucier, Biochem. Biophys. Res. Commun. 1988, 151, 1233-1240.
28. B. Norden, T. Kurucsev, J. Mol. Recognit. 1994, 7, 141-156.
29. B. Norden, M. Kubista, T. Kurucsev, Quart. Rev. Biophys. 1992, 25, 51-170.
30. J. N. Demas, G. A. Crosby, J. Phys. Chem. 1971, 75, 991-1024
31. D. F. Eaton, Pure Appl. Chem. 1988, 60, 1108-1114.