Indolo[2,3-b]-quinolizinium bromide: An efficient intercalator with DNA-photodamaging properties

ChemBioChem

Volumn 3, Issue 6, 2002, Pages 550-558

  Viola, Giampietro ^a   Dall'Acqua, Francesco ^a   Gabellini, Nadia ^a   Moro, Stefano ^a   Vedaldi, Daniela ^a   Ihmels, Heiko ^b  

^a UNIVERSITY OF PADOVA   (Italy)

^b UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Bioorganic chemistry; DNA cleavage; Molecular modeling; Photobiology; Quinolizinium salts

Indexed keywords

BROMINE DERIVATIVE; DNA; DYE; INDOLO[2,3 B]QUINOLIZINIUM BROMIDE; INTERCALATING AGENT; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; BASE PAIRING; DNA BINDING; DNA CLEAVAGE; DNA DAMAGE; ENERGY TRANSFER; FLAME PHOTOMETRY; LINEAR DICHROISM; MOLECULAR MODEL; PRIORITY JOURNAL; ULTRAVIOLET A RADIATION;

AUTORADIOGRAPHY; BASE SEQUENCE; BINDING SITES; BROMIDES; DNA; DNA DAMAGE; ENERGY TRANSFER; FLUOROMETRY; INDOLES; INTERCALATING AGENTS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PHOTOCHEMISTRY; QUINOLIZINES; RADIATION-SENSITIZING AGENTS; SPECTROPHOTOMETRY; THERMODYNAMICS; TITRIMETRY;

EID: 0036902167     PISSN: 14394227     EISSN: None     Source Type: Journal    
DOI: 10.1002/1439-7633(20020603)3:6<550::AID-CBIC550>3.0.CO;2-Z     Document Type: Article

References (50)

1. E. Kochevar, D. D. Dunn in Bioorganic Photochemistry (Ed.: H. Morrison), John Wiley and Sons, New York, 1990, p. 273.
2. G. Pratviel, J. Bernadou, B. Meunier, Angew. Chem. 1995, 107, 819; Angew. Chem. Int. Ed. Engl. 1995, 34, 746.
3. G. Pratviel, J. Bernadou, B. Meunier, Angew. Chem. 1995, 107, 819; Angew. Chem. Int. Ed. Engl. 1995, 34, 746.
4. B. Armitage, Chem. Rev. 1998, 98, 1171.
5. D. T Croke, L. Perroault, M. A. Sari, J. P. Battioni, D. Mansuy, C. Hèlene, T. Le Doan, J. Photochem. Photobiol. B 1993, 18, 41.
6. H. Y. Mei, J. K. Barton, Proc. Natl. Acad. Sci. USA 1988, 85, 1939.
7. T. Saito, M. Takayama, T. Matsura, J. Am. Chem. Soc. 1990, 112, 883.
8. S. Matsugo, S. Kawanishi, K. Yamamoto, H. Sugiyama, T. Matsuura, T. Saito, Angew. Chem. 1991, 103, 1343; Angew. Chem. Int. Ed. Engl. 1991, 30, 1351.
9. S. Matsugo, S. Kawanishi, K. Yamamoto, H. Sugiyama, T. Matsuura, T. Saito, Angew. Chem. 1991, 103, 1343; Angew. Chem. Int. Ed. Engl. 1991, 30, 1351.
10. M. Bouziane, C. Ketterle, P. Helissey, P. Herfeld, M. Le Bret, S. Giorgi-Renault, C. Auclair, Biochemistry 1995, 34, 14051.
11. P. E. Nilsen, Bioconjugate Chem. 1991, 2, 1.
12. D. T. Breslin, G. B. Schuster, J. Am. Chem. Soc. 1996, 118, 2311.
13. M. P. Fontaine-Aupart, E. Renault, C. Videlot, F. Tfibel, R. Pansu, M. Charlier, P. Pernot, Photochem. Photobiol. 1999, 70, 929.
14. W. D. Wilson in Nucleic Acids in Chemistry and Biology (Eds.: G.M. Blackburn, M.J. Gait) IRL Press, Oxford, 1996, pp. 331-374.
15. W. D. Wilson, A. N. Gough, J. J. Doyle, M. W. Davidson, J. Med. Chem. 1976, 19, 1261.
16. D.S. Pilch, C. Yu, D. Makhey, E. J. LaVoie, A. R. Srinivasan, W. K. Olson, R. S. Sauers, K. J. Breslauer, N. E. Geacintov, L. F. Liu, Biochemistry 1997, 36, 12542.
17. 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.
18. 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.
19. H. Ihmels, K. Faulhaber, C. Sturm, G. Bringmann, K. Messer, N. Gabellini, D. Vedaldi, G. Viola, Photochem. Photobiol. 2001, 74, 505.
20. A. Hörmann, B. Chaudhuri, H. Fretz, Bioorg. Med. Chem. 2001, 9, 917.
21. H. Ihmels, G. Bringmann, K. Faulhaber, K. Messer, C. Sturm, D. Vedaldi, G. Viola, Eur. J. Org. Chem. 2001, 1157.
22. J. D. McGhee, P. H. von Hippel, J. Mol. Biol. 1974, 86, 469.
23. G. Schatchard, Ann. N. Y. Acad. Sci. 1949, 51, 660.
24. M. T Record Jr., C. F. Anderson, T. M. Lohman, Q. Rev. Biophys. 1978, 11, 103.
25. J. B. Chaires, Anti-Cancer Drug Des. 1996, 11, S69.
26. B. Nordén, M. Kubista, T. Kurucsev, Q. Rev. Biophys. 1992, 25, 51.
27. B. Nordén, T. Kurucsev, J. Mol. Recognit. 1994, 7, 141.
28. D. S. Suh, J. B. Chaires, Bioorg. Med. Chem. 1995, 3, 723.
29. T. Förster, Ann. Phys. 1948, 2, 55.
30. H. Kyung-Mee, C. Sang-Doh, L. Saeyun, K. K. Soeg, Biochim. Biophys. Acta 1997, 1334, 312.
31. M. Rayner, A.G. Szabo, R. O. Loufty, R. W. Ylp, J. Phys. Chem. 1980, 84, 289.
32. M. Ponti, S. M. Farrow, R. L. Souhami, M. D'Incalci, J. A. Hartley, Nucleic Acids Res. 1991, 19, 2929.
33. Sanger, S. Nicklen, A. R. Coulsen, Proc. Natl. Acad. Sci. USA 1977, 74, 5463.
34. M. Saito, H. Takayama, K. Sugiyama, Nakatani, J. Am. Chem. Soc. 1995, 117, 6406.
35. J. E. Rogers, S. J. Weiss, L. A. Kelly, J. Am. Chem. Soc. 2000, 122, 427.
36. C. H. Kumar, E. H. A. Punzalan, W. B. Tan, Tetrahedron 2000, 56, 7027.
37. S. Steenken, S. V Jovanovic, J. Am. Chem. Soc. 1997, 119, 618.
38. J. Burrows, J. G. Muller, Chem. Rev. 1998, 98, 1109.
39. S. Neidle, T. C. Jenkins, Methods Enzymol. 1991, 203, 433.
40. C. J. Alden, S. Arnott, Nucleic Acids Res. 1975, 10, 1701.
41. G. Berhens, G. Kroneburg, D. Schulte-Frohlinde, Z. Naturforsch, C: J. Biosci. 1982, 37, 1205.
42. B. Giese, X. Beirich-Graf, J. Burger, C. Kesselheim, M. Senn, T. Schäfer, Angew. Chem. 1993, 105, 1850; Angew. Chem. Int. Ed. Engl. 1993, 32, 1742.
43. B. Giese, X. Beirich-Graf, J. Burger, C. Kesselheim, M. Senn, T. Schäfer, Angew. Chem. 1993, 105, 1850; Angew. Chem. Int. Ed. Engl. 1993, 32, 1742.
44. J. R. Lakowicz, Principles of Fluorescence Spectroscopy, Plenum Press, New York, 1983, pp. 257.
45. NAMOT2 (Nucleic Acid Modeling Tool), Los Alamos National Laboratory, Los Alamos, NM, USA.
46. Molecular Operating Environment (MOE 2001.01), Chemical Computing Group, Inc, 1255 University Street, Suite 1600, Montreal, PQ, Canada.
47. S. J. Weiner, P. A. Kollman, D. T. Nguyen, J. Comput. Chem. 1986, 7, 230.
48. Gaussian98 (Revision A.7), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1998.
49. D. Qiu, S. Shenkin, F. P. Hollinger, W. C. Still, J. Phys. Chem. 1997, 101, 3005.
50. T. A. Ciulla, J. R. Van Camp, E. Rosenfeld, I. E. Kochevar, Photochem. Photobiol. 1989, 49, 293.