Synthesis, DNA binding, and cleaving properties of an ellipticine-salen·copper conjugate

Bioconjugate Chemistry

Volumn 8, Issue 6, 1997, Pages 789-792

  Routier, Sylvain ^a   Bernier, Jean Luc ^a   Catteau, Jean Pierre ^a   Colson, Pierre ^b   Houssier, Claude ^b   Rivalle, Christian ^a   Bisagni, Emile ^a   Bailly, Christian ^c  

^a CNRS   (France)

^b UNIVERSITY OF LIÈGE   (Belgium)

^c CENTRE OSCAR LAMBRET   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMOPHORES; COPPER COMPOUNDS;

COPPER COMPLEXES; COPPER CONJUGATES; CU COMPLEXES; DNA-BINDING; ELLIPTICINE; ETHYLENE DIAMINE; PROPERTY; SCHIFF-BASE COPPER COMPLEXES; SPECTROSCOPIC MEASUREMENTS;

DNA;

EID: 0031281392     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc970131y     Document Type: Article

References (21)

1. (a) Sigman, D. S., Mazumder, A., and Perrin, D. M. (1993) Chemical nucleases. Chem. Rev. 93, 2295-2316.
2. (b) Pratviel, G., Bernadou, J., and Meunier, B. (1995) Carbon-hydrogen bonds of DNA sugar units as targets for chemical nucleases and drugs. Angew. Chem., Int. Ed. Engl. 34, 746-769.
3. (a) Muller, J. G., Chen, X., Dadiz, A. C., Rokita, S. E., and Burrows, C. J. (1992) Ligands effects associated with the intrinsic selectivity of DNA oxidation promoted by nickel(II) macrocyclic complexes. J. Am. Chem. Soc. 114, 6407-6411.
4. (b) Woodson, S. A., Muller, J. G., Burrows, C. J., and Rokita, S. E. (1993) A primer extension assay for modification of guanine by Ni(II) complexes. Nucleic Acids Res. 21, 5524-5525.
5. (c) Cheng, C.-C., Rokita, S. E., and Burrows, C. J. (1993) Nickel(III)-promoted DNA cleavage with ambient dioxygen. Angew. Chem., Int. Ed. Engl. 32, 277-278.
6. (d) Muller, J. G., Paikoff, S. J., Rokita, S. E., and Burrows, C. J. (1994) DNA modification promoted by water-soluble nickel(II) salen complexes: a switch to DNA alkylation. J. Inorg. Biochem. 54, 199-206.
7. (e) Burrows, C. J., and Rokita, S. E. (1994) Recognition of guanine structure in nucleic acids by nickel complexes. Acc. Chem. Res. 27, 295-301.
8. (f) Gravert, D. J., and Griffin, J. H. (1993) Specific DNA cleavage mediated by [salenMn(III)]. J. Org. Chem. 58, 820-822.
9. +. Inorg. Chem. 35, 4837-4847.
10. (h) Bhattacharya, S., and Mandal, S. S. (1995) Ambient oxygen activating water soluble cobalt-salen complex for DNA cleavage. J. Chem. Soc., Chem. Commun., 2489-2490.
11. (i) Sato, K., Chikira, M., Fujii, Y., and Komatsu, A. (1994) Stereospecific binding of chemically modified salen-type Schiff base complexes of copper(II) with DNA. J. Chem. Soc., Chem. Commun., 625-626.
12. Routier, S., Bernier, J.-L., Waring, M. J., Colson, P., Houssier, C., and Bailly, C. (1996) Synthesis of a functionalized salen-copper complex and its interaction with DNA. J. Org. Chem. 61, 2326-2331.
13. Routier, S., Cotelle, N., Catteau, J.-P., Bernier, J.-L., Waring, M. J., Riou, J.-F., and Bailly, C. (1996) Salen-anthraquinone conjugates. Synthesis, DNA-binding and cleaving properties, effects on topoisomerases and cytotoxicity. BioOrg. Med. Chem. 4, 1185-1196.
14. Routier, S., Bernier, J.-L., Catteau, J.-P., and Bailly, C. (1997) Recognition and cleavage of DNA by a distamycin-salen·copper conjugate. BioOrg. Med. Chem. Lett. 7, 1729-1732.
15. Rivalle, C., Wendling, F., Tambourin, P., Lhoste, J.-M., Bisagni, E., and Chermann, J.-C. (1983) Antitumor amino-substituted pyrido[3′,4′:4,5]pyrrolo[2,3-g]isoquinolines and pyrido[4,3-b]carbazole derivatives: Synthesis and evaluation of compounds resulting from new side chain and heterocycle modifications. J. Med. Chem. 26, 181-185.
16. Bourdouxhe, C., Colson, P., Houssier, C., Sun, J.-S., Montenay-Garestier, T., Hélène, C., Rivalle, C., Bisagni, E., Waring, M. J., Hénichart, J.-P., and Bailly, C. (1992) Binding of a distamycin-ellipticine hybrid molecule to DNA and chromatin: spectroscopic, biochemical and molecular modeling investigations. Biochemistry 31, 12385-12396.
17. (a) Houssier, C., Hardy, B., and Fredericq, E. (1974) Interaction of ethidium bromide with DNA. Optical and electrooptical study. Biopolymers 13, 1141-1160.
18. (b) Fredericq, E., and Houssier, C. (1972) Study of the interaction of DNA and acridine orange by various optical methods. Biopolymers 11, 2281-2308.
19. Houssier, C. (1981) Investigating nucleic acids, nucleoproteins, polynucleotides, and their interactions with small ligands by electrooptical systems. In Molecular Electro-Optics (S. Krause, Ed.) pp 363-398, Plenum Publishing, New York.
20. Chou, P.-J., and Johnson, W. C., Jr (1993) Base inclinations in natural and synthetic DNAs. J. Am. Chem. Soc. 115, 1205-1214.
21. Bailly, C., OhUigin, C., Rivalle, C., Bisagni, E., Hénichart, J. P., and Waring, M. J. (1990) Sequence-selective binding of an ellipticine derivative to DNA. Nucleic Acids Res. 18, 6283-6291.