Threading bis-intercalation of a macrocyclic bisacridine at abasic sites in DNA: Nuclear magnetic resonance and molecular modeling study

Biochemistry

Volumn 38, Issue 43, 1999, Pages 14205-14213

  Jourdan, Muriel ^a   Garcia, Julian ^a   Lhomme, Jean ^a   Teulade Fichou, Marie Paule ^b   Vigneron, Jean Pierre ^b   Lehn, Jean Marie ^b  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

^b l'alimentation et l'Environnement   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACRIDINE DERIVATIVE; BISACRIDINE; DNA; MACROCYCLIC COMPOUND; OLIGONUCLEOTIDE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DNA DRUG COMPLEX; INTERCALATION COMPLEX; MOLECULAR MODEL; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

ACRIDINES; BINDING SITES; DNA; DNA ADDUCTS; FURANS; INTERCALATING AGENTS; KINETICS; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; NUCLEIC ACID CONFORMATION; OLIGONUCLEOTIDES; PROTONS;

EID: 0033607302     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi991111h     Document Type: Article

References (60)

1. Lindahl, T., and Nyberg, B. (1972) Biochemistry 11, 3610-3618.
2. Singer, B., and Grunberger, D. (1983) Molecular Biology of Mutagens and Carcinogens ; Plenum Press: New York, pp 16-19.
3. Price, A. (1993) Cancer Biology 4, 61-71.
4. Teoule, R. (1987) J. Radiat. Biol. 51, 573-589.
5. Laval, E., and Laval, F. (1980) Molecular and Cellular Aspects of Carcinogens Screening Tests ; Oxford University Press: Oxford, U.K., Vol. 27, pp 55-73.
6. Weiss, B., and Grossman, L. (1987) Adv. Enzymol. Relat. Areas Mol. Biol., 60, 1-34.
7. Sancar, A., and Sancar, G. B. (1988) Annu. Rev. Biochem. 57, 29-67.
8. Myles, G. M., and Sancar, A. (1989) Chem. Res. Toxicol. 2, 197-226.
9. Bailly, V., and Verly, W. G. (1987) Biochem. J. 242, 565-572.
10. Kim, J., and Lin, S. (1988) Nucl. Acids Res. 146, 229-241.
11. Bailly, V., and Verly, W. G. (1989) Nucl. Acids Res. 17, 3617-3618.
12. Demple, B., and Harrison, L. (1994) Annu. Rev. Biochem. 63, 915-948.
13. Gentil, A., Margot, A., and Sarasin, A. (1984) Mutat. Res. 129, 141-147.
14. Loeb, L. A., and Preston, B. D. (1986) Annu. Rev. Genet. 20, 201-230.
15. Hickson, I. D. (1997) Base Excision Repair of DNA Damage, Springer-Verlag, Heidelberg, Germany, pp 81-102.
16. Lown, J. W., and McLaughlin, L. W. (1979) Biochem. Pharmacol. 28, 1631-1638.
17. Lown, J. W., Joshua, A. V., and McLaughlin, L. W. (1980) J. Med. Chem. 23, 798-805.
18. Malvy, C., Prevost, P., Gansser, C., and Paoletti, C. (1986) Chem. Biol. Interact. 57, 41-53.
19. Bertrand, J.-R., Vasseur, J.-J., Gouyette, A., Rayner, B., Imbach, J.-L., Paoletti, C., and Malvy, C. (1989) J. Biol. Chem. 264, 14172-14178
20. Vasseur, J.-J., Rayner, B., Imbach, J.-L., Verna, S., McCloskey, J. A., Lee, M., Chang, D. K., and Lown, J. L. (1987) J. Org. Chem. 52, 4994-4998.
21. Vasseur, J.-J., Peoc'h, D., Rayner, B., and Imbach, J.-L. (1991) Nucleosides Nucleotides 10, 107-117.
22. Behmoaras, T., Toulme, J.-J., and Hélène, C. (1981) Nature 78, 926-930.
23. Pierre, J., and Laval, J. (1981) J. Biol. Chem. 256, 10217-10220.
24. Hélène, C., Toulme, J.-J., Behmoaras, T., and Cazenave, C. (1982) Biochimie 64, 697-705.
25. Male, R., Fosse, V., and Kleppe, K. (1982) Nucl. Acids Res. 20, 6305-6308.
26. Boturyn, D., Boudali, A., Constant, J. F., Defrancq, E., and Lhomme, J. (1997) Tetrahedron 53, 5485-5492.
27. Liuzzi, M., Weinfeld, M., and Paterson, M. C. (1987) Biochemistry 26, 3315-3321.
28. Lefrançois, M., Bertrand, J.-R., and Malvy, C. (1990) Mutation Res. 236, 9-17.
29. Malvy, C., Pierre, J., Lefrançois, M., Markovits, J., Garbay, C., and Roques, B. P. (1990) Chem.-Biol. Interact. 73, 249-260.
30. O'Reilly, S., Baker, S. D., Sartorius, S., Rowinsky, E. K., Finizio, M., Lubiniecki, G. M., Grochow, L. B., Gray, J. E., Pieniazek, H. J. Jr, and Donehower, R. C. (1998) Ann. Oncol. 9, 101-104.
31. Constant, J.-F., O'Connor, T. R., Lhomme, J., and Laval, J. (1988) Nucl. Acids Res. 16, 2691-2703.
32. Fkyerat, A., Demeunynck, M., Constant, J.-F., Michon, P., Lhomme, J. (1993) J. Am. Chem. Soc. 115, 9952-9959.
33. Fkyerat, A., Demeunynck, M., Constant, J.-F., and Lhomme, J. (1993) Tetrahedron 49, 11237-11252.
34. Constant, J.-F., Fkyerat, A., Demeunynck, M., Laval, J., O'Connor, T. R., and Lhomme, J. (1990) Anticancer Drug Design 5, 59-62.
35. Berthet, N., Boudali, A., Constant, J.-F., Decout, J. L., Demeunynck, M., Fkyerat, A., Garcia, J., Laayoun, A., Michon, P., and Lhomme, J. (1994) J. Mol. Recognition 7, 99-107.
36. Belmont, P., Boudali, A., Constant, J.-F., Demeunynck, M., Fkyerat, A., Lhomme, J., Michon, P., and Serratrice, G. (1997) New J. Chem. 21, 47-54.
37. Berthet, N., Constant, J.-F., Demeunynck, M., Michon, P, Lhomme, J. (1997) J. Med. Chem. 40, 3346-3352.
38. Coppel, Y., Constant, J.-F., Coulombeau, C., Demeunynck, M., Garcia, J., and Lhomme, J. (1997) Biochemistry 36, 4831-4843.
39. Barret, J. M., Fahy, J., Ethiévant, C., Lhomme, J., and Hill, B. T. (1999) Anti-Cancer Drugs 10, 55-65.
40. Wilson, W. D., Ratmeyer, L., Cegla, M. T., Spychala, J., Boykin, D., Demeunynck, M., Lhomme, J., Krishnan, G., Kennedy, D., Vinayak, R., and Zon, G. (1994) New. J. Chem 18, 419-423.
41. Teulade-Fichou, M. P., Vigneron, J. P., and Lehn, J. M. (1995) Supramol. Chem. 5, 139-147.
42. Slama-Schwok, A., Peronnet, F., Hantz-Brachet, E., Taillandier, E., Teulade-Fichou, M. P., Vigneron, J. P., Best-Belpomme, M., and Lehn, J. M. (1997) Nucl. Acids Res. 25, 2574-2581.
43. Slama-Schwok, A., Teulade-Fichou, M. P., Vigneron, J. P., Taillandier, E., and Lehn, J. M. (1995) J. Am. Chem. Soc. 117, 6822-6830.
44. Blacker, A. J., Teulade-Fichou, M. P., Vigneron, J. P., Fauquet, M., and Lehn, J. M. (1998) Bioorg. Medic. Chem. Lett. 8, 601-606.
45. Berthet, N., Michon, J., Teulade-Fichou, M. P., Vigneron, J. P., Lehn, J. M., and Lhomme, J. (1999) Chem. Eur. J., in press.
46. Takeshita, M., Chang, C. N., Johnson, F., Will, S., and Grollman, A. P. (1987) J. Biol. Chem. 262, 10171-10179.
47. Coppel, Y., Berthet, N., Coulombeau, C., Coulombeau, Ce., Garcia, J., and Lhomme, J. (1997) Biochemistry 36, 4817-4830.
48. Freeman, R., Friedrich, and J., Xi-Li, W. (1988) J. Magn. Reson. 79, 561-567.
49. Plateau, P., and Gueron, M. (1982) J. Am. Chem. Soc. 104, 7310-7311.
50. Insight II 97.0/Discover 97.0 of Biosym/MSI 9685 Strandon Road-San Diego.
51. Weiner, S. J., Kollman, P. A., Nguyen, D. T., and Case, D. A. (1986) J. Comput. Chem. 7, 230-252.
52. Arnott, S., Chandrasekaran, R., Birdsall, D. L., Leslie, A. G. W., and Ratliff, R. L. (1980) Nature (London) 283, 743-745.
53. Lavery, R., and Sklenar, H. (1996) Curves 5.1 Manual, CNRS, Paris.
54. Lavery, R., and Sklenar, H. (1989) J. Biomol. Struct. Dyn. 6, 655-667.
55. Feigon, J., Leupin, W., Denny, W. A., and Kearns, D. R. (1983) Biochemistry 22, 5943-5951.
56. Scheek, R. M., Russo, N., Boelens, R., Kaptein, R., and Van Boom, J. H. (1983) J. Am. Chem. Soc. 105, 2914-2916.
57. Wüthrich, K. (1986) NMR of Proteins and Nucleic Acids, John Wiley and Sons, New York, pp 203-255.
58. Zhang, X.; Patel, D. J. (1990) Biochemistry 29, 9451-9466.
59. Kochoyan, M., Leroy, J.-L., and Gueron, M. (1987) J. Mol. Biol. 196, 599-609.
60. Leroy, J.-L., Kochoyan, M., Huynh-Dinh, T., and Gueron, M. (1988) J. Mol. Biol. 200, 223-238.