Abasic site recognition in DNA as a new strategy to potentiate the action of anticancer alkylating drugs?

Journal of Medicinal Chemistry

Volumn 42, Issue 25, 1999, Pages 5153-5159

  Belmont, Philippe ^a   Jourdan, Muriel ^a   Demeunynck, Martine ^a   Constant, Jean François ^a   Garcia, Julian ^a   Lhomme, Jean ^a   Carez, Danièle ^b   Croisy, Alain ^b  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

^b INSERM   (France)

Author keywords

[No Author keywords available]

Indexed keywords

6 AMINO 9 [3,7 BIS(DIAMINOMETHYLENE) 11 (6 CHLORO 2 METHOXYACRIDIN 9 YL) 3,7,11 TRIAZA UNDECYL] 9H PURINE; ALKYLATING AGENT; ANTINEOPLASTIC AGENT; CARMUSTINE; DNA; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG DNA BINDING; DRUG POTENCY; HUMAN; HUMAN CELL; MOLECULAR RECOGNITION; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYSICAL CHEMISTRY;

ANIMALS; ANTINEOPLASTIC AGENTS, ALKYLATING; CATTLE; DNA, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MICE; MICE, INBRED DBA; MOLECULAR STRUCTURE; NUCLEIC ACID DENATURATION; TUMOR CELLS, CULTURED;

EID: 0033576725     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9901428     Document Type: Article

References (36)

1. Hemminki, K.; Ludlum, D. B. Covalent modification of DNA by antineoplastic agents. J. Natl. Cancer Inst. 1984, 73, 1021-1028.
2. Chaney, S. G. DNA Repair: Enzymatic Mechanisms and Relevance to Drug Response. J. Nat. Cancer Inst. 1996, 88, 346.
3. Erickson, L. C. The role of O-6 methylguanine DNA methyl-transferase (MGMT) in drug resistance ans strategies for its inhibition. Semin. Cancer Biol. 1991, 2, 257-265.
4. Barret, J. M.; Hill, B. T. DNA repair mechanisms associated with cellular resistance to antitumor drugs: potential novel targets. Anti-Cancer Drugs 1998, 9, 105-123.
5. Dolan, M. E. Inhibition of DNA repair as a means of increasing the antitumor activity of DNA reactive agents. Adv. Drug Delivery Rev. 1997, 26, 105-118.
6. Frankfurt, O. S. Inhibition of DNA repair and the enhancement of cytotoxicity of alkylating agents. Int. J. Cancer 1991, 48, 916-923.
7. Bowman, K. J.; White, A.; Golding, B. T.; Griffin, R. J.; Curtin, N. J. Potentiation of anti-cancer agent cytotoxicity by the potent poly(ADP-ribose)polymerase inhibitors NU1025 and NU1064. Br. J. Cancer 1998, 78, 1269-1277.
8. Lindahl, T.; Nyberg, B. Rate of depurination of native deoxyribonucleic acid. Biochemistry 1972, 11, 3610-3618.
9. Sancar, A. DNA Excision Repair. Annu. Rev. Biochem. 1996, 65, 43-81.
10. Weiss, B.; Grossman, L. Phosphodiesterases involved in DNA repair. Adv. Enzymol. Relat. Areas Mol. Biol. 1987, 1987, 1-34.
11. Liuzzi, M.; Weinfeld, M.; Paterson, M. C. Selective inhibition by methoxyamine of the apurinic/apyrimidinic endonuclease activity associated with pyrimidine dimer-DNA glycosylase from Micrococcus luteus and bacteriophage T4. Biochemistry 1987, 26, 3315-3321.
12. Lefrançois, M.; Bertrand, J. R.; Malvy, C. 9-Amino-ellipticine inhibits the apurinic site-dependent base excision-repair pathway. Mutation Res. 1990, 236, 9-17.
13. Malvy, C.; Safraoui, H.; Bloch, E.; Bertrand, J. R. Involvement of apurinic sites in the synergistic action of alkylating and intercalating drugs in Escherichia coli. Anti-Cancer Drug Des. 1988, 2, 361-370.
14. Grafström, R. H.; Sun, T.; Doleniak, D. AP endonuclease: a possible target for a novel tumoricidal compound. J. Cell Biochem. 1995, 279.
15. Bobola, M. S.; Berger, M. S.; Stevens, B.; Silber, J. R. Variation of DMP840 resistance and relationship to apurinic/apyrimidic endonuclease activity and alkylation agent sensitivity in 12 brain tumor cell lines. Proc. Am. Assoc. Cancer Res. 1997, 38, 3314.
16. Pourquier, P.; Ueng, L.-M.; Kohlhagen, G.; Mazumder, A.; Gupta, M.; Kohn, K. W.; Pommier, Y. Effects of uracil incorporation, DNA mismatches, and abasic sites on cleavage and religation activities of mammalian topoisomerase I. J. Biol. Chem. 1997, 272, 7792-7796.
17. Kingma, P. S.; Corbett, A. H.; Burcham, P. C.; Marnett, L. J.; Osheroff, N. Abasic sites stimulate double-stranded DNA cleavage mediated by topoisomerase II. DNA lesions as endogenous topoisomerase II poisons. J. Biol. Chem. 1995, 270, 21441-21444.
18. Kingma, P. S.; Osheroff, N. Spontaneous DNA damage stimulates topoisomerase II-mediated DNA cleavage. J. Biol. Chem. 1997, 272, 7488-7493.
19. Kingma, P. S.; Osheroff, N. Topoisomerase II-mediated DNA cleavage and religation in the absence of base-pairing. Abasic lesions as a tool to dissect enzyme mechanism. J. Biol. Chem. 1998, 273, 17999-18002.
20. Kingma, P. S.; Osheroff, N. Apurinic sites are position-specific topoisomerase II poisons. J. Biol. Chem. 1997, 272, 1148-1155.
21. Kingma, P. S.; Osheroff, N. The response of eukariotic topoisomerases to DNA damage. Biochim. Biophys. Acta 1998, 1400, 223-232.
22. Fkyerat, A.; Demeunynck, M.; Constant, J.-F.; Michon, P.; Lhomme, J. A new class of artificial nucleases that recognize and cleave apurinic sites in DNA with great selectivity and efficiency. J. Am. Chem. Soc. 1993, 115, 9952-9959.
23. Berthet, N.; Boudali, A.; Constant, J.-F.; Decout, J.-L.; Demeunynck, M.; Fkyerat, A.; Garcia, J.; Laayoun, A.; Michon, P.; Lhomme, J. Design of molecules that specifically recognize and cleave apurinic sites in DNA. J. Mol. Recognit. 1994, 7, 99-107.
24. Belmont, P.; Boudali, A.; Constant, J.-F.; Demeunynck, M.; Fkyerat, A.; Michon, P.; Serratrice, G.; Lhomme, J. Efficient and Versatiles chemical tools for cleavage of abasic sites in DNA. New J. Chem. 1997, 21, 47-54.
25. Coppel, Y.; Constant, J.-F.; Coulombeau, C.; Demeunynck, M.; Garcia, J.; Lhomme, J. NMR and molecular modeling studies of the interaction of artificial AP lyases with a DNA duplex containing an apurinic abasic site model. Biochemistry 1997, 36, 4831-4843.
26. Thomas, F.; Michon, J.; Lhomme, J. Interaction of a spin-labeled adenine-acridine conjugate with a DNA duplex containing an abasic site model. Biochemistry 1999, 38, 1930-1937.
27. Barret, J. M.; Fahy, J.; Etievant, C.; Lhomme, J.; Hill, B. T. Novel artificial endonucleases inhibit base excision repair and potentiate the cytotoxkity of DNA-damaging agents on L1210 cells. Anti-Cancer Drugs 1999, 10, 55-65.
28. Iwanowicz, E. J.; Poss, M. A.; Lin, J. Preparation of N,N′-bistert-butoxycarbonylthiourea. Synth. Commun. 1993, 23, 1443-1445.
29. Berthet, N.; Constant, J.-F.; Demeunynck, M.; Michon, P.; Lhomme, J. Search for DNA repair inhibitors: selective binding of nucleic bases-acridine conjugates to a DNA duplex containing an abasic site. J. Med. Chem. 1997, 40, 3346-3352.
30. Millican, T. A.; Mock, G. A.; Chauncey, M. A.; Patel, T. P.; Eaton, M. A.; Gunning, J.; Cutloush, S. D.; Neidle, S.; Mann, J. Synthesis and biophysical studies of short oligodeoxynucleotides with novel modifications: a possible approach to the problem of mixed base oligodeoxynucleotide synthesis. Nucleic Acids Res. 1984, 12, 7435-7453.
31. Takeshita, M.; Chang, C. N.; Johnson, F.: Will, S.; Grollman, A. P. Oligodeoxynucleotides containing synthetic abasic sites. J. Biol. Chem. 1987, 262, 10171-10179.
32. Fkyerat, A.; Demeunynck, M.; Constant, J.-F.; Lhomme, J. Synthesis of purine-acridine hybrid molecules related to artificial endonucleases. Tetrahedron 1993, 49, 11237-11252.
33. Pierre, J.; Laval, J. Specific nicking of DNA at apurinic sites by peptides containing aromatic residues. J. Biol. Chem. 1981, 256, 10217-10220.
34. Marky, L. A.; Breslauer, K. J. The melting behavior of a DNA junction structure: a calorimetric and spectroscopic study. Biopolymers 1987, 26, 1601-1620.
35. Freeman, R.; Friedrich, J.; Xi-Li, W. A pulse for all seasons. Fourier transform spectra without a phase gradient. J. Magn. Reson. 1988, 79, 561-567.
36. Plateau, P.; Guéron, M. Exchangeable proton NMR without baseline distortion, using new strong-pulse sequences. J. Am. Chem. Soc. 1982, 104, 7310-7311.