New approach for the preparation of efficient DNA cleaving agents: Ditopic copper-platinum complexes based on 3-clip-phen and cisplatin

Journal of Medicinal Chemistry

Volumn 50, Issue 13, 2007, Pages 3148-3152

  De Hoog, Paul ^a   Boldron, Christophe ^a   Gamez, Patrick ^a   Sliedregt Bol, Karen ^a   Roland, Isabelle ^c   Pitié, Marguerite ^b   Kiss, Robert ^d   Meunier, Bernard ^b   Reedijk, Jan ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

^c Unibioscreen SA   (Belgium)

^d UNIVERSITÉ LIBRE DE BRUXELLES   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; COPPER [1 (1,10 PHENANTHROLIN 3 YLOXY) 3 (1,10 PHENANTHROLIN 8 YLOXY)PROPAN 2 AMINE]; COPPER COMPLEX; DNA CLEAVING AGENT; PLATINUM COMPLEX; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL STRAIN MCF 7; COVALENT BOND; DRUG CYTOTOXICITY; DRUG EFFICACY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CISPLATIN; DNA CLEAVAGE; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; ORGANOMETALLIC COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34347267664     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0614331     Document Type: Article

References (38)

1. Chabner, B. A.; Roberts, T. G. Timeline - Chemotherapy and the war on cancer. Nat. Rev. Cancer 2005, 5, 65-72.
2. Hurley, L. H. DNA and its associated processes as targets for cancer therapy. Nat. Rev. Cancer 2002, 2, 188-200.
3. Reedijk, J. New clues for platinum antitumor chemistry: Kinetically controlled metal binding to DNA. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 3611-3616.
4. Chen, J. Y.; Stubbe, J. Bleomycins: Towards better therapeutics. Nat. Rev. Cancer 2005, 5, 102-112.
5. Pitié, M.; Sudres, B.; Meunier, B. Dramatic increase of the DNA cleavage activity of Cu(Clip-phen) by fixing the bridging linker on the C-3 position of the phenanthroline units. Chem. Commun. 1998, 2597-2598.
6. Pitié, M.; Burrows, C. J.; Meunier, B. Mechanisms of DNA cleavage by copper complexes of 3-Clip-Phen and of its conjugate with a distamycin analogue. Nucleic Acids Res. 2000, 28, 4856-4864.
7. Fuertes, M. A.; Alonso, C.; Perez, J. M. Biochemical modulation of cisplatin mechanisms of action: Enhancement of antitumor activity and circumvention of drug resistance. Chem. Rev. 2003, 103, 645-662.
8. Kartalou, M.; Essigmann, J. M. Mechanisms of resistance to cisplatin. Mutat. Res. 2001, 478, 23-43.
9. Kartalou, M.; Essigmann, J. M. Recognition of cisplatin adducts by cellular proteins. Mutat. Res. 2001, 478, 1-21.
10. Kopp, H. G.; Kuczyk, M.; Classen, J.; Stenzl, A.; Kanz, L.; Mayer, F.; Bamberg, M.; Hartmann, J. T. Advances in the treatment of testicular cancer. Drugs 2006, 66, 641-659.
11. van Zutphen, S.; Reedijk, J. Targeting platinum anti-tumour drugs: Overview of strategies employed to reduce systemic toxicity. Coord. Chem. Rev. 2005, 249, 2845-2853.
12. Baruah, H.; Rector, C. L.; Monnier, S. M.; Bierbach, U. Mechanism of action of non-cisplatin type DNA-targeted platinum anticancer agents: DNA interactions of novel acridinylthioureas and their platinum conjugates. Biochem. Pharmacol. 2002, 64, 191-200.
13. Bowler, B. E.; Ahmed, K. J.; Sundquist, W. I.; Hollis, L. S.; Whang, E. E.; Lippard, S. J. Synthesis, characterization, and DNA-binding properties of (1,2-diaminoethane)platinum(11) complexes linked to the DNA intercalator acridine-orange by trimethylene and hexamethylene chains. J. Am. Chem. Soc. 1989, 111, 1299-1306.
14. Cullinane, C.; Wickham, G.; McFadyen, W. D.; Denny, W. A.; Palmer, B. D.; Phillips, D. R. The use of bidirectional transcription footprinting to detect platinum-DNA cross-links by acridine-tethered platinum diamine complexes and cisplatin. Nucleic Acids Res. 1993, 21, 393-400.
15. Palmer, B. D.; Lee, H. H.; Johnson, P.; Baguley, B. C.; Wickham, G.; Wakelin, L. P. G.; McFadyen, W. D.; Denny, W. A. DNA-directed alkylating agents. 2. Synthesis and biological activity of platinum complexes linked to 9-anilinoacridine. J. Med. Chem. 1990, 33, 3008-3014.
16. Perrin, L. C.; Prenzler, P. D.; Cullinane, C.; Phillips, D. R.; Denny, W. A.; McFadyen, W. D. DNA targeted platinum complexes: Synthesis, cytotoxicity and DNA interactions of cis-dichloroplatinum-(II) complexes tethered to phenazine-1-carboxamides. J. Inorg. Biochem. 2000, 81, 111-117.
17. Whittaker, J.; McFadyen, W. D.; Wickham, G.; Wakelin, L. P. G.; Murray, V. The interaction of DNA-targeted platinum phenanthridinium complexes with DNA. Nucleic Acids Res. 1998, 26, 3933-3939.
18. Bowler, B. E.; Hollis, L. S.; Lippard, S. J. Synthesis and DNA-binding and photonicking properties of acridine-orange linked by a polymethylene tether to (1,2-diaminoethane)dichloroplatinum(II). J. Am. Chem. Soc. 1984, 106, 6102-6104.
19. Holmes, R. J.; McKeage, M. J.; Murray, V.; Denny, W. A.; McFadyen, W. D. cis-Dichloroplatinum(II) complexes tethered to 9-aminoacridine-4- arboxamides: synthesis and action in resistant cell lines in vitro. J. Inorg. Biochem. 2001, 85, 209-217.
20. Martins, E. T.; Baruah, H.; Kramarczyk, J.; Saluta, G.; Day, C. S.; Kucera, G. L.; Bierbach, U. Design, synthesis, and biological activity of a novel non-cisplatin-type platinum-acridine pharmacophore. J. Med. Chem. 2001, 44, 4492-4496.
21. Takahara, P. M.; Rosenzweig, A. C.; Frederick, C. A.; Lippard, S. J. Crystal structure of double-stranded DNA containing the major adduct of the anticancer drug cisplatin. Nature 1995, 377, 649-652.
22. Pitié, M.; Boldron, C.; Gornitzka, H.; Hemmert, C.; Donnadieu, B.; Meunier, B. DNA cleavage by copper complexes of 2- and 3-Clip-Phen derivatives. Eur. J. Inorg. Chem. 2003, 528-540.
23. Detmer, C. A.; Pamatong, F. V.; Bocarsly, J. R. Molecular recognition effects in metal complex mediated double-strand cleavage of DNA: Reactivity and binding studies with model substrates. Inorg. Chem. 1997, 36, 3676-3682.
24. Pamatong, F. V.; Detmer, C. A.; Bocarsly, J. R. Double-strand cleavage of DNA by a monofunctional transition metal cleavage agent. J. Am. Chem. Soc. 1996, 118, 5339-5345.
25. Povirk, L. F.; Houlgrave, C. W. Effect of apurinic apyrimidinic endonucleases and polyamines on DNA treated with bleomycin and neocarzinostatin - Specific formation and cleavage of closely opposed lesions in complementary strands. Biochemistry 1988, 27, 3850-3857.
26. Povirk, L. F.; Wubker, W.; Kohnlein, W.; Hutchinson, F. DNA double-strand breaks and alkali-labile bonds produced by bleomycin. Nucleic Acids Res. 1977, 4, 3573-3580.
27. Budiman, M. E.; Alexander, R. W.; Bierbach, U. Unique base-step recognition by a platinum-acridinylthiourea conjugate leads to a DNA damage profile complementary to that of the anticancer drug cisplatin. Biochemistry 2004, 43, 8560-8567.
28. Temple, M. D.; McFadyen, W. D.; Holmes, R. J.; Denny, W. A.; Murray, V. Interaction of cisplatin and DNA-targeted 9-aminoacridine platinum complexes with DNA. Biochemistry 2000, 39, 5593-5599.
29. Bassett, E.; Vaisman, A.; Havener, J. M.; Masutani, C.; Hanaoka, F.; Chaney, S. G. Efficiency of extension of mismatched primer termini across from cisplatin and oxaliplatin adducts by human DNA polymerases β and η in vitro. Biochemistry 2003, 42, 14197-14206.
30. Vaisman, A.; Chaney, S. G. The efficiency and fidelity of translesion synthesis past cisplatin and oxaliplatin GpG adducts by human DNA polymerase beta. J. Biol. Chem. 2000, 275, 13017-13025.
31. Woynarowski, J. M.; Chapman, W. G.; Napier, C.; Herzig, M. C. S.; Juniewicz, P. Sequence- and region-specificity of oxaliplatin adducts in naked and cellular DNA. Mol. Pharmacol. 1998, 54, 770-777.
32. Zou, Y.; Vanhouten, B.; Farrell, N. Sequence specificity of DNA-DNA interstrand cross-link formation by cisplatin and dinuclear platinum complexes. Biochemistry 1994, 33, 5404-5410.
33. 3)(thiazole). Protein recognition and nucleotide excision repair of monofunctional adductst. Biochemistry 2003, 42, 792-800.
34. Murray, V.; Motyka, H.; England, P. R.; Wickham, G.; Lee, H. H.; Denny, W. A.; McFadyen, W. D. An investigation of the sequence-specific interaction of cis-diamminedichloroplatinum(II) and four analogs, including two acridine-tethered complexes, with DNA inside human cells. Biochemistry 1992, 31, 11812-11817.
35. Murray, V.; Motyka, H.; England, P. R.; Wickham, G.; Lee, H. H.; Denny, W. A.; McFadyen, W. D. The use of TAQ DNA-polymerase to determine the sequence specificity of DNA damage caused by cis-diamminedichloroplatinum(II), acridine-tethered platinum(II) diammine complexes or two analogs. J. Biol. Chem. 1992, 267, 18805-18809.
36. Temple, M. D.; Recabarren, P.; McFadyen, W. D.; Holmes, R. J.; Denny, W. A.; Murray, V. The interaction of DNA-targeted 9-amino acridine-4-carboxamide platinum complexes with DNA in intact human cells. Biochim. Biophys. Acta 2002, 1574, 223-230.
37. Fasman, G. Handbook of biochemistry and molecular biology: nucleic acids; CRC: Boca Raton, 1975; Vol. 3, p 175.
38. Sambrook, J.; Fritsch, E. F.; Maniatis, T. Molecular Cloning: A Laboratory Manuel; Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY, 1989; Vol. 2.