Monofunctionally trans-diammine platinum(II)-modified peptide nucleic acid oligomers: A new generation of potential antisense drugs

Chemistry - A European Journal

Volumn 8, Issue 24, 2002, Pages 5566-5570

  Schmidt, Kathrin S ^a,b   Boudvillain, Marc ^c   Schwartz, Annie ^c   Van der Marel, Gijs A ^b   Van Boom, Jacques H ^b   Reedijk, Jan ^b   Lippert, Bernhard ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

^b LEIDEN UNIVERSITY   (Netherlands)

^c CENTRE DE BIOPHYSIQUE MOLÉCULAIRE   (France)

Author keywords

Antisense agents; Nucleic acids; Peptide nucleic acids; Platinum; Solid phase synthesis

Indexed keywords

MASS SPECTROMETRY; NUCLEIC ACIDS; OLIGOMERS; SYNTHESIS (CHEMICAL);

ANTISENSE STRATEGIES;

PLATINUM;

DIAMINE; DOUBLE STRANDED DNA; NUCLEIC ACID; OLIGOMER; OLIGONUCLEOTIDE; PEPTIDE; PLATINUM DERIVATIVE;

ARTICLE; CROSS LINKING; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; SOLID; SYNTHESIS;

EID: 0346666966     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20021216)8:24<5566::aid-chem5566>3.0.co;2-%23     Document Type: Article

References (37)

1. P. E. Nielsen, M. Egholm, R. H. Berg, O. Buchardt, Science 1991, 254, 1497.
2. D. A. Dean, Adv. Drug Deliv. Rev. 2000, 44, 81.
3. P. E. Nielsen, Expert Opin. Invest. Drugs 2001, 10, 331.
4. M. Egholm, O. Buchardt, L. Christensen, C. Behrens, S. M. Freier, D. A. Driver, R. H. Berg, S. K. Kim, B. Norden, P. E. Nielsen, Nature 1993, 265, 566.
5. V. V. Demidov, V. N. Potaman, M. D. Frank-Kamenetskii, M. Egholm, O. Buchardt, S. H. Sonnichsten, P. E. Nielsen, Biochem. Pharmacol. 1994, 48, 1310.
6. J. C. Hanvey, N. J. Peffer, J. E. Bisi, S. A. Thomson, R. Cadilla, J. A. Josey, D. J. Ricca, C. F. Hassman, M. A. Bonham, K. G. Au, S. G. Carter, D. A. Bruckenstein, A. L. Boyd, S. A. Noble, L. E. Babiss, Science 1992, 258, 1481.
7. H. Knudsen, P. E. Nielsen, Nucleic Acids Res. 1996, 24, 494,
8. C. Gambacorti-Passerini, L. Mologni, C. Bertazzoli, P. le Coutre, E. Marchesi, F. Grignani, P. E. Nielsen, Blood 1996, 88, 1411.
9. L. Mologni, P. le Coutre, P. E. Nielsen, C. Gambacorti-Passerini, Nucleic Acids Res. 1998, 26, 1934.
10. J. E. Gee, I. Robbins, A. C. van der Laan, J. H. van Boom, C. Colombier, M. Leng, A. R. Raible, J. S. Nelson, B. Lebleu, Antisense Nucleic Acid Drug Dev. 1998, 8, 103.
11. A. S. Boutorine, D. Brault, M. Tagasugi, O. Delgado, C. Hélène, J. Am. Chem. Soc. 1996, 118, 9469, and references therein.
12. I. V. Kutyavin, H. B. Gamper, A. A. Gall, R. B. Meyer, J. Am. Chem. Soc. 1993, 115, 9303.
13. H. Maruenda, M. Tomasz, Bioconjugate Chem. 1996, 7, 541, and references therein.
14. B. Lippert, M. Leng in Topics in Biological Inorganic Chemistry, Vol. 1 (Metallopharmaceuticals 1) (Eds. M. J. Clarke, P. J. Sadler), Springer, Berlin, 1999, pp. 117-142, and references therein.
15. C. Colombier, B. Lippert, M. Leng, Nucleic Acids Res. 1996, 24, 4519.
16. M. B. L. Janik, B. Lippert, J. Biol. Inorg. Chem. 1999, 4, 645.
17. F. Paquet, M. Boudvillain, G. Lancelot, M. Leng, Nucleic Acids Res. 1999, 27, 4261.
18. J. Müller, M. Drumm, M. Boudvillain, M. Leng, E. Sletten, B. Lippert, J. Biol. Inorg. Chem. 2000, 5, 603.
19. B. Andersen, E. Bernal-Mendez, M. Leng, E. Sletten, Eur. J. Inorg. Chem. 2000, 1201.
20. M. Boudvillain, M. Guérin, R. Dalbiès, T. Saison-Behmoaras, M. Leng, Biochemistry 1997, 36, 2925.
21. K. Aupeix-Scheidler, S. Chabas, L. Bidou, J.-P. Rousset, M. Leng, J.-J. Toulmé, Nucleic Acids Res. 2000, 28, 438.
22. U. Berghoff, K. Schmidt, M. Janik, G. Schöder, B. Lippert, Inorg. Chim. Acta 1998, 269, 135.
23. R. Manchanda, S. U. Dunham, S. J. Lippard, J. Am. Chem. Soc. 1996, 118, 5144.
24. J. Schliepe, U. Berghoff, B. Lippert, D. Cech, Angew. Chem. 1996; 108, 705; Angew. Chem. Int. Ed. Engl. 1996, 35, 646.
25. J. Schliepe, U. Berghoff, B. Lippert, D. Cech, Angew. Chem. 1996; 108, 705; Angew. Chem. Int. Ed. Engl. 1996, 35, 646.
26. K. S. Schmidt, D. V. Filippov, N. J. Meeuwenoord, G. A. van der Marel, J. H. van Boom, B. Lippert, J. Reedijk, Angew. Chem. 2000, 112, 383; Angew. Chem. Int. Ed. 2000, 39, 375.
27. K. S. Schmidt, D. V. Filippov, N. J. Meeuwenoord, G. A. van der Marel, J. H. van Boom, B. Lippert, J. Reedijk, Angew. Chem. 2000, 112, 383; Angew. Chem. Int. Ed. 2000, 39, 375.
28. R. Casale, I. S. Jensen, M. Egholm in Peptide Nucleic Acids: Protocols and Applications (Eds.: P. E. Nielsen, M. Egholm), Horizon Scientific, Wymondham, UK, 1999, pp. 39-50.
29. J. Reedijk, Chem. Commun. 1996, 801, and references therein.
30. M. Egholm, O. Buchardt, L. Christensen, C. Behrens, S. M. Freier, D. A. Driver, R. H. Berg, S. K. Kim, B. Nordén, P. E. Nielsen, Nature 1993, 365, 566.
31. A. M. Maxam, W. Gilbert, Proc. Natl. Acad. Sci. USA 1977, 74, 560.
32. M. A. Lemaire, A. Schwartz, A. R. Rahmouni, M. Leng, Proc. Natl. Acad. Sci. USA 1991, 88, 1982.
33. T. D. Tullius, B. A. Dombroski, Proc. Natl. Acad. Sci. USA 1986, 83, 5469.
34. E. Bernal-Méndez, J.-S. Sun, F. González-Vílchez M. Leng, New J. Chem. 1998, 1479.
35. B. Hyrup, M. Egholm, O. Buchardt, P. E. Nielsen, Bioorg. Med. Chem. Lett. 1996, 6, 1083.
36. For PNA-transition metal complexes with coordinatively saturated metal entities at the N terminus rather than a heterocyclic base, see: J. C. Verheijen, G. A. van der Marel, J. H. van Boom, N. Metzler-Nolte, Bioconjugate Chem. 2000, 11, 741.
37. G. B. Kauffman, D. O. Cowan, Inorg. Synth. 1963, 7, 239.