RNA-selective modification by a platinum(II) complex conjugated to amino- and guanidinoglycosides

Angewandte Chemie - International Edition

Volumn 44, Issue 6, 2005, Pages 927-932

  Boer, Jürgen ^a   Blount, Kenneth F ^a   Luedtke, Nathan W ^a   Elson Schwab, Lev ^a   Tor, Yitzhak ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Aminoglycosides; Antiviral agents; Drug design; Platinum; RNA

Indexed keywords

AMINO ACIDS; CROSSLINKING; DNA; DRUG PRODUCTS; ONCOLOGY; PLATINUM; RNA; SYNTHESIS (CHEMICAL);

CONJUGATES; COVALENT CROSS-LINKS; NUCLEIC ACID; SELECTIVITY;

ORGANOMETALLICS;

AMINOGLYCOSIDE ANTIBIOTIC AGENT; ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; CISPLATIN; DNA; FRAMYCETIN; GUANIDINE DERIVATIVE; GUANIDINOGLYCOSIDE DERIVATIVE; GUANIDINONEOMYCIN B; PLATINUM COMPLEX; RNA; RNA DIRECTED DNA POLYMERASE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CROSS LINKING; DRUG DESIGN; DRUG DNA BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; GENE TARGETING; PROTEIN RNA BINDING; STRUCTURE ANALYSIS;

AMINOGLYCOSIDES; CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; ELECTROPHORESIS, POLYACRYLAMIDE GEL; GUANIDINES; MOLECULAR SEQUENCE DATA; ORGANOPLATINUM COMPOUNDS; RNA;

EID: 13744261523     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461182     Document Type: Article

References (43)

1. E. R. Jamieson, S. J. Lippard, Chem. Rev. 1999, 99, 2467-2498.
2. a) A. M. J. Fichtinger-Schepman, J. L. van der Veer, J. H. J. denHartog, P. H. M. Lohman, J. Reedijk, Biochemistry 1985, 24, 707-713;
3. b) A. Eastman, Biochemistry 1986, 25, 3912-3915.
4. H. Huang, J. Woo, S. C. Alley, P. B. Hopkins, Bioorg. Med. Chem. 1995, 5, 659-669.
5. R. N. Bose, Mini-Rev. Med. Chem. 2002, 2, 103-111.
6. G. Speelmans, R. W. Staffhorst, K. Versluis, J. Reedijk, B. de Kruijff, Biochemistry 1997, 36, 10545-10550.
7. T. Ishikawa, F. Ali-Osman, J. Biol. Chem. 1993, 268, 20116-20125.
8. Selected examples: a) B. E. Bowler, L. S. Hollis, S. J. Lippard, J. Am. Chem. Soc. 1984, 106, 6102-6104;
9. b) B. D. Palmer, H. H. Lee, P. Johnson, B. C. Baguley, G. Wickham, L. P. G. Wakelin, W. D. McFadyen, W. A. Denny, J. Med. Chem. 1990, 33, 3008-3014;
10. c) D. Gibson, K. F. Gean, J. Katzhendle, R. Ben-Shoshan, A. Ramu, I. Ringel, J. Med. Chem. 1991, 34, 414-420;
11. d) J. Whittaker, W. D. McFadyen, G. Wickham, L. P. Wakelin, V. Murray, Nucleic Acids Res. 1998, 26, 3933-3939;
12. e) L. C. Perrin, C. Culliname, W. D. McFayden, D. R. Phillips, Anti-Cancer Drug Des. 1999, 14, 243-252;
13. f) Y. S. Chen, M. J. Heeg, PG. Brauschweiger, W. H. Xie, P. G. Wang, Angew. Chem. 1999, 111, 1882-1884; Angew. Chem. Int. Ed. 1999, 38, 1768-1769;
14. f) Y. S. Chen, M. J. Heeg, PG. Brauschweiger, W. H. Xie, P. G. Wang, Angew. Chem. 1999, 111, 1882-1884; Angew. Chem. Int. Ed. 1999, 38, 1768-1769;
15. g) M. S. Robillard, A. R. P. M. Valentijn, N. J. Meeuwenoord, G. A. van der Marel, J. H. van Boom, J. Reedijk, Angew. Chem. 2000, 112, 3226-3229; Angew. Chem. Int. Ed. 2000, 39, 3096-3099;
16. g) M. S. Robillard, A. R. P. M. Valentijn, N. J. Meeuwenoord, G. A. van der Marel, J. H. van Boom, J. Reedijk, Angew. Chem. 2000, 112, 3226-3229; Angew. Chem. Int. Ed. 2000, 39, 3096-3099;
17. h) Y. Mikata, Y. Shinohara, K. Yoneda, Y. Nakamura, I. Brudzinska, T. Tanase, T. Kitayama, R. Takagi, T. Okamoto, I. Kinoshita, M. Doe, C. Orvig, S. Yano, Bioorg. Med. Chem. Lett. 2001, 11, 3045-3047;
18. i) S. K. Sharma, L. W. McLaughlin, J. Am. Chem. Soc. 2002, 124, 9658-9659;
19. j) M. S. Robillard, N. P. Davies, G. A. van der Marel, J. H. van Boom, J. Reedijk, V. Murray, J. Inorg. Biochem. 2003, 96, 331-338;
20. k) R. J. Heetebrij, M. de Kort, N. J. Meeuwenoord, H. den Dulk, G. A. van der Marel, J. H. van Boom, J. Reedijk, Chem. Eur. J. 2003, 9, 1823-1827.
21. a) Y. Tor, ChemBioChem 2003, 4, 998-1007;
22. N. W. Luedtke, Y. Tor in Small Molecule DNA and RNA Binders: From Synthesis to Nucleic Acid Complexes (Eds.: M. Demeunynck, C. Bailly, D. Wilson), Wiley-VCH, Weinheim, 2003, pp. 18-40.
23. a) V. W. Pollard, M. H. Malim, Annu. Rev. Microbiol. 1998, 52, 491-532;
24. b) A. D. Frankel, J. A. T. Young, Annu. Rev. Biochem. 1998, 67, 1-25.
25. J. L. Battiste, H. Mao, N. S. Rao, R. Tan, D. R. Muhandiram, L. E. Kay, A. D. Frankel, J. R. Williamson, Science, 1996, 275, 1547-1551.
26. N. W. Luedtke, Y. Tor, Biopolymers 2003, 70, 103-119.
27. M. L. Zapp, S. Stern, M. R. Green, Cell 1993, 74, 969-978.
28. N. W. Luedtke, T. J. Baker, M. Goodman, Y. Tor, J. Am. Chem. Soc. 2000, 122, 12035-12036.
29. K. Li, T. M. Davis, C. Bailly, A. Kumar, D. W. Boykin, W. D. Wilson, Biochemistry 2001, 40, 1150-1158.
30. a) K. Michael, H. Wang, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1361-1371;
31. b) S. R. Kirk, N. W. Luedtke, Y. Tor, J. Am. Chem. Soc. 2000, 122, 980-981.
32. See the Supporting Information for detailed experimental procedures and additional data.
33. T. J. Baker, N. W Luedtke, Y. Tor, M. Goodman, J. Org. Chem. 2000, 65, 9054-9058.
34. We have found it is beneficial to install the guanidinium groups at early stages of the synthetic scheme.
35. Attempts to reduce the azide by catalytic hydrogenation, a method that was successfully employed for 4, led to several by-products.
36. 2] coordination sphere.
37. Noncovalent complexes are denatured under such conditions and yield no gel-mobility shift. See, for example, Figure 2 b which illustrates the case with neomycin B (a molecule that is known to associate with the RRE noncovalently).
38. --treated 1 and 2 indicate that these derivatives have approximately the same affinity to the RRE JW compared to the nonmodified parent compounds (neomycin B and guanidinoneomycin B, respectively).[16] This indicates that the conjugated metal center does not significantly alter the RNA-binding characteristics of the glycoside skeleton.
39. 2) minus two chloride ions (70) yields an expected mass of m/z 11 917. Since the aminoglycoside carries six positive charges under the acidic conditions of the matrix used, six fewer protons are required to form a single-charged positive ion of the Pt-conjugated RRE JW. For an oligonucleotide of this size, MALDI-TOF MS can be expected to show an accuracy of ±4 amu. As such, good agreement between the expected and experimentally observed mass is established.
40. Similar mass spectral characterization of 2 with the RRE reveals its binding and covalent modification are slightly less specific than those of 1. This agrees with a previous determination of the RRE-binding specificity of amino- and guanidinoglycosides[13] and underscores the link between specific binding and platinum conjugation to the RNA.
41. Since the mass spectra indicate that both chloride ions are displaced, a similar mechanism to the coordination of cis-Pt to DNA is implied.
42. L. Wang, D. E. Ruffner, Nucleic Acids Res. 1997, 25, 4344-4361.
43. J. A. Ippolito, T. A. Steitz, J. Mol. Biol. 2000, 295, 711-717.