G-G base-pairing in nucleobase adducts of the anticancer drug cis-[PtCl2(NH3)(2-picoline)] and its trans isomer

Chemistry - A European Journal

Volumn 11, Issue 15, 2005, Pages 4396-4404

  McGowan, Geraldine ^a   Parsons, Simon ^a   Sadler, Peter J ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

Author keywords

Anticancer drug; Guanine; Hydrogen bonding; Platinum; X ray crystallography

Indexed keywords

CRYSTAL STRUCTURE; HYDROGEN BONDS; ISOMERS; PLATINUM; PLATINUM COMPOUNDS; TUMORS; X RAY CRYSTALLOGRAPHY;

2-PICOLINE; ANTICANCER DRUGS; GUANINE; NUCLEOBASE ADDUCTS;

DRUG DOSAGE;

ANTINEOPLASTIC AGENT; GUANINE; PLATINUM DERIVATIVE;

ARTICLE; BASE PAIRING; CHEMICAL STRUCTURE; CHEMISTRY; DNA ADDUCT; ELECTROSPRAY MASS SPECTROMETRY; ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; BASE PAIRING; CRYSTALLOGRAPHY, X-RAY; DNA ADDUCTS; GUANINE; HYDROGEN-ION CONCENTRATION; ISOMERISM; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; PLATINUM COMPOUNDS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 22944485048     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200500122     Document Type: Article

References (47)

1. E. R. Jamieson, S. J. Lippard, Chem. Rev. 1999, 99, 2467-2498.
2. A. M. J. Fichtinger-Schepman, J. L. van der Veer, J. H. J. den Hartog, P. H. M. Lohman, J. Reedijk, Biochemistry 1985, 24, 707-713.
3. S. O. Ano, F. P. Intini, G. Natile, L. G. Marzilli, J. Am. Chem. Soc. 1997, 119, 8570-8571.
4. J. S. Saad, T. Scarcia, K. Shinozuka, G. Natile, L. G. Marzilli, Inorg. Chem. 2002, 41, 546-557.
5. J. Holford, F. Raynaud, B. A. Murrer, K. Grimaldi, J. A. Hartley, M. Abrams, L. R. Kelland, Anti-Cancer Drug Des. 1998, 13, 1-18.
6. Y. Chen, Z. Guo, S. Parsons, P. J. Sadler, Chem. Eur. J. 1998, 4, 672-676.
7. K. Harrap, The Institute of Cancer Research Study Report, November 1992, unpublished results, AnorMED Inc.
8. B. Lippert, G. Raudaschl, C. J. L. Lock, P. Pilon, Inorg. Chim. Acta 1984, 93, 43-50.
9. H. Schöllhorn, G. Raudaschl-Sieber, G. Müller, U. Thewalt, B. Lippert, J. Am. Chem. Soc. 1985, 107, 5932-5937.
10. S. E. Sherman, D. Gibson, A. H.-J. Wang, S. J. Lippard, J. Am. Chem. Soc. 1988, 110, 7368-7381.
11. G. Frommer, H. Schöllhorn, U. Thewalt, B. Lippert, Inorg. Chem. 1990, 29, 1417-1422.
12. G. Schröder, J. Kozelka, M. Sabat, M.-H. Fouchet, R. Beyerle-Pfnür, B. Lippert, Inorg. Chem. 1996, 55, 1647-1652.
13. R. E. Cramer, P. L. Dahlstrom, M. J. T. Seu, T. Norton, M. Kashiwagi, Inorg. Chem. 1980, 19, 148-154.
14. R. W. Gellert, R. Bau, J. Am. Chem. Soc. 1975, 97, 7379-7380.
15. S. Grabner, J. Plavec, N. Bukovec, D. Di Leo, R. Cini, G. Natile, J. Chem. Soc. Dalton Trans. 1998, 1447-1451.
16. R. Cini, S. Grabner, N. Bukovec, L. Cerasino, G. Natile, Eur. J. Inorg. Chem. 2000, 1601-1607.
17. R. K. O. Sigel, E. Freisinger, B. Lippert, J. Biol. Inorg. Chem. 2000, 5, 287-299.
18. F. Schwarz, B. Lippert, H. Schöllhorn, U. Thewalt, Inorg. Chim. Acta 1990, 176, 113-121.
19. R. Beyerle-Pfnür, B. Brown, R. Faggiani, B. Lippert, C. J. L. Lock, Inorg. Chem. 1985, 24, 4001-4009.
20. G. Schröder, B. Lippert, M. Sabat, C. J. L. Lock, R. Faggiani, B. Song, H. Sigel, J. Chem. Soc. Dalton Trans. 1995, 3767-3775.
21. R. Faggiani, B. Lippert, C. J. L. Lock, R. A. Speranzini, Inorg. Chem. 1982, 21, 3216-3225.
22. G. Schröder, M. Sabat, I. Baxter, J. Kozelka, B. Lippert, Inorg. Chem. 1997, 36, 490-493.
23. B. Lippert, J. Am. Chem. Soc. 1981, 103, 5691-5697.
24. B. Lippert, Met. Ions Biol. Syst. 1996, 33, 106-141.
25. S. Yao, J. P. Plastaras, L. G. Marzilli, Inorg. Chem. 1994, 33, 6061-6077.
26. C. Meiser, E. Freisinger, B. Lippert, J. Chem. Soc. Dalton Trans. 1998, 2059-2064.
27. A. Schreiber, M. S. Lüth, A. Erxleben, E. C. Fusch, B. Lippert, J. Am. Chem. Soc. 1996, 118, 4124-4132.
28. O. Krizanovic, M. Sabat, R. Beyerle-Pfnür, B. Lippert, J. Am. Chem. Soc. 1993, 115, 5538-5548.
29. I. Dieter-Wurm, M. Sabat, B. Lippert, J. Am. Chem. Soc. 1992, 114, 357-359.
30. E. Freisinger, I. B. Rother, M. S. Lüth, B. Lippert, Proc. Natl. Acad. Sci. USA 2003, 100, 3748-3753.
31. R. K. O. Sigel, S. M. Thompson, E. Freisenger, F. Glahé, B. Lippert, Chem. Eur. J. 2001, 7, 1968-1980.
32. E. Freisenger, S. Meier, B. Lippert, J. Chem. Soc. Dalton Trans. 2000, 3274-3280.
33. H. C. Wong, K. Shinozuka, G. Natile, L. G. Marzilli, Inorg. Chim. Acta 2000, 297, 36-46.
34. N. Margiotta, P. Papadia, F. P. Fanizzi, G. Natile, Eur. J. Inorg. Chem. 2003, 6, 1136-1144.
35. A. T. M. Marcelis, J. L. van der Veer, J. C. M. Zwetsloot, J. Reedijk, Inorg. Chim. Acta 1983, 78, 195-203.
36. R. Griesser, G. Kampf, L. E. Kapinos, S. Komeda, B. Lippert, J. Reedijk, H. Sigel, Inorg. Chem. 2003, 42, 32-41.
37. B. Song, J. Zhao, R. Griesser, C. Meiser, H. Sigel, B. Lippert, Chem. Eur. J. 1999, 5, 2374-2387.
38. G. B. Kauffman, D. O. Cowan, Inorg. Synth. 1963, 7, 239-245.
39. P. T. Beurskens, G. Beurskens, W. P. Bosman, R. de Gelder, S. Garcia-Granda, R. O. Gould, R. Israel, J. M. M. Smits, The DIRDIF96 Program System, Technical Report of the Crystallography Laboratory, University of Nijmegen, Nijmegen (The Netherlands), 1996.
40. G. M. Sheldrick, SHELXTL, University of Göttingen, Göttingen (Germany), 2001.
41. A. L. Spek, PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht (The Netherlands), 2004.
42. I. J. Bruno, J. C. Cole, P. R. Edgington, M. Kessler, C. F. Macrae, P. McCabe, J. Pearson, R. Taylor, Acta Crystallogr. Sect. B 2002, 58, 389-397.
43. P. van der Sluis, A. L. Spek, Acta Crystallogr. Sect. A 1990, 46, 194-201.
44. R. A. Sparks, GEMINI, Bruker AXS, Madison, Wisconsin (USA), 1999.
45. Bruker AXS, SAINT Version 7, Madison, Wisconsin (USA), 2003.
46. Y. Le Page, J. Appl. Crystallogr. 1982, 15, 255-259.
47. H. D. Flack, Acta Crystallogr. Sect. A 1987, A43, 564-568.