Mono- and bis-guanosine adducts of platinum complexes with carrier ligands having in-plane steric bulk: The case of 1,10-phenanthroline and 2,9-dimethyl-1,10-phenanthroline

European Journal of Inorganic Chemistry

Volumn , Issue 6, 2003, Pages 1136-1144

  Margiotta, Nicola ^a   Papadia, Paride ^a   Fanizzi, Francesco P ^b,c   Natile, Giovanni ^a  

^a UNIVERSITY OF BARI   (Italy)

^b UNIVERSITY OF SALENTO   (Italy)

^c Consortium CARSO Cancer Res Centre ^*  (Italy)

Author keywords

Antitumour agents; Atropisomerism; NMR spectroscopy; Nucleobases; Platinum

Indexed keywords

BIOMOLECULES; CHEMICAL SHIFT; CHLORINE COMPOUNDS; LIGANDS; PLATINUM; PLATINUM COMPOUNDS; POSITIVE IONS;

ANTITUMOUR AGENTS; ATROPISOMERISM; CARRIER LIGANDS; GUANINE; GUANOSINES; NMR-SPECTROSCOPY; NUCLEOBASES; PHENANTHROLINES; ROTAMERS; STERIC BULK;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

1,10 PHENANTHROLINE; 2,9 DIMETHYL 1,10 PHENANTHROLINE; CHLORIDE ION; CISPLATIN; DIAMINE DERIVATIVE; DNA; GUANINE DERIVATIVE; GUANOSINE DERIVATIVE; LIGAND; NUCLEIC ACID BASE; PLATINUM COMPLEX; SOLVENT; WATER;

ARTICLE; CHEMICAL BOND; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; DIELECTRIC CONSTANT; DRUG CONFORMATION; DRUG STABILITY; ISOMERISM; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; ROTATION; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0037354453     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejic.200390145     Document Type: Article

References (43)

1. J. Reedijk, Chem. Commun. 1996, 801-806.
2. Cisplatin. Chemistry and Biochemistry of a Leading Anticancer Drug (Ed.: B. Lippert), Wiley VCH, Zurich, 1999.
3. S. E. Sherman, S. J. Lippard, Chem. Rev. 1987, 87, 1153-1181.
4. A. Eastman, Pharmacol. Ther. 1987, 34, 155-166.
5. 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.
6. L. G. Marzilli, S. O. Ano, F. P. Intini, G. Natile, J. Am. Chem. Soc. 1999, 42, 9133-9142.
7. K. M. Williams, L. Cerasino, F. P. Intini, G. Natile, L. G. Marzilli, Inorg. Chem. 1998, 37, 5260-5268.
8. M. Carlone, F. P. Fanizzi, F. P. Intini, N. Margiotta, L. G. Marzilli, G. Natile, Inorg. Chem. 2000, 39, 634-641.
9. S. T. Sullivan, A. Ciccarese, F. P. Fanizzi, L. G. Marzilli, Inorg. Chem. 2000, 39, 836-842.
10. S. T. Sullivan, A. Ciccarese, F. P. Fanizzi, L. G. Marzilli, Inorg. Chem. 2001, 40, 455-462.
11. H. C. Wong, R. Coogan, F. P. Intini, G. Natile, L. G. Marzilli, Inorg. Chem. 1999, 38, 777-787.
12. D. Kiser, F. P. Intini, Y. Xu, G. Natile, L. G. Marzilli, Inorg. Chem. 1994, 33, 4149-4158.
13. R. E. Cramer, P. L. Dahlstrom, J. Am. Chem. Soc. 1979, 101, 3679-3681.
14. R. E. Cramer, P. L. Dahlstrom, Inorg. Chem. 1985, 24, 3420-3424.
15. P. G. Sammes, G. Yahioglu, Chem. Soc. Rev. 1994, 23, 327-334.
16. M. Nozaki, K. Ono, T. Nakazawa, S. Kotani, O. Hayaishi, J. Biol. Chem. 1968, 243, 2682-2690.
17. A. R. Katritzky, A. J. Boulton, Adv. Heteroc. Chem. 1978, 22, 1-69 and references therein.
18. J. Leiter, J. L. Hartwell, J. S. Kahler, I. Kline. M. J. Shear, J. Natl. Cancer Inst. 1953, 14, 365-374.
19. Z. Broda, S. Bulba, Res. Commun. Chem. Pathol. Pharmacol. 1972, 3, 383-391.
20. O. Clement, D. Macartney, E. Buncel, Inorg. Chim. Acta 1997, 264, 117-124.
21. F. P. Fanizzi, F. P. Intini, L. Maresca, G. Natile, M. Lanfranchi, A. Tiripicchio, J. Chem. Soc., Dalton Trans. 1991, 1007-1015.
22. F. P. Fanizzi, M. Lanfranchi, G. Natile, A. Tiripicchio, J. Chem. Soc., Dalton Trans. 1994, 33, 3331-3339.
23. R. J. H. Clark, F. P. Fanizzi, G. Natile, C. Pacifico, C. G: van Rooyen, D. A. Tocher, Inorg. Chim. Acta 1995, 235, 205-213.
24. S. O. Ano, Z. Kuklenyik, L. G. Marzilli, in Cisplatin. Chemistry and Biochemistry of a Leading Anticancer Drug (Ed.: B. Lippert), Wiley VCH, Zurich, 1999.
25. G. Admiraal, J. H. van der Veer, R. A. G. de Graaff, J. H. J. den Hartog, J. Reedijk, J. Am. Chem. Soc. 1987, 109, 592-594.
26. S. O. Ano, F. P. Intini, G. Natile, L. G. Marzilli, J. Am. Chem. Soc. 1998, 120, 12017-12022.
27. S. O. Ano, F. P. Intini, G. Natile, L. G. Marzilli, J. Am. Chem. Soc. 1997, 119, 8570-8571.
28. S. J. Berners-Price, U. Frey, J. D. Ranford, P. J. Sadler, J. Am. Chem. Soc. 1993, 115, 8649-8659.
29. K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, John Wiley & Sons, inc., New York, 1997.
30. K. Wuthrich, NMR of Proteins and Nucleic Acids, John Wiley & Sons, New York, 1986.
31. J. S. Saad, T. Scarcia, K. Shinozuka, G. Natile, L. G. Marzilli, Inorg. Chem. 2002, 41, 546-557.
32. L. G. Marzilli, S. O. Ano, F. P. Intini, G. Natile, J. Am. Chem. Soc. 1999, 121, 9133-9142.
33. M. Polak, J. Plavec, A. Trifonova, A. Földesi, J. Chattopadhyaya, J. Chem. Soc., Perkin Trans. 1999, 1, 2835-2843.
34. F. Basolo, R. G. Pearson, in Mechanism of Inorganic Reactions, John Wiley & Sons, New York, 1967, Chapt. 5.
35. J. A. Beaty, M. M. Jones, Inorg. Chem. 1992, 31, 2547-2551.
36. M. Mikola, K. D. Kilka, A. Hakala, J. Arpalahti, Inorg. Chem. 1999, 38, 571-578.
37. A. Habtemariam, J. A. Parkinson, N. Margiotta, T. W. Hambley, S. Parsons, P. J. Sadler, J. Chem. Soc., Dalton Trans. 2001, 362-372.
38. N. Margiotta, F. P. Fanizzi, J. Kobe, G. Natile, Eur. J. Inorg. Chem. 2001, 5, 1303-1310.
39. L. G. Marzilli, F. P. Intini, D. Kiser, H. C. Wong, S. O. Ano, P. A. Marzilli, G. Natile, Inorg. Chem. 1998, 37, 6898-6905.
40. S. O. Ano, F. P. Intini, G. Natile, L. G. Marzilli, Inorg. Chem. 1999, 38, 2989-2999.
41. Y. Xu, G. Natile, F. P. Intini, L. G. Marzilli, J. Am. Chem. Soc. 1990, 112, 8172-8179.
42. Kaleidagraph, Version 3.0 for Macintosh Computers, Abelbeck Software, 1993.
43. Yu. N. Kukushkin, Yu. E. Vyaz'menskii, L. I. Zorina, Yu. L. Pazukhina, Zh. Neorg. Khim. 1968, 13, 1595-1599.