DNA binding mode of the cis and trans geometries of new antitumor nonclassical platinum complexes containing piperidine, piperazine, or 4-picoline ligand in cell-free media. Relations to their activity in cancer cell lines

Biochemistry

Volumn 42, Issue 20, 2003, Pages 6321-6332

  Kasparkova, Jana ^a   Marini, Victoria ^a   Najajreh, Yousef ^b   Gibson, Dan ^b,c   Brabec, Viktor ^a  

^a INSTITUTE OF BIOPHYSICS   (Czech Republic)

^b HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^c HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; DRUG PRODUCTS; PLATINUM; TUMORS;

LIGANDS;

CELLS;

AMINE; ANTINEOPLASTIC AGENT; AROMATIC COMPOUND; CISPLATIN; CISPLATIN DERIVATIVE; DNA; HETEROCYCLIC COMPOUND; LIGAND; PICOLINE DERIVATIVE; PIPERAZINE; PIPERIDINE; PLASMID DNA; PLATINUM COMPLEX; TRANSPLATIN;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CANCER RESISTANCE; CELL FREE SYSTEM; CHEMICAL MODIFICATION; CIS ISOMER; CONTROLLED STUDY; CROSS LINKING; CYTOTOXICITY; DNA DAMAGE; DNA HELIX; DRUG DNA BINDING; DRUG SENSITIVITY; DRUG UPTAKE; GEOMETRY; HUMAN; HUMAN CELL; PRIORITY JOURNAL; TRANS ISOMER;

ANIMALS; ANTINEOPLASTIC AGENTS; BASE SEQUENCE; BINDING SITES; CATTLE; CELL-FREE SYSTEM; CISPLATIN; CROSS-LINKING REAGENTS; DNA; DNA ADDUCTS; HUMANS; KINETICS; NUCLEIC ACID DENATURATION; ORGANOPLATINUM COMPOUNDS; STEREOISOMERISM; TUMOR CELLS, CULTURED;

MAMMALIA;

EID: 0037845097     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi0342315     Document Type: Article

References (49)

1. Wong, E., and Giandomenico, C. M. (1999) Chem. Rev. 99, 2451-2466.
2. O'Dwyer, P. J., Stevenson, J. P., and Johnson, S. W. (1999) in Cisplatin. Chemistry and Biochemistry of a Leading Anticancer Drug (Lippert, B., Ed.), pp 31-72, Wiley-VCH, Weinheim, Germany.
3. Giaccone, G. (2000) Drugs 59, 9-17.
4. Johnson, N. P., Butour, J.-L., Villani, G., Wimmer, F. L., Defais, M., Pierson, V., and Brabec, V. (1989) Prog. Clin. Biochem. Med. 10, 1-24.
5. Kartalou, M., and Essigmann, J. M. (2001) Mutat. Res. 478, 1-21.
6. Cohen, S. M., and Lippard, S. J. (2001) Prog. Nucleic Acid Res. Mol. Biol. 67, 93-130.
7. Gelasco, A., and Lippard, S. J. (1999) in Metallopharmaceuticals I. DNA Interactions (Clarke, M. J., and Sadler, P. J., Eds.), pp 1-43, Springer, Berlin.
8. Jamieson, E. R., and Lippard, S. J. (1999) Chem. Rev. 99, 2467-2498.
9. Zamble, D. B., and Lippard, S. J. (1999) in Cisplatin. Chemistry and Biochemistry of a Leading Anticancer Drug (Lippert, B., Ed.), pp 73-110, Wiley-VCH, Weinheim, Germany.
10. Brabec, V. (2002) Prog. Nucleic Acid Res. Mol. Biol. 71, 1-68.
11. Dalbies, R., Payet, D., and Leng, M. (1994) Proc. Natl. Acad. Sci. U.S.A. 91, 8147-8151.
12. Boudvillain, M., Dalbies, R., Aussourd, C., and Leng, M. (1995) Nucleic Acids Res. 23, 2381-2388.
13. Leng, M., Schwartz, A., and Giraud-Panis, M. J. (2000) in Platinum-Based Drugs in Cancer Therapy (Kelland, L. R., and Farrell, N. P., Eds.), pp 63-85, Humana Press Inc., Totowa, NJ.
14. Kelland, L. R. (2000) in Platinum-Based Drugs in Cancer Therapy (Kelland, L. R., and Farrell, N. P., Eds.), pp 299-319, Humana Press Inc., Totowa, NJ.
15. Farrell, N. (1996) in Metal Ions in Biological Systems (Sigel, A., and Sigel, H., Eds.), pp 603-639, Marcel Dekker, Inc., New York, Basel, and Hong Kong.
16. Natile, G., and Coluccia, M. (1999) in Metallopharmaceuticals (Clarke, M. J., and Sadler, P. J., Eds.), pp 73-98, Springer, Berlin.
17. Perez, J. M., Fuertes, M. A., Alonso, C., and Navarro-Ranninger, C. (2000) Crit. Rev. Oncol. Hematol. 35, 109-120.
18. Brabec, V., and Kasparkova, J. (2002) in Small Molecule DNA and RNA Binders: From Synthesis to Nucleic Acid Complexes (Demeunynck, M., Bailly, C., and Wilson, D., Eds.), pp 178-223, Wiley-VCH, Weinheim, Germany.
19. Farrell, N., Kelland, L. R., Roberts, J. D., and Van Beusichem, M. (1992) Cancer Res. 52, 5065-5072.
20. Eastman, A., Jennerwein, M. M., and Nagel, D. L. (1988) Chem.-Biol. Interact. 67, 71-80.
21. Najajreh, Y., Perez, J. M., Navarro-Ranninger, C., and Gibson, D. (2002) J. Med. Chem. 45, 5189-5195.
22. Khazanov, E., Barenholz, Y., Gibson, D., and Najajreh, Y. (2002) J. Med. Chem. 45, 5196-5204.
23. Kartalou, M., and Essigmann, J. M. (2001) Mutat. Res. 478, 23-43.
24. Brabec, V., and Kasparkova, J. (2002) Drug Resist. Updates 5, 147-161.
25. Brabec, V., and Palecek, E. (1970) Biophysik 6, 290-300.
26. Brabec, V., and Palecek, E. (1976) Biophys. Chem. 4, 76-92.
27. Brabec, V., Reedijk, J., and Leng, M. (1992) Biochemistry 31, 12397-12402.
28. Kim, S. D., Vrana, O., Kleinwächter, V., Niki, K., and Brabec, V. (1990) Anal. Lett. 23, 1505-1518.
29. Brabec, V., and Leng, M. (1993) Proc. Natl. Acad. Sci. U.S.A. 90, 5345-5349.
30. Comess, K. M., Costello, C. E., and Lippard, S. J. (1990) Biochemistry 29, 2102-2110.
31. Lemaire, M. A., Schwartz, A., Rahmouni, A. R., and Leng, M. (1991) Proc. Natl. Acad. Sci. U.S.A. 88, 1982-1985.
32. Brabec, V., Sip, M., and Leng, M. (1993) Biochemistry 32, 11676-11681.
33. Farrell, N., Appleton, T. G., Qu, Y., Roberts, J. D., Fontes, A. P. S., Skov, K. A., Wu, P., and Zou, Y. (1995) Biochemistry 34, 15480-15486.
34. Brabec, V., Kasparkova, J., Vrana, O., Novakova, O., Cox, J. W., Qu, Y., and Farrell, N. (1999) Biochemistry 38, 6781-6790.
35. Keck, M. V., and Lippard, S. J. (1992) J. Am. Chem. Soc. 114, 3386-3390.
36. Brabec, V., Neplechova, K., Kasparkova, J., and Farrell, N. (2000) J. Biol. Inorg. Chem. 5, 364-368.
37. Kelland, L. R., Abel, G., McKeage, M. J., Jones, M., Goddard, P. M., Valenti, M., Murrer, B. A., and Harrap, K. R. (1993) Cancer Res. 53, 2581-2586.
38. Alley, M. C., Scudiero, D. A., Monks, A., Hursey, M. L., Czerwinski, M. J., Fine, D. L., Abbott, B. J., Mayo, J. G., Shoemaker, R. H., and Boyd, M. R. (1988) Cancer Res. 48, 589-601.
39. Vrana, O., Boudny, V., and Brabec, V. (1996) Nucleic Acids Res. 24, 3918-3925.
40. Brabec, V., Kleinwächter, V., Butour, J. L., and Johnson, N. P. (1990) Biophys. Chem. 35, 129-141.
41. Cohen, G. L., Bauer, W. R., Barton, J. K., and Lippard, S. J. (1979) Science 203, 1014-1016.
42. Scovell, W. M., and Collart, F. (1985) Nucleic Acids Res. 13, 2881-2895.
43. Fichtinger-Schepman, A. M. J., Van der Veer, J. L., Den Hartog, J. H. J., Lohman, P. H. M., and Reedijk, J. (1985) Biochemistry 24, 707-713.
44. Eastman, A. (1987) Pharmacol. Ther. 34, 155-166.
45. Bancroft, D. P., Lepre, C. A., and Lippard, S. J. (1990) J. Am. Chem. Soc. 112, 6860-6871.
46. Eastman, A., and Barry, M. A. (1987) Biochemistry 26, 3303-3307.
47. Brabec, V., Vrana, O., Novakova, O., Kleinwachter, V., Intini, F. P., Coluccia, M., and Natile, G. (1996) Nucleic Acids Res. 24, 336-341.
48. Zaludova, R., Kleinwächter, V., and Brabec, V. (1996) Biophys. Chem. 60, 135-142.
49. Dalbies, R., Boudvillain, M., and Leng, M. (1995) Nucleic Acids Res. 23, 949-953.