Cu(II) complexes with heterocyclic substituted thiosemicarbazones: The case of 5-formyluracil. Synthesis, characterization, X-ray structures, DNA interaction studies, and biological activity

Inorganic Chemistry

Volumn 42, Issue 6, 2003, Pages 2049-2055

  Baldini, Monica ^a   Belicchi Ferrari, Marisa ^a   Bisceglie, Franco ^a   Pelosi, Giorgio ^a   Pinelli, Silvana ^a   Tarasconi, Pieralberto ^a  

^a UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

5 FORMYLURACIL; COPPER CHLORIDE; COPPER COMPLEX; DNA; HETEROCYCLIC COMPOUND; OXYGEN; THIOSEMICARBAZONE; UNCLASSIFIED DRUG; URACIL DERIVATIVE; WATER;

ANALYTIC METHOD; ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL ANALYSIS; CONTROLLED STUDY; CRYSTAL STRUCTURE; DENATURATION; DNA BINDING; HUMAN; HUMAN CELL; MOLECULAR INTERACTION; SYNTHESIS; TECHNIQUE; TITRIMETRY; TUMOR CELL LINE; X RAY ANALYSIS;

COPPER; CRYSTALLOGRAPHY, X-RAY; DNA; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; THIOSEMICARBAZONES; TUMOR CELLS, CULTURED; U937 CELLS; URACIL;

EID: 0037464350     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic026131d     Document Type: Article

References (44)

1. Padhyé, S.; Kauffman, G. B. Coord. Chem. Rev. 1985, 63, 127-160.
2. Byrnes, R. W.; Mohan, M.; Antholine, W. E.; Xu, R. X.; Petering, D. H. Biochemistry 1990, 29, 7046-7053.
3. Agrawal, K. C.; Booth, B. A.; Sartorelli, A. C. J. Med. Chem. 1968, 11, 700-703.
4. Agrawal, K. C.; Sartorelli, A. C. J. Med. Chem. 1969, 12, 771-774.
5. Antholine, W. E.; Knight, J.; Whelan, H.; Petering, D. H. Mol. Pharmacol. 1977, 13, 89-98.
6. Klayman, D. L.; Bartosovich, J. F.; Griffin, T. S.; Mason, C. J.; Scovill, J. P. J. Med. Chem. 1979, 22, 855-862.
7. Klayman, D. L.; Scovill, J. P.; Bartosovich, J. F.; Mason, C. J. J. Med. Chem. 1979, 22, 1367-1373.
8. Ronen, D.; Sherman, L.; Bar-Nun, S.; Teitz, Y. Amtimicrob. Agents Chemother. 1987, 31, 1798-1802.
9. Condit, R. C.; Easterly, R.; Pacha, R. F.; Fathi, Z.; Meis, R. J. Virology 1991, 185, 857-861.
10. Belicchi-Ferrari, M.; Gasparri-Fava, G.; Tarasconi, P.; Albertini, R.; Pinelli, S.; Starcich, R. J. Inorg. Biochem. 1994, 53, 13-25.
11. Cory, J. G.; Cory, A. H.; Rappa, G.; Lorico, A.; Liu, M.-C.; Lin, T.-S.; Sartorelli, A. C. Biochem. Pharmacol. 1994, 48, 335-344.
12. Kovala-Demertzi, D.; Nath Yadav, P.; Demertzis, M. A.; Coluccia, M. J. Inorg. Biochem. 2000, 78, 347-354.
13. Scovill, J. P.; Klayman, D. L.; Franchino, C. F. J. Med. Chem. 1982, 25, 1261-1264.
14. Campbell, M. J. M. Coord. Chem. Rev. 1975, 15, 279-319.
15. Lakovidou, Z.; Papageorgiou, A.; Demertzis, M. A.; Mioglou, E.; Mourelatos, D.; Kotsis, A.; Yadav, P. N.; Kovala-Demertzi, D. AntiCancer Drugs 2001, 12, 65-70.
16. Liberta, A. E.; West, D. X. BioMetals 1992, 5, 121-126.
17. Hussain Reddy, K.; Sambasiva Reddy, P.; Ravindra Babu, P. Transition Met. Chem. (Dordrecht, Neth.) 2000, 25, 154-160.
18. Wolmark, N.; Rockette, H. J. Clin. Oncol. 1999, 17, 3553-3559.
19. Denny, W. A. Eur. J. Med. Chem. 2001, 36, 577-595.
20. Belicchi-Ferrari, M.; Gasparri-Fava, G.; Leporati, E.; Pelosi, G.; Rossi, R.; Tarasconi, P.; Albertini, R.; Bonati, A.; Lunghi, P.; Pinelli, S. J. Inorg. Biochem. 1998, 70, 145-154.
21. Belicchi-Ferrari, M.; Bisceglie, F.; Pelosi, G.; Tarasconi, P.; Albertini, R.; Bonati, A.; Lunghi, P.; Pinelli, S. J. Inorg. Biochem. 2001, 83, 169-179.
22. West, D. X.; Swearingen, J. K.; Valdés-Martínez, J.; Hernández-Ortega, S.; El-Sawaf, A. K.; van Meurs, F.; Castineiras, A.; Garcia, I.; Bermejo, I.; Polyhedron 1999, 18, 2919-2929.
23. Belicchi-Ferrari, M.; Capacchi, S.; Reffo, G.; Pelosi, G.; Tarasconi, P.; Albertini, R.; Pinelli, S.; Lunghi, P. J. Inorg. Biochem. 2000, 81, 89-97.
24. Abram, U.; Ortner, K.; Gust, R.; Sommer, K. J. Chem. Soc., Dalton Trans. 2000, 735-744.
25. Belicchi-Ferrari, M.; Capacchi, S.; Bisceglie, F.; Pelosi, G.; Tarasconi, P. Inorg. Chim. Acta 2001, 312, 81-87.
26. Belicchi-Ferrari, M.; Bisceglie, F.; Pelosi, G.; Tarasconi, P.; Albertini, R.; Pinelli, S. J. Inorg. Biochem. 2001, 87, 137-147.
27. Belicchi-Ferrari, M.; Bisceglie, F.; Leporati, E.; Pelosi, G.; Tarasconi, P.; Pinelli, S. Bull. Chem. Soc. Jpn. 2002, 75, 781-788.
28. Mudasir; Yoshioka, N.; Inoue, H. J. Inorg. Biochem. 1999, 77, 239-247.
29. Reichmann, M. E.; Rice, S. A.; Thomas, C. A.; Doty, P. J. Am. Chem. Soc. 1954, 76, 3047-3051
30. Ugozzoli, F. Comput. Chem. 1987, 11, 109-120.
31. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. SIR 92. J. Appl. Crystallogr. 1993, 26, 343-350.
32. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. SIR 97. J. Appl. Crystallogr. 1999, 32, 115-122.
33. Sheldrick, G. SHELXL 97 A Program for Structure Refinement; University of Goettingen: Goettingen, Germany, 1997.
34. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, U.K., 1974.
35. Nardelli, M. PARST95. An update to PARST: a system of Fortran routines for calculating molecular structure parameters from the results of crystal structure analyses. J. Appl. Crystallogr. 1995, 28, 659.
36. Johnson, C. K.; Burnett, M. N. ORTEPIII; Report ORNL-6895; Oak Ridge National Laboratory: Oak Ridge, TN, 1996.
37. Spek, A. L. PLATON. A Multipurpose Crystallographic Tool; Utrecht University: Utrecht, The Netherlands, 1999.
38. Wolfe, A.; Shimer, G. H., Jr.; Meehan, T. Biochemistry 1987, 26, 6392-6396.
39. Liu, J.; Zhang, T.; Lu, T.; Qu, L.; Zhou, H.; Zhang, Q.; Ji, L. J. Inorg. Biochem. 2002, 91, 269-276.
40. Wilson, W. D.; Tanious, F. A.; Fernandez-Saiz, M.; Rigl, C. T. In Methods in Molecular Biology; Fox, K. R., Ed.; Humana: Clifton, NJ, 1997; Vol. 90.
41. Cremer, D.; Pople, J. A. J. Am. Chem. Soc. 1975, 97, 1354.
42. Liu, F.; Meadows, K. A.; McMillin, D. R. J. Am. Chem. Soc. 1993, 115, 6699-6704.
43. Pastenack, R. F.; Gibbs, E. J.; Villafranca, J. J. Biochemistry 1983, 22, 2406-2412.
44. Pyle, A. M.; Remann, J. P.; Meshoyrer, R.; Kumar, C. V.; Turro, N. J.; Barton, J. K. J. Am. Chem. Soc. 1989, 111, 3051-3058.