Novel tetranuclear orthometalated complexes of Pd(II) and Pt(II) derived from p-isopropylbenzaldehyde thiosemicarbazone with cytotoxic activity in cis-DDP resistant tumor cell lines. Interaction of these complexes with DNA

Journal of Medicinal Chemistry

Volumn 41, Issue 9, 1998, Pages 1399-1408

  Quiroga, Adoración G ^a   Pérez, José M ^a   López Solera, Isabel ^a   Masaguer, José R ^a   Luque, Antonio ^b   Román, Pascual ^b   Edwards, Andy ^c   Alonso, Carlos ^a   Navarro Ranninger, Carmen ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^c NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

4 ISOPROPYLBENZALDEHYDE THIOSEMICARBAZONE DERIVATIVE; CYTOTOXIC AGENT; DOXORUBICIN; ETOPOSIDE; PALLADIUM COMPLEX; PALLADIUM(4 ISOPROPYLBENZALDEHYDE THIOSEMICARBAZONE) DERIVATIVE; PLATINUM DERIVATIVE; PLATINUM(4 ISOPROPYLBENZALDEHYDE THIOSEMICARBAZONE) DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CANCER INHIBITION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DNA CROSS LINKING; DRUG CYTOTOXICITY; DRUG DNA BINDING; HUMAN; HUMAN CELL; METAL BINDING; MOUSE; NONHUMAN; STRUCTURE ANALYSIS;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE; CELL SURVIVAL; CIRCULAR DICHROISM; CISPLATIN; CROSS-LINKING REAGENTS; CRYSTALLOGRAPHY, X-RAY; DNA; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MOLECULAR STRUCTURE; NUCLEIC ACID CONFORMATION; ORGANOMETALLIC COMPOUNDS; RATS; THIOSEMICARBAZONES; TUMOR CELLS, CULTURED;

EID: 0032560227     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970520d     Document Type: Article

References (57)

1. (a) Dobek, A. S.; Klayman, D. L.; Dickson, E. T.; Scovill, J. P.; Oster, C. N. Thiosemicarbazones of 2-Acetylpyridine, 2-Aeetylquinoline, 1- and 3-Acetylisoquinoline and Related Compounds as Inhibitors of Clinically Significant Bacteria In Vitro. Arzneim. Forsch. 1983, 33, 1583.
2. (b) Scovill, J. P.; Klayman, D. L.; Franchino, C. F. 2-Acetylpyridine Thiosemicarbazones Complexes With Transition Metals as Antimalarial and Antileukemic Agents. J. Med. Chem. 1982, 25, 1261.
3. (c) Klayman, D. L.; Scovill, J. P.; Mason, C. J.; Bartosevich, J. F.; Bruce, J.; Lin, A. 2-Acetylpyridine Thiosemicarbazones. 6. 2-Acetylpyridine and 2-Butyrylpyridine Thiosemicarbazones as Anti-leukemic Agents. Arzneim. Forsch. 1983, 33, 909.
4. (d) Shipman, C., Jr.; Smith, S. H.; Drach, J. C.; Klayman, D. L. Thiosemicarbazones of 2-Acetylpyridine, 2-Acetylquinoline, 1-Acetylisoquinoline, and Related-Compounds as Inhibitors of Herpes-simplex Virus In Vitro and In a Cutaneous Herpes Guinea-pig Model. Antiviral Res. 1986, 6, 197.
5. (e) Pandeya, S. N.; Dimmock, J. R. Recent Evaluations of Thiosemicarbazones and Semicarbazones and Related Compounds for Antineoplastic and Anticonvulsant Activities. Pharmazie 1993, 48, 659.
6. (a) Aravindakshan, K. K.; Nair, C. G. R. Preparation and Characterization of Solid Complexes of 2-Furaldehyde Thiosemicarbazone with Some Transition Metal Ions. Indian J. Chem., Sect. A 1981, 20, 684.
7. (b) Crim, J. A.; Petering, H. G. Antitumor Activity of Cu(II)KTS, the Cu(II) Chelate of 3-Ethoxy-2-oxobutyraldehydeBis(thiosemicarbazone). Cancer Res. 1967, 27, 1278.
8. (c) Petering, D. H.; Antholine, W. E.; Saryan, L. A. Metal Complexes as Antitumor Agents, α-N-Heterocyclic carboxaldehyde Thiosemicarbazones. In Anticancer and Interferon Agents. Syntheses and Properties; Ottenbrite, R. H., Butler, G. B., Eds.; Marcel Dekker: New York, 1984; p 221.
9. (d) Kovala-Demertzi, D.; Domopuolou, A.; Demertzi, M. Coordinating Properties of 2-Acetylpyridine Thiosemicarbazone. Palladium(II) Complexes with Neutral and Deprotonated Ligand. X-ray Structure of Bromo(2-Acetylpiridine Thiosemicarbazonato) Palladium(II). Polyhedron 1994, 13, 1917.
10. (a) West, D. X.; Liberta, A. E.; Padhye, S. B.; Chikate, R. C.; Sonawane, P. B.; Kumbhar, A. S.; Yerande, R. G. Thiosemicarbazone Complexes of Copper(II): Structural and Biological Studies. Coord. Chem. Rev. 1993, 123, 49.
11. (b) Campbell, M. J. M. Transitioin Metal Complexes of Thiosemicarbazide and Thiosemicarbazone. Ibid. 1975, 15, 279.
12. (c) Wiles, D. M.; Gingras, B. A.; Suprunchuk, T. The C=S Stretching Vibration in the Infrared Spectra of Some Thiosemicarbazones. Can. J. Chem. 1967, 45, 469.
13. (d) West, D. X.; Bain, G. A.; Butcher, J.; Jasinski, J. P.; Li, Y.; Pozdniakv, Y.; Valdés-Martinez, J.; Toscano, A. R.; Hernández-Ortega, S. Structural Studies of Three Isomeric Forms of Heterocyclic N4-Sustituted Thiosemicarbazones and Two Nickel(II) Complexes. Polyhedron 1996, 15, 665.
14. (e) Bingham, A. G.; Bogge, H.; Muller, A.; Ainscoing, E. W.; Brodie, A. M. Synthetic, Spectroscopic, and X-ray Crystallographic Studies on Binuclear Copper(II) Complexes with a Tridentate NNS-bonding 2-Formylpyridine Thiosemicarbazone Ligand. The Characterization of Both Neutral and Deprotonated Co-ordinated Ligand Structures. J. Chem. Soc., Dalton Trans. 1987, 493.
15. 2}] (X = Cl or Br). Ibid. 1994, 2233 .
16. (a) Hingorani, S.; Agarwala, B. V. Structural Investigation of Pd(II) and Pt(II) Complexes with o-Vainillin Thiosemicarbazone and 4-Phenylthiosemicarbazone and Their Mixed Ligand Complexes. Spectrosc. Lett 1990, 23, 1097.
17. (b) Kovala-Demertzi, D.; Domopoulo, A.; Demertzis, M. A.; Valdés-Martínez, J.; Hernández-Hortega, S.; Espinosa-Pérez, G.; West, D. X.; Salberg, M. M.; Bain, G. A.; Bloom, P. D. Palladium(II) Complexes of 2-Acetylpyridine N4-Propyl, N4-Dipropyl- and 3-Hexamethyleneimyl Thiosemicarbazones with Potencially Interesting Biological Activity. Synthesis, Spectral Properties, Antifungal and In Vitro Antitumor Activity. Polyhedron 1996, 15, 2587.
18. (a) Garcia-Ruano, J. L.; Lopez-Solera, I.; Masaguer, J. R.; Navarro-Ranninger, C.; Rodriguez, J. H.; Martinez-Carrera, S. Cyclometalation of N-(4-Methoxyphenyl)-α-benzoylidenamine with Palladium(II) Acetate. Evidence for a New Kind of Diastereoisomerism. Organometallics 1992, 11, 3013.
19. (b) Navarro-Ranninger, C.; Lopez-Solera, I.; Alvarez-Valdés, A.; RodríguezRamos, J. H.; Masaguer, J. R.; García-Ruano, J. L.; Solans, X. Cyclometalated Complexes of Palladium(II) and Platinum(II) with N-Benzyl- and N-(Phenylethyl)-α-Benzoylidenamine. Delocalization in the Cyclometalated Ring as a Driving Force for the Orthometalation. Ibid. 1993, 12, 4104.
20. (c) García-Ruano, J. L.; Gonzalez, A. M.; López-Solera, I.; Masaguer, J. R.; Navarro-Ranninger, C.; Raithby, P. R.; Rodríguez, J. H. Enantiomerically Pure Palladacycles Derived from β-Ketosulfoxides. Angew. Chem., Int. Ed. Engl. 1995, 34, 1351.
21. (a) Navarro-Ranninger, C.; López-Solera, I.; Pérez, J. M.; Masaguer, J. R.; Alonso, C. In Vitro Antitumor Activity of Two Isomeric Cyclopalladated Compounds Derived from Benzoyl-benzylidenimines. Appl. Organomet. Chem. 1993, 7, 57.
22. (b) Navarro-Ranninger, C.; López-Solera, I.; Pérez, J. M.; Rodríguez, J.; García-Ruano, J. L.; Raithby, P. R.; Masaguer, J. R.; Alonso, C. Analysis of Two Cycloplatinated Compounds Derived from N-(4-Methoxyphenyl)-α-benzoylbenzylidenamine. Comparison of the Activity of These Compounds with Other Isostructural Cyclopalladated Compounds. J. Med. Chem. 1993, 36, 3795.
23. (c) Navarro-Ranninger, C.; Lopez-Solera, I.; Gonzalez, V. M.; Pérez, J. M.; Alvarez-Valdés, A.; Martín, A.; Raithby, P. R.; Masaguer, J. R.; Alonso, C. Cyclometalated Complexes of Platinum and Palladium with N-(4-Chlorophenyl)-α-benzoylbenzylidenamine. In Vitro Cytostatic activity, DNA Modification, and Interstrand Cross-Link Studies. Inorg. Chem. 1996, 35, 5181.
24. (a) Teixidor, F.; Sánchez, G.; Lucena, N.; Escriche, L.; Kivekäs, R.; Casabó, J Palladium-promoted Benzothiophene Condensation in NS2 Ligands. J. Chem. Soc., Chem. Commun. 1992, 163.
25. 2CO. Angew. Chem., Int. Ed. Engl. 1987, 26, 768.
26. (c) Mimoun, H.; Charpentier, R.; Mitschier, A.; Fisher, J.; Weiss, R. Palladium(II) tert-Butyl Peroxide Carboxylates. New Reagents for the Selective Oxidation of Terminal Olefins to Methyl Ketones. On the Role of Peroxymetalation in Selective Oxidative Processes. J. Am. Chem. Soc. 1980, 102, 1047.
27. 4] (Hpro = L-proline) J. Chem. Soc., Dalton Trans. 1996, 4031.
28. (e) Gibson, D.; Lippard, S. J. Preparation and Structural Characterization of a Novel Hexanuclear Complex of Platinum(II) with 2-Aminoethanethiolate. Inorg. Chem. 1986, 25, 219.
29. n+. Inorg. Chem. 1992, 31, 2501.
30. (a) Kawamoto, T.; Kushi, Y. Crystal and Molecular Structure of Tetra-palladium Cluster with a C,N,S-Tridentate Ligand. Chem. Lett. 1992, 1057.
31. (b) Kawamoto, T.; Nagasawa, I.; Kuma, H.; Kushi, Y. Pd·H-C Interactions. Preparation and Structure of Orthometalated Tetranuclear Complexes of Palladium(II) and Platinum(II). Inorg. Chem. 1996, 35, 2427.
32. 13C NMR studies of some monomeric derivatives of N-(4-MethoxyphenyDα-benzoylbenzilideneamine. J. Organomet. Chem. 1994, 476, 111.
33. (b) Steel, P. J.; Caygill, G. B. Cyclometalated Compounds. II. Proton and Carbon-13 Nuclear Magnetic Resonance Spectral Assignments of Cyclopalladated Compounds. J. Organomet. Chem. 1987, 327, 101.
34. (a) Adams, R. D.; Horvath, Y. T.; Segmuller, B. E.; Yang, L. W. Metal-induced Cleavage of Carbon-sulfur Bonds in Thiolato Ligands. Thermolysis of HOs3(CO)10(μ-SC6H5) under Carbon Monoxide Pressure. The Synthesis and Crystal and Molecular Structures of Os4(CO)13(μ3S) and Os5(CO)15(μ4S). Organometallics 1983, 2, 1301.
35. (b) Ghilardi, C. A.; Midollini, S.; Sacconi, L. An Enneanuclear Nickel Sulfide with a Cofacial Bi-octahedral Geometry. X-ray Crystal Structure of [Ni9(μ4-S)3(μ3-S)6(PET3)6][BHP4]2 J. Chem. Soc., Chem. Commun. 1981, 47.
36. (c) Bodensieck, U.; Santiago, J.; Stoeckli-Evans, H.; Suss-Fink, G. Tetranuclear Ruthenium Clusters Containing a Pseudo-octahedral Ru4S2 Framework and Diaminocarbene Ligands. J. Chem. Soc., Dalton Trans. 1992, 255.
37. (a) Casas, J. S.; Sánchez, A.; Sordo, J.; Vázquez-López, A.; Castellano, E. E.; Zukermann-Schpector, J.; Rodríguez-Arguelles, M. C.; Russo, U. Diorganotin (IV) Derivatives of Salicylaldehydethiosemicarbazone. The Crystal Structure of Dimethyl- and Diphenyl- (Salicylaldehydethiosemicarbazonato)tin(IV). Inorg. Chim. Acta 1994, 276, 169
38. (b) Casas, J. S.; Castiñeiras, A.; Sánchez, A.; Sordo, J.; Vázquez-López, A.; Rodríguez-Arguelles, M. C.; Russo, U. Synthesis and Spectroscopic Propierties of Diorganotin(IV) Derivatives of 2,6-Diacetylpyridine Bis(thiosemicarbazone). Crystal Structure of Diphenyl{2,6-diacetylpyridine Bis(thiosemicarbazonato)}tin(IV) Bis(dimethylformamide) solvate. Ibid. 1994, 221, 61.
39. (c) Mohan, M.; Sharma, P.; Kumar, M.; Jha, N. K. Metal Complexes of 2,6-Diacetylpyridine Bis(thiosemicarbazone): Their Preparation, Characterization and Antitumour Activity. Ibid. 1986, 125, 9.
40. 2. J. Chem. Soc., Dalton Trans. 1991, 2669.
41. Gutierrez, M. A.; Newkome, G. R.; Selbin, J. Cyclometalation Palladium 2-Arylpyridine Complexes. J. Organomet. Chem. 1980, 202, 341.
42. Albert, J.; Ceder, R. M.; Gómez, M.; Granell, J.; Sales, J. Cyclopalladation of N-Mesitylbenzilidenamines. Aromatic versus aliphatic C.-H Activation. Organometallics 1992, 11, 1536.
43. Thimmaiah, K. N.; Chandrappa, G. T.; Rangeswany; Jayarama. Structural Studies of Biologically active Complexes of Zinc(II) Cadmium(II), Mercury(II) and Copper(II) with p-Anísaldehyde Thiosemicarbazone. Polyhedron 1984, 3, 1237.
44. Alley, M. C.; Scudiero, D. A.; Monks, A.; Huresey, M. L.; Czerwinski, M. J.; Fine, D. L.; Abbott, B. J.; Mayo, J. G.; Shoemaker, R. H.; Boyd, M. R. Feasibility of Drug Screening with Panels of Human-tumor Cell-lines Using a Microculture Tetrazolium Assay. Cancer Res. 1988, 48, 589.
45. Sherman, S. E.; Lippard, S. J. Structural Aspects of Platinum Anticancer Drug-interactions with DNA. Chem. Rev. 1987, 87, 1153.
46. Johnson, A.; Qu, Y.; Houten, B. V.; Farrell, N. β-Z DNA Conformational-changes Induced by a Family of Dinuclear Bis(platinum) Complexes Nucl. Acids Res. 1992, 20, 1697.
47. Roberts, J. R.; Houten, B. V.; Qu, Y.; Farrell, N. O. Interaction of Novel Bis(platinum) Complexes with DNA. Nucl. Acids Res. 1989, 17, 9719.
48. Bax, A.; Morris, G. A. An Improved Method for Heteronuclear Chemical-shift Correlation by 2-Dimensional NMR. J. Magn. Reson. 1981, 42, 501.
49. Sah, P. P. T.; Daniels, T. C. Thiosemicarbazide as a Reagent for the Identification of Aldehydes, Ketones and Quinones. Recl. Trav. Chim. Pays-Bas 1950, 69, 1545.
50. Walker, N.; Stuart, D. An Empirical Method for Correcting Diffractometer Data for Absorption Effects. Acta Crystallogr. 1983, A39, 158.
51. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, 1974; Vol. IV.
52. Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; García-Granda, S.; Gould, R. O.; Smith J. M. M.; Smykalla, C. The DIRDIF Program System; Technical Report of the Crystallography Laboratory, Tournooiveld 6525 ED, Nijmegen, The Netherlands, 1992.
53. Stewart, J. M.; Machin, P. A.; Dickinson, C. W.; Ammon, H. L.; Heck, H.; Flack, H. The X-RAY 76 System of Crystallographic Program; Computer Science Center, University of Maryland: College Park, Maryland, 1976.
54. Martínez-Ripoll M.; Cano, F. H. Programa PESOS; Institute Rocasolano, CSIC, Madrid, Spain, 1975.
55. Spek A. L. PLATON, An Integrated Tool for the Analysis of the Results of a Single-Crystal Structure Determination. Acta Crystallogr. 1990, A46, C34.
56. Sheldrick, G. M. Phase Annealing in SHELX-90 Direct Methods for Larger Structures. Acta Crystallogr. 1990, A46, 467.
57. Sheldrick, G. M. SHELX-96, Program for the refinement of crystal structure; University of Göttingen: Göttingen, Germany, 1996.