Cinnamaldehyde and cuminaldehyde thiosemicarbazones and their copper(II) and nickel(II) complexes: A study to understand their biological activity

Journal of Inorganic Biochemistry

Volumn 140, Issue , 2014, Pages 111-125

  Bisceglie, Franco ^a,b   Pinelli, Silvana ^a,b   Alinovi, Rossella ^a,b   Goldoni, Matteo ^a   Mutti, Antonio ^a   Camerini, Alessandro ^a   Piola, Lorenzo ^a   Tarasconi, Pieralberto ^a,b   Pelosi, Giorgio ^a,b  

^a UNIVERSITY OF PARMA   (Italy)

^b CIRCMSB Consorzio Interuniversitario di Ric in Chimica Dei Metalli Nei Sistemi Biologici Parma Local Unit   (Italy)

Author keywords

Caspase; Copper; DNA; Nickel; Thiosemicarbazone; Topoisomerase IIa

Indexed keywords

ANTILEUKEMIC AGENT; CASPASE 3; CASPASE 8; CASPASE 9; CINNAMALDEHYDE; COPPER COMPLEX; CUMINALDEHYDE; DNA TOPOISOMERASE (ATP HYDROLYSING); DNA TOPOISOMERASE IIA INHIBITOR; GYRASE INHIBITOR; NICKEL COMPLEX; THIOSEMICARBAZONE DERIVATIVE; TRANS CINNAMALDEHYDE THIOSEMICARBAZONE; TRANS CUMINALDEHYDE THIOSEMICARBAZONE; UNCLASSIFIED DRUG; ACROLEIN; BENZALDEHYDE DERIVATIVE; COPPER; NICKEL; CUPRIC ION; DNA; DNA TOPOISOMERASE; LIGAND; METAL COMPLEX; REACTIVE OXYGEN METABOLITE;

APOPTOSIS; ARTICLE; ATOMIC ABSORPTION SPECTROMETRY; BIOLOGICAL ACTIVITY; CELL PROLIFERATION; CONFORMATIONAL TRANSITION; DRUG CYTOTOXICITY; FIBROBLAST; G2 PHASE CELL CYCLE CHECKPOINT; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; NORMAL HUMAN; U937 CELL LINE; ULTRAVIOLET SPECTROSCOPY; ANALOGS AND DERIVATIVES; CHEMISTRY; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ANTINEOPLASTIC ACTIVITY; ATOMIC ABSORPTION; CELL CYCLE; CONTROLLED STUDY; CYTOPLASM; DRUG SYNTHESIS; HISTIOCYTIC LYMPHOMA; IC50; M PHASE CELL CYCLE CHECKPOINT; MOLECULE;

ACROLEIN; BENZALDEHYDES; COPPER; MAGNETIC RESONANCE SPECTROSCOPY; NICKEL; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; THIOSEMICARBAZONES;

EID: 84906967108     PISSN: 01620134     EISSN: 18733344     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2014.07.014     Document Type: Article

References (50)

1. G.M. Cragg, and D.J. Newman Biochim. Biophys. Acta 1830 2013 3670 3695
2. B.M. Kwon, S.H. Lee, S.U. Choi, S.H. Park, C.O. Lee, Y.K. Cho, N.D. Sung, and S.H. Bok Arch. Pharm. Res. 21 1998 147 152
3. C.M. Cabello, W.B. Bair, S.D. Lamore, S. Ley, A.S. Bause, S. Azimian, and G.T. Wondrak Free Radic. Biol. Med. 46 2009 220 231
4. T. Nitoda, M.D. Fan, and I. Kubo Phytother. Res. 22 2008 809 813
5. N.S. Moorthy, N.M. Cerqueira, M.J. Ramos, and P.A. Fernandes Recent Pat. Anticancer Drug Discov. 8 2013 168 182
6. H. Beraldo, and D. Gambino Mini-Rev. Med. Chem. 4 2004 31 39
7. B.M. Paterson, and P.S. Donnelly Chem. Soc. Rev. 40 2011 3005 3018
8. G. Pelosi Open Crystallogr. J. 3 2010 16 28
9. Y. Yu, E. Gutierrez, Z. Kovacevic, F. Saletta, P. Obeidy, Y.S. Rahmanto, and D.R. Richardson Curr. Med. Chem. 19 2012 2689 2702
10. F. Bisceglie, M. Baldini, M. Belicchi Ferrari, E. Buluggiu, M. Careri, G. Pelosi, S. Pinelli, and P. Tarasconi Eur. J. Med. Chem. 42 2007 627 634
11. M.B. Ferrari, F. Bisceglie, G. Pelosi, M. Sassi, P. Tarasconi, M. Cornia, S. Capacchi, R. Albertini, and S. Pinelli J. Inorg. Biochem. 90 2002 113 126
12. D. Kovala-Demertzi, A. Papageorgiou, L. Papathanasis, A. Alexandratos, P. Dalezis, J.R. Miller, and M.A. Demertzis Eur. J. Med. Chem. 44 2009 1296 1302
13. G.L. Parrilha, J.G. da Silva, L.F. Gouveia, A.K. Gasparoto, R.P. Dias, W.R. Rocha, D.A. Santos, N.L. Speziali, and H. Beraldo Eur. J. Med. Chem. 46 2011 1473 1482
14. M. Belicchi-Ferrari, F. Bisceglie, A. Buschini, S. Franzoni, G. Pelosi, S. Pinelli, P. Tarasconi, and M. Tavone J. Inorg. Biochem. 104 2010 199 206
15. F. Bisceglie, S. Pinelli, R. Alinovi, P. Tarasconi, A. Buschini, F. Mussi, A. Mutti, and G. Pelosi J. Inorg. Biochem. 116 2012 195 203
16. A. Buschini, S. Pinelli, C. Pellacani, F. Giordani, M.B. Ferrari, F. Bisceglie, M. Giannetto, G. Pelosi, and P. Tarasconi J. Inorg. Biochem. 103 2009 666 677
17. P. Tarasconi, S. Capacchi, G. Pelosi, M. Cornia, R. Albertini, A. Bonati, P.P. Dall'Aglio, P. Lunghi, and S. Pinelli Bioorg. Med. Chem. 8 2000 157 162
18. Q.X. Chen, K.K. Song, Q. Wang, and H. Huang J. Enzym. Inhib. Med. Chem. 18 2003 491 496
19. Y.J. Zhu, K.K. Song, Z.C. Li, Z.Z. Pan, Y.J. Guo, J.J. Zhou, Q. Wang, B. Liu, and Q.X. Chen J. Agric. Food Chem. 57 2009 5518 5523
20. P.M. Krishna, and K.H. Reddy Inorg. Chim. Acta 362 2009 4185 4190
21. P.M. Krishna, K.H. Reddy, J.P. Pandey, and D. Siddavattam Transit. Met. Chem. 33 2008 661 668
22. A.G. Quiroga, J.M. Perez, I. Lopez-Solera, J.R. Masaguer, A. Luque, P. Roman, A. Edwards, C. Alonso, and C. Navarro-Ranninger J. Med. Chem. 41 1998 1399 1408
23. Y.M. Chumakov, N.M. Samus, G. Bocelli, K.Y. Suponitskii, V.I. Tsapkov, and A.P. Gulya Russ. J. Coord. Chem. 32 2006 14 20
24. P.P.T. Sah, and T.C. Daniels Recl. Trav. Chim. Pays-Bas 69 1950 1545 1556
25. G. Sheldrick SADABS. Program for Empirical Absorption Correction of Area Detector 1996 University of Göttingen Göttingen
26. A. Altomare, M.C. Burla, M. Camalli, G.L. Cascarano, C. Giacovazzo, A. Guagliardi, A.G.G. Moliterni, G. Polidori, and R. Spagna J. Appl. Crystallogr. 32 1999 115 119
27. G. Sheldrick SHELXL 97. A Program for Structure Refinement 1997 University of Göttingen Göttingen
28. L.J. Farrugia J. Appl. Crystallogr. 32 1999 837 838
29. M. Nardelli J. Appl. Crystallogr. 28 1995 659
30. A.L. Spek PLATON, A Multipurpose Crystallographic Tool 1998 University of Utrecht Utrecht
31. C.F. Macrae, I.J. Bruno, J.A. Chisholm, P.R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek, and P.A. Wood J. Appl. Crystallogr. 41 2008 466 470
32. M.E. Reichmann, S.A. Rice, C.A. Thomas, and P. Doty J. Am. Chem. Soc. 76 1954 3047 3053
33. S. Tagliaferri, A. Caglieri, M. Goldoni, S. Pinelli, R. Alinnovi, D. Poli, C. Pellacani, G. Giordano, A. Mutti, and L.G. Costa Toxicol. in Vitro 24 2010 116 122
34. E. Erba, D. Bergamaschi, L. Bassano, G. Damia, S. Ronzoni, G.T. Faircloth, and M. D'Incalci Eur. J. Cancer 37 2001 97 105
35. VCCLAB, Virtual Computational Chemistry Laboratory http://www.vcclab.org 2005
36. I.V. Tetko, J. Gasteiger, R. Todeschini, A. Mauri, D. Livingstone, P. Ertl, V.A. Palyulin, E.V. Radchenko, N.S. Zefirov, A.S. Makarenko, V.Y. Tanchuk, and V.V. Prokopenko J. Comput. Aided Mol. Des. 19 2005 453 463
37. M.B. Ferrari, S. Capacchi, G. Reffo, G. Pelosi, P. Tarasconi, R. Albertini, S. Pinelli, and P. Lunghi J. Inorg. Biochem. 81 2000 89 97
38. A. Diaz, I. Garcia, R. Cao, H. Beraldo, M.M. Salberg, D.X. West, L. Gonzalez, and E. Ochoa Polyhedron 16 1997 3549 3555
39. M.J.M. Campbell Coord. Chem. Rev. 15 1975 279 319
40. V.I. Ivanov, L.E. Minchenkova, A.K. Schyolkina, and A.I. Poletayev Biopolymers 12 1973 89 110
41. R.V. Person, K. Monde, H.U. Humpf, N. Berova, and K. Nakanishi Chirality 7 1995 128 135
42. C.A. Sprecher, W.A. Baase, and W.C. Johnson Jr. Biopolymers 18 1979 1009 1019
43. B. Norden, and F. Tjerneld Biopolymers 21 1982 1713 1734
44. J. Kypr, I. Kejnovska, D. Renciuk, and M. Vorlickova Nucleic Acids Res. 37 2009 1713 1725
45. A. Silvestri, G. Barone, G. Ruisi, D. Anselmo, S. Riela, and V.T. Liveri J. Inorg. Biochem. 101 2007 841 848
46. N.J. Zuidam, Y. Barenholz, and A. Minsky FEBS Lett. 457 1999 419 422
47. J.C. Sitko, E.M. Mateescu, and H.G. Hansma Biophys. J. 84 2003 419 431
48. S. Mahadevan, and M. Palaniandavar Chem. Commun. 1996 2547 2548
49. A. Wolfe, G.H. Shimer Jr., and T. Meehan Biochemistry 26 1987 6392 6396
50. F.H. Allen, and O. Kennard Chem. Des. Autom. News 1993 31 37