Synthesis, crystal structure and pharmacological evaluation of two new Cu(II) complexes of 2-oxo-1,2-dihydroquinoline-3-carbaldehyde (benzoyl) hydrazone: A comparative investigation

European Journal of Medicinal Chemistry

Volumn 47, Issue 1, 2012, Pages 73-85

  Senthil Raja, Duraisamy ^a   Bhuvanesh, Nattamai S P ^b   Natarajan, Karuppannan ^a  

^a BHARATHIAR UNIVERSITY   (India)

^b TEXAS A AND M UNIVERSITY   (United States)

Author keywords

Antioxidant; Copper(II) complexes; Cytotoxicity; DNA binding; Protein binding

Indexed keywords

2 OXO 1,2 DIHYDROQUINOLINE 3 CARBALDEHYDE(BENZOYL)HYDRAZONE; ANTINEOPLASTIC AGENT; ANTIOXIDANT; CHLORIDE; CISPLATIN; COPPER COMPLEX; HYDRAZONE DERIVATIVE; NITRATE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; BINDING COMPETITION; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG CYTOTOXICITY; DRUG DNA BINDING; DRUG PROTEIN BINDING; DRUG SCREENING; DRUG SYNTHESIS; FEMALE; FLUORESCENCE; HUMAN; HUMAN CELL; IC 50; MOUSE; NONHUMAN; POLYMERIZATION; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; CATTLE; CELL LINE, TUMOR; CHLORIDES; COPPER; CRYSTALLOGRAPHY, X-RAY; DNA; FREE RADICAL SCAVENGERS; HEXANOIC ACIDS; HUMANS; HYDRAZINES; HYDRAZONES; MICE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NIH 3T3 CELLS; NITRATES; ORGANOMETALLIC COMPOUNDS; SERUM ALBUMIN, BOVINE;

EID: 84855820822     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.10.024     Document Type: Article

References (55)

1. R.A. Sanchez-Delgado, M. Navarro, H. Perez, and J.A. Urbina J. Med. Chem. 39 1996 1095 1099
2. J.A. Drewry, and P.T. Gunning Coord. Chem. Rev. 255 2011 459 472
3. V. Milacic, and Q.P. Dou Coord. Chem. Rev. 253 2009 1649 1660
4. R. Malhotra, J.P. Singh, M. Dudeja, and K.S. Dhindsa J. Inorg. Biochem. 46 1992 119 127
5. D.R. Richardson Antimicrob. Agents Chemother. 41 1997 2061 2063
6. F. Lebon, M. Ledecq, Z. Benatallah, S. Sicsic, R. Lapouyade, O. Kahan, A. Garcon, M. Reboud-Ravaux, and F. Durant J. Chem. Soc. Perkin Trans. 2 1999 795 800
7. N. Bharti, M.R. Maurya, F. Naqvi, A. Bhattacharya, S. Bhattacharya, and A. Azam Eur. J. Med. Chem. 35 2000 481 486
8. P. Krishnamoorthy, P. Sathyadevi, A.H. Cowley, R.R. Butorac, and N. Dharmaraj Eur. J. Med. Chem. 46 2011 3376 3387
9. D.S. Raja, N.S.P. Bhuvanesh, K. Natarajan, J. Biol. Inorg. Chem., doi:10.1007/s00775-011-0844-1.
10. Y.-C. Liu, and Z.-Y. Yang Eur. J. Med. Chem. 44 2009 5080 5089
11. Y.-C. Liu, and Z.-Y. Yang J. Inorg. Biochem. 103 2009 1014 1022
12. S. Banerjee, S. Mondal, W. Chakraborty, S. Sen, R. Gachhui, R.J. Butcher, A.M.Z. Slawin, C. Mandal, and S. Mitra Polyhedron 28 2009 2785 2793
13. C.D. Fan, H. Su, J. Zhao, B.X. Zhao, S.L. Zhang, and J.Y. Miao Eur. J. Med. Chem. 45 2010 1438 1446
14. Y. Li, and Z.-Y. Yang Inorg. Chim. Acta 362 2009 4823 4831
15. Z.-C. Liu, B.-D. Wang, Z.-Y. Yang, Y. Li, D.D. Qin, and T.-R. Li Eur. J. Med. Chem. 44 2009 4477 4484
16. D.S. Raja, G. Paramaguru, N.S.P. Bhuvanesh, J.H. Reibenspies, R. Renganathan, and K. Natarajan Dalton Trans. 40 2011 4548 4559
17. Z.-C. Liu, B.-D. Wang, B. Li, Q. Wang, Z.-Y. Yang, T.-R. Li, and Y. Li Eur. J. Med. Chem. 45 2010 5353 5361
18. A.W. Addison, T.N. Rao, J. Reedijk, J. van Rijn, and G.C. Veschoor J. Chem. Soc. Dalton Trans. 1984 1349 1356
19. E.C. Miller, and J.A. Miller Cancer 47 1981 1055 1064
20. A.E. Friedman, C.V. Kumar, N.J. Turro, and J.K. Barton Nucleic Acids Res. 19 1991 2595 2602
21. A.M. Pyle, T. Morri, and J.K. Barton J. Am. Chem. Soc. 112 1990 9432 9434
22. J.K. Barton, J.M. Goldberg, C.V. Kumar, and N.J. Turro J. Am. Chem. Soc. 108 1986 2081 2088
23. P.H. Proctor, and E.S. Reynolds Physiol. Chem. Phys. Med. NMR. 16 1984 175 195
24. K.E. Erkkila, D.T. Odom, and J.K. Barton Chem. Rev. 99 1999 2777 2795
25. B.N. Trawick, A.T. Danihe, and J.K. Bashkin Chem. Rev. 98 1998 939 960
26. J.K. Barton, A.T. Danishefsky, and J.M. Goldberg J. Am. Chem. Soc. 106 1984 2172 2176
27. F.Q. Liu, Q.X. Wang, K. Jiao, F.F. Jian, G.Y. Liu, and R.X. Li Inorg. Chim. Acta 359 2006 1524 1530
28. D. Lawrence, V.G. Vaidyanathan, and B.U. Nair J. Inorg. Biochem. 100 2006 1244 1251
29. D.S. Raja, N.S.P. Bhuvanesh, and K. Natarajan Eur. J. Med. Chem. 46 2011 4584 4594
30. M. Eriksson, M. Leijon, C. Hiort, B. Norden, and A. Graeslund Biochemistry 33 1994 5031 5040
31. A. Wolf, G.H. Shimer, and T. Meehan Biochemistry 26 1987 6392 6396
32. G. Zhao, H. Lin, S. Zhu, H. Sun, and Y. Chen J. Inorg. Biochem. 70 1998 219 226
33. M. Howe-Grant, K.C. Wu, W.R. Bauer, and S.J. Lippard Biochemistry 15 1976 4339 4446
34. F.J. Meyer-Almes, and D. Porschke Biochemistry 32 1993 4246 4253
35. G.M. Howe, K.C. Wu, and W.R. Bauer Biochemistry 19 1976 339 347
36. Y.B. Zeng, N. Yang, W.S. Liu, and N. Tang J. Inorg. Biochem. 97 2003 258 264
37. B.D. Wang, Z.-Y. Yang, Q. Wang, T.K. Cai, and P. Crewdson Bioorg. Med. Chem. 14 2006 1880 1888
38. B.P. Kamat, and J. Seetharamappa J. Pharm. Biomed. Anal. 35 2008 655 664
39. X.Z. Feng, Z. Yang, L.J. Wang, and C. Bai Talanta 47 1998 1223 1229
40. G.Z. Chen, X.Z. Huang, Z.Z. Zheng, J.G. Xu, and Z.B. Wang Methods of Fluorescence Analysis second ed. 1990 Science Press Beijing
41. J.N. Miller Proc. Anal. Div. Chem. Soc. 16 1979 203 208
42. J.H. Tang, F. Luan, and X.G. Chen Bioorg. Med. Chem. 149 2006 3210 3217
43. M. Sankaran, C. Kumarasamy, U. Chokkalingam, and P.S. Mohan Bioorg. Med. Chem. Lett. 20 2010 7147 7151
44. M.G. Malakyan, S.A. Badzhinyan, L.A. Vardevanyan, D.S. Grigoryan, D.E. Egiazaryan, A.A. Avetisyan, I.L. Aleksanyan, L.P. Ambartsumyan, and K.S. Sargsyan Pharm. Chem. J. 43 2009 8 11
45. A. Ahmad, S.F. Asad, S. Singh, and S.M. Hadi Cancer Lett. 154 2000 29 37
46. A.S. Azmi, S.H. Bhat, and S.M. Hadi FEBS Lett. 579 2005 3131 3135
47. S.H. Bhat, A.S. Azmi, and S.M. Hadi Toxicol. Appl. Pharmacol. 218 2007 249 255
48. M.K. Singh, A. Chandra, B. Singh, and R.M. Singh Tetrahedron Lett. 48 2007 5987 5990
49. APEX2 "Program for Data Collection on Area Detectors" BRUKER AXS Inc. 5465 East Cheryl Parkway, Madison, WI 53711-5373 USA.
50. G.M. Sheldrick SADABS (Version 2008/1): Program for Absorption Correction for Data from Area Detector Frames 2008 University of Gottingen
51. M.S. Blois Nature 29 1958 1199 1200
52. T. Nash Biochem. J. 55 1953 416 421
53. L.C. Green, D.A. Wagner, J. Glogowski, P.L. Skipper, J.S. Wishnok, and S.R. Tannenbaum Anal. Biochem. 126 1982 131 138
54. C. Beauchamp, and I. Fridovich Anal. Biochem. 44 1971 276 287
55. M. Blagosklonny, and W.S. EI-diery Int. J. Cancer 67 1996 386 392