Synthesis, structure, DNA-binding properties and antioxidant activity of a nickel(II) complex with bis(N-allylbenzimidazol-2-ylmethyl)benzylamine

Journal of Photochemistry and Photobiology B: Biology

Volumn 107, Issue 1, 2012, Pages 65-72

  Wu, Huilu ^a   Yuan, Jingkun ^a   Bai, Ying ^a   Pan, Guolong ^a   Wang, Hua ^a   Shu, Xingbin ^a  

^a LANZHOU JIAOTONG UNIVERSITY   (China)

Author keywords

Antioxidant property; Benzimidazole; Crystal structure; DNA binding property; Nickel(II) complex

Indexed keywords

[NICKEL BIS(N ALLYLBENZIMIDAZOL 2 YLMETHYL)BENZYLAMINE]BISPICRATE; BENZYLAMINE DERIVATIVE; BIS(N ALLYLBENZIMIDAZOL 2 YLMETHYL)BENZYLAMINE; NICKEL COMPLEX; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; BINDING AFFINITY; DRUG DNA BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS;

ABSORPTION; ANTIOXIDANTS; BENZIMIDAZOLES; CHEMISTRY TECHNIQUES, SYNTHETIC; DNA; LIGANDS; NICKEL; ORGANOMETALLIC COMPOUNDS; SPECTRUM ANALYSIS; VISCOSITY;

EID: 84855906795     PISSN: 10111344     EISSN: 18732682     Source Type: Journal    
DOI: 10.1016/j.jphotobiol.2011.11.010     Document Type: Article

References (57)

1. J.B. Wright The chemistry of the benzimidazoles Chem. Rev. 48 1951 397 541
2. S.Y. Hong, K.W. Kwak, C.K. Ryu, S.J. Kang, and K.H. Chung Antiproliferative effects of 6-anilino-5-chloro-1H-benzo[d]imidazole-4,7-dione in vascular smooth muscle cells Bioorg. Med. Chem. 16 2008 644 649
3. J.Y. Xu, Y. Zeng, Q. Ran, Z. Wei, Y. Bi, Q.H. He, Q.J. Wang, S. Hu, J. Zhang, M.Y. Tang, W.Y. Hua, and X.M. Wu Synthesis and biological activity of 2-alkylbenzimidazoles bearing a N-phenylpyrrole moiety as novel angiotensin II AT1 receptor antagonists Bioorg. Med. Chem. Lett. 17 2007 2921 2926 (Pubitemid 46636234)
4. P.D. Patel, M.R. Patel, N. Kaushik-Basu, and T.T. Talele 3D QSAR and molecular docking studies of benzimidazole derivatives as hepatitis C virus NS5B polymerase Inhibitors J. Chem. Inf. Model. 48 2008 42 55 (Pubitemid 351271049)
5. K. Taniguchi, S. Shigenaga, T. Ogahara, T. Fujitsu, and M. Matsuo Synthesis and antiinflammatory and analgesic properties of 2-amino-1H- benzimidazole and 1,2-dihydro-2-iminocycloheptimidazole derivatives Chem. Pharm. Bull. 41 1993 301 309 (Pubitemid 23128192)
6. S. Estrada-Soto, R. Villalobos-Molina, F. Aguirre-Crespo, J. Vergara-Galicia, H. Oreno-DÍaz, M. Torres-Piedra, and G. Navarrete-Vázquez Relaxant activity of 2-(substituted phenyl)-1H-benzimidazoles on isolated rat aortic rings: design and synthesis of 5-nitro derivatives Life Sci. 79 2006 430 435 (Pubitemid 43870298)
7. Ö.Ö. Guven, T. Erdǒgan, H. Göker, and S. Yildiz Synthesis and antimicrobial activity of some novel phenyl and benzimidazole substituted benzyl ethers Bioorg. Med. Chem. Lett. 17 2007 2233 2236 (Pubitemid 46505260)
8. Z. Ates-Alagoz, S. Yildiz, and E. Buyukbingol Antimicrobial activities of some tetrahydronaphthalene-benzimidazole derivatives Chemotherapy 53 2007 110 113 (Pubitemid 46377217)
9. B.G. Mohamed, A.A. Abdel-Alim, and M.A. Hussein Synthesis of 1-acyl-2-alkylthio-1,2,4-triazolobenzimidazoles with antifungal, anti-inflammatory and analgesic effects Acta Pharm. 56 2006 31 48 (Pubitemid 43253971)
10. H.Y. Liu, H. Wu, J. Yang, Y.Y. Liu, B. Liu, Y.Y. Liu, and J.F. Ma pH-Dependent assembly of 1D to 3D octamolybdate hybrid materials based on a new flexible bis-[(pyridyl)-benzimidazole] ligand Cryst. Growth Des. 11 2011 2920 2927
11. M.S. Diaz-Cruz, J. Mendieta, A. Monjonelli, R. Tauler, and M. Esteban Specific interactions of bovine and human β-casomorphin-7 with Cu(II) ions J. Inorg. Biochem. 70 1998 91 95
12. K.E. Erkkila, D.T. Odom, and J.K. Barton Recognition and reaction of metallointercalators with DNA Chem. Rev. 99 1999 2777 2796
13. L.N. Ji, X.H. Zou, and J.G. Lin Shape- and enantioselective interaction of Ru(II)/Co(III) polypyridyl complexes with DNA Coord. Chem. Rev. 216-217 2001 513 536
14. B.M. Zeglis, V.C. Pierre, and J.K. Barton Metallo-intercalators and metallo-insertors Chem. Commun. 44 2007 4565 4579 (Pubitemid 350077044)
15. J.A. Cowan Metal activation of enzymes in nucleic acid biochemistry Chem. Rev. 98 1998 1067 1088
16. C.L. Liu, M. Wang, T.L. Zhang, and H.Z. Sun DNA hydrolysis promoted by di- and multi-nuclear metal complexes Coord. Chem. Rev. 248 2004 147 168
17. H.L. Wu, X.C. Huang, J.K. Yuan, F. Kou, F. Jia, B. Liu, and K.T. Wang A V-shaped ligand 2,6-bis(2-benzimidazolyl)pyridine and its picrate Mn(II) complex: Synthesis, crystal structure and DNA-binding properties Eur. J. Med. Chem. 45 2010 5324 5330
18. H.L. Wu, K. Li, T. Sun, F. Kou, F. Jia, J.K. Yuan, B. Liu, and B.L. Qi Synthesis, structure, and DNA-binding properties of manganese(II) and zinc(II) complexes with tris(N-methylbenzimidazol-2-ylmethyl)amine ligand Transition. Met. Chem. 36 2011 21 28
19. H.L. Wu, R.R. Yun, K.T. Wang, K. Li, X.C. Huang, and T. Sun Synthesis, crystal structure, and spectrum properties of cobalt(II) complexes based on tridentate 1, 3-bis(benzimidazol-2-yl)-2-oxopropane ligand and derivative Z. Anorg. Allg. Chem. 636 2010 629 633
20. H.L. Wu, X.C. Huang, J.K. Yuan, K. Li, J. Ding, R.R. Yun, W.K. Dong, and X.Y. Fan A five-coordinate copper(II) perchlorate complex with tris(N-methylbenzimidazol-2-ylmethyl)amine and salicylate J. Coord. Chem. 62 2009 3446 3453
21. H.L. Wu, J.K. Yuan, Y. Bai, F. Kou, F. Jia, and B. Liu Synthesis crystal structure and spectra properties of the cadmium (II) complex with bis(N-allylbenzimidazol-2-ylmethyl)benzylamine Bioinorg. Chem. Appl. 2011 2011 705989
22. S. Satyanarayana, J.C. Dabrowiak, and J.B. Chaires Tris(phenanthroline) ruthenium(II) enantiomer interactions with DNA: mode and specificity of binding Biochemistry 32 1993 2573 2584 (Pubitemid 23090644)
23. M.E. Reichmann, S.A. Rice, C.A. Thomas, and P. Doty A further examination of the molecular weight and size of desoxypentose nucleic acid J. Am. Chem. Soc. 76 1954 3047 3051
24. K. Takahashi, Y. Nishida, and S. Kida Crystal structure of copper(II) complex with N, N-bis(2-benzimidazolylmethyl)benzylamine Polyhedron 3 1984 113 116
25. Bruker Smart saint and sadabs 2000 Bruker Axs, Inc. Madison, WI
26. G.M. Sheldrick, SHELXTL, Siemens Analytical X-ray Instruments, Inc., Madison, Wisconsin, USA, 1996.
27. A.M. Pyle, J.P. Rehmann, R. Meshoyrer, C.V. Kumar, N.J. Turro, and J.K. Barton Mixed-ligand complexes of ruthenium(II): factors governing binding to DNA J. Am. Chem. Soc. 111 1989 3051 3058
28. A. Wolf, G.H. Shimer, and T. Meehan Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA Biochemistry 26 1987 6392 6396 (Pubitemid 17155512)
29. B.C. Baguley, and M.L. Bret Quenching of DNA-ethidium fluorescence by amsacrine and other antitumor agents: a possible electron-transfer effect Biochemistry 23 1984 937 943 (Pubitemid 14168073)
30. J.R. Lakowicz, and G. Webber Quenching of fluorescence by oxygen Probe for structural fluctuations in macromolecules Biochemistry 12 1973 4161 4170
31. C.P. Tan, J. Liu, L.M. Chen, S. Shi, and L.N. Ji Synthesis, structural characteristics, DNA binding properties and cytotoxicity studies of a series of Ru(III) complexes J. Inorg. Biochem. 102 2008 1644 1653
32. C.C. Winterbourn Hydroxyl radical production in body fluids. Roles of metal ions, ascorbate and superoxide Biochem. J. 198 1981 125 131 (Pubitemid 11063361)
33. C.C. Winterbourn Comparison of superoxide with other reducing agents in the biological production of hydroxyl radicals Biochem. J. 182 1979 625 628
34. Z.Y. Guo, R.E. Xing, S. Liu, H.H. Yu, P.B. Wang, C.P. Li, and P.C. Li The synthesis and antioxidant activity of the Schiff bases of chitosan and carboxymethyl chitosan Bioorg. Med. Chem. Lett. 15 2005 4600 4603 (Pubitemid 41253902)
35. W.J. Geary The use of conductivity measurements in organic solvents for the characterization of coordination compounds Coord. Chem. Rev. 7 1971 81 122
36. 3-symmetric tripodal benzimidazole ligands Inorg. Chem. 39 2000 4843 4849
37. T.J. Lane, I. Nakagawa, J.L. Walter, and A.J. Kandathil Infrared investigationof certain imidazole derivatives and their metal chelates Inorg. Chem. 1 1962 267 276
38. E.K. Chec, M. Kubiak, T. Glowiak, and J.J. Ziolkowski Synthesis, crystal and molecular structure of the novel complex [dinitrato{N, N-bis(1- methylbenzimidazol-2-ylmethyl)methylamine}]cobalt(II) Transition. Met. Chem. 23 1998 641 644
39. M. McKee, M. Zvagulis, and C.A. Reed Further insight into magnetostructural correlations in binuclear copper(II) species related to methemocyanin: x-ray crystal structure of 1, 2-.mu.-nitrito complex Inorg. Chem. 24 1985 2914 2919
40. K. Nakamoto Infrared and Raman Spectra of Inorganic and Coordination Compounds 1978 Wiley New York 305
41. H.L. Wu, K.T. Wang, R.R. Yun, and X.C. Huang Studies on copper(II), cobalt (II) and nickel (II) picrate complexes with the ligand 1,3-bis(2-benzimidazyl)-2-thiapropane Synth. React. Inorg., Met.-Org., Nano-Met. Chem. 39 2009 629 632
42. L.E. Xiao, M. Zhang, and W.H. Sun Synthesis, characterization and ethylene oligomerization and polymerization of 2-(1H-2-benzimidazolyl)-6-(1- (arylimino)ethyl)pyridylchromium chlorides Polyhedron 29 2010 142 147
43. D. Kang, J. Seo, S.Y. Lee, and J.Y. Lee First dicadmium(II) complex of tripodal amide ligand with one edge-sharing monocapped octahedral geometry Inorg. Chem. Commun. 10 2007 1425 1428
44. N. Yoshikawa, S. Yamabe, N. Kanehisa, Y. Kai, H. Takashima, and K. Tsukahara Synthesis, characterization, and DFT investigation of Ir(III) tolylterpyridine complexes Eur. J. Inorg. Chem. 13 2007 1911 1919
45. J.P. Collin, I.M. Dixon, J.P. Sauvage, J.A.G. Williams, F. Barigelletti, and L. Flamigni Synthesis and photophysical properties of Iridium(III) bisterpyridine and its homologues: a family of complexes with a long-lived excited state J. Am. Chem. Soc. 121 1999 5009 5016
46. J. Liu, T.X. Zhang, and L.N. Ji DNA-binding and cleavage studies of macrocyclic copper(II) complexes J. Inorg. Biochem. 91 2002 269 276 (Pubitemid 34727777)
47. S. Nafisi, A.A. Saboury, N. Keramat, J.F. Neault, and H.A. Tajmir-Riahi Stability and structural features of DNA intercalation with ethidium bromide, acridine orange and methylene blue J. Mol. Struct. 827 2007 35 43 (Pubitemid 46161521)
48. H.L. Wu, J.K. Yuan, Y. Bai, F. Jia, B. Liu, F. Kou, and J. Kong Synthesis, structure, DNA-binding properties, and antioxidant activity of copper(II) and cobalt(II) complexes with bis(N-allylbenzimidazol-2-ylmethyl) benzylamine Transition. Met. Chem. 36 2011 819 827
49. S. Yellappa, J. Seetharamappa, L.M. Rogers, R. Chitta, R.P. Singhal, and F. D'Souza Binding, electrochemical activation, and cleavage of DNA by cobalt(II)tetrakis-N-methylpyridyl porphyrin and its b-pyrrole brominated derivative Bioconjug. Chem. 17 2006 1418 1425 (Pubitemid 44851485)
50. M. Shakir, M. Azam, M.-F. Ullah, and S.-M. Hadi Synthesis, spectroscopic and electrochemical studies of N, N-bis[(E)-2-thienylmethylidene]-1,8- naphthalene -diamine and its Cu(II) complex: DNA cleavage and generation of superoxide anion J. Photoch. Photobio. B 104 2011 449 456
51. J.B. LePecq, and C. Paoletti A fluorescent complex between ethidium bromide and nucleic acids: Physical-Chemical characterization J. Mol. Biol. 27 1967 87 106
52. Q.H. Zhou, and P. Yang Synthesis, crystal structure and DNA binding studies of Zn(II) complex with 1,3-bis(benzimidazol-2-yl)-2-oxapropane Acta Chim. Sinica 64 2006 793 798 (Pubitemid 44663021)
53. S. Satyanarayana, J.C. Dabroniak, and J.B. Chaires Neither.DELTA.- nor.LAMBDA.-tris(phenanthroline)ruthenium(II) binds to DNA by classical intercalation Biochemistry 31 1992 9319 9324
54. S.B. Bukhari, S. Memon, M. Mahroof-Tahir, and M.I. Bhanger Synthesis, characterization and antioxidant activity copper-quercetin complex Spectrochim. Acta A. Mol. Biomol. Spectrosc. 71 2009 1901 1906
55. F.V. Botelho, J.I. Alvarez-Leite, V.S. Lemos, A.M.C. Pimenta, H.D.R. Calado, T. Matencio, C.T. Miranda, and E.C. Pereira-Maia Physicochemical study of floranol, its copper(II) and iron(III) complexes, and their inhibitory effect on LDL oxidation J. Inorg. Biochem. 101 2007 935 943 (Pubitemid 46770854)
56. Q. Wang, Z.Y. Yang, G.F. Qi, and D.D. Qin Synthesis, crystal structure, antioxidant activities and DNA-binding studies of the Ln(III) complexes with 7-methoxychromone-3-carbaldehyde-(4′-hydroxy) benzoyl hydrazone Eur. J. Med. Chem. 44 2009 2425 2433
57. T.R. Li, Z.Y. Yang, B.D. Wang, and D.D. Qin Synthesis, characterization, antioxidant activity and DNA-binding studies of two rare earth(III) complexes with naringenin-2-hydroxy benzoyl hydrazone ligand Eur. J. Med. Chem. 43 2008 1688 1695