Share This Article:

Photocleavage Properties and DNA-Binding Studies of Oxovanadium Complexes Incorporating 2-(2-Hydroxybenzylideneamino) Isoindoline-1,3-Dione and Fluoro-Phenanthroline Derivatives

Abstract Full-Text HTML XML Download Download as PDF (Size:3249KB) PP. 51-63
DOI: 10.4236/ojic.2014.44007    4,342 Downloads   5,295 Views  

ABSTRACT

Three mononuclear oxovanadium complexes [VO(Hbid)(CF3PIP)] (1) (Hbid=(E)-2-(2-hydroxybenzylideneamino) isoindoline-1,3-dione, CF3PIP=2-(2-trifluoromethyl phenyl)imidazole[4,5-f][1,10] phenanthroline), [VO(Hbid)(m-CF3PIP)]; (2) (m-CF3PIP=2-(3-trifluoromethyl phenyl)imidazole [4, 5-f][1,10]phenanthroline) and [VO(Hbid)(p-CF3PIP)]; (3) (p-CF3PIP=2-(4-trifluoromethyl phenyl) imidazole[4,5-f][1,10]phenanthroline) have been synthesized and characterized by elemental analysis, IR, molar conductance, ES-MS and 1H NMR. The DNA-binding properties of these complexes were studied by using UV-Vis absorption titration, fluorescence spectra, viscosity measurements and thermal denaturation studies. The results show that 1, 2 and 3 interact with calf thymus DNA (CT-DNA) by intercalation modes and the magnitude of their intrinsic binding constants (Kb values) follows the order: 2 < 1 < 3. Furthermore, their photocleavage properties with pBR322 plasmid DNA were investigated by agarose gel electrophoresis experiments. The DNA cleavage capacity of complex 3 is also stronger than that of 1 and 2.

Conflicts of Interest

The authors declare no conflicts of interest.

Cite this paper

Ying, P. , Zeng, P. , Lu, J. , Yang, N. and Chen, H. (2014) Photocleavage Properties and DNA-Binding Studies of Oxovanadium Complexes Incorporating 2-(2-Hydroxybenzylideneamino) Isoindoline-1,3-Dione and Fluoro-Phenanthroline Derivatives. Open Journal of Inorganic Chemistry, 4, 51-63. doi: 10.4236/ojic.2014.44007.

References

[1] Chen, Z.F., Liu, Y.C., Huang, K.B. and Liang, H. (2013) Alkaloid-Metal Based Anticancer Agents. Current Topics in Medicinal Chemistry (Sharjah, United Arab Emirates), 13, 2104-2115.
http://dx.doi.org/10.2174/15680266113139990146
[2] Rafique, S., Idrees, M., Nasim, A., Akbar, H. and Athar, A. (2010) Transition Metal Complexes as Potential Therapeutic Agents. Biotechnology and Molecular Biology Reviews, 5, 38-45.
[3] Gu, J. and Codd, R. (2012) Copper(II)-Based Metal Affinity Chromatography for the Isolation of the Anticancer Agent Bleomycin from Streptomyces verticillus Culture. Journal of Inorganic Biochemistry, 115, 198-203.
http://dx.doi.org/10.1016/j.jinorgbio.2012.01.015
[4] Leon, I. E., Porro, V., Di, V.A.L., Naso, L.G., Williams, P.A.M., Bollati-Fogolin, M. and Etcheverry, S.B. (2014) Antiproliferative and Apoptosis-Inducing Activity of an Oxidovanadium(IV) Complex with the Flavonoid Silibinin against Osteosarcoma Cells. Journal of Biological Inorganic Chemistry, 19, 59-74.
http://dx.doi.org/10.1007/s00775-013-1061-x
[5] Anupama, B. and Gyana Kumari, C. (2011) Synthesis, Characterization, DNA Binding and Antimicrobial Activity of 4-Amino Antipyrine Schiff Base Metal Complexes. Research Journal of Pharmaceutical, Biological and Chemical Sciences, 2, 140-159.
[6] Walmsley, R.S., Litwinski, C., Antunes, E., Hlangothi, P., Hosten, E., McCleland, C., Nyokong, T., Torto, N. and Tshentu, Z.R. (2013) Oxovanadium(IV)-Containing Poly(Styrene-co-4'-Ethenyl-2-Hydroxyphenylimidazole) Electrospun Nanofibers for the Catalytic Oxidation of Thioanisole. Journal of Molecular Catalysis A: Chemical, 379, 94-102.
http://dx.doi.org/10.1016/j.molcata.2013.07.018
[7] Parihar, S., Jadeja, R.N. and Gupta, V.K. (2014) Novel Oxovanadium(IV) Complexes with 4-Acyl Pyrazolone Ligands: Synthesis, Crystal Structure and catalytic Activity towards the Oxidation of Benzylic Alcohols. RSC Advances, 4, 10295-10302. http://dx.doi.org/10.1039/c3ra46896h
[8] Sanna, D., Micera, G. and Garribba, E. (2013) Interaction of Insulin-Enhancing Vanadium Compounds with Human Serum holo-Transferrin. Inorganic Chemistry, 52, 11975-11985.
http://dx.doi.org/10.1021/ic401716x
[9] Yamaguchi, T., Watanabe, S., Matsumura, Y., Tokuoka, Y. and Yokoyama, A. (2012) Synthesis of Oxovanadium Complexes and Their Apoptosis-Inducing Activity in Leukemia Cells. Chemical & Pharmaceutical Bulletin, 60, 508-512. http://dx.doi.org/10.1248/cpb.60.508
[10] Yamaguchi, T., Watanabe, S., Matsumura, Y., Tokuoka, Y. and Yokoyama, A. (2012) Oxovanadium Complexes with Quinoline and Pyridinone Ligands: Syntheses of the Complexes and Effect of Alkyl Chains on Their Apoptosis-Inducing Activity in Leukemia Cells. Bioorganic & Medicinal Chemistry, 20, 3058-3064.
http://dx.doi.org/10.1016/j.bmc.2012.02.063
[11] Liao, X.W., Pan, W.J., He, R.W., Guo, H.W., Ying, P. and Lu, J.Z. (2014) Unsymmetrical Oxovanadium Complexes Derived from Salicylaldehyde and Phenanthroline: Synthesis, DNA Interactions and Antitumor Activities. Chemical Biology & Drug Design, 83, 367-378. http://dx.doi.org/10.1111/cbdd.12248
[12] Zhai, S.S., Guo, Q., Dong, J.F., Xu, T. and Li, L.Z. (2014) An Oxovanadium(IV) Complex of an L-Serine Schiff Base and 1,10-Phenanthroline: Synthesis, Crystal Structure, and DNA and Albumin-Binding Properties. Transition Metal Chemistry, 39, 271-280. http://dx.doi.org/10.1007/s11243-014-9800-6
[13] Sumrra, S.H. and Chohan, Z.H. (2013) In Vitro Antibacterial, Antifungal and Cytotoxic Activities of Some Triazole Schiff Bases and Their Oxovanadium(IV) Complexes. Journal of Enzyme Inhibition and Medicinal Chemistry, 28, 1291-1299. http://dx.doi.org/10.3109/14756366.2012.735666
[14] Liao, X.W., Lu, J.Z., Ying, P., Zhao, P., Bai, Y.L., Li, W.J. and Liu, M.P. (2013) DNA Binding, Antitumor Activities and Hydroxyl Radical Scavenging Properties of Novel Oxovanadium(IV) Complexes with Substituted Isoniazid. Journal of Biological Inorganic Chemistry, 18, 975-984.
http://dx.doi.org/10.1007/s00775-013-1046-9
[15] Jing, B.Q., Dong, J.F., Li, J.H., Xu, T. and Li, L.Z. (2013) Synthesis, Crystal Structure and DNA Interaction of an Oxovanadium(IV) Complex Containing L-Valine Schiff Base and 1,10-Phenanthroline. Journal of Coordination Chemistry, 66, 520-529. http://dx.doi.org/10.1080/00958972.2013.763939
[16] Shiva, K.L. and Revanasiddappa, H.D. (2011) Synthesis, Characterization, Antimicrobial, DNA Binding and Oxidative Cleavage Activities of Cu(II) and Co(II) Complexes with 2-(2-Hydroxybenzylideneamino) Isoindoline-1, 3-Dione. Journal of Coordination Chemistry, 64, 699-714.
http://dx.doi.org/10.1080/00958972.2011.554544
[17] Sugihara, H. and Hiratani, K. (1996) 1,10-Phenanthroline Derivatives as Ionophores for Alkali Metal Ions. Coordination Chemistry Reviews, 148, 285-299. http://dx.doi.org/10.1016/0010-8545(95)01178-1
[18] Sun, D.D., Wang, W.Z., Mao, J.W., Mei, W.J. and Liu, J. (2012) Imidazo [4,5-f][1,10] Phenanthroline Derivatives as Inhibitor of C-Myc Gene Expression in A549 Cells via NF-κB Pathway. Bioorganic & Medicinal Chemistry Letters, 22, 102-105. http://dx.doi.org/10.1016/j.bmcl.2011.11.063
[19] Gomathi Sankareswari, V., Vinod, D., Mahalakshmi, A., Alamelu, M., Kumaresan, G., Ramaraj, R. and Rajagopal, S. (2014) Interaction of Oxovanadium(IV)-Salphen Complexes with Bovine Serum Albumin and Their Cytotoxicity against Cancer. Dalton Transactions, 43, 3260-3272.
http://dx.doi.org/10.1039/c3dt52505h
[20] Naso, L.G., Lezama, L., Rojo, T., Etcheverry, S.B., Valcarcel, M., Roura, M., Salado, C., Ferrer, E.G. and Williams, P.A.M. (2013) Biological Evaluation of Morin and Its New Oxovanadium(IV) Complex as Antio-Xidant and Specific Anti-Cancer Agents. Chemico-Biological Interactions, 206, 289-301.
http://dx.doi.org/10.1016/j.cbi.2013.10.006
[21] Zhang, Y.L., Wang, X.S., Fang, W., Cai, X.Y., Li, H.Z., Mao, J.W., Jin, X.B., Bai, Y.L. and Lu, J.Z. (2013) In Vitro Study of the Cytotoxicities of Two Mixed-Ligand Oxovanadium Complexes on Human Hepatoma Cells. Pharmazie, 68, 827-834.
[22] El-Asmy, A.A., Al-Gammal, O.A., Saad, D.A. and Ghazy, S.E. (2009) Synthesis, Characterization, Molecular Modeling and Eukaryotic DNA Degradation of 1-(3,4-Dihydroxybenzylidene) Thiosemicarbazide Complexes. Journal of Molecular Structure, 934, 9-22. http://dx.doi.org/10.1016/j.molstruc.2009.05.039
[23] Du, Y.f., Lu, J.Z., Guo, H.W., Jiang, J., Chao, P., Chen, F. and Pan, J.M. (2010) DNA Binding and Photocleavage Properties of Two Mixed-Ligand Oxovanadium Complexes. Transition Metal Chemistry, 35, 859-864.
http://dx.doi.org/10.1007/s11243-010-9404-8
[24] Lu, J.Z., Guo, H.W., Zeng, X.D., Zhang, Y.L., Zhao, P., Jiang, J. and Zang, L.Q. (2012) Synthesis and Characterization of Unsymmetrical Oxidovanadium Complexes: DNA-Binding, Cleavage Studies and Antitumor Activities. Journal of Inorganic Biochemistry, 112, 39-48.
http://dx.doi.org/10.1016/j.jinorgbio.2012.02.034
[25] Guo, H.W., Lu, J.Z., Ruan, Z.G., Zhang, Y.L., Liu, Y.J. Zang, L.Q. Jiang, J. and Huang, J.W. (2012) Synthesis, DNA-Binding, Cytotoxicity, and Cleavage Studies of Unsymmetrical Oxovanadium Complexes. Journal of Coordination Chemistry, 65, 191-204. http://dx.doi.org/10.1080/00958972.2011.645204
[26] Jeslin Kanaga Inba, P., Annaraj, B., Thalamuthu, S. and Neelakantan, M.A. (2013) Cu(II), Ni(II), and Zn(II) Complexes of Salan-Type Ligand Containing Ester Groups: Synthesis, Characterization, Electrochemical Properties and in Vitro Biological Activities. Bioinorganic Chemistry and Applications, 2013, 439848-439860.
http://dx.doi.org/10.1155/2013/439848
[27] Liu, Y.J., Li, Z.Z., Liang, Z.H., Yao, J.H. and Huang, H.L. (2011) Cytotoxicity, Apoptosis, Cellular Uptake, Cell Cycle Arrest, Photocleavage and Antioxidant Activity of 1,10-Phenanthroline Ruthenium(II) Complexes. DNA and Cell Biology, 30, 839-848. http://dx.doi.org/10.1089/dna.2011.1243
[28] Reichmann, M.E., Rice, C.A., Thomas, C.A. and Doty, P. (1954) A Further Examination of the Molecular Weight and Size of Deoxypentose Nucleic Acid. Journal of the American Chemical Society, 76, 3047-3053.
http://dx.doi.org/10.1021/ja01640a067
[29] Wu, Q., Fan, C.D., Chen, T.F., Liu, C.R., Mei, W.J., Chen, S.D., Wang, B.G., Chen, Y.Y. and Zheng, W.J. (2013) Microwave-Assisted Synthesis of Arene Ruthenium(II) Complexes That Induce S-Phase Arrest in Cancer Cells by DNA Damage-Mediated p53 Phosphorylation. European Journal of Medicinal Chemistry, 63, 57-63.
http://dx.doi.org/10.1016/j.ejmech.2013.01.037
[30] Cai, Z.B., Liu, L.F., Hong, Y.Q. and Zhou, M. (2013) Synthesis, Characterization and Nonlinear Optical Responses of Nickel(II) Complexes with Phenanthroline-Based Ligands. Journal of Coordination Chemistry, 66, 2388-2397.
http://dx.doi.org/10.1080/00958972.2013.805322
[31] Tang, T.T., Tang, G.D., Kou, S.S., Zhao, J.Y., Culnane, L.F. and Zhang, Y. (2014) Experimental and DFT Studies on the Vibrational and Electronic Spectra of 2-(1H-Imidazo [4,5-f][1,10] Phenanthrolin-2-yl) phenol. Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 117, 144-151. http://dx.doi.org/10.1016/j.saa.2013.07.108
[32] Raman, N. and Selvan, A. (2011) DNA Interaction, Enhanced DNA Photocleavage, Electrochemistry, Thermal Investigation and Biopotential Properties of New Mixed-Ligand Complexes of Cu(II)/VO(IV) Based on Schiff Bases. Journal of Molecular Structure, 985, 173-183.
http://dx.doi.org/10.1016/j.molstruc.2010.10.038
[33] Hazari, P.P., Pandey, A.K., Chaturvedi, S., Tiwari, A.K., Chandna, S., Dwarakanath, B.S. and Mishra, A.k. (2012) Synthesis of Oxovanadium(IV) Schiff Base Complexes Derived from C-Substituted Diamines and Pyridoxal-5-Phosphate as Antitumor Agents. Chemical Biology & Drug Design, 79, 223-234.
http://dx.doi.org/10.1111/j.1747-0285.2011.01265.x
[34] Li, C.Z., Wu, J.G., Wang, L.F., Min, R., Jia, N.Y. and Guo, J. (1999) Synthesis, Characterization and Antitumor Activity of Copper(II) Complex with Nicotinamido-4-Bis(2-Chloroethyl) Aminobenzaldimine. Journal of Inorganic Biochemistry, 73, 195-202. http://dx.doi.org/10.1016/S0162-0134(99)00005-7
[35] Zhao, P., Xu, L.C., Huang, J.W., Fu, B., Yu, H.C., Zhang, W.H., Chen, J., Yao, J.H. and Ji, L.N. (2008) DNA-Binding and Photocleavage Properties of Cationic Porphyrin-Anthraquinone Hybrids with Different Lengths of Links. Bioorganic Chemistry, 36, 278-287. http://dx.doi.org/10.1016/j.bioorg.2008.08.002
[36] Tabatabaee, M., Bordbar, M., Ghassemzadeh, M., Tahrir, M., Mehri Lighvan, Z. and Neumuller, B. (2013) Two New Neutral Copper(II) Complexes with Dipicolinic Acid and 3-Amino-1H-1,2,4-Triazole Formed under Different Reaction Conditions: Synthesis, Characterization, Molecular Structures and DNA-Binding Studies. European Journal of Medicinal Chemistry, 70, 364-371.
http://dx.doi.org/10.1016/j.ejmech.2013.10.009
[37] Gabra, N.M., Mustafa, B., Kumar, Y.P., Shobha Devi, C., Shilpa, M., Reddy, K.L. and Satyanarayana, S. (2014) DNA-Binding and Cleavage, Cytotoxicity Properties of Ru(II) Complexes with 2-(4’-Chloro-Phenyl) Imidazo[4,5-f][1,10] Phenanthroline, Ligand and Their “Light Switch” on-off Effect. Medicinal Chemistry Research, 23, 224-235. http://dx.doi.org/10.1007/s00044-013-0617-1
[38] Hazari, P.P., Pandey, A.K., Chaturvedi, S., Tiwari, A.K., Chandna, S., Dwarakanath, B.S. and Mishra, A.K. (2012) Synthesis of Oxovanadium(IV) Schiff Base Complexes Derived from C-Substituted Diamines and Pyridoxal-5-Phosphate as Antitumor Agents. Chemical Biology & Drug Design, 79, 223-234.
http://dx.doi.org/10.1111/j.1747-0285.2011.01265.x
[39] Zhou, C.Q., Lin, Y.L., Chen, J.X. and Chen, W.H. (2012) Synergetic DNA-Cleaving Activities of the Metal Complexes of a Polyether-Tethered Pyrrole-Polyamide Dimer. Chemistry & biodiversity, 9, 1125-1132.
http://dx.doi.org/10.1002/cbdv.201100183
[40] Chen, C., Bai, F.Y., Zhang, R., Song, G., Shan, H., Xing, N. and Xing, Y.H. (2013) Synthesis, Structure and Catalytic Bromination of Supramolecular Oxovanadium Complexes Containing Oxalate. Journal of Coordination Chemistry, 66, 671-688. http://dx.doi.org/10.1080/00958972.2013.765561
[41] Bian, L., Li, L.Z., Zhang, Q.F., Dong, J.F., Xu, T., Li, J.H. and Kong, J.M. (2012) Synthesis, Crystal Structures, DNA Binding and Cleavage Studies of Two Oxovanadium(IV) Complexes of 1,10-Phenanthroline and Schiff Bases Derived from Tryptophan. Transition Metal Chemistry, 37, 783-790. http://dx.doi.org/10.1007/s11243-012-9653-9
[42] Lewis, N.A., Liu, F., Seymour, L., Magnusen, A. and Erves, T.R. (2012) Synthesis, Characterisation and Preliminary In Vitro Studies of Vanadium(IV) Complexes with a Schiff Base and Thiosemicarbazones as Mixed Ligands. European Journal of Inorganic Chemistry, 2012, 664-677.
http://dx.doi.org/10.1002/ejic.201100898
[43] Benitez, J., Becco, L., Correia, I., Leal, S.M. and Guiset, H. (2011) Vanadium Polypyridyl Compounds as Potential Antiparasitic and Antitumoral Agents: New Achievements. Journal of Inorganic Biochemistry, 105, 303-312.
http://dx.doi.org/10.1016/j.jinorgbio.2010.11.001
[44] Mezo, G., Herenyi, L., Habdas, J., Majer, Z., Mysliwa-Kurdziel, B., Toth, K. and Csik, G. (2011) Syntheses and DNA Binding of New Cationic Porphyrin-Tetrapeptide Conjugates. Biophysical Chemistry, 155, 36-44.
http://dx.doi.org/10.1016/j.bpc.2011.02.007
[45] Jang, Y.J., Yeo, G.Y., Park, B. and Kim, S.K. (2011) The Relationship between the Structures of Periphery Ligands and the DNA Binding Mode of [Ru(II) (1,10-Phenanthroline) (L1L2) Dipyrido[3,2-a:2’,3’-c] Phenazine] n+ (L1 = Cl or Pyridine and L2 = Pyridine, n = 1, 2). Biophysical Chemistry, 158, 38-45. http://dx.doi.org/10.1016/j.bpc.2011.04.014
[46] Tan, D.J., He, Y., Qiu, L. and Zhang, Z.T. (2007) Studies on the Interactions of Sodium Chrysin-6-Sulfonate and Its Dinuclear Zinc, Tetra-Nuclear Calcium Complex with DNA. Chemical Research and Application, 19, 502-506.
[47] McCrate, A., Carlone, M., Nielsen, M. and Swavey, S. (2010) Anaerobic Photocleavage of Supercoiled DNA by a Ruthenium(II) Substituted Fluorinated Porphyrin. Inorganic Chemistry Communications, 13, 537-539.
http://dx.doi.org/10.1016/j.inoche.2010.01.031
[48] Surendra, D.C., Siva Kumar, V., John Venison, S., Vetha Potheher, I. and Rajalaxmi Subahashini, D. (2013) Synthesis, Structural Characterisation, Bio-Potential Efficiency and DNA Cleavage Applications of Nicotinamide Metal Complexes. Journal of Molecular Structure, 1040, 192-205.
http://dx.doi.org/10.1016/j.molstruc.2013.02.019
[49] Li, H.J., Bo, H.B., Wang, J.Q., Shao, H.W. and Huang, S.L. (2011) Separation of Supercoiled from Open Circular Forms of Plasmid DNA and Biological Activity Detection. Cytotechnology, 63, 7-12.
http://dx.doi.org/10.1007/s10616-010-9322-9
[50] Nejedly, K., Sykorova, E., Diekmann, S. and Paleeek, E. (1998) Analysis of a Curved DNA Constructed from Alternating dAn:dTn-Tracts in Linear and Supercoiled Form by High Resolution Chemical Probing. Biophysical Chemistry, 73, 205-216. http://dx.doi.org/10.1016/S0301-4622(98)00145-8
[51] Benitez, J., Guggeri, L., Tomaz, I., Pessoa, J.C., Moreno, V., Lorenzo, J., Aviles, F.X., Garat, B. and Gambino, D. (2009) A Novel Vanadyl Complex with a Polypyridyl DNA Intercalator as Ligand: A Potential Anti-Protozoa and Anti-Tumor Agent. Journal of Inorganic Biochemistry, 103, 1386-1394.
http://dx.doi.org/10.1016/j.jinorgbio.2009.07.013

  
comments powered by Disqus

Copyright © 2019 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.