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Synthesis and Investigation of DNA Effect of [N,N'-bis (salicylidene)-1,3-propanediaminato]nickel(II) Complex

Year 2010, Volume: 5 Issue: 1, 67 - 74, 25.06.2010

Mürsel Arıcı Hasan Nazır

Abstract

In this study, N,N'-bis(salicylidene)-1,3-propanediaminato]nickel(II) (NiL) complex was synthesized from reaction of bis(salicylidene)-1,3-propanediamine (H2L) with nickel(II) chloride
hexahydrate in ethanolic medium. The interaction of synthesized NiL complex with pBR322 plasmid DNA was investigated by ultraviolet absorption spectroscopy (UV), cyclic voltammetry (CV) and agarose jel electrophoresis. It was found that the absorption spectrum of NiL complex in the presence of plasmid DNA showed hyperchromism and its peak current was significantly decreased at recorded voltammogram. Effect of NiL complex on DNA in the absence of reductant agents showed by ajarose jel electrophoresis. Moreover, the geometry of the lowest-energy structure of NiL complex calculated by Hyperchem® program gave a good result to be associated with partial intercalation and electrostatic binding modes of the DNA.

Keywords

Ni(II) complex plasmid DNA cleavage partial intercalation electrostatic interaction

References

  • [1] Sigman D.S., Mazumdar A., Perrin D.M., 1993. Chemical nucleases, Chemical Review, 93: 2295- 2316.
  • [2] Barton J., Golgberg J.M., Kumar C.V., Turro N.J., 1986. Binding Modes and Base Specificity of Tris(phenanthroline)ruthenium(II) Enantiomers with Nucleic Acids: Tuning the Stereoselectivity, Journal of. American Chemical Society, 108: 2081-2088.
  • [3] Vijayalakshmi R., Kanthimathi M., Parthasarathi R., Nair B.U., 2006. Interaction of chromium(III) complex of chiral binaphthyl tetradentate ligand with DNA, Bioorganic & Medicinal Chemistry, 14: 3300-3306.
  • [4] Vaidyanathan V.G., Weyhermuller T., Nair B.U., Subramanıan J., 2005. DNA damage induced by a chromium(III) Schiff base complex is reversible under physiological condition, Journal of Inorganic Biochemistry, 99: 2248–2255.
  • [5] Vijayalakshmi R., Kanthimathi M., Subramanian V., Nair, B.U., 2000. Interaction of DNA with [Cr(Schiff base)(H2O)2]CIO4, Biochimica et Biophysica Acta, 1475: 157-164.
  • [6] Arslantas A., Devrim A.K., Necefoglu H., 2007. DNA-Binding Study of Tetraaqua-bis(pnitrobenzoato)cobalt(II) Dihydrate Complex: [Co(H2O)4(p-NO2C6H4COO)2]·2H2O, International Journal of Molecular Sciences, 8: 564-571.
  • [7] Gupta T., Patra A.K., Dhar S., Nethaji M., Chakravarty Ar, 2005. Effect of copper–sulphur bond on the DNA photo-cleavage activity of 2-(methylthio)ethylpyridine-2 carbaldimine copper(II) complexes, Journal of Chemical Science, 117: 123-132.
  • [8] Patra A.K., Gupta T., Roy S., Chakravarty A.R., 2008. Synthesis, structure, DNA-binding and photocleavage activity of a binuclear copper(II) complex, Indian Journal of Chemistry, 47: 643- 649.
  • [9] Pitié M., Burrows C.J., Meunler B., 2000. Mechanisms of DNA cleavage by copper complexes of 3- Clip-Phen and of its conjugate with a distamycin analogue, Nucleic Acids Research, 28: 4856- 4864.
  • [10] Yang Z.S., Yu J.S., Chen H.Y., 2002. Electrochemically Induced DNA Cleavage by CopperPhenanthroline Complex, Electroanalysis, 14: 747-752.
  • [11] Lu L.P., Zhu M.L., Yang P., 2003. Crystal structure and nuclease activity of mono(1,10- phenanthroline)copper complex, Journal of Inorganic Biochemistry, 95: 31-36.
  • [12] Routier S., Vezin H., Lamour E., Bernier J.L., Catteau J.P., Baılly C., 1999. DNA cleavage by hydroxy-salicylidene-ethylendiamine-iron complexes, Nucleic Acids Research, 27: 4160-4166.
  • [13] Wang M., Wang L.F., Li Y.Z., Li Q.X., Xu Z.D., Qu D.Q., 2001. Antitumour activity of transition metal complexes with the thiosemicarbazone derived from 3-acetylumbelliferone, Transition Metal Chemistry, 26: 307-310.
  • [14] Reddy K.H., Reddy S., Babu P.R., 2000. Nuclease activity of 2-substituted heteroaromatic thiosemicarbazone and semicarbazone copper(II) complexes, Transition Metal Chemistry, 25: 154-160.
  • [15] Lei Y., Yin-Zhuang Z., Jin-Li L., Shu-Jie T., Ling-Mei X., 2009. Synthesis, Crystal Structure and Interaction with DNA of a Novel Chromium(III) Complex Containing Salicylaldehyde Semicarbazone, Chinese Journal of. Structural Chemistry, 28: 789-796.
  • [16] Reddy P.R., Raju N., Manjula P., Reddy K.V.G., 2007. Synthesis and DNA Binding/Cleavage of Mononuclear Copper(II) Phenanthroline/Bipyridine Proline Complexes, Chemistry & Biodiversity, 4: 1565-1577.
  • [17] Reddy P.R., Raju N., Reddy K.V., 2009. Synthesis, characterization and DNA binding and cleavage properties of copper (II)-tryptophan-tryptophan complex, Indian Journal of Chemistry, 48A: 1638-1643.
  • [18] Colak A., Cekirge E., Karaböcek S., Kücükdumlu A., Ertunga N.S., Col M., Abbasoğlu R., 2009. Investigation of DNA cleavage activities of new oxime-type ligand complexes and molecular modeling of complex-DNA interactions, Chemical Paper, 63: 554-561.
  • [19] Drew G.B., 1985. Structure of (N,N’-Trimethylenesalicylideneaminato)nickel(II) (1) and (N,N’- Trimethylenesalicylideneaminato)copper(II) (2), Acta Crystallography, 41: 1755-1758.
  • [20] Atakol O., Nazir H., Arici C., Durmus S., Svoboda I., Fuess H., 2003. Some new Ni-Zn heterodinuclear complexes: square-pyramidal nickel(II) coordination, Inorganica Chimica Acta, 342: 295-300.
  • [21] HyperChem, Hypercube Inc., Gainesville, USA.
  • [22] Reichmann M.E., Rice S.A., Thomas C.A., Doty P., 1954. A further examination of the molekuler weight and size of desoxypentose nucleic acid, Molekuler Weight and Size of Deoxypentose Nucleic Acid, 76: 3047-3050.
  • [23] Kumar C.V., Asuncion E.H., 1993. DNA Binding Studies and Site Selective Fluorescence Sensitization of an Anthryl Probe, Journal of American Chemical Society, 115: 8547-8553.
  • [24] Mahadevan S., Palaniandavar M., 1998. Spectroscopic and Voltammetric Studies on Copper Complexes of 2,9-Dimethyl-1,10-phenanthrolines Bound to Calf Thymus DNA, Inorganic Chemistry, 37: 693-700.
  • [25] Indumathy R., Radhika S., Kanthimathi M., Weyhermuller T., Nair B.U., 2007. Cobalt complexes of terpyridine ligand: Crystal structure and photocleavage of DNA, Journal of Inorganic Biochemistry, 101: 434–443.
  • [26] Arjmand F., Aziz M., 2008. Synthesis and characterization of dinuclear macrocyclic cobalt(II), copper(II) and zinc(II) complexes derived from 2,2,2’,2’-S,S[bis(bis-N,N-2- thiobenzimidazolyloxato-1,2-ethane)]: DNA binding and cleavage studies, Europian Journal of Medicinal Chemistry, XX: 1-11.
  • [27] Tamilarasan R., Mcmillin D.R., 1990. Photophysical Studies of Copper Phenanthrolines Bound to DNA, Inorganic Chemistry, 29: 2798-2802.
  • [28] Wang Y.L., Liu Y.C., Yang Z.S., Zhao G.C., 2004. Electrochemical cleavage of DNA in the presence of copper–sulfosalicylic acid complex, Bioelectrochemistry, 65: 77– 81.
  • [29] Ibrahim M.S., 2001.Voltammetric studies of the interaction of nogalamycin antitumor drug with DNA, Analytica Chimica Acta, 443: 63–72.

[N,N'-Bis(salisiliden)-1,3-propandiaminato]nikel(II) Kompleksinin Sentezi ve DNA Etkisinin İncelenmesi

Year 2010, Volume: 5 Issue: 1, 67 - 74, 25.06.2010

Mürsel Arıcı Hasan Nazır

Abstract

Özet: Bu çalışmada, bis(salisiliden)-1,3-diaminopropan (H2L) Schiff bazı ile nikel(II) klorür hekzahidrat'ın etanoldeki reaksiyonundan [N,N'-bis(salisiliden)-1,3-propandiaminato]nikel(II) (NiL) kompleksi sentezlendi. Sentezlenen NiL kompleksinin pBR322 plazmid DNA ile etkileşimi ultraviyole absorpsiyon spektroskopisi (UV), dönüşümlü voltametri (CV) ve agaroz jel elektroforez ile incelendi.
NiL kompleksinin DNA varlığında absorpsiyon spektrumunun hiperkromik etki gösterdiği ve kaydedilen dönüşümlü voltamogramında pik akımının azaldığı bulundu. NiL kompleksinin indirgeyici maddeler olmadan plazmid DNA'yı etkilediği agaroz jel elektroforez ile gösterildi. Ayrıca NiL kompleksinin Hyperchem® programıyla hesaplanan en düşük enerjili yapısının geometrisi, DNA'nın kısmi interkalasyon ve elektrostatik bağlama modlarıyla ilişkilendirilebilir bir sonuç vermektedir.

Anahtar kelimeler: Nikel(II) kompleks, plazmid DNA yarılması, kısmi interkalasyon, elektrostatik etkileşim

Synthesis and Investigation of DNA Effect of [N,N'-bis
(salicylidene)-1,3-propanediaminato]nickel(II) Complex

Abstract: In this study, N,N'-bis(salicylidene)-1,3-propanediaminato]nickel(II) (NiL) complex was synthesized from reaction of bis(salicylidene)-1,3-propanediamine (H2L) with nickel(II) chloride hexahydrate in ethanolic medium. The interaction of synthesized NiL complex with pBR322 plasmid
DNA was investigated by ultraviolet absorption spectroscopy (UV), cyclic voltammetry (CV) and agarose jel electrophoresis. It was found that the absorption spectrum of NiL complex in the presence of plasmid DNA showed hyperchromism and its peak current was significantly decreased at recorded voltammogram. Effect of NiL complex on DNA in the absence of reductant agents showed by ajarose jel electrophoresis. Moreover, the geometry of the lowest-energy structure of NiL complex calculated by
Hyperchem® program gave a good result to be associated with partial intercalation and electrostatic binding modes of the DNA.

Key words: Ni(II) complex, plasmid DNA cleavage, partial intercalation, electrostatic interaction

Keywords

Nikel(II) kompleks plazmid DNA yarılması kısmi interkalasyon elektrostatik etkileşim

References

  • [1] Sigman D.S., Mazumdar A., Perrin D.M., 1993. Chemical nucleases, Chemical Review, 93: 2295- 2316.
  • [2] Barton J., Golgberg J.M., Kumar C.V., Turro N.J., 1986. Binding Modes and Base Specificity of Tris(phenanthroline)ruthenium(II) Enantiomers with Nucleic Acids: Tuning the Stereoselectivity, Journal of. American Chemical Society, 108: 2081-2088.
  • [3] Vijayalakshmi R., Kanthimathi M., Parthasarathi R., Nair B.U., 2006. Interaction of chromium(III) complex of chiral binaphthyl tetradentate ligand with DNA, Bioorganic & Medicinal Chemistry, 14: 3300-3306.
  • [4] Vaidyanathan V.G., Weyhermuller T., Nair B.U., Subramanıan J., 2005. DNA damage induced by a chromium(III) Schiff base complex is reversible under physiological condition, Journal of Inorganic Biochemistry, 99: 2248–2255.
  • [5] Vijayalakshmi R., Kanthimathi M., Subramanian V., Nair, B.U., 2000. Interaction of DNA with [Cr(Schiff base)(H2O)2]CIO4, Biochimica et Biophysica Acta, 1475: 157-164.
  • [6] Arslantas A., Devrim A.K., Necefoglu H., 2007. DNA-Binding Study of Tetraaqua-bis(pnitrobenzoato)cobalt(II) Dihydrate Complex: [Co(H2O)4(p-NO2C6H4COO)2]·2H2O, International Journal of Molecular Sciences, 8: 564-571.
  • [7] Gupta T., Patra A.K., Dhar S., Nethaji M., Chakravarty Ar, 2005. Effect of copper–sulphur bond on the DNA photo-cleavage activity of 2-(methylthio)ethylpyridine-2 carbaldimine copper(II) complexes, Journal of Chemical Science, 117: 123-132.
  • [8] Patra A.K., Gupta T., Roy S., Chakravarty A.R., 2008. Synthesis, structure, DNA-binding and photocleavage activity of a binuclear copper(II) complex, Indian Journal of Chemistry, 47: 643- 649.
  • [9] Pitié M., Burrows C.J., Meunler B., 2000. Mechanisms of DNA cleavage by copper complexes of 3- Clip-Phen and of its conjugate with a distamycin analogue, Nucleic Acids Research, 28: 4856- 4864.
  • [10] Yang Z.S., Yu J.S., Chen H.Y., 2002. Electrochemically Induced DNA Cleavage by CopperPhenanthroline Complex, Electroanalysis, 14: 747-752.
  • [11] Lu L.P., Zhu M.L., Yang P., 2003. Crystal structure and nuclease activity of mono(1,10- phenanthroline)copper complex, Journal of Inorganic Biochemistry, 95: 31-36.
  • [12] Routier S., Vezin H., Lamour E., Bernier J.L., Catteau J.P., Baılly C., 1999. DNA cleavage by hydroxy-salicylidene-ethylendiamine-iron complexes, Nucleic Acids Research, 27: 4160-4166.
  • [13] Wang M., Wang L.F., Li Y.Z., Li Q.X., Xu Z.D., Qu D.Q., 2001. Antitumour activity of transition metal complexes with the thiosemicarbazone derived from 3-acetylumbelliferone, Transition Metal Chemistry, 26: 307-310.
  • [14] Reddy K.H., Reddy S., Babu P.R., 2000. Nuclease activity of 2-substituted heteroaromatic thiosemicarbazone and semicarbazone copper(II) complexes, Transition Metal Chemistry, 25: 154-160.
  • [15] Lei Y., Yin-Zhuang Z., Jin-Li L., Shu-Jie T., Ling-Mei X., 2009. Synthesis, Crystal Structure and Interaction with DNA of a Novel Chromium(III) Complex Containing Salicylaldehyde Semicarbazone, Chinese Journal of. Structural Chemistry, 28: 789-796.
  • [16] Reddy P.R., Raju N., Manjula P., Reddy K.V.G., 2007. Synthesis and DNA Binding/Cleavage of Mononuclear Copper(II) Phenanthroline/Bipyridine Proline Complexes, Chemistry & Biodiversity, 4: 1565-1577.
  • [17] Reddy P.R., Raju N., Reddy K.V., 2009. Synthesis, characterization and DNA binding and cleavage properties of copper (II)-tryptophan-tryptophan complex, Indian Journal of Chemistry, 48A: 1638-1643.
  • [18] Colak A., Cekirge E., Karaböcek S., Kücükdumlu A., Ertunga N.S., Col M., Abbasoğlu R., 2009. Investigation of DNA cleavage activities of new oxime-type ligand complexes and molecular modeling of complex-DNA interactions, Chemical Paper, 63: 554-561.
  • [19] Drew G.B., 1985. Structure of (N,N’-Trimethylenesalicylideneaminato)nickel(II) (1) and (N,N’- Trimethylenesalicylideneaminato)copper(II) (2), Acta Crystallography, 41: 1755-1758.
  • [20] Atakol O., Nazir H., Arici C., Durmus S., Svoboda I., Fuess H., 2003. Some new Ni-Zn heterodinuclear complexes: square-pyramidal nickel(II) coordination, Inorganica Chimica Acta, 342: 295-300.
  • [21] HyperChem, Hypercube Inc., Gainesville, USA.
  • [22] Reichmann M.E., Rice S.A., Thomas C.A., Doty P., 1954. A further examination of the molekuler weight and size of desoxypentose nucleic acid, Molekuler Weight and Size of Deoxypentose Nucleic Acid, 76: 3047-3050.
  • [23] Kumar C.V., Asuncion E.H., 1993. DNA Binding Studies and Site Selective Fluorescence Sensitization of an Anthryl Probe, Journal of American Chemical Society, 115: 8547-8553.
  • [24] Mahadevan S., Palaniandavar M., 1998. Spectroscopic and Voltammetric Studies on Copper Complexes of 2,9-Dimethyl-1,10-phenanthrolines Bound to Calf Thymus DNA, Inorganic Chemistry, 37: 693-700.
  • [25] Indumathy R., Radhika S., Kanthimathi M., Weyhermuller T., Nair B.U., 2007. Cobalt complexes of terpyridine ligand: Crystal structure and photocleavage of DNA, Journal of Inorganic Biochemistry, 101: 434–443.
  • [26] Arjmand F., Aziz M., 2008. Synthesis and characterization of dinuclear macrocyclic cobalt(II), copper(II) and zinc(II) complexes derived from 2,2,2’,2’-S,S[bis(bis-N,N-2- thiobenzimidazolyloxato-1,2-ethane)]: DNA binding and cleavage studies, Europian Journal of Medicinal Chemistry, XX: 1-11.
  • [27] Tamilarasan R., Mcmillin D.R., 1990. Photophysical Studies of Copper Phenanthrolines Bound to DNA, Inorganic Chemistry, 29: 2798-2802.
  • [28] Wang Y.L., Liu Y.C., Yang Z.S., Zhao G.C., 2004. Electrochemical cleavage of DNA in the presence of copper–sulfosalicylic acid complex, Bioelectrochemistry, 65: 77– 81.
  • [29] Ibrahim M.S., 2001.Voltammetric studies of the interaction of nogalamycin antitumor drug with DNA, Analytica Chimica Acta, 443: 63–72.
There are 29 citations in total.

Details

Primary Language Turkish
Subjects Chemical Engineering
Journal Section Makaleler
Authors

Mürsel Arıcı This is me

Hasan Nazır

Publication Date June 25, 2010
Published in Issue Year 2010 Volume: 5 Issue: 1

Cite

IEEE M. Arıcı and H. Nazır, “[N,N’-Bis(salisiliden)-1,3-propandiaminato]nikel(II) Kompleksinin Sentezi ve DNA Etkisinin İncelenmesi”, Süleyman Demirel University Faculty of Arts and Science Journal of Science, vol. 5, no. 1, pp. 67–74, 2010.
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