مطالعه برهمکنش کمپلکس های نیکل (II) دارای لیگاندهای آروماتیک مسطح با DNA غده تیموس

نوع مقاله: علمی-پژوهشی

نویسندگان

1 زاهدان، دانشگاه آزاد اسلامی، واحد علوم و تحقیقات سیستان و بلوچستان

2 تهران، دانشگاه تهران، مرکز تحقیقات بیوشیمی و بیوفیزیک

3 زاهدان، دانشگاه سیستان و بلوچستان، دانشکده علوم، گروه شیمی

4 کرج، پژوهشگاه مواد و انرژی، پژوهشکده فناوری نانو و مواد پیشرفته

5 تهران، دانشگاه خوارزمی، گروه علوم زیستی

چکیده

سه کمپلکس نیکل با فرمول های 2)3](NO2[Ni(en)، 2)3](NO2[Ni(phen)، 2)3](NO2[Ni(bpy)(به ترتیب a، b و c) که در آنها =en اتیلن دی آمین، =bpy 2 و 2- بی پیریدین و =phen 1و 10 فنانترولین است تهیه شد. ساختار این کمپلکس ها توسط روش های طیف سنجی فرا بنفش، فروسرخ، رزونانس مغناطیسی هسته و روش‌های هدایت سنجی و تجزیه عنصری شناسایی شد. برهمکنش این سه کمپلکس محلول در آب با DNA غده تیموس به روش های جذب الکترونیکی، فلوئورسانس و ژل فیلتراسیون مطالعه شد. این کمپلکس ها می‌ توانند DNAرا در غلظت های بسیار کم، غیرطبیعی کنند. برهمکنش بین کمپلکس‌های bو cکه دارای لیگاندهای آروماتیک و مسطح هستند، شاید از نوع اینترکیلیشن باشد. همچنین، کمپلکس c می‌تواند DNAرا به دو قطعه برش داده و با هر دو برهمکنش داشته باشد.

کلیدواژه‌ها

موضوعات


[1] Hillman R.E., Dandliker P.J., Barton J.K., Charge Transfer through the DNA Base Stack, Angew. Chem., Int. Ed. Engl., 36, p. 2714 (1977).

[2] Dupureur C., Barton J.K, "Comprehensive Supramolecular Chemistry", Lehn J-M., (ed.) Pergamon, New York, 5, p. 295 (1977).

[3] Amani S., Zolgharnein J., Theriot L.J., Synthesis of Binuclear MonohydroxoBridged Copper (II) Complexes with 1,10-Phenanthroline and 4,4 -dimethyl - 2,2 – bipyrdine, Iran. J. Chem. Chem. Eng., 19(1), p. 1 (1998).

[4] Mesmaeker A. K-D., Lecomte.J-P., Kelly J.M., Photoreactions of Metal Complexes with DNA, Especially those Involving a Primary Photo-Electron Transfer, Topics Curr. Chem., 177, p.25 (1996).

[5] Norden B., Lincoln P., Akerman B., Tuite E., "Metalions in Biological Systems: Probing of Nucleic Acids by Metal Ion Complexes of Small Molecules", Sigel A., Sigel H., (eds) Marcel Dekker, New York, 33, p. 177 (1996).

[6] Sigman D.S, Mazumder. A., Perrin D.M., Chemical Nucleases, J. Chem. Rev., 93, p. 2295 (1993).

[7] Murphy C.J., Barton. J. K., Ruthenium Complexes as Luminescent Reporters of DNA, Meth.Enzymol., 226, p. 576 (1993).

[8] Turro N.J, Barton J. K, Tamalia. D.A,Molecular Recognition and Chemistry in Restricted Reaction Spaces. Photophysics and Photoinduced Electron Transfer onthe Surfaces of Micelles, Dendrimers and DNA, J.Acc. Chem. Res, 24, p. 332 (1991)

[9] Pyle A.M, Barton J.K, Probing Nucleic Acids with Transition Metal Complexes, J.Prog.Inorg.Chem., 38, p. 413 (1990).

[10] Tullis T.D (ed.), "Metal-DNA chemistry. ACS Symposium Series", Am. Chem. Soc., Washington, DC, 402 (1989).

[11] Barton J.K, Metals and DNA: Molecular Left – Handed Complements,  Science, 233, p. 727 (1986). 

[12] Kawanishi S, Oikawa S, Inoue S, Nishino K, Distinct Mechanisms of Oxidative DNA Damage Induced by Carcinogenic Nickel Subsulfide and Nickel Oxides, J. Environ.Health Perspect., 110, p. 789 (2002).

[13] Badisa V.L, Latinwo L.M, Odewumi C.O, Ikediobi C.O, Badisa R.B., Ayuk-Takem L.T., Woga J.N., West J., Mechanism of DNA Damage by Cadmium and Interplay of Antioxidant Enzymes and Agents, J. Environ. Toxical., 22, p. 144 (2007).

[14] Matkar S.S., Wrischnik L.A, Jones P.R., Hellman-Blumberg U.,Two Closely Related Nickel Complexes Have Different Effects on DNA Damage and Cell Viability, Biochem. Biophys. Res. Commun, 343, p. 754 (2006).

[15] Illan-Cabeza N.A, Vilaplana R.A, Alvarez Y., Akdi K., Kamah S., Hueso-Urena F., Quiros M., Gonzalez-Vilchez F., Moreno-Carretero M.N., Synthesis, Structure and Biological Activity of a New and Efficient Cd(II)-uracil Derivative Complex System for Cleavage of DNA, J. Biol. Inorg. Chem., 10, p. 924 (2005).

[16] Afrasiabi Z., Sinn E., Lin W., Ma Y., Campana C., Padhye S., Nickel(II) Complexes of Naphthaquinone Thiosemicarbazone and Semicarbazone: Synthesis, Structure, Spectroscopy and Biological Activity, J. Inorg. Biochem., 98, p. 1526 (2005).

[17] Fang Y.Y., Claussen C.A., Lipkowitz K.B., Long E.C., Diastereoselective DNA Cleavage Recognition by Ni(II) x Gly-Gly-His-Derived Metallopeptides, J. Am. Chem. Soc., 128, p. 3198 (2006).

[18] Kaczmarek P., Szczepanik W., Jezowska-Bojczuk M., Acid-base, Coordination and Oxidative Properties of Systems Containing ATP, L-histidineand Ni(II) Ions, Dalton Trans., 34, p. 3653 (2005).

[19] Kirin S.I, Happel C.M, Hrubanova S., Weyhermuller T., Klein C., Metzler-Nolte N.,Synthesis, structure and DNA Cleavage Propensity of Metal Complexes M(II)L with the N-(2-ethoxyethanol)-bis(2-picolyl)amine Ligand L (M = Co, Ni, Cu and Zn), Dalton. Trans., 33, p. 1201 (2004).

[20] Muller J.G., Chen X., Dadiz C., Rokita S.E., Burrows C. J., Ligand Effects Associated with the Intrinsic Selectivity of DNA Oxidation Promoted by Nickel(II) Macrocyclic Complexes, J. Am. Chem. Soc., 114, p. 6407 (1992).

[21] Reddy P.R, Rao K.S, Ternary Nickel(II) Complexes as Hydrolytic DNA-Cleavage Agents, Chem.Biodivers., 3, p. 231 (2006).

[22] Rodriguez-Arguelles M.C, Ferrari M.B, Biscegli F., Pellizi C, Pelosi.G., Pinelli S., Sassi M., Synthesis, Characterization and Biological Activity of Ni, Cu and Zn Complexes of IsatinHydrazones, J. Inorg.Biochem., 98, p. 313  (2004).

[23] Song Y.M, Wu Q., Yang P.J., Luan N.N, Wang L.F, Liu Y.M, DNA Binding and Cleavage Activity of Ni(II) Complexwith All-trans Retinoic Acid, J. Inorg. Biochem., 100, p. 1685 (2006).

[24] Rahimizadeh M., Rajabzadeh G., Preparation of Ethylenediamine by Ammonolysis of 1,2-ichioroethane  NonaqueousMedia, Iran. J. Chem. Chem. Eng., 14(2), p. 1 (1995).

[25] Lindoy L.F, Livingstone S.E., Complexes of Iron(II), Cobalt(II) and Nickel(II) with α-Diimines and Related BidentateLigands, Coord. Chem. Rev., 2, p. 173 (1967).

[26] McWhinnie W.R., Miller J.D., The Chemistry of Complexes Containing 2,2′-Bipyridyl, 1, 10-Phenanthroline, or 2,2′,6′,2”-Terpyridyl as Ligands, Adv. Inorg. Chem. Radiochem., 12, p. 135 (1970). 

[27] McKenzie E.D.,The Steric Effect in Bis(2,2'-bipyridyl) and Bis(1,10-phenanthroline) Metal Compounds, Coord. Chem. Rev., 6, p. 187 (1971).

[28] Wada A., Katayama C.,  Tanaka J., The Crystal Structure and Absolute Configuration of (+)589Tris(2,2'-bipyridyl)nickel(II) chloride (+)589-tartrate Hydrate, [Ni(C10H8N2)3]2Cl2.C4H4O6.nH2O, Acta Crystallogr., Sect. B, 32, p. 3194 (1976).

[29] Wada A., Sakabe N., Tanaka. J, The Crystal Structure of Tris(2,2'-bipyridyl)nickel(II) SulphateHydrate, [Ni(C10H8N2)3]SO4.7.5H2O, Acta Crystallogr. Sect. B,32, p. 1121 (1976).

[30] Butler K.R, Snow M.R., The Structure and Absolute Configuration of the (+)589Tris(1, 2-dithiooxalation) cobaltate (III) Ion, J. Chem. Soc. (A), p. 565 (1971

[31] Frenz B.A, Ibers J.A., Crystal and Molecular Structure of Tris (1,10-phenanthroline)nickel(II) Pentacarbonylmanganate(-I), [Ni(1,10-phen)3][Mn(CO)5]2, J. Inorg. Chem., 11, p. 1109 (1972).

[32] Butcher R.J., Sinn E., Synthesis and Relation between Magnetic and Structural Properties of a Series of Monomeric and DimericNickel(II) Complexes. Crystal and Molecular Structures of [Ni(biq)Cl2]2, Ni(biq)Br2, [Ni(dmp)Cl2]2, [Ni(dmp)Br2]2 and Ni(bc)I2, J. Inorg. Chem., 16, p. 2334 (1977).

[33] Butcher R.J., O’Connor C.J., Sinn E., Magnetic Properties of Some Monomeric and DimericNickel(II) Complexes NiLX2 (L = 2,9-dimethyl-1,10-phenanthroline (dmp), 2,2'-biquinolyl, bathocuproine; X = chlorine, bromine, iodine) and the Crystal Structure of Ni(dmp)I2, J. Inorg. Chem.,18, p. 492 (1979).

[34]Arora S.K., Carter D.E., Fernando Q., (2,2'-Bipyridyl)bis(O,O'-dimethyl Dithiophosphato) Nickel(II), Acta Crystallogr., Sect. B, 33, p. 3230 (1977).

[35] Shetty P.S., Fernando Q., Structures of Five- and Six-Coordinated Mixed-Ligand Chelates of Nickel(II) Containing Sulfur and Nitrogen Donor Atoms, J. Am. Chem. Soc., 92, p. 3964 (1970).

[36]Moosavi-Movahedi A.A., Godarzi M., Interaction Studies of Sodium N- Dodecyl Sulfate and Proton to Histon H1, Iran. J. Chem. Chem. Eng., 3, p. 3 (1989)

[37] Omoregie O., Woods J., Synthesis and Physicochemical Studies of Nickel(II) Complexes of Various 2-Alkyl-1-phenyl-1,3-butanediones and Their 2,2’-Bipyridine and 1,10-Phenanthroline Adducts, Int. J. Chem.3, p. 24 (2011).

[38] Mansouri-Torshizi H., Saeidifar M., Divsalar A., Saboury A.A., Binding Studies of a Novel Antitumor Palladium(II) Complex to Calf Thymus DNA, J.Nucleous. Nucleot.Nuc.Acids, 30, p. 405 (2011).

[39] Divsalar A., Saboury A.A., Ahadi A., Zemanatiyar E., Bagheri M.J., Mansoori-Torshizi H., Ajloo D., Sarma R.H., Biological Evaluation and Interaction of a Newly Designed Anti-Cancer Pd(II) Complex and Human Serum Albumin, J. Biomol. Struc. Dyn., 29, p. 283, (2011).

[40] Masouri-Torshizi H., Saeidifar M., Khosravi F., Divsalar A., Saboury A.A., Yekke-Ghasemi Z., DNA-Binding and Thermodynamic Parameters, Structure and Cytotoxicity of Newly Designed Platinum(II) and Palladium(II) Anti-Tumor Complexes, Bull. Korean Chem. Soc., 32, p. 947 (2011).

[41] Masouri-Torshizi H, Saeidifar M., YekkeGhasemi Z, Khastan M., Divsalar A.,  Saboury A.A.,  DNA Binding Studies and Cytotoxicity of the Novel 1,10-phenanthrolinePalladium(II) Complexes of Dithiocarbamate Derivatives,  J. Korean Chem. Soc., 55, p. 70 (2011).

[42] Masouri-Torshizi H., Saeidifar M., Divsalar A., Saboury A.A, Study on Interaction of DNA from Calf Thymus with 1,10-phenanthrolinehexyldithiocarbamatopalladium(II) nitrate as Potential Antitumor Agent, J. Biomol. Struc. Dyn., 28, p. 805 (2011).

[43] Zhang Z., Wang S., Dong X.,Photodynamic Activity of a Nickel Diimine Complex and Its Interaction with DNA, J. Trans. Met. Chem., 37, p. 379 (2012).

[44] Van-Der Poel H., Van- Koten G., Vrieze K., Five-Coordinate [PtIICl2(.eta.2-olefin)L2] (L2 = .sigma., SigmaN,N'-Bonded alpha-Diimine or N,N'-Disubstituted 1,2-Diaminoethane) Complexes. Solution Conformation, eta.2-olefin Rotational Barriers (NMR), and the x-Ray Molecular Structure of [PtCl2(.eta.2-styrene) (t-Bu-N:CHCH:N-t-Bu)], J. Inorg. Chem., 19, p. 1145 (1980).

[45] Rejitha K., Suresh M., ThermoanalyticalInvestigations of Tris(ethylenediamine)nickel(II) Oxalate and Sulphate Complexes, J. Therm. Anal. Cal., 102(3), p. 931 (2010).

[46] Elduque A., Finestra C., Lopez C., Lahoz J.A., Merchan F.J., Oro F., Pinillos M.T., Rhodium Dithiocarbamate Compounds as Metalloligands:  A Controlled Way for the Construction of Binuclear Complexes, J.Inorg.Chem.,37, p. 824 (1998).

[47] Mansuri-Torshizi H., Akhbari-Shad M.H, Srivastava T.S, Synthesis, Two–Dimensional 1HNMR Spectrum, and DNA Binding Studies of 2,2’–Bipyridine– 2-pyridinecarboxylato -Platinum (II) Nitrate, Iran. J. Sci. Technol., 25, p. 153 (2001).

[48] Manav N., Mishra A.K., Kaushik N.K., In Vitro Antitumour and Antibacterial Studies of Some Pt(IV) Dithiocarbamate Complexes, Spectrochim.Acta Part A, 65, p. 32 (2006).

[49] Angelici R.J., "Synthesis Technique in Inorganic Chemistry", p. 17, Saunders, Philadelphia, (1969).

[50] Lepecq J.B., Paoletti C., A Fluorescent Complex between EthidiumBromide and Nucleic Acids: Physical-Chemical Characterization, J. Mol. Biol., 27, p. 87 (1967).

[51] Howe-Grant M., Wu K.C., Bauer W.K., Lippard S.J., Binding of Platinum and Palladium Metallo Intercalation Reagents and Antitumor Drugs to Closed and Open DNAs, Biochemistry, 15(19), p.4339 (1976).