Reactions of Zn2+, Cd2+ and Hg2+ with Free Adenine
DOI:
https://doi.org/10.6000/1929-5030.2013.02.02.1Keywords:
Adenine, Group 12, Fluorescence, IR, Raman, NMR, Potentiometry, SpeciationAbstract
We are reporting the fluorescence quenching, IR, Raman, 1H-NMR, and potentiometric studies for the Zn2+:adenine and the Cd2+:adenine systems under ambient conditions. IR and Raman spectra suggest that Zn2+ and Cd2+ interact with adenine but the modes of interaction differ. Fluorescence spectra indicate that the interaction involving Zn2+ is more favorable than that of Cd2+, and this effect is due to the difference in ionic radii. 1H-NMR, potentiometry, and speciation diagrams indicate the formation of strong metal ion adenine complexes. Potentiometric titrations of the heavier member of group 12 metals (Hg2+) show similar results to that of Zn2+ and Cd2+. Some differences in the 1H-NMR experiments appeared between both (Zn2+ and Cd2+) compared to that of Hg2+. Due to the fluorescence quenching of adenine, adenine can be used as a sensor of Zn2+ and Cd2+.References
[1] Verma S, Mishra AK, Kumar J. The many facets of adenine: coordination, crystal patterns, and catalysis. Acct Chem Res 2010; 43: 1-79. http://dx.doi.org/10.1021/ar9001334
[2] Ghose R. Metal Complexation with Adenine and Thymine. Synth React Inorg Met-Org Chem 1992; 22:4-379.
[3] Lanir A, Yu N-T. A Raman spectroscopic study of the interaction of divalent metal ions with adenine moiety of adenosine 5'-triphosphate. J Biol Chem 1979; 254: 13-5882.
[4] Hamada YZ, Greene JT, Shields V, Pratcher M, Gardiner S, Waddell E, et al. Spectroscopic and potentiometric studies of the interaction of adenine with trivalent metal ions. J Coord Chem 2010; 63: 2-284. http://dx.doi.org/10.1080/00958970903377279
[5] Mishima A, Kaji T, Yamamoto C, Sakamoto M, Kozuka H. Zinc-induced tolerance to cadmium cytotoxicity without metallothionein induction in cultured bovine aortic endothelial cells. Toxicol Lett 1995; 75: 85. http://dx.doi.org/10.1016/0378-4274(94)03164-3
[6] Shipman MA, Price C, Gibson AE, Elsegood MRJ, Clegg W, Houlton A. Monomer dimer tetramer polymer: structural diversity in zinc and cadmium complexes of chelate-tethered nucleobases. Chem Eur J 2000; 6: 23-4371. http://dx.doi.org/10.1002/1521- 3765(20001201)6:23<4371::AID-CHEM4371>3.0.CO;2-X
[7] Kaji T, Mishima A, Koyanagi E, Yamamoto C, Sakamoto M, Kozuka H. Possible mechanism for zinc protection against cadmium cytotoxicity in cultured vascular endothelial cells. Toxicology 1992; 76: 3-257. http://dx.doi.org/10.1016/0300-483X(92)90194-J
[8] Tek JW, Owski TP, Siorowski KG. Differential pulsepolarographic approach to zinc(II)- and cadmium(II)-DNA systems. Inorg Chimi Acta 1987; 138: 1-79.
[9] Beringhelli T, Freni H, Morazzoni F, Romiti P, Servida R. Spectroscopic and spectromagnetic study of adenosine chloroderivatives of bivalent Co, Ni, Cu, Zn, Cd. Comparison with the corresponding adenine chloroderivatives. Spectrochimica Acta part A: Mol Spectrosc 1981; 37: 9-763. http://dx.doi.org/10.1016/0584-8539(81)80078-5
[10] Saha N, Sigel H. Ternary complexes in solution as models for enzyme-metal ion-substrate complexes. Comparison of the coordination tendency of imidazole and ammonia toward the binary complexes of Mn(II), Co(II), Ni(II), Cu(II), Zn(II), or Cd(II) and uridine 5-triphosphate or adenosine 5- triphosphate. J Am Chem Soc 1982; 104: 4100. http://dx.doi.org/10.1021/ja00379a010
[11] Sponer J, Sabat M, Burda JV, Leszczynski J, Hobza P. Interaction of the adenine-thymine Watson-Crick and adenine-adenine reverse-Hoogsteen and DNA base pairs with hydrated group IIA (Mg2+, Ca2+, Sr2+, Ba2+) and IIB (Zn2+, Cd2+, Hg2+) metal cations: Absence of the base pair stabilization by metal-induced polarization effects. J Phys Chem B 1999; 103: 2528. http://dx.doi.org/10.1021/jp983744w
[12] Mamardashvili GM, Berezin BD. Interaction of porphyrins with adenine and adenosine complexes. Effect of a metal nature. Russian J Coord Chem 2006; 32: 4-276. http://dx.doi.org/10.1134/S1070328406040087
[13] Gasowska A, Lomozik L. Investigation of the solution structure of Cu(II) mixed-ligand complexes of adenosine 5- monophosphate and cytidine 5-monophosphate and polyamines. J Coord Chem 2001; 52: 4-375. http://dx.doi.org/10.1080/00958970108028185
[14] Qian L, Sun Z, Gao J, Movassagh B, Morales L, Mertes KB. Structural Aspects of the Dephosphorylation of Adenosine Triphosphate Catalyzed by Polyammonium Macrocycles. J Coord Chem 1991; 23: 1-155. http://dx.doi.org/10.1080/00958979109408248
[15] Mikulski CM, Minutella R, De Franco N, Borges Jr.G, Renn A, Karayannis NM. Adenosine N(1)-Oxide Complexes with Divalent 3d Metal Perchlorates. J Coord Chem 1989; 20: 1- 39. http://dx.doi.org/10.1080/00958978909408846
[16] Alderighi L, Dominguez S, Gans P, Midollini S, Sabatini A, Vacca A. Beryllium binding to adenosine 5'-phosphates in aqueous solution at 25o C. J Coord Chem 2009; 62: 1-14. http://dx.doi.org/10.1080/00958970802474862
[17] Strasak M, Durcova Z. Spectroscopic studies of metal ion mediated interactions with components of nucleic acids. I, ESR study of ternary copper(II) complexes of -amino acids and dipeptides with adenosine. J Coord Chem 1990; 22: 2- 99. http://dx.doi.org/10.1080/00958979009410032
[18] Mohan MS, Khan MMT. Ternary complexes of transition metal ions with adenosine 5'-triphosphate and 1,10- phenanthorline. J Coord Chem 1979; 8: 4-207. http://dx.doi.org/10.1080/00958977908076499
[19] Jarzebowska RB, Lomozik L. Interactions of cadmium(II) ions with adenosine as well as adenosine-5'-mono phosphate and diamine or triamines in the ternary systems. J Coord Chem 2007; 60: 23-2567.
[20] Al-Najjar AA, Mohamed MMA, Shoukry MM. Interaction of dipropyltin(IV) with amino acids, peptides, dicarboxylic acids and DNA constituents. J Coord Chem 2006; 59: 2-193. http://dx.doi.org/10.1080/00958970500270786
[21] Mohamed MMA, Shehata MR, Shoukry MM. Trimethyltin(IV) complexes with some selected DNA constituents. J Coord Chem 2001; 53: 2-125. http://dx.doi.org/10.1080/00958970108022607
[22] Li Q, Yang P, Hua E, Tian C. Diorganotin(IV) antitumor agents. Aqueous and solid-state coordination chemistry of nucleotides with R2SnCl2. J Coord Chem 1996; 40: 3-227. http://dx.doi.org/10.1080/00958979608024347
[23] Operschall BP, Bianchi EM, Griesser R, Sigel H. Influence of decreasing solvent polarity (1,4-dioxane/water mixtures) onthe stability and structure of complexes formed by copper(II), 2,2'-bipyridine or 1,10-phenanthroline and guanosine 5'- diphosphate: evaluation of isomeric equilibria. J Coord Chem 2009; 62: 1-23. http://dx.doi.org/10.1080/00958970802474888
[24] Arrambide G, Gambino D. Synthesis and spectroscopic characterization of hydroxylamido/amino acid complexes of oxovanadium(V). J Coord Chem 2009; 62: 1-63. http://dx.doi.org/10.1080/00958970802474821
[25] Kazuo N. Infrared and Raman Spectra of Inorganic and Coordination Compounds, 5th ed. New York: Wiley & Sons 1977; (Part B): pp. 120-187.
[26] Silverstine RM, Clayton BG, Terence CM. Spectroscopic Identification of Organic Compounds, in Ultraviolet Spectrometry, 5th ed. New York: John Wiley & Sons 1991; pp. 289-315.
[27] Martell AE, Smith RM, Motekaitis RJ. Critical Stability Constants Database, Version 6.0, NIST; Texas A & M University, College Station, TX, USA 2001.
[28] Hamada YZ, Bayakly N, George D, Greer T. Speciation of molybdenum(VI)-citric acid complexes in aqueous solutions. Synth React Inorg Met-Orga Nano-Met Chem 2008; 38: 664.
[29] Hamada YZ, Roger C. Interaction of L-3,4- dihydroxyphenylalanine (L-DOPA) as a coordinating ligand wwith a series of metal ions; reaction of L-DOPA. J Coord Chem 2007; 60: 20-2149. http://dx.doi.org/10.1080/00958970701256634
[30] Hamada YZ, Bayakly N, Peipho A, Carlson B. Accurate potentiometric studies of chromium-citrate and ferric citrate complexes in aqueous solutions at physiological and alkaline pH values. Synth React Inorg Met-Orga Nano-Met Chem 2006; 36: 469.
[31] Hamada YZ, Harris WR. Stability constants and multinuclaer NMR measurements of phosphonic acid derivatives with aluminum in aqueous solutions. Inorg Chim Acta 2006; 359: 4-1135. http://dx.doi.org/10.1016/j.ica.2005.11.027
[32] Mathlouthi M, Seuvre A, Koenig JL. F.t.-i.r. and laser-Raman spectra of adenine and adenosine. Carbohydr Res 1984; 131: 1. http://dx.doi.org/10.1016/0008-6215(84)85398-7
[33] Golcuk K, Altun A, Kumru M. Thermal studies and vibrational analyses of m-methylaniline complexes of Zn(II), Cd(II) and Hg(II) bromides. Spectrochimica Acta Part A 2003; 59: 1841. http://dx.doi.org/10.1016/S1386-1425(02)00415-8
[34] Torreggiani A, Esposti AD, Tamba M, Marconi G, Fini G. Experimental and theoretical Raman investigation on interactions of Cu(II) with histamine. J Raman Spec 2006; 37: 291. http://dx.doi.org/10.1002/jrs.1431
[35] Wu SP, Ding BL, Wu JB, Jiang ZQ. Fluorescence quenching study on the interaction of bases of nucleic acid with electron-accepting sensitizer and serum albumin containing electron-rich tryptophan residue. Res Chem Intermed 2000; 26(Suppl 7/8): 727.
[36] Williams NJ, Gan W, Reibenspies JH, Hancock RD. Possible steric control of the relative strength of chelation enhanced fluorescence for zinc(II) compared to cadmium(II): metal ion complexing properties of tris(2-quinolylmethyl)amine, a crystallographic, UV-visible, and fluorometric study. Inorg Chem 2009; 48: 4-1407. http://dx.doi.org/10.1021/ic801403s
[37] Joshi BP, Park J, Lee WI, Lee KH. Ratiometric and turn-on monitoring for heavy and transition metal ions in aqueous solution with a fluorescent peptide sensor. Talanta 2009; 78: 903. http://dx.doi.org/10.1016/j.talanta.2008.12.062
[38] Al-Kady AS, Gaber M, Hussein MM, Ebeid EZM. Fluorescence Enhancement of Coumarin Thiourea Derivatives by Hg2+, Ag+ , and Silver Nanoparticles. J Phys Chem A 2009; 113: 9474. http://dx.doi.org/10.1021/jp905566z
[39] Baes CF, Mesmer RE. The hydrolysis of cations, New York: Wiley and Sons 1967.
[40] Alderighi L, Gans P, Ienco A, Perters D, Sabatini A, Vacca A. Hyperquad simulation and speciation (HySS): a utility program for the investigation of equilibria involving soluble and partially soluble species. Coord Chem Rev 1999; 184: 311. http://dx.doi.org/10.1016/S0010-8545(98)00260-4
[41] Huang X-H, Lu Y, He YB, Chen ZH. A Metal–Macrocycle Complex as a Fluorescent Sensor for Biological Phosphate Ions in Aqueous Solution. Eur J Org Chem 2010; 10: 1921. http://dx.doi.org/10.1002/ejoc.200901328
[42] Aravind P, Prasad MNV. Modulation of cadmium-induced oxidative stress in Ceratophyllum demersum by zinc involves ascorbate-glutathione cycle and glutathione metabolism. Plant Physiol Biochem 2005; 43: 107. http://dx.doi.org/10.1016/j.plaphy.2005.01.002
[43] Daniels PJ, Bittel D, Smirnova IV, Winge DR, Andrews GK. Mammalian metal response element-binding transcription factor-1 functions as a zinc sensor in yeast, but not as a sensor of cadmium or oxidative stress. Nucleic Acids 2002; 30: 3130. http://dx.doi.org/10.1093/nar/gkf432
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2013-05-24
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Hamada, Y. Z., Burkey, T., Waddell, E., Aitha, M., & Phambu, N. (2013). Reactions of Zn2+, Cd2+ and Hg2+ with Free Adenine. Journal of Applied Solution Chemistry and Modeling, 2(2), 77–84. https://doi.org/10.6000/1929-5030.2013.02.02.1
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