Fluorescence and electrochemical recognition of nucleosides and DNA by a novel luminescent bioprobe Eu(lll) -TNB

Journal of Fluorescence

Volumn 22, Issue 3, 2012, Pages 971-992

  Azab, Hassan A ^a   Mogahed, E M ^a   Awad, F K ^a   El Aal, R M Abd ^a   Kamel, Rasha M ^a  

^a SUEZ CANAL UNIVERSITY   (Egypt)

Author keywords

Adenosine; Cytidine; DNA; Europium TNB; Glassy carbon electrode; Guanosine; Inosine; Time resolved luminescence; Voltammetry

Indexed keywords

ADENOSINE; CYTIDINE; EUROPIUM-TNB; GLASSY CARBON ELECTRODES; GUANOSINES; INOSINE; TIME-RESOLVED LUMINESCENCE;

CYCLIC VOLTAMMETRY; DNA; EUROPIUM; FLUORESCENCE; GLASS MEMBRANE ELECTRODES; IONIC STRENGTH; NAPHTHALENE; THERMOANALYSIS; VOLTAMMETRY;

BIOMOLECULES;

2,3 BUTANEDIONE; 4,4,4 TRIFLUORO 1 (2 NAPHTHYL)1,3 BUTANEDIONE; 4,4,4 TRIFLUORO-1-(2-NAPHTHYL)1,3-BUTANEDIONE; DNA; DRUG DERIVATIVE; EUROPIUM; FLUORESCENT DYE; NAPHTHALENE DERIVATIVE; NUCLEOSIDE; ORGANOMETALLIC COMPOUND;

ARTICLE; CHEMISTRY; ELECTROCHEMISTRY; FLUORESCENCE; LUMINESCENCE; METHODOLOGY; SYNTHESIS; THERMODYNAMICS;

DIACETYL; DNA; ELECTROCHEMISTRY; EUROPIUM; FLUORESCENCE; FLUORESCENT DYES; LUMINESCENT MEASUREMENTS; NAPHTHALENES; NUCLEOSIDES; ORGANOMETALLIC COMPOUNDS; THERMODYNAMICS;

TRIFLUORO;

EID: 84862226386     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-011-1036-7     Document Type: Article

References (88)

1. Jiao K, Wang QX, Sun W, Jian FF (2005) Synthesis, characterization and DNA-binding properties of a new cobalt(II) complex: Co (bbt)2Cl2. J Inorg Biochem 99:1369-1375 (Pubitemid 40726033)
2. Sigman DS, Graham DR, Aurora VD, Stern AM (1979) Oxygendependent cleavage of DNA by the 1, 10-phenanthroline. cuprous complex. Inhibition of Escherichia coli DNA polymerase I. J Biol Chem 254:12269-12272 (Pubitemid 10138153)
3. Yang ZS, Wang YL (2004) Electrochemically induced DNA cleavage by copper-bipyridyl complex. Electrochem Commun 6:158-163
4. Cater MT, Bard AJ (1987) Voltammetric studies of the interaction of tris(1, 10-phenanthroline)cobalt(III) with DNA. J Am Chem Soc 109:7528-7530
5. Kawanishi S, Inoue S, Sano S (1986) Mechanism of DNA cleavage induced by sodium chromate(VI) in the presence of hydrogen peroxide. J Biol Chem 261:5952-5958 (Pubitemid 17207430)
6. Chen QY, Li DH (1999) Interaction of a novel red-region fluorescent probe. Nile Blue, with DNA and its application to nucleic acids assay. Analyst 124:901-906
7. Li YF, Huang CZ, Huang XH (2001) Determination of DNA by its enhancement effect of resonance light scattering by azur A. Anal Chim Acta 429:311-319 (Pubitemid 32112699)
8. Wang J, Xu D, Kawde AN, Polsky R (2001) Metal nanoparticlebased electrochemical stripping potentiometric detection of DNA Hybridization. Anal Chem 73:5576-5581 (Pubitemid 33108570)
9. Wang H, Li WR, Lu Y, Fu NN, Zhang HS (2005) Vibrational frequencies and infrared intensities of the hydrogen-bonded complexes of nitrous acid with ethers: ab initio and DFT studies. Spectrochim Acta A 61:2103-2107
10. Zhang S, Zhong H, Ding C (2008) Chronocoulometric detection of DNA hybridization using reporter DNA probe modified with Au nanoparticles based on porous gold leaf electrode. Anal Chem 80:7206-7212
11. Zou QC, Yan QJ, Song GW, Zhang SL, Wu LM (2007) Detection of DNA using cationic polyhedral oligomeric silsesquioxane nanoparticles as the probe by resonance light technique. Biosens Bioelectron 22:1461-1465
12. Niu S, Singh G, Saraf RF (2007) Label-less fluorescence-based method to detect hybridization with applications to DNA microarray. Biosens Bioelectron 23:714-720 (Pubitemid 350101188)
13. Fernandez MR, Gonzalez MJV, Garcia MED (1997) Roomtemperature phosphorescent palladium-porphine probe for DNA determination. Anal Chem 69:2406-2410
14. Churchwell MI, Beland FA, Doerge DR (2002) Quantification of multiple DNA adducts formed through oxidative stress using liquid chromatography and electrospray tandem mass spectrometry. Chem Res Toxicol 15:1295-1301 (Pubitemid 35222199)
15. Hason S, Pivonkova H, Vetter V, Fojta M (2008) Label-free sequence-specific DNA sensing using copper-enhanced anodic stripping of purine bases at boron-doped diamond electrodes. Anal Chem 80:2391-2399 (Pubitemid 351499820)
16. Benedict JD, Forsham PH, Stetten D (1949) The metabolism of uric acid in the normal and gouty human studied with the aid of isotopic uric acid. J Biol Chem 181:183
17. Waslien CI, Calloway DH, Margen S (1968) Uric acid production of men fed graded amounts of egg protein and yeast nucleic acid. Am J Med 21:892
18. Griebsch A, Zollner N (1974) Effect of ribomononucleotides given orally on uric acid production in man. Adv Exp Med Biol 41:443
19. Garrel DR, Verdy M, PetitClerc C, Martin C, Bruke D, Hamet P (1991) Lowering of HDL2-cholesterol and lipoprotein A-I particle levels by increasing the ratio of polyunsaturated to saturated fatty acids. Am J Clin Nutr 53:665
20. Loffler W, Grobner W, Medina R, Zollner N (1982) Influence of dietary purines on pool size, turnover, and excretion of uric acid during balance conditions. Isotope studies using 15N-uric acid. Res Exp Med (Berl) 181:113
21. Yu TS, Berfe L, Gutman AB (1962) Renal function in gout. II. Efect of uric acid loading on renal excretion of uric acid. Am J Med 33:829
22. Choi HK, Liu S, Curhan G (2005) Intake of purine-rich foods, protein, and dairy products and relationship to serum levels of uric acid: the Third National Health and Nutrition Examination Survey. Arthritis Rheum 52:283
23. Harris MD, Siegel LB, Alloway JA (1999) Gout and hyperuricemia. Am Fam Physician 59:925
24. Gibson T, Rodgers AV, Simmonds HA, Court-Brown F, Todd E, Meilton V (1983) A controlled study of diet in patients with gout. Ann Rheum Dis 42:123
25. Faller J, Fox IH (1982) Ethanol-induced hyperuricemia: evidence for increased urate production by activation of adenine nucleotide turnover. N Engl J Med 307:1598
26. Cao G, Russel RM, Lischner N, Prior RL (1998) Serum antioxidant capacity is increased by consumption of strawberries, spinach, red wine or vitamin C in elderly women. J Nutr 128:2383
27. Yamaoka N, Kaneko K, Kudo Y, Aoki M, Yasuda M, Mawatari K, Yamada Y, Yamamoto T (2010) Analysis of purine in purine-rich cauliflower. Nucleos Nucleot Nucleic Acids 29:518
28. Clifford AJ, Riumallo JA, Young VR, Scrimshaw NS (1976) Effect of oral purines on serum and urinary uric acid of normal. Hyperuricemic and gouty humans. J Nutr 106:428
29. QianbT CZ, Yang MS (2004) Determination of adenosine nucleotides in cultured cells by ion-pairing liquid chromatographyelectrospray ionization mass spectrometry. Anal Biochem 325:77
30. Cordell RL, Hill SJ, Ortori CA, Barrett DA (2008) Quantitative profiling of nucleotides and related phosphate-containing metabolites in cultured mammalian cells by liquid chromatography tandem electrospray mass spectrometry. J Chromatogr B 871:115
31. Cai Z, Song F, Yang MS (2002) Capillary liquid chromatographichigh- resolution mass spectrometric analysis of ribonucleotides. J Chromatogr A 976:135
32. Vela JE, Olson LY, Huang A, Fridland A, Ray AS (2007) Simultaneous quantitation of the nucleotide analog adefovir, its phosphorylated anabolites and 2'-deoxyadenosine triphosphate by ionpairing LC/MS/MS. J Chromatogr B 848:335
33. Carli D, Honorat M, Cohen S, Megherbi M, Vignal B, Dumontet C, Payen L, Guitton J (2009) Simultaneous quantification of 5-FU, 5-FUrd, 5-FdUrd, 5-FdUMP, dUMP and TMP in cultured cell models by LCMS/MS. J Chromatogr B 877:2937
34. De Abreu RA, Van Baal JM, De Bruyn CH, Bakkeren JA, Schretlen ED (1982) Investigation of catecholamine metabolism using high-performance liquid chromatography. J Chromatogr 229:67
35. Klawitter J, Schmitz V, Klawitter J, Leibfritz D, Christians U (2007) Development and validation of an assay for the quantification of 11 nucleotides using LC/LC-electrospray ionization-MS. Anal Biochem 365:230
36. Gill BD, Indyk HE (2007) Determination of nucleotides and nucleosides in milks and pediatric formulas: a review. J AOAC Int 90:1354
37. Crauste C, Lefebvre I, Hovaneissian M, Puy JY, Roy B, Peyrottes S, Cohen S, Guitton J, Dumontet C, Perigaud C (2009) Validation and long-term evaluation of a modified on-line chiral analaytical method for therapeutic drug monitoring of (R, S)-methadone in clinical samples. J Chromatogr B 877:1417
38. Elbanovski M, Makowska B (1996) The lanthanides as luminescent probes in investigations of biochemical systems J. Photochem Photobiol A 99:85
39. Gudgin Dickson EF, Pollak A, Diamandis EP (1995) Timeresolved detection of lanthanide luminescence for ultrasensitive bioanalytical assays. J Photochem Photobiol B 27:3
40. Lis S, Elbanowski M, Makowska B, Hnatejko Z (2002) Energy transfer in solution of lanthanide complexes. Photobiology A 150:233
41. Azab HA, Anwar ZM, Ahmed RG (2010) Pyrimidine and purine mononucleotides recognition by trivalent lanthanide complexes with N-acetyl amino acids. J Chem Eng Data 55(1):459-475
42. Azab HA, El-Korashy SA, Anwar ZM, Hussein BHM, Khairy GM (2010) Synthesis and fluorescence properties of Eu-anthracene-9-carboxylic acid towards N-acetyl amino acids and nucleotides in different solvents. Spectrochim Acta A Mol Biomol Spectrosc 75:21-27
43. Azab HA, AboElNour KM, Sherif S (2007) Metal ion complexes containing di-, tripeptides and biologically important zwitterionic buffers. J Chem Eng Data 52:381-390 (Pubitemid 46480675)
44. Azab HA, El-Korashy SA, Anwar ZM, Hussein BHM, Khairy GM (2010) Eu(lll)-anthracene-9-carboxylic acid as a responsive luminescent bioprobe and its electroanalytical Interactions with Nacetyl amino acids, nucleotides and DNA. J Chem Eng Data 55:3130-3141
45. Azab HA, Abd El-Gawad II, Kamel RM (2009) Ternary complexes formed by the fluorescent probe Eu (III)-9-anthracene carboxylic acid with pyrimidine and purine nucleobases. J Chem Eng Data 54:3069-3078
46. Filip W, Mojmir S, Li AX, Azab HA, Bartha R, Hudson RHE (2007) A robust and convergent synthesis of dipeptides-DOTAM conjugates as chelators for lanthanide ions: new PARACEST MRI agents. Bioconjug Chem 18(5):1625-1636 (Pubitemid 47464073)
47. Orabi AS, Azab HA, ElDeghidy FS, Said H (2010) Ternary complexes of La(III), Ce(III), Pr(III) or Er(III) with adenosine 5'-mono, 5'-di, and 5'-triphosphate as primary ligands and some biologically important zwitterionic buffers as secondary ligands. J Solution Chem 39:319-334
48. Azab HA, Al-Deyab SS, Anwar ZM, Gharib RA (2011) Fluorescence and electrochemical probing of N-acetylamino acids, nucleotides and DNA by Eu(lll) -bathophenanthroline complex. J Chem Eng Data 56(4):833-849
49. Azab HA, Al-Deyab SS, Anwar ZM, Kamel RM (2011) Potentiometric, electrochemical and fluorescence study of the coordination properties of the monomeric and dimeric complexes of Eu(lll) with nucleobases and PIPES. J Chem Eng Data 56:1960-1969
50. Azab HA, Al-Deyab SS, Anwar ZM, Abd El-Gawad II, Kamel RM (2011) Comparison of the coordination tendency of amino acids, Nucleobases or mononucleotides towards the monomeric and dimeric lanthanide complexes with biologically important compounds. J Chem Eng Data 56:2613-2625
51. Bates GR, Roy NR, Robinson AR (1964) Determination of pH: theory and practice. Wiley, New York
52. Gran G (1952) Determination of the equivalence point in potentiometric titration part II. Analyst 77:661
53. May PM, Williams DR (1985) Computational methods for the determination of Formation Constants. In: Leggett DJ (ed). Plenum Press, New York, pp. 37-70.
54. Bjerrum J (1941) Metal amine complex formation in aqueous solution. Haase, Copenhagen
55. Irving H, Rossotti HS (1953) Methods for computing successive stability constants from experimental formation curves. J Chem Soc 3397.
56. De Stefano C, Princi P, Rigano C, Sammartano S (1987) Computer analysis of equilibrium data in solution. ESAB2M: An improved version of the ESAB program. Ann Chim (Rome) 77:643
57. Gans P, Vacca AJ (1996) Investigation of equilibria in solution. Determination of equilibrium constants with the HYPERQUAD suite of programs. Talanta 43:1739
58. Kumar CV, Turner RS, Asunction EH (1993) Groove binding of a styrylcyanine dye to the DNA double helix: the salt effect. J Photochem Photobiol A Chem 74:231-238
59. Son GS, Yeo JA, Kim JM, Kim SK, Moon HR, Nam W (1998) Base specific complex formation of norfloxacin with DNA. Biophys Chem 74:225-236 (Pubitemid 28454655)
60. Palu G, Valisena G, Ciarrocchi G, Gatto B, Palumbo M (1992) Quinolone binding to DNA is mediated by magnesium ions. Proc Natl Acad Sci USA 89:9671
61. Ocaña JA, Barragán FJ, Callejon M (2004) Fluorescence and terbium sensitised luminescence determination of garenoxacin in human urine and serum. Talanta 63:691
62. Teixeira LS, Grasso AN, Monteiro AM, Neto AMF, Vieira ND, Gidlund M, Courrol LC (2010) Enhancement on the europium emission band of europium chlortetracycline complex in the presence of LDL. Anal Biochem 400:19
63. Lakowicz JR (1999) Principles of fluorescence spectroscopy, 2nd edn. Plenum Press, New York, pp. 87, 95, 237-249, 331.
64. Benesi HA, Hildebrand JH (1949) Spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J Am Chem Soc 71:2703
65. Wei XF, Liu HZ (2000) The interaction between Triton X-100 and bovine serum albumin. Chin J Anal Chem 28:699
66. Kang J, Liu Y, Xie M, Li S, Jiang M, Wang Y (2004) Interactions of human serum albumin with chlorogenic acid and ferulic acid. Biochim Biophys Acta 1674:205
67. Ross PD, Subranmanian S (1981) Thermodynamics of protein association reactions-forced contributing to stability. Biochemistry 20:3096
68. Martin RB, Mariam YH (1979) Interactions between metal ions and nucleic bases, nucleosides, and nucleotides in solution. Met Ions Biol Syst 8:57
69. Martin RB (1985) Nucleoside sites for transition metal ion binding. Accounts Chem Res 18:32
70. Patterson GS, Holm RH (1972) Effects of chelate ring substituents on the polarographic redox potentials of tris(β-diketonato)ruthenium( II, III) complexes. Inorg Chem 11:2285
71. Takeuchi T, Endo A, Shimizu K, Sato GP (1985) Electrochemical oxidation of tris(β-diketonato)-ruthenium(III) in acetonitrile solutions at platinum electrodes. J Electroanal Chem 185:185
72. Collman JP (1965) Reactions of metal acetylacetonates. Angew Chem Int Ed Engl 4:132
73. Brad AJ, Faulkner LR (1980) Electrochemical methods. Fundamentals and applications. Wiley, New York, 218
74. Oliveria-Brett AM, Piedade JAP, Silva LA, Diculescu VC (2004) Voltammetric determination of all DNA nucleotides. Anal Biochem 332:321
75. Neidle S, Balasubramanian S (2006) Quadruplex nucleic acids. RSC Publishing, Cambridge
76. Huppert JL (2008) Four-stranded nucleic acids: structure, function and targeting of G-quadruplexes. Chem Soc Rev 37:1375-1384
77. Burge S, Parkinson GN, Hazel P, Todd AK, Neidle S (2006) Quadruplex DNA: sequence, topology and structure. Nucleic Acids Res 34:5402-5415 (Pubitemid 44742430)
78. Patel DJ, Phan AT, Kuryavyi V (2007) Human telomere, oncogenic promoter and 5'-UTR G-quadruplexes: diverse higher order DNA and RNA targets for cancer therapeutics. Nucleic Acids Res 35:7429-7455
79. Parkinson GN, Lee MP, Neidle S (2002) Crystal structure of parallel quadruplexes from human telomeric DNA. Nature 417:876-880 (Pubitemid 34670337)
80. Haider S, Parkinson GN, Neidle S (2002) Crystal structure of the potassium form of an Oxytricha nova G-quadruplex. J Mol Biol 320:189-200 (Pubitemid 34722211)
81. Haider SM, Parkinson GN, Neidle S (2003) Structure of a Gquadruplex-ligand complex. J Mol Biol 326:117-125
82. Phan AT, Kuryavyi V, Burge S, Neidle S, Patel DJ (2007) Structure of an unprecedented G-quadruplex scaffold in the human c-kit promoter. J Am Chem Soc 129:4386-4392 (Pubitemid 46595454)
83. Schaffitzel C, Berger I, Postberg J, Hanes J, Lipps HJ, Plückthun A (2001) In vitro generated antibodies specific for telomeric guaninequadruplex DNA react with Stylonychia lemnae macronuclei. Proc Natl Acad Sci USA 98:8572-8577 (Pubitemid 32678069)
84. Paeschke K, Simonsson T, Postberg J, Rhodes D, Lipps HJ (2005) Telomere end-binding proteins control the formation of Gquadruplex DNA structures in vivo. Nat Struct Mol Biol 12:847-854 (Pubitemid 41486707)
85. Oganesian L, Bryan TM (2007) Physiological relevance of telomeric G-quadruplex formation: a potential drug target. Bioessays 29:155-165 (Pubitemid 46340250)
86. De Cian A, Grellier P, Mouray E, Depoix D, Bertrand H, Monchaud D, Teulade-Fichou MP, Mergny JL, Alberti P (2008) Plasmodium telomeric sequences: structure, stability and quadruplex targeting by small compounds. Chembiochem 9:2730-2739
87. Balasubramanian S, Neidle S (2009) G-quadruplex nucleic acids as therapeutic targets. Curr Opin Chem Biol 13:345-353
88. Baraldi PG, Tabrizi MA, Preti D, Fruttarolo F, Avitabile B, Bovero A, Pavani G, Carretero MCN, Romagnoli R (2003) DNA minorgroove binders. Design, synthesis, and biological evaluation of ligands structurally related to CC-1065, distamycin, andanthramycin. Pure Appl Chem 75:187-194