Synthesis of novel Eu(III) luminescent probe based on 9-acridinecarboxylic acid skelton for sensing of ds-DNA

Journal of Fluorescence

Volumn 22, Issue 2, 2012, Pages 639-649

  Azab, Hassan A ^a   Hussein, Belal H M ^a   El Falouji, Abdullah I ^b  

^a Suez Canal University   (Egypt)

^b SUEZ CANAL UNIVERSITY   (Egypt)

Author keywords

Ds DNA; Eu(III) 9 acridinecarboxylate; Luminescent probe; Nucleotides

Indexed keywords

CALF THYMUS DNA; CARBONYL GROUPS; CONDUCTIVITY MEASUREMENTS; DETECTION LIMITS; DIPHOSPHATES; EFFECT OF PH; EU COMPLEXES; EXPERIMENTAL CONDITIONS; FLUORESCENCE INTENSITIES; GUANOSINES; INOSINE; LINEAR RANGE; LUMINESCENT PROBES; MASS SPECTROSCOPY; MONOPHOSPHATES; STABILITY CONSTANTS;

COORDINATION REACTIONS; DNA; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; MASS SPECTROMETRY; NUCLEOTIDES; PH EFFECTS; PROBES; THERMOANALYSIS; ULTRAVIOLET SPECTROSCOPY;

EUROPIUM;

ACRIDINE DERIVATIVE; CALF THYMUS DNA; COORDINATION COMPOUND; DNA; EUROPIUM; LUMINESCENT AGENT;

ANIMAL; ARTICLE; CATTLE; CHEMICAL STRUCTURE; CHEMISTRY; SPECTROFLUOROMETRY; SYNTHESIS;

ACRIDINES; ANIMALS; CATTLE; COORDINATION COMPLEXES; DNA; EUROPIUM; LUMINESCENT AGENTS; MOLECULAR STRUCTURE; SPECTROMETRY, FLUORESCENCE;

EID: 84862235738     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-011-1000-6     Document Type: Article

References (62)

1. Erkkila KE, Odom DT, Barton JK (1999) Recognition and reaction of metallointercalators with DNA. Chem Rev 99:2777-2796
2. Jakupec MA, Unfried P, Keppler BK (2005) Pharmacological properties of cerium compound. Rev Physiol Biochem Pharmacol 153:101-11
3. Di GC, De MM, Chiron J, Delmas F (2005) Synthesis and antileishmanial activities of 4, 5-di-substituted acridines as compared to their 4-mono-substituted homologues. Bioorg Med Chem 13:5560-5568
4. Rauf S, Gooding J, Akhtar K, Ghauri M, Rahman M, Anwar M, Khalid A (2005) Electrochemical approach of anticancerdrugs-DNA interaction. J Pharm Biomed Anal 37:205-217
5. Gamage S, Tepsiri N, Wilairat P, Wojcik S, Figgit D, Ralph R, Denny W (1994) Synthesis and in vitro evaluation of 9-anilino-3, 6-diaminoacridines active against a multidrug-resistant strain of the malaria parasite plasmodium falciparum. J Med Chem 37:1486-1494 (Pubitemid 24174086)
6. Gamage SA, Figgit DP, Wojcik SJ, Ralph RK, Ransijn A, Mauel J, Yardly V, Snowdon D, Croft SL, Denny WA (1997) Structure -activity relationships for the antileishmanial and antitrypanosomal activities of 1'-substituted 9-anilinoacridines. J Med Chem 40:2634-2642 (Pubitemid 27347028)
7. Mauel J, Denny WA, Gamage SA, Ransijn A, Wojcik SL, Figgit DP, Ralph R (1993) 9-anilinoacridines as potential antileishmanial agents. Antimicrob Agents Chemother 37:991-996 (Pubitemid 23141309)
8. Rewcastle GW, Atwell GJ, Chambers D, Baguley BC, Denny WA (1986) Potential antitumor agents. 46. Structure-activity relationships for acridine monosubstituted derivatives of the antitumor agent N-[2-(dimethylamino)ethyl]-9- aminoacridine-4-carboxamide. J Med Chem 29:472-477 (Pubitemid 16034763)
9. Li J, Wei Y, Guo L, Zhang C, Jiao Y, Shuang S, Dong C (2008) Study on spectroscopic characterization of Cu porphyrin/ Co porphyrin and their interactions with ctDNA. Talanta 76:34-39
10. Ni Y, Lin D, Kokot S (2008) Synchronous fluorescence and UV-vis spectroscopic studies of interactions between the tetracycline antibiotic, aluminium ions and DNAwith the aid of the Methylene Blue dye probe. Anal Chim Acta 606:19-25 (Pubitemid 350212838)
11. Araya F, Huchet G, McGroarty I, Skellern GS, Waigh RD (2007) Capillary electrophoresis for studying drug-DNA interactions. Methods 42:141-149 (Pubitemid 46654813)
12. Sandstrom K, Warmlander S, Leijon M, Graslund A (2003) 1H NMR studies ofselective interactions of norfloxacin with doublestranded DNA. Biochem Biophys Res Commun 304:55-59 (Pubitemid 36434193)
13. Wang L, Lin L, Ye B (2006) Electrochemical studies of the interaction of the anticancer herbal drug emodin with DNA. J Pharm Biomed Anal 42:625-629 (Pubitemid 44636093)
14. Atwell GJ, Rewcastle GW, Baguley BC, Denny WA (1987) Potential antitumor agents. 50. In vivo solid-tumor activity of derivatives of N-[2-(dimethylamino) ethyl]acridine-4-carboxamide. J Med Chem 30:664-669 (Pubitemid 17065201)
15. Graves DE, Velea LM (2000) Intercalative binding of small molecules to nucleic acids. Curr Org Chem 4:915-929
16. Atwell GJ, Cain BF, Baguley BC, Finlay GJ, Denny WA (1984) Potential antitumor agents. Part 43. Synthesis and biological activity of dibasic 9-aminoacridine-4-carboxamides, a new class of antitumor agent. J Med Chem 27:1481-1485 (Pubitemid 15200571)
17. Bi S, Zhang H, Qiao C, Sun Y, Liu C (2008) Studies of interaction of emodin and DNA in the presence of ethidium bromide by spectroscopic method. Spectrochim Acta 69:123-129 (Pubitemid 350297060)
18. Sabolova D, Kozurkova M, Kristian P, Danihel I, Podhradsky D, Imrich J (2006) Determination of the binding affinities of plasmid DNA using fluorescent intercalators possessing an acridine skeletonInt. J Biol Macromol 38:94-98
19. Liu R, Yang J, Sun C, Li L, Wu X, Li Z, Qi C (2003) Study of the interaction of nucleic acids with acridine orange-CTMAB and determination of nucleic acids at nanogram levels based on the enhancement of resonance light scattering. Chem Phys Lett 376:108-115 (Pubitemid 36860504)
20. Liu SP, Chen S, Liu ZF, Hu XL, Shan T (2005) Resonance Rayleigh scattering spectra of interaction of sodium carboxymethylcellulose with cationic acridine dyes and their analytical applications. Anal Chim Acta 535:169-175 (Pubitemid 40410509)
21. Wang M, Yang J, Wu X, Huang F (2000) Study of the interaction of nucleic acids with acridine red and CTMAB by a resonance light scattering technique and determination of nucleic acids at nanogram levels. Anal Chim Acta 422:151-158
22. Azab HA, Anwar ZM, Ahmed RG (2010) Pyrimidine and purine mononucleotid es recognition by trivalent lanthanide complexes with N-acetyl amino acids. J Chem Eng Data 55:459-475
23. Azab HA, El-Korashy SA, Anwar ZM, Hussein BHM, Khairy GM (2010) Synthesis and fluorescence properties of Euanthracene-9-carboxylic acid towards Nacetylamino acids and nucleotides in different solvents. Spectrochim Acta Part A 75:21-27
24. Azab HA, Abd El-Gwad II, Kamel RM (2009) Ternary complexes formed by the fluorescent probe Eu(III)-anthracene-9-carboxylic acid with pyrimidine and purine nucleobases. J Chem Eng Data 54:3069-3078
25. 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
26. Azab HA, Al-Deyab SS, Anwar ZM, Gharib RA (2011) Fluorescence and electrochemical probing of N-acetylamino acids, nucleotides and DNA by Eu(III)-bathophenanthroline complex. J Chem Eng Data 56:833-849
27. 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(III) with Nucleobases and PIPES. J Chem Eng Data 56:1960-1969
28. 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
29. Ali R, Saleh SM, Meier RJ, Azab HA, Abdelgawad II, Wolfbeis OS (2010) Upconverting nanoparticle based optical sensor for carbon dioxide. Sensors and Actuators B 150:126-131
30. Liu XW, Li J, Li H, Zheng KC, Chao H, Ji LN (2005) Synthesis, characterization, DNA-binding and photocleavage of complexes [Ru(phen)2(6-OH-dppz)]2+ and [Ru(phen)2(6-NO2-dppz)]2+. J Inorg Biochem 99:2372-2380
31. Kumar CV, Asuncion EH (1993) DNA binding studies and site selective fluorescence sensitization of an anthryl probe. J Am Chem Soc 115:8547-8553
32. Welcher FJ (1965) The analytical uses of ethylene diaminetetraacetic acid. D. Von Nostrand Co., Inc., Princeton
33. Hart FA, Laming FP (1964) Complexes of 1, 10-phenanthroline with lanthanide chlorides and thiocyanates. J Inorg Nucl Chem 26:579-585
34. Wang Y, Wang Y, Yang ZY (2007) Synthesis, characterization and DNA-binding studies of 2-carboxybenzaldehydeisonicotinoylhydrazone and its La(III), Sm(III) and Eu(III) complexes. Spectrochim Acta A 66:329-334 (Pubitemid 46027681)
35. Nakamoto K (1986) Infrared and Raman spectra of inorganic and coordination compounds. Wiley, New York
36. Deacon GB, Phillips RJ (1980) Relationships between the carbonoxygen stretching frequencies of carboxylato complexes and the type of carboxylate coordination. Coord Chem Rev 33:227-250
37. Ryu CK, Endicott JF (1988) Synthesis, spectroscopy, and photophysical behavior of mixed-ligand mono-and bis(polypyridyl) chromium(III) complexes. Examples of efficient, thermally activated excited-state relaxation without back intersystem crossing. Inorg Chem 27:2203-2214
38. Choppin GR, Peterman DR (1998) Applications of lanthanide luminescence spectroscopy to solution studies of coordination chemistry. Coord Chem Rev 174:283-299 (Pubitemid 128452113)
39. Fischer G, Naaman R (1976) Near Resonance vibronic coupling. Isoquinoline J Chem Phys 12:367-379
40. Schulman SG (1977) Fluorescence and phosphorescence spectroscopy: Physicochemical principles and practice. Pergamon, New York, p 60
41. Pasternack RF, Gibbs EJ, Villafranca JJ (1983) Interactions of porphyrins with nucleic acids. Biochemistry 22:2406-2414 (Pubitemid 13093549)
42. Ling LS, He ZK, Chen F, Chen F, Zeng YE (2003) Singlemismatch detection using nucleic acid molecular 'light switch'. Talanta 59:269-275
43. Kumar CV, Barton JK, Turro NJ (1985) Photophysics of ruthenium complexes bound to double helical DNA. J Am Chem Soc 107:5518-5523
44. Xu H, Zheng KC, Chen Y, Li YZ, Lin LJ, Li H, Zhang PX, Ji LN (2003) Effects of ligand planarity on the interaction of polypyridyl Ru(II) complexes with DNA. Dalton Trans 11:2260-2268
45. Hirohama T, Kuranuki Y, Ebina E, Sugizaki T, Arii H, Chikira M, Selvi PT, Palaniandavar M (2005) Copper(II) complexes of 1, 10-phenanthroline-derived ligands: Studies on DNA binding properties and nuclease activity. J Inorg Biochem 99:1205-1219
46. Barton JK, Danishefsky A, Goldberg J (1984) Tris (phenanthroline) ruthenium(II): stereoselectivity in binding to DNA. J Am Chem Soc 106:2172-2176 (Pubitemid 14568819)
47. Benesi HA, Hildebrand JH (1949) A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J Am Chem Soc 71:2703-2707
48. 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 1674:205-214 (Pubitemid 40125392)
49. Elbanovski M, Makowska B (1996) The lanthanides as luminescent probes in investigations of biochemical systems. J Photochem Photobiol A 99:85
50. Gudgin Dickson EF, Pollak A, Diamandis EP (1995) Timeresolved detection of lanthanide luminescence for ultrasensitive bioanalytical assays. J Photochem Photobiol B 27:3
51. Lis S, Elbanowski M, Makowska B, Hnatejko Z (2002) Energy transfer in solution of lanthanide complexes. Photobiology A 150:233
52. Lepecq JB, Paoletti C (1966) A new fluorometric method for RNA and DNA determination. Anal Biochem 17:100-107
53. Labara C, Paigen K (1980) A simple, rapid, and sensitive DNA assay procedure. Anal Biochem 102:344-352 (Pubitemid 10115803)
54. Li WY, Xu JG, Guo XQ, Zhu QZ, Zhao YB (1997) A novel fluorometric method for DNA and RNA determination. Anal Lett 30:527-536
55. Li WY, Xu JG, Guo XQ, Zhu QZ, Zhao YB (1997) Application of vitamin K3 as a photochemical fluorescence probe in the determination of nucleic acids. 30:245-257
56. Huang CZ, Li KA, Tong SY (1996) Fluorescent complexes of nucleic acids/8-hydroxyqulnollne/lanthanum(III) and the fluorometry of nucleic acids. Anal Lett 29:1705-1717 (Pubitemid 126452296)
57. Huang CZ, Li KA, Tong SY (1997) Spectrofluorimetric determination of nucleic acids with aluminum(III)/8-hydroxyquinoline complex. Anal Lett 30:1305-1319 (Pubitemid 27482007)
58. Ci YX, Li YZ, Chang WB (1991) Fluorescence reaction of terbium(III) with nucleic acids in the presence of phenanthroline. Anal Chim Acta 248:589-594
59. Wu X, Yang J, Huang F, Wang M, Sun L, Xu G (1999) Study of the reaction between nucleic acids and Tb-BPMPHD-CTMAB complex and its analytical application. Anal Lett 32:2417-2425 (Pubitemid 29455901)
60. 3+-benzoylacetone-cetyltrimethylammonium bromide-nucleic acid system. J Fluorescence 15:655-660 (Pubitemid 41795588)
61. 3+ and its analytical application. J Luminescence 96:201-209 (Pubitemid 34222945)
62. Haugland RP (Ed.) (2003) Handbook of Fluorescent Probes and Research Products. Molecular Probes 9:301-304