Quenching of tryptophan and 4,4'-diaminostilbene fluorescence by dinitrophenyl ethers: Use of 1-allyloxy-2,4-dinitrobenzene, as a quencher

Romanian Biotechnological Letters

Volumn 16, Issue 1 SUPPL., 2011, Pages 130-140

  Rusu, Elena ^a   Airinei, A ^a   Tigoianu, R I ^a  

^a PETRU PONI INSTITUTE OF MACROMOLECULAR CHEMISTRY   (Romania)

Author keywords

1 allyoxy 2,4 dinitrobenzene; 4,4' diaminostilbene; Fluorescence quenching; Tryptophan

Indexed keywords

EID: 79952307031     PISSN: 12245984     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (42)

1. X.F. YAN, H.-M. XIAO, X.-D. GONG, X.-H. JU, Quantitative structure-activity relationships of nitroaromatics toxicity to the algae (Scenedesmus obliguus), Chemosphere, 59, 467-471 (2005)
2. A. UZER, E. ERCAG, H. PARLAR, R. APAKA, H. FILIK, Spectrophotometric determination of 4,6-dinitro-o-cresol (DNOC) in soil and lemon juice, Anal. Chim. Acta, 580, 83-90 (2006)
3. S. PALIWAL, M. WALESA, T. GOOD, J. GRIMSLEY, J. WILD, A. SIMONIAN, Fluorescence-based sensing of p-nitrophenol and p-nitrophenyl substituent organophosphates, Anal. Chim. Acta, 596, 9-15 (2007)
4. M. GRUBE, O. MUTER, S. STRIKAUSKA, M. GAVARE, B. LIMANE, Application of FT-IR for control of the medium composition during biodegradation of nitro aromatic compounds, J. Ind. Microbiol. Biotechnol., 35, 1545-1549 (2008)
5. J. ČERNOHLAVKOVA, J. JARKOVSKY, M. NESPOROVA, J. HOFMAN, Variability of soil microbial properties: Effects of sampling, handling and storage, Ecotoxicol. Environ. Saf., 72, 80-85 (2009).
6. S.C. NYBURG, C.H. FAERMAN, L. PRASAD, D. PALLEROS, N. NUDELMAN, Structures of 2,4-dinitroanisole and 2,6-dinitroanisole, Acta Cryst., C43, 686-689 (1987).
7. G. DROCHIOIU, Laser-Induced ATP Formation: Mechanism and Consequences, Photomed. Laser Surg., 28(4), 573-574 (2010)
8. C.A. DUMITRAS-HUTANU, A. PUI, S. JURCOANE, E. RUSU, G. DROCHIOIU, Biological effect and the toxicity mechanisms of some dinitrophenyl ethers, Roum. Biotechnol. Lett., 14(6), 4893-4899 (2009)
9. G. DROCHIOIU, A. ADOCHITEI, L. HABASESCU, G. ZBANCIOC, A. PUI, R. GRADINARU, E. RUSU, CD and FT-IR study of some adducts of albumin with toxic dinitrophenyl derivatives, Bull. Polytechnic Inst. Iaşi, Tom 55(4), 23-28, 2009.
10. W. ZHANG, C. R. WILSON, N.D. DANIELSON, Indirect fluorescent determination of selected nitro-aromatic and pharmaceutical compounds via UV-photolysis of 2-phenylbenzimidazole-5-sulfonate, Talanta, 74, 1400-1407 (2008).
11. X. WANG, H. ZENG, L. ZHAO, J.M. LIN, A selective optical chemical sensor for 2,6-dinitrophenol based on fluorescence quenching of a novel functional polymer, Talanta, 70, 160-168 (2006)
12. G.H. SHI, Z.B. SHANG, Y. WANG, W.J. JIN, T.C. ZHANG, Fluorescence quenching of CdSe quantum dots by nitroaromatic explosives and their relative compounds, Spectrochim. Acta, Part A, 70, 247-252 (2008)
13. R.C. STRINGER, S. GANGOPADHYAY, S.A. GRANT, Detection of Nitroaromatic Explosives Using a Fluorescent-Labeled Imprinted Polymer, Anal. Chem., 82, 4015-4019 (2010).
14. S. ZHANG, F. LU, L. GAO, L. DING, Y. FANG, Fluorescent Sensors for Nitroaromatic Compounds Based on Monolayer Assembly of Polycyclic Aromatics, Langmuir, 23, 1584-1590, (2007)
15. H. LI, J. KANG, L. DING, F. LU, Y. FANG, A dansyl-based fluorescent film: Preparation and sensitive detection of nitroaromatics in aqueous phase, J. Photochem. Photobiol. A: Chem., 197, 226-231 (2008)
16. R.M. MELAVANKI, R.A. KUSANUR, J.S. KADADEVARAMATH, M.V. KULAKARNI, Effect of Solvent Polarity on the Fluorescence Quenching of Biologically Active 5BAMC by Aniline in Binary Solvent Mixtures, J. Lumin., 129, 1298-1303 (2009).
17. W. ZHANG, C.R. WILSON, N.D. DANIELSON, Indirect fluorescent determination of selected nitro-aromatic and pharmaceutical compounds via UV-photolysis of 2-phenylbenzimidazole-5-sulfonate, Talanta, 74, 1400-1407 (2008)
18. J.V. GOODPASTER, V.L. MCGUFFIN, Fluorescence Quenching as a Novel Indirect Detection Method for Nitrated Explosives, Anal. Chem., 73, 2004-2011 (2001)
19. M.R. CARTER, R.C. BLAKE, T. D. NGUYEN, L. A. BOSTANIAN, Near real-time biosensor-based detection of 2,4-dinitrophenol, Biosens. Bioelectron., 18, 69-72 (2003).
20. L. CHEN, D.W. MCBRANCH, H.L. WANG, R. HELGESON, F. WUDL, D.G. WHITTEN, Highly sensitive biological and chemical sensors based on reversible fluorescence quenching in a conjugated polymer, PNAS 96, 12287-12292 (1999).
21. J.T. VIVIAN, P.R. CALLIS, Mechanisms of tryptophan fluorescence shifts in proteins, J. Biophys., 80, 2093-2109 (2001)
22. T. YUAN, A.M. WELJIE, H.J. VOGEL, Tryptophan fluorescence quenching by methionine and selenomethionine residues of calmodulin: orientation of peptide and protein binding, Biochem., 37, 3187-3195 (1998).
23. D.K. SMITH, L. MULLER, Dendritic biomimicry: microenvironmental effects on tryptophan fluorescence, Chem. Commun., 1915-1916 (1999)
24. O.K. GASYMOV, A.R. ABDURAGIMOV, T.N. YUSIFOV, B.J. GLASGOW, Resolution of ligand positions by site-directed tryptophan fluorescence in tear lipocalin, Protein Sci., 9, 325-331 (2000).
25. K.J. SMIT, K.P. GHIGGINO, Influence of solvent on the photochemistry of 4,4'-diaminostilbene, Chem. Phys. Lett., 122, (1985) 369-374
26. A.M. EL-TONI, S. YIN, T.J. SATO, Silica coating and photochemical properties of layered double hydroxide/4,4'-diaminostilbene-2,2'-disulfonic acid nanocomposite, Colloid Interface Sci., 293, 449-54 (2006)
27. M. SEYDACK, J. BENDING, The Anomalous Excited-State Temperature Behavior of trans-4,4'-Diaminostilbene and trans-4,4'-Di(phenyl-ureanyl)-stilbene, J. Phys. Chem. A, 105, 5731-5733 (2001).
28. E.B. de VARGAS, E.L. SETTI, M.L. AIMAR, R.H. de ROSSI, Hydrolysis of ethers of 2,4-dinitrophenol. No evidence for a single electron transfer mechanism, J. Org. Chem., 58, 7364-7367 (1993).
29. Y.J. KIM, I.S. CHUNG, S.Y. KIM, Synthesis of poly(phenylene oxide) containing trifluoromethyl groups via selective and sequential nucleophilic aromatic substitution reaction, Macromolecules, 36, 3809-3811 (2003).
30. J.R. LAKOWITCZ, Principles of Fluorescence Spectroscopy, third ed., Springer, New York, 2006
31. B. VALEUR, Molecular Fluorescence. Principles and Applications, Wiley-VCH, Weinhem, 2002
32. F.L. CUI, J.L. WANG, Y.R. CUI, J.P. LI, Fluorescent investigation of the interactions between N-(p-chlorophenyl)-N'-(1-naphthyl) thiourea and serum albumin: Synchronous fluorescence determination of serum albumin, Anal. Chim. Acta, 571, 175-183 (2006).
33. J.V. GRAZULEVICIUS, I. SOUTAR, L. SWANSON, Photophysics of carbazole-containing systems. Fluorescence of carbazole containing oligoethers in dilute solution, Macromolecules 31, 4820-4827 (1998)
34. B.G. EVALE, S.M. HANAGODIMATH, Effect of temperature and quencher on the fluorescence of 4-(5-methyl-3-furan-2-yl-benzofuran-2-yl)-7-methyl-chromen-2-one in different solvents, Spectrochim Acta Part A, 75, 1592-1599 (2010).
35. I.S. LEE, H. SUZUKI, Quenching Dynamics Promoted by Silver Nanoparticles, J. Photochrm. Photobiol. Part A: Chem., 195, 254-260 (2008).
36. L.A. SKLAR, B.S. HUDSON, R.D. SIMONI, Conjugated polyene fatty acids as fluorescent probes: binding to bovine serum albumin, Biochemistry, 16, 5100-5108 (1977).
37. B. VALEUR, J.C. BROCHON, New Trends in Fluorescence Spectroscopy, Springer, Berlin, 1999.
38. W.C. ABERT, W.M. GREGORY, G.S. ALLAN, The binding interaction of coomassie blue with proteins, Anal. Biochem., 213, 407-413 (1993)
39. A. VARLAN, M. HILLEBRAND, Study on the interaction of 2-carboxyphenoxathiin with bovine serum albumin and human serum albumin by fluorescence spectroscopy and circular dichroism, Rev. Roum. Chim., 55, 69-77 (2010).
40. A.F. JONES, J. LUNES, Protein fluorescence and its relationship to free radical activity, Br. J. Cancer, 55, Suppl. VIII, 60-65 (1987).
41. Y.J. HU, Y. LIN, Z.B. PI, S.S. QU, Interaction of cromolyn sodium with human serum albumin: A fluorescence quenching study, Bioorg. Med. Chem., 13, 6609-6614 (2005)
42. G. ZHANG, Y. WANG, H. ZHANG, S. TANG, W. TAO, Human serum albumin interaction with paraquat studied using spectroscopic methods, Pesticide Biochem. Physiol., 87, 23-29 (2007).