Flavone modified-β-cyclodextrin as a highly selective and efficient fluorescent chemosensor for Cu2+ ions and l-histidine

Sensors and Actuators, B: Chemical

Volumn 188, Issue , 2013, Pages 59-64

  Azath, Ismail Abulkalam ^a   Pitchumani, Kasi ^a  

^a MADURAI KAMARAJ UNIVERSITY   (India)

Author keywords

Aqueous medium; Copper (II) sensor; Flavone modified cyclodextrin; Fluorescent sensor; Histidine sensor

Indexed keywords

AQUEOUS MEDIUM; CYCLODEXTRIN CAVITIES; EMISSION SPECTRUMS; FLUORESCENCE ENHANCEMENT; FLUORESCENT CHEMOSENSOR; FLUORESCENT SENSORS; MODIFIED CYCLODEXTRINS; TURN-ON SENSORS;

AMINO ACIDS; CYCLODEXTRINS; EMISSION SPECTROSCOPY; FLAVONOIDS; FLUORESCENCE; METAL IONS; SENSORS;

COPPER COMPOUNDS;

EID: 84881309269     PISSN: 09254005     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.snb.2013.07.009     Document Type: Article

References (44)

1. Excellent review by Y. Zhou, J. Yoon, Recent progress in fluorescent and colorimetric chemosensors for detection of amino acids, Chemical Society Reviews 41 (2012) 52-67 and references therein.
2. T.E. Creighton Encyclopedia of Molecular Biology vol. 2 1999 Wiley New York 1147
3. J.D. Kopple, and M.E. Swendseid Evidence that histidine is an essential amino acid in normal and chronically uremic man Journal of Clinical Investigation 55 1975 881 891
4. G.N. Chen, X.P. Wu, J.P. Duan, and H.Q. Chen A study on electrochemistry of histidine and its metabolites based on the diazo coupling reaction Talanta 49 1999 319 330
5. Y. Kusakari, S. Nishikawa, S.-i. Ishiguro, and M. Tamai Histidine-like immunoreactivity in the rat retina Current Eye Research 16 1997 600 604
6. M. Watanabe, M.E. Suliman, A.R. Qureshi, E. Garcia-Lopez, P. Barany, O. Heimburger, P. Stenvinkel, and B. Lindholm Consequences of low plasma histidine in chronic kidney disease patients: associations with inflammation, oxidative stress, and mortality American Journal of Clinical Nutrition 87 2008 1860 1866 (Pubitemid 351872652)
7. A.L. Jones, M.D. Hulettand, and C.R. Parish Histidine-rich glycoprotein: a novel adaptor protein in plasma that modulates the immune, vascular and coagulation systems Immunology and Cell Biology 83 2005 106 118 (Pubitemid 40469318)
8. D.J. Sullivan Jr., I.Y. Gluzmanand, and D.E. Goldberg Plasmodium hemozoin formation mediated by histidine-rich proteins Science 271 1996 219 222
9. F.W.G. Leebeek, C. Kluft, E.A.R. Knot, and M.P.M. De Maat Histidine-rich glycoprotein is elevated in mild liver cirrhosis and decreased in moderate and severe liver cirrhosis Journal of Laboratory and Clinical Medicine 113 1989 493 497 (Pubitemid 19109409)
10. H. Saito, L.T. Goodnough, J.M. Boyleand, and N. Heimburger Reduced histidine-rich glycoprotein levels in plasma of patients with advanced liver cirrhosis. Possible implications for enhanced fibrinolysis American Journal of Medicine 73 1982 179 182 (Pubitemid 13203912)
11. J.K. Lim, Y. Kim, S.Y. Lee, and S.W. Joo Spectroscopic analysis of l-histidine adsorbed on gold and silver nanoparticle surfaces investigated by surface-enhanced Raman scattering Spectrochimica Acta A 69 2008 286 289 (Pubitemid 350297084)
12. J. Ruta, C. Grosset, C. Ravelet, J. Fize, A. Villet, A. Ravel, and E. Peyrin Chiral resolution of histidine using an anti-d-histidine l-RNA aptamer microbore column Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences 845 2007 186 190 (Pubitemid 46073914)
13. Colorimetric sensing: J.F. Folmer-Andersen, V.M. Lynch, E.V. Anslyn, Naked-eye detection of histidine by regulation of CuII coordination modes, Chemistry - A European Journal 11 (2005) 5319-5326. (Pubitemid 41285087)
14. Y.Y. Liu, M.G. Fan, S.X. Zhang, X.H. Sheng, and J.N. Yao Basic amino acid induced isomerization of a spiropyran: towards visual recognition of basic amino acids in water New Journal of Chemistry 31 2007 1878 1881
15. Examples of amino acid sensors: E.K. Feusterand, T.E. Glass, Detection of amines and unprotected amino acids in aqueous conditions by formation of highly fluorescent iminium ions, Journal of the American Chemical Society 125 (2003) 16174-16175. (Pubitemid 38020628)
16. A.T. Wright, and E.V. Anslyn Cooperative metal-coordination ion pairing in tripeptide recognition Organic Letters 6 2004 1341 1344 (Pubitemid 38626299)
17. J.-S. You, X.-Q. Yu, G.-L. Zhang, Q.-X. Xiang, J.-B. Lan, and R.G. Xie Novel chiral imidazole cyclophane receptors: synthesis and enantioselective recognition for amino acid derivatives Chemical Communications 2001 1816 1817 (Pubitemid 32906795)
18. W.-L. Wong, K.-A. Huang, P.-F. Teng, C.-S. Lee, and H.-L. Kwong A novel chiral terpyridine macrocycle as a fluorescent sensor for enantioselective recognition of amino acid derivatives Chemical Communications 2004 384 385 (Pubitemid 38270825)
19. L.-D. Li, Z.-B. Chen, H.-T. Zhao, and L. Guo Electrochemical real-time detection of l-histidine via self-cleavage of DNAzymes Biosensors and Bioelectronics 26 2011 2781 2785
20. J. Liang, Z. Chen, L. Guo, and L. Li Electrochemical sensing of l-histidine based on structure-switching DNAzymes and gold nanoparticle-graphene nanosheet composites Chemical Communications 47 2011 5476 5478
21. M.A. Hortala, L. Fabbrizzi, N. Marcotte, F. Stomeo, and A. Taglietti Designing the selectivity of the fluorescent detection of amino acids: a chemosensing ensemble for histidine Journal of the American Chemical Society 125 2003 20 21 (Pubitemid 36068628)
22. H. Li, J. Liu, Y. Fang, Y. Qin, S. Xu, Y. Liu, and E. Wang G-quadruplex-based ultrasensitive and selective detection of histidine and cysteine Biosensors and Bioelectronics 41 2013 563 568
23. 2+ ligand Organic & Biomolecular Chemistry 9 2011 4032 4034
24. 2+ specific triazole based calix[4] arene conjugate (L) as a fluorescence sensor for histidine and cysteine in HEPES buffer milieu Analyst 137 2012 4069 4075
25. Z. Huang, J. Du, J. Zhang, X.-Q. Yu, and L. Pu A simple and efficient fluorescent sensor for histidine Chemical Communications 48 2012 3412 3414
26. F. Hapiot, A. Ponchel, S. Tillowy, and E. Monflier Cyclodextrins and their applications in aqueous-phase metal-catalyzed reactions Comptes Rendus Chimie 14 2011 149 166
27. V. Ramamurthy Photochemistry in Organized and Constrained Media 1991 VCH, Publishers Cambridge, UK
28. S. Pagliari, R. Corradini, G. Galaverna, S. Sforza, A. Dossena, and R. Marchelli Enantioselective sensing of amino acids by copper(II) complexes of phenylalanine-based fluorescent β-cyclodextrins Tetrahedron Letters 41 2000 3691 3695 (Pubitemid 30322047)
29. R. Corradini, C. Paganuzzi, R. Marchelli, S. Pagliari, S. Sforza, A. Dossena, G. Galaverna, and A. Duchateau Design and synthesis of fluorescent β-cyclodextrins for the enantioselective sensing of α-amino acids Chirality 15 2003 S30 S39
30. R. Corradini, C. Paganuzzi, R. Marchelli, S. Pagliari, S. Sforza, A. Dossena, G. Galaverna, and A. Duchateau Fast parallel enantiomeric analysis of unmodified amino acids by sensing with fluorescent β-cyclodextrins Journal of Materials Chemistry 15 2005 2741 2746 (Pubitemid 41048669)
31. R. Corradini, C. Paganuzzi, R. Marchelli, S. Pagliari, A. Dossena, and A. Duchateau Fluorescent cyclodextrins bearing metal binding sites and their use for chemo- and enantioselective sensing of amino acid derivatives Journal of Inclusion Phenomena and Macrocyclic Chemistry 57 2007 625 630
32. R. Corradini, A. Dossena, G. Galaverna, R. Marchelli, A. Panagia, and G. Sartor Fluorescent chemosensor for organic guests and copper(II) ion based on dansyldiethylenetriamine-modified β-cyclodextrin Journal of Organic Chemistry 62 1997 6283 6289 (Pubitemid 27427591)
33. 3+ in water: colorimetric and ratiometric sensor based on per-6-amino-β-cyclodextrin/p-nitrophenol Sensors and Actuators B 146 2010 273 277
34. I.A. Azath, P. Suresh, and K. Pitchumani Per-6-ammonium-β- cyclodextrin/p-nitrophenol complex as a colorimetric sensor for phosphate and pyrophosphate anions in water Sensors and Actuators B 155 2011 909 912
35. K. Kanagaraj, A. Affrose, S. Sivakolunthu, and K. Pitchumani Highly selective fluorescent sensing of fenitrothion using per-6-amino-β- cyclodextrin:Eu(III) complex Biosensors and Bioelectronics 35 2012 452 455
36. V. Tharmaraj, and K. Pitchumani A highly selective ratiometric fluorescent chemosensor for Cu(II) based on dansyl-functionalized thiol stabilized silver nanoparticles Journal of Materials Chemistry 2013 10.1039/C3TB00534H
37. V. Tharmaraj, and K. Pitchumani An intramolecular charge transfer (ICT) based chemosensor for silver ion using 4-methoxy-N-((thiophen-2-yl)methyl) benzenamine Analyst 137 2012 5320 5324
38. D. Sriram, P. Yogeeswari, P. Dhakla, P. Senthilkumar, D. Banerjee, and T.H. Manjashetty 5-Nitrofuran-2-yl derivatives: synthesis and inhibitory activities against growing and dormant mycobacterium species Bioorganic and Medicinal Chemistry Letters 19 2009 1152 1154
39. D. Vizitiu, C.S. Walkinshaw, B.I. Gorin, and G.R.J. Thatcher Synthesis of monofacially functionalized cyclodextrins bearing amino pendent groups Journal of Organic Chemistry 62 1997 8760 8766 (Pubitemid 28013395)
40. M. Zhao, X.-F. Yang, S. He, and L. Wang A rhodamine-based chromogenic and fluorescent chemosensor for copper ion in aqueous media Sensors and Actuators B 135 2009 625 631
41. W. Lu, H. Jiang, F. Hu, L. Jiang, and Z. Shen A novel chemosensor based on Fe(III)-complexation for selective recognition and rapid detection of fluoride anions in aqueous media Tetrahedron 67 2011 7909 7912
42. S. Chandra, S. Raizada, and R. Verma Synthesis, characterisation and biological activities of copper(II) complexes with semicarbazones and thiosemicarbazones Journal of Chemical and Pharmaceutical Research 4 2012 1612 1618
43. A. Nakamura, S. Okutsu, Y. Oda, A. Ueno, and F. Toda Synthesis of a rhenium complex appending a cyclodextrin unit on a ligand Tetrahedron Letters 35 1994 7241 7244 (Pubitemid 24293156)
44. M.A. Mortellaro, and D.G. Nocera A supramolecular chemosensor for aromatic hydrocarbons Journal of the American Chemical Society 118 1996 7414 7415 (Pubitemid 26270636)