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http://dx.doi.org/10.5764/TCF.2015.27.4.261

Charge Transfer Dye Probe for Thiol-containing Amino Acid  

Shin, In Sub (Graduate School of Environment and Information Sciences, Yokohama National University)
Gwon, Seon Yeong (Department of Textile System Engineering, Kyungpook National University)
Matsumoto, Shinya (Graduate School of Environment and Information Sciences, Yokohama National University)
Kim, Sung Hoon (Department of Textile System Engineering, Kyungpook National University)
Publication Information
Textile Coloration and Finishing / v.27, no.4, 2015 , pp. 261-269 More about this Journal
Abstract
Two new D-${\pi}$-A dyes were synthesized by the condensation reaction between active methyl and aromatic aldehyde and its biothiol sensing properties in DMSO/water were investigated by UV-vis spectroscopy. Upon addition of $Hg^{2+}$, the solution of D-${\pi}$-A dyes showed color change and the absorption band shows a formation of a dye-$Hg^{2+}$ coordination complex. These dyes exhibited high selectivity for $Hg^{2+}$ as compared with other cations. The dye-$Hg^{2+}$ could be recovered by adding glutathion(GSH). The absorption intensity of dye-$Hg^{2+}$ increased only by the addition of glutathione(GSH). The competition experiments revealed that no obvious interference was observed by performing the titration with the mixture of glutathione(GSH) and other amino acids. The results indicated that these D-${\pi}$-A dyes were highly selective for glutathione(GSH) detection.
Keywords
cysteine(Cys); glutathione(GSH); homocysteine(Hcy); biothiol sensing; D-${\pi}$-A dyes;
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1 S. H. Lee, J. Kumar, and S. K. Tripathy, Thin Film Optical Sensors Employing Polyelectrolyte Assembly, Langmuir, 16, 10482(2000).   DOI
2 Y. Lio, R. C. Mills, J. M. Boncella, and K. S. Schanze, Fluorescent Polyacetylene Thin Film Sensor for Nitroaromatics, Langmuir, 17, 7452(2001).   DOI
3 T. A. Dickinson, J. White, J. S. Kauer, and D. R. Walt, A Chemical-detecting System Based on a Cross-reactive Optical Sensor Array, Nature, 382, 697(1996).   DOI
4 J. S. Bae, S. Y. Gwon, and S. H. Kim, Anthraquinone- carbamodithiolate Assembly as Selective Chromogenic Chemosensor for $Fe^{3+} $, Textile Coloration and Finishing, 25(1), 13(2013).   DOI
5 Y. A. Son and S. H. Kim, Anthraquinone and Indole based Chemosensor for Fluoride Anions Detection, Textile Coloration and Finishing, 26(1), 1(2014).   DOI
6 D. G. Myszka, Improving Biosensor Analysis, J. Mol. Recognit., 12, 279(1999).   DOI
7 J. Liu and Y. Lu, A Colorimetric Lead Biosensor Using DNAzyme-Directed Assembly of Gold Nanoparticles, J. Am. Chem. Soc., 125, 6642(2003).   DOI
8 J. B. Schulz, J. Lindenau, J. Seyfried, and J. Dichgans, Glutathione, Oxidative Stress and Neurodegeneration, European J. of Biochemistry, 267, 4904 (2000).   DOI
9 S. Seshadri, A. Beiser, J. Selhub, P. F. Jacques, I. H. Rosenberg, R. B. D. Agostino, P. W. F. Wilson, and P. A. Wolf, Plasma Homocysteine as a Risk Factor for Dementia and Alzheimer's Disease, New Engl. J. Med., 346, 476(2002).   DOI
10 R. O. Ball, G. C. Martin, and P. B. Pencharz, The In Vivo Sparing of Methionine by Cysteine in Sulfur Amino Acid Requirements in Animal Models and Adult Humans, J. Nutr, 136, 1682S (2006).   DOI
11 R. Hong, G. Han, J. M. Fernandez, B. J. Kim, N. S. Forbes, and V. M. Rotello, Glutathione-Mediated Delivery and Release Using Monolayer Protected Nanoparticle Carriers, J. Am. Chem. Soc., 128, 1078(2006).   DOI
12 S. Shahrokhian, Lead Phthalocyanine as a Selective Carrier for Preparation of a Cysteine-Selective Electrode, Anal. Chem., 73, 5972(2001).   DOI
13 H. Refsum, P. M. Ueland, O. Nygard, and S. E. Vollset, Homocysteine and Cardiovascular Disease, Annual Review of Medicine, 49, 31(1998).   DOI
14 J. B. Schulz, J. Lindenau, J. Seyfried, and J. Dichgans, Glutathione, Oxidative Stress and Neurodegeneration, Eur. J. Biochem., 267, 4904(2000).   DOI
15 Z. A. Wood, E. Schroder, J. R. Harris, and L. B. Poole, Structure, Mechanism and Regulation of Peroxiredoxins, Trends Biochem. Sci., 28, 32(2003).   DOI
16 I. S. Shin, S. Y. Gwon, and S. H. Kim, Chromogenic Sensing of Biological Thiols Using Squarylium Dye, Dyes and Pigments, 120, 642(2014).
17 L. E. Khairy, P. M. Ueland, H. Refsum, I. M. Graham, and S. E. Vollset, Plasma Total Cysteine as a Risk Factor for Vascular Disease, Circulation, 103, 2544(2001).   DOI
18 B. S. V. Asbeck, J. Hoidal, G. M. Vercellotti, B. A. Schwartz, C. F. Moldow, and H. S. Jacob, Protection against Lethal Hyperoxia by Tracheal Insufflation of Erythrocytes: Role of Red Cell Glutathione, Science, 227, 756(1985).   DOI
19 V. P. Wellner, M. E. Anderson, R. N. Puri, G. L. Jensen, and A. Meister, Radioprotection by Glutathione Ester: Transport of Glutathione Ester into Human Lymphoid Cells and Fibroblasts, Proceedings of Natl. Acad. Sci., USA, Vol.81, p.4732, 1984.   DOI
20 L. H. Lash, T. M. Hagen, and D. P. Jones, Exogenous Glutathione Protects Intestinal Epithelial Cells from Oxidative Injury, Proceedings of Natl. Acad. Sci., USA, Vol.83, p.4641, 1986.   DOI
21 Y. Suzuki and K. Yokoyama, Design and Synthesis of Intramolecular Charge Transfer-Based Fluorescent Reagents for the Highly-Sensitive Detection of Proteins, J. Am. Chem. Soc., 127, 17799(2005).   DOI
22 L. Yuanyuan, W. Fangfang, L. Yan, H. Song, and Z. Xianshung, Novel Mercury Sensor based on Water Soluble Styrylindolium Dye, Dyes and Pigments, 96, 424(2013).   DOI