황원자를 함유한 아미노산 검출용 전하이동형 색소에 관한 연구

DOI QR코드

DOI QR Code

신인섭;권선영;마츠모토 신야;김성훈
Shin, In Sub;Gwon, Seon Yeong;Matsumoto, Shinya;Kim, Sung Hoon

  • 투고 : 2015.10.07
  • 심사 : 2015.11.26
  • 발행 : 2015.12.27

초록

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.

키워드

cysteine(Cys);glutathione(GSH);homocysteine(Hcy);biothiol sensing;D-${\pi}$-A dyes

참고문헌

  1. S. H. Lee, J. Kumar, and S. K. Tripathy, Thin Film Optical Sensors Employing Polyelectrolyte Assembly, Langmuir, 16, 10482(2000). https://doi.org/10.1021/la0011836
  2. Y. Lio, R. C. Mills, J. M. Boncella, and K. S. Schanze, Fluorescent Polyacetylene Thin Film Sensor for Nitroaromatics, Langmuir, 17, 7452(2001). https://doi.org/10.1021/la010696p
  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). https://doi.org/10.1038/382697a0
  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). https://doi.org/10.5764/TCF.2013.25.1.13
  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). https://doi.org/10.5764/TCF.2014.26.1.1
  6. D. G. Myszka, Improving Biosensor Analysis, J. Mol. Recognit., 12, 279(1999). https://doi.org/10.1002/(SICI)1099-1352(199909/10)12:5<279::AID-JMR473>3.0.CO;2-3
  7. J. Liu and Y. Lu, A Colorimetric Lead Biosensor Using DNAzyme-Directed Assembly of Gold Nanoparticles, J. Am. Chem. Soc., 125, 6642(2003). https://doi.org/10.1021/ja034775u
  8. J. B. Schulz, J. Lindenau, J. Seyfried, and J. Dichgans, Glutathione, Oxidative Stress and Neurodegeneration, European J. of Biochemistry, 267, 4904 (2000). https://doi.org/10.1046/j.1432-1327.2000.01595.x
  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). https://doi.org/10.1056/NEJMoa011613
  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). https://doi.org/10.1093/jn/136.6.1682S
  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). https://doi.org/10.1021/ja056726i
  12. S. Shahrokhian, Lead Phthalocyanine as a Selective Carrier for Preparation of a Cysteine-Selective Electrode, Anal. Chem., 73, 5972(2001). https://doi.org/10.1021/ac010541m
  13. H. Refsum, P. M. Ueland, O. Nygard, and S. E. Vollset, Homocysteine and Cardiovascular Disease, Annual Review of Medicine, 49, 31(1998). https://doi.org/10.1146/annurev.med.49.1.31
  14. J. B. Schulz, J. Lindenau, J. Seyfried, and J. Dichgans, Glutathione, Oxidative Stress and Neurodegeneration, Eur. J. Biochem., 267, 4904(2000). https://doi.org/10.1046/j.1432-1327.2000.01595.x
  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). https://doi.org/10.1016/S0968-0004(02)00003-8
  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). https://doi.org/10.1161/01.CIR.103.21.2544
  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). https://doi.org/10.1126/science.2982213
  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. https://doi.org/10.1073/pnas.81.15.4732
  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. https://doi.org/10.1073/pnas.83.13.4641
  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). https://doi.org/10.1021/ja054739q
  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). https://doi.org/10.1016/j.dyepig.2012.09.010

과제정보

연구 과제 주관 기관 : 한국연구재단