IJOC  Vol.3 No.4 , December 2013
A Fluorescence Ratiometric Probe for Cysteine/Homocysteine and Its Application for Living Cell Imaging
ABSTRACT

A fluorescence ratiometric probe 1 for cysteine (Cys) and homocysteine (Hcy) has been rationally constructed based on intramolecular charge transfer (ICT) mechanism. Upon treatment with Cys/Hcy, probe 1 exhibited a fluorescence ratiometric response, with the emission wavelength displaying a large shift (from 526 nm to 446 nm). When 90 μM Cys were added, the emission ratios (I446/I526) of the probe changed dramatically from 0.01797 to 4.65472. The detection limit was also measured to be 0.18 μM (S/N = 3). The theoretical calculations have confirmed that the ratiometric response of probe 1 to Cys/Hcy is due to the inhibition of ICT process upon the reaction of probe 1 with Cys/Hcy. Furthermore, the fluorescence imaging experiments in living cell demonstrated that probe 1 was favourable for intracellular Cys/Hcy imaging.


Cite this paper
L. Long, L. Wang and Y. Wu, "A Fluorescence Ratiometric Probe for Cysteine/Homocysteine and Its Application for Living Cell Imaging," International Journal of Organic Chemistry, Vol. 3 No. 4, 2013, pp. 235-239. doi: 10.4236/ijoc.2013.34033.
References
[1]   Z. A. Wood, E. Schroder, J. R. Harris and L. B. Poole, “Structure, Mechanism and Regulation of Peroxiredoxins,” Trends in Biochemical Sciences, Vol. 28, No. 1, 2003, pp. 32-40.
http://dx.doi.org/10.1016/S0968-0004(02)00003-8

[2]   S. Shahrokhian, “Lead Phthalocyanine as a Selective Carrier for Preparation of a Cysteine-Selective Electrode,” Analytical Chemistry, Vol. 73, No. 24, 2001, pp. 5972-5978.
http://dx.doi.org/10.1021/ac010541m

[3]   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,” The New England Journal of Medicine, Vol. 346, No. 7, 2002, pp. 476-483.
http://dx.doi.org/10.1056/NEJMoa011613

[4]   X. Chen, T. Pradhan, F. Wang, J. S. Kim and J. Yoon, “Fluorescent Chemosensors Based on Spiroring-Opening of Xanthenes and Related Derivatives,” Chemical Reviews, Vol. 112, No. 3, 2012, pp. 1910-1956.
http://dx.doi.org/10.1021/cr200201z

[5]   H. S. Jung, X. Chen, J. S. Kim and J. Yoon, “Recent Progress in Luminescent and Colorimetric Chemosensors for Detection of Thiols,” Chemical Society Reviews, Vol. 42, No. 14, 2013, pp. 6019-6031.
http://dx.doi.org/10.1039/c3cs60024f

[6]   D. Srikun, E. W. Miller, D. W. Domaille and C. J. Chang, “An ICT-Based Approach to Ratiometric Fluorescence Imaging of Hydrogen Peroxide Produced in Living Cells,” Journal of the American Chemical Society, Vol. 130, No. 14, 2008, pp. 4596-4597.
http://dx.doi.org/10.1021/ja711480f

[7]   K. Kikuchi, H. Takakusa and T. Nagano, “Recent Advances in the Design of Small Molecule-Based FRET Sensors for Cell Biology,” TrAC, Trends in Analytical Chemistry, Vol. 23, No. 6, 2004, pp. 407-415.
http://dx.doi.org/10.1016/S0165-9936(04)00608-9

[8]   C. S. Lim, G. Masanta, H. J. Kim, J. H. Han, H. M. Kim and B. R. Cho, “Ratiometric Detection of Mitochondrial Thiols with a Two-Photon Fluorescent Probe,” Journal of the American Chemical Society, Vol. 133, No. 29, 2011, pp. 11132-11135.
http://dx.doi.org/10.1021/ja205081s

[9]   G. Kim, K. Lee, H. Kwon and H. Kim, “Ratiometric Fluorescence Imaging of Cellular Glutathione,” Organic Letters, Vol. 13, No. 11, 2011, pp. 2799-2801.
http://dx.doi.org/10.1021/ol200967w

[10]   S. Lim and H. Kim, “Ratiometric Detection of Cysteine by a Ferrocenyl Michael Acceptor,” Tetrahedron Letters, Vol. 52, No. 25, 2011, pp. 3189-3190.
http://dx.doi.org/10.1016/j.tetlet.2011.03.153

[11]   L. Niu, Y. Guan, Y. Chen, L. Wu, C. Tung and Q. Yang, “BODIPY-Based Ratiometric Fluorescent Sensor for Highly Selective Detection of Glutathione Over Cysteine and Homocysteine,” Journal of the American Chemical Society, Vol. 134, No. 46, 2012, pp. 18928-18931.
http://dx.doi.org/10.1021/ja309079f

[12]   P. Das, A. K. Mandal, N. B. Chandar, M. Baidya, H. B. Bhatt, B. Ganguly, S. K. Ghosh and A. Das, “New Chemodosimetric Reagents as Ratiometric Probes for Cysteine and Homocysteine and Possible Detection in Living Cells and in Blood Plasma,” Chemistry—A European Journal, Vol. 18, No. 48, 2012, pp. 15382-15393.
http://dx.doi.org/10.1002/chem.201201621

[13]   L. Long, W. Lin, B. Chen, W. Gao and L. Yuan, “Construction of a FRET-Based Ratiometric Fluorescent Thiol Probe,” Chemical Communications, Vol. 47, No. 3, 2011, pp. 893-895. http://dx.doi.org/10.1039/c0cc03806g

[14]   Z. Guo, S. Nam, S. Park and J. Yoon, “A Highly Selective Ratiometric Near-Infrared Fluorescent Cyanine Sensor for Cysteine with Remarkable Shift and Its Application in Bioimaging,” Chemical Science, Vol. 3, No. 9, 2012, pp. 2760-2765.
http://dx.doi.org/10.1039/c2sc20540h

[15]   H. Li, J. Xu and H. Yan, “Ratiometric Fluorescent Determination of Cysteine Based on Organic Nanoparticles of Naphthalene-Thiourea-Thiadiazole-Linked Molecule,” Sensors and Actuators B, Vol. 139, No. 2, 2009, pp. 483-487. http://dx.doi.org/10.1016/j.snb.2009.03.028

[16]   X. Zeng, X. Zhang, B. Zhu, H. Jia and Y. Li, “A Highly Selective Wavelength-Ratiometric and Colorimetric Probe for Cysteine,” Dyes and Pigments, Vol. 94, No.1, 2012, pp. 10-15. http://dx.doi.org/10.1016/j.dyepig.2011.10.013

[17]   O. Rusin, N. N. S. Luce, R. A. Agbaria, J. O. Escobedo, S. Jiang, I. M. Warner, F. B. Dawan, K. Lian and R. M. Strongin, “Visual Detection of Cysteine and Homocysteine,” Journal of the American Chemical Society, Vol. 126, No. 2, 2004, pp. 438-439.
http://dx.doi.org/10.1021/ja036297t

[18]   T. Kim, D. Lee and H. Kim, “Highly Selective Fluorescent Sensor for Homocysteine and Cysteine,” Tetrahedron Letters, Vol. 49, No. 33, 2008, pp. 4879-4881.
http://dx.doi.org/10.1016/j.tetlet.2008.06.003

[19]   B. Zhu, C. Gao, Y. Zhao, C. Liu, Y. Li, Q. Wei, Z. Ma, B. Du and X. Zhang, “A4-Hydroxynaphthalimide-derived ratiometric Fluorescent Chemodosimeter for Imaging Palladium in Living Cells,” Chemical Communications, Vol. 47, No. 30, 2011, pp. 8656-8658.
http://dx.doi.org/10.1039/c1cc13215f

[20]   C. R. Yellaturu, M. Bhanoori, I. Neeli and G. N. Rao, “N-Ethylmaleimide Inhibits Platelet-Derived Growth Factor BB-Stimulated Akt Phosphorylation via Activation of Protein Phosphatase 2A,” The Journal of Biological Chemistry, Vol. 277, No. 42, 2002, pp. 40148-40155.
http://dx.doi.org/10.1074/jbc.M206376200

 
 
Top