14
X. Zeng et al. / Dyes and Pigments 94 (2012) 10e15
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pyrroloquinoline quinone modified electrode. Analytical Chemistry 2000;
72(23):5755e60.
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nanoparticles with tunable length for electrocatalysis and electrochemical
determination of thiols. Chemical Communications; 2009:4530e2.
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agent) and Cys was added to the solution of 1, as expected, no
obvious changes in the absorption spectra was observed (Fig. 8),
implying the reaction of 1 to thiol of Cys. Next, to further confirm
the reaction of 1 with Cys by the SNArBr, the product of SNArBr
between 2-aminoethanethiol (to facilitate the purification of thiol
adduct, 2-aminoethanethiol substituted for Cys.) and 1 was isolated
and characterized by 1H-NMR, 13C-NMR, and HRMS [47]. Thus,
combined with the previous study [45], a possible mechanism was
proposed as shown in Scheme 1.
[16] Fei SD, Chen JH, Yao SZ, Deng GH, He DL, Kuang YF. Electrochemical behavior
of L-cysteine and its detection at carbon nanotube electrode modified with
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cysteine and glutathione complexes of bismuth by mass spectrometry:
assessing the biochemical fate of bismuth pharmaceutical agents. Chemical
Communications; 2003:146e7.
4. Conclusions
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throughput and simultaneous measurement of homocysteine and cysteine in
human plasma and urine by liquid chromatographyeelectrospray tandem
mass spectrometry. Analytical Biochemistry 2007;371(1):71e81.
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fluorescent probe for thiol bioimaging. Organic Letters 2008;10(1):37e40.
[20] Tanaka F, Mase N, Barbas III CF. Determination of cysteine concentration by
In summary, we have described a new probe molecule which
exhibits excellent Cys-selectivity over GSH and other amino acids,
and a 58 nm red-shift of absorption spectrum accompanied with
the color change from colorless to yellow upon reaction with Cys.
The probe could be used for the quantification of Cys by both
normal and ratiometric absorption spectrometry methods with the
working range covering the physiological level of Cys in normal
organisms, and also by “naked-eye” with a minimum detectable
fluorescence increase: reaction of cysteine with
Chemical Communicaiton; 2004:1762e3.
a fluorogenic aldehyde.
[21] Lin WY, Long LL, Yuan L, Cao ZM, Chen BB, Tan W. A ratiometric fluorescent
probe for cysteine and homocysteine displaying
a large emission shift.
concentration of approximately 50 mM. These present results may
Organic Letters 2008;10(24):5577e80.
provide a useful approach for the development of colorimetric
probe for Cys and other thiol-containing amino acids, especially for
their ratiometric detection.
[22] Zhang M, Li MY, Zhao Q, Li FY, Zhang DQ, Zhang JP, et al. Novel Y-type two-
photon active fluorophore: synthesis and application in fluorescent sensor
for cysteine and homocysteine. Tetrahedron Letters 2007;48(13):2329e33.
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cysteine and cysteine in water. Chemical Communications; 2008:6173e5.
[24] Zeng Y, Zhang GX, Zhang DQ. A selective colorimetric chemosensor for thiols
based on intramolecular charge transfer mechanism. Analytica Chimica Acta
2008;627(2):254e7.
Acknowledgments
This work was supported by the National Nature Science
Foundation of China (No. 20975012) and the 111 Project (B07012).
[25] Guo Y, Shao SJ, Xu J, Shi YP, Jiang SX. A specific colorimetric cysteine sensing
probe based on dipyrromethaneeTCNQ assembly. Tetrahedron Letters 2004;
45(34):6477e80.
[26] Zhang XH, Li C, Cheng XX, Wang XS, Zhang BW. A near-infrared croconium
dye-based colorimetric chemodosimeter for biological thiols and cyanide
anion. Sensors and Actuators B 2008;129(1):152e7.
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