658
W. Dong et al. / Dyes and Pigments 96 (2013) 653e658
[16] Chen XQ, Zhou Y, Peng XJ, Yoon JY. Fluorescent and colorimetric probes for
detection of thiols. Chem Soc Rev 2010;39(6):2120e35.
[17] Rusin O, St Luce NN, Agbaria RA, Escobedo JO, Jiang S, Warner IM, et al.
Visual detection of cysteine and homocysteine. J Am Chem Soc 2004;126(2):
438e9.
[18] Wang WH, Rusin O, Xu XY, Kim KK, Escobedo JO, Fakayode SO, et al. Detection
of homocysteine and cysteine. J Am Chem Soc 2005;127(45):15949e58.
[19] Li HL, Fan JL, Wang JY, Tian MZ, Du JJ, Sun SG, et al. A fluorescent chemo-
dosimeter specific for cysteine: effective discrimination of cysteine from
homocysteine. Chem Commun 2009;39:5904e6.
Department (No. 2012JM2004) and the Education Department (No.
12JK0518) of Shaanxi Province of China.
Appendix A. Supplementary material
Supplementary data related to this article can be found at http://
[20] Tanaka F, Mase N, Barbas III CF. Determination of cysteine concentration by
fluorescence increase: reaction of cysteine with a fluorogenic aldehyde. Chem
Commun 2004;15:1762e3.
References
[21] Yuan L, Lin W, Yang Y. A ratiometric fluorescent probe for specific detection of
cysteine over homocysteine and glutathione based on the drastic distinction
in the kinetic profiles. Chem Commun 2011;47:6275e7.
[1] De Groote J, Van Steenbergen W. Paracetamol intoxication and N-acetyl-
cysteine treatment. Acta Gastro Enter Belg 1995;58:326e34.
[2] Pocernich CB, La Fontaine M, Butterfield DA. In-vivo glutathione elevation
protects against hydroxyl free radical-induced protein oxidation in rat brain.
Neurochem Int 2000;36(3):185e91.
[22] Lim S, Escobedo JO, Lowry M, Xu XY, Strongin R. Selective fluorescence
detection of cysteine and N-terminal cysteine peptide residues. Chem Com-
mun 2010;46(31):5707e9.
[3] Benrahmoune M, Therond P, Abedinzadeh Z. The reaction of superoxide
radical with N-acetylcysteine. Free Radic Biol Med 2000;29(8):775e82.
[4] Tzanavaras Paraskevas D. A green HPLC method for the determination of N-
acetylcysteine using post-column derivatization with methyl-propiolate.
Instrum Sci Technol 2012;40(2e3):150e60.
[23] Jiang W, Fu QQ, Fan HY, Ho J, Wang W. A highly selective fluorescent probe for
thiophenols. Angew Chem Int Ed 2007;46(44):8445e8.
[24] Yang XF, Guo YX, Strongin RM. Conjugate addition/cyclization sequence
enables selective and simultaneous fluorescence detection of cysteine and
homocysteine. Angew Chem Int Ed 2011;50(45):10690e3.
[5] Nozal MJ, Bernal JL, Toribio L, Marinero P, Moral O, Manzanas L, et al. Deter-
mination of glutathione, cysteine and N-acetylcysteine in rabbit eye tissues
using high performance liquid chromatography and post-column derivatiza-
tion with 5,50-dithiobis(2-nitrobenzoic acid). J Chromatogr A 1997;778(1e2):
347e53.
[6] Tsikas D, Sandmann J, Ikic M, Fauler J, Stichtenoth DO, Frölich JC. Analysis of
cysteine and N-acetylcysteine in human plasma by high-performance liquid
chromatography at the basal state and after oral administration of N-ace-
tylcysteine. J Chromatogr B Biomed Sci Appl 1998;708(1e2):55e60.
[7] Lu C, Liu GY, Jia JY, Gui YZ, Liu YM, Zhang MQ, et al. Liquid chromatography
tandem mass spectrometry method for determination of N-acetylcysteine in
human plasma using an isotope-labeled internal standard. Biomed Chroma-
togr 2011;25(4):427e31.
[25] Yang XF, Guo YX, Strongin RM. A seminaphthofluorescein-based fluorescent
chemodosimeter for the highly selective detection of cysteine. Org Biomol
Chem 2012;10(14):2739e41.
[26] Lindkvist B, Weinander R, Engman L, Koetse M, Engberts JB, Morgenstern R.
Glutathione transferase mimics: micellar catalysis of an enzymic reaction.
Biochem J 1997;323(1):39e43.
[27] Tang SS, Chang GG. Nucleophilic aromatic substitution of glutathione and l-
chloro-2,4-dinitrobenzene in reverse micelles. A model system to assess the
transition-state stabilization in glutathione transferase catalyzed conjugation.
J Org Chem 1995;60(19):6183e5.
[28] Liou JY, Huang TM, Chang GG. Reverse micelles as a catalyst for the nucleophilic
aromatic substitution between glutathione and 2,4-dinitrochlorobenzene.
J Chem Soc Perkin Trans 1999;2:2171e6.
_
_
ꢀ
[8] Longo A, Di Toro M, Galimberti C, Carenzi A. Determination of N-acetylcys-
teine in human plasma by gas chromatography-mass spectrometry.
J Chromatogr B Biomed Sci Appl 1991;562(1e2):639e45.
[29] Svensson R, Pamedytyte V, Juodaityte J, Makuska R, Morgenstern R. Charac-
terisation of polymeric surfactants that are glutathione transferase mimics.
Toxicology 2001;168(3):251e8.
[9] Glowacki R, Bald E. Determination of N-acetylcysteine and main endogenous
thiols in human plasma by HPLC with ultraviolet detection in the form of their s-
quinolinium derivatives. J Liq Chromatogr Relat Technol 2009;32(17):2530e44.
[10] Jaworska M, Szulinska Z, Wilk M, Anuszewska E. Capillary electrophoresis for
the determination of N-acetyltyrosine and N-acetylcysteine in products for
parenteral nutrition: method development and comparison of two CE
systems. Acta Chromatogr 2011;23(4):595e602.
[30] Nakata E, Yukimachi Y, Kariyazono H, Im S, Abe C, Uto Y, et al. Design of
a bioreductively-activated fluorescent pH probe for tumor hypoxia imaging.
Bioorg Med Chem 2009;17(19):6952e8.
[31] Yang XF, Su Z, Liu CH, Qi HQ, Zhao ML. A thiol-selective fluorogenic probe
based on the cleavage of 4-methylumbelliferyl-20,40,60-trinitropheyl ether.
Anal Bioanal Chem 2010;396(7):2667e74.
[32] Hirabayashi K, Hanaoka K, Shimonishi M, Terai T, Komatsu T, Ueno T, et al.
Selective two-step labeling of proteins with an off/on fluorescent probe. Chem
Eur J 2011;17(52):14763e71.
[33] Whitaker JE, Haugland RP, Ryan D, Hewitt PC, Haugland RP, Prendergast FG.
Fluorescent rhodol derivatives: versatile, photostable labels and tracers. Anal
Biochem 1992;207(2):267e79.
[11] Ogwu V, Cohen G.
A simple colorimetric method for the simultaneous
determination of N-acetylcysteine and cysteine. Free Radic Biol Med 1998;
25(3):362e4.
[12] Suarez WT, Pessoa-Neto OD, Janegitz BC, Vieira HJ, Faria RC, Fatibello-Filho O.
Flow injection spectrophotometric determination of N-acetylcysteine and
captopril employing Prussian blue generation reaction. Anal Lett 2011;44(14):
2394e405.
[13] Garcia-Molina F, Penalver MJ, Rodriguez-Lopez JN, Garcia-Canovas F, Tudela J.
Enzymatic method with polyphenol oxidase for the determination of cysteine
and N-acetylcysteine. J Agric Food Chem 2005;53(16):6183e9.
[14] Pipi ARF, do Carmo DR. Voltammetric studies of titanium (IV) phosphate
modified with copper hexacyanoferrate and electroanalytical determination
of N-acetylcysteine. J Appl Electrochem 2011;41(7):787e93.
[15] Beitollahi H, Raoof JB, Hosseinzadeh R. Fabrication of a nanostructure-based
electrochemical sensor for simultaneous determination of N-acetylcysteine
and acetaminophen. Talanta 2011;85(4):2128e34.
[34] Kwon JY, Jang YJ, Lee YJ, Kim KM, Seo MS, Nam W, et al.
A highly
selective fluorescent chemosensor for Pb2þ. J Am Chem Soc 2005;127(8):
10107e11.
[35] Dean JA. Lange’s handbook of chemistry. 15th ed. New York: McGraw-Hill;
1998.
[36] Chen XQ, Pradhan T, Wang F, Kim JS, Yoon J. Fluorescent chemosensors based
on spiroring-opening of xanthenes and related derivatives. Chem Rev 2012;
112(13):1910e56.
[37] Cifuentes A, Bernal JL, Diez-Masa JC. Determination of critical micelle
concentration values using capillary electrophoresis instrumentation. Anal
Chem 1997;69(20):4271e4.