Highly selective colorimetric sensor for cysteine and homocysteine based on azo derivatives

A simple colorimetric method for the determination of cysteine and homocysteine has been developed. The reaction of the azo dyes containing an aldehyde group with cysteine or homocysteine afforded very stable derivatives thiazolidines or thiazinanes under neutral pH conditions. The method is selective and sensitive for cysteine and homocysteine detection without the interference of other amino acids. Importantly, the recognition of Cys and Hcy could be observed by naked eyes.

[1]  R. Głowacki,et al.  Urinary excretion measurement of cysteine and homocysteine in the form of their S-pyridinium derivatives by high-performance liquid chromatography with ultraviolet detection. , 1998, Journal of chromatography. A.

[2]  Sudha Seshadri,et al.  Plasma Homocysteine as a Risk Factor for Dementia and Alzheimer's Disease , 2002 .

[3]  Y V Tcherkas,et al.  Simultaneous determination of several amino acids, including homocysteine, cysteine and glutamic acid, in human plasma by isocratic reversed-phase high-performance liquid chromatography with fluorimetric detection. , 2001, Journal of chromatography. A.

[4]  Abraham Weizman,et al.  Cysteine-induced hypoglycemic brain damage: an alternative mechanism to excitotoxicity , 2004, Amino Acids.

[5]  G. Chwatko,et al.  Determination of different species of homocysteine in human plasma by high-performance liquid chromatography with ultraviolet detection. , 2002, Journal of chromatography. A.

[6]  Y. Kai,et al.  Synthesis, coloration, and crystal structure of the dibasic chromoacerand-piperazine 1:1 salt complex , 1988 .

[7]  I. Warner,et al.  Visual detection of cysteine and homocysteine. , 2004, Journal of the American Chemical Society.

[8]  Yasuteru Urano,et al.  Highly sensitive fluorescence probes for nitric oxide based on boron dipyrromethene chromophore-rational design of potentially useful bioimaging fluorescence probe. , 2004, Journal of the American Chemical Society.

[9]  Anil Kumar Singh,et al.  Novel Bacteriorhodopsin Analogues Based on Azo Chromophores , 1996 .

[10]  I. Warner,et al.  Detection of Homocysteine and Cysteine , 2005 .

[11]  V. Lynch,et al.  Fluorinated Calix[4]pyrrole and Dipyrrolylquinoxaline: Neutral Anion Receptors with Augmented Affinities and Enhanced Selectivities , 2000 .

[12]  D. Jacobsen,et al.  Homocysteine in health and disease , 2001 .

[13]  Jonathan L. Sessler,et al.  Naked-Eye Detection of Anions in Dichloromethane: Colorimetric Anion Sensors Based on Calix[4]pyrrole , 2000 .

[14]  S. Vollset,et al.  Homocysteine and cardiovascular disease. , 1998, Annual review of medicine.

[15]  H. Kwong,et al.  A novel chiral terpyridine macrocycle as a fluorescent sensor for enantioselective recognition of amino acid derivatives. , 2004, Chemical communications.

[16]  T. Inoue,et al.  Electrochemical detection of thiols with a coenzyme pyrroloquinoline quinone modified electrode. , 2000, Analytical chemistry.

[17]  T. Gunnlaugsson,et al.  Highly selective colorimetric naked-eye Cu(II) detection using an azobenzene chemosensor. , 2004, Organic letters.

[18]  F. Tanaka,et al.  Rapid fluorescent screening for bifunctional amine-acid catalysts: efficient syntheses of quaternary carbon-containing aldols under organocatalysis. , 2003, Organic Letters.

[19]  R. Strongin,et al.  Direct detection of homocysteine. , 2004, Journal of the American Chemical Society.

[20]  A. P. Silva,et al.  Fluorescence “Off–On” Signalling upon Linear Recognition and Binding of α,ω‐Alkanediyldiammonium Ions by 9,10‐Bis{(1‐aza‐4,7,10,13,16‐pentaoxacyclooctadecyl)methyl}anthracene , 1990 .

[21]  S. Shahrokhian,et al.  Lead phthalocyanine as a selective carrier for preparation of a cysteine-selective electrode. , 2001, Analytical chemistry.

[22]  M. Han,et al.  Rationally designed chromogenic chemosensor that detects cysteine in aqueous solution with remarkable selectivity , 2004 .

[23]  M. Levene,et al.  Determination of plasma total homocysteine and cysteine using HPLC with fluorescence detection and an ammonium 7-fluoro-2, 1, 3-benzoxadiazole-4-sulphonate (SBD-F) derivatization protocol optimized for antioxidant concentration, derivatization reagent concentration, temperature and matrix pH. , 1996, Biomedical chromatography : BMC.

[24]  V. Amarnath,et al.  A specific HPLC-UV method for the determination of cysteine and related aminothiols in biological samples. , 2003, Talanta.

[25]  Z. A. Wood,et al.  Structure, mechanism and regulation of peroxiredoxins. , 2003, Trends in biochemical sciences.

[26]  Manfred T. Reetz,et al.  2,15-Dihydroxy-hexahelicene (HELIXOL): synthesis and use as an enantioselective fluorescent sensor , 2001 .

[27]  Keiji Hirose,et al.  Enantioselective complexation of phenolic crown ethers with chiral aminoethanol derivatives: effects of substituents of aromatic rings of hosts and guests on complexation , 2000 .

[28]  Vojtech Adam,et al.  Simultaneous femtomole determination of cysteine, reduced and oxidized glutathione, and phytochelatin in maize (Zea mays L.) kernels using high-performance liquid chromatography with electrochemical detection. , 2005, Journal of chromatography. A.

[29]  H. Tian,et al.  A colorimetric and fluorescent chemodosimeter: fluoride ion sensing by an axial-substituted subphthalocyanine , 2005 .

[30]  U. Spichiger-Keller,et al.  Application of Chromogenic and Fluorogenic Reactands in the Optical Sensing of Dissolved Aliphatic Amines , 1998 .

[31]  Neil Burford,et al.  Definitive identification of cysteine and glutathione complexes of bismuth by mass spectrometry: assessing the biochemical fate of bismuth pharmaceutical agents. , 2003, Chemical communications.

[32]  Hong Wang,et al.  Spectrofluorimetic determination of cysteine based on the fluorescence inhibition of Cd(II)-8-hydroxyquinoline-5-sulphonic acid complex by cysteine. , 2001, Talanta.

[33]  Hideki Kandori,et al.  Reactive cysteine is protonated in the triplet excited state of the LOV2 domain in Adiantum phytochrome3. , 2005, Journal of the American Chemical Society.

[34]  Y. Kanaoka Organic fluorescence reagents in the study of enzymes and proteins. , 1977, Angewandte Chemie.

[35]  S. Kitagawa,et al.  Porphyrin Receptors for Amines, Amino Acids, and Oligopeptides in Water , 1999 .

[36]  P. Houzé,et al.  Simultaneous determination of total plasma glutathione, homocysteine, cysteinylglycine, and methionine by high‐performance liquid chromatography with electrochemical detection , 2001, Journal of clinical laboratory analysis.

[37]  V. Lynch,et al.  Achieving large color changes in response to the presence of amino acids: a molecular sensing ensemble with selectivity for aspartate. , 2001, Journal of the American Chemical Society.

[38]  Jonathan L Sessler,et al.  Off-the-Shelf Colorimetric Anion Sensors. , 2001, Angewandte Chemie.

[39]  K. Okabe,et al.  Development of hydrophilic fluorogenic derivatization reagents for thiols: 4-(N-acetylaminosulfonyl)-7-fluoro-2,1,3-benzoxadiazole and 4-(N-trichloroacetylaminosulfonyl)-7-fluoro-2,1,3-benzoxadiazole. , 2002, Journal of chromatography. A.

[40]  F. Tanaka,et al.  Fluorescent detection of carbon-carbon bond formation. , 2003, Journal of the American Chemical Society.

[41]  Sumio Tokita,et al.  Colorimetric chiral recognition by a molecular sensor , 1996, Nature.

[42]  T. Glass,et al.  Detection of amines and unprotected amino acids in aqueous conditions by formation of highly fluorescent iminium ions. , 2003, Journal of the American Chemical Society.

[43]  F. Tanaka,et al.  Rapid analysis of solvent effects on enamine formation by fluorescence: how might enzymes facilitate enamine chemistry with primary amines? , 2004 .

[44]  T. Kinoshita,et al.  Visualization of Molecular Length of α, ω-Diamines and Temperature by a Receptor Based on Phenolphthalein and Crown Ether (SYNTHETIC ORGANIC CHEMISTRY-Fine Organic Synthesis) , 1999 .

[45]  G Chwatko,et al.  Determination of cysteine in human plasma by high-performance liquid chromatography and ultraviolet detection after pre-column derivatization with 2-chloro-1-methylpyridinium iodide. , 2000, Talanta.

[46]  Y. Uemori,et al.  Water-Soluble Zinc Porphyrins as Receptors for Amino Carboxylates , 2001 .

[47]  Shouzhuo Yao,et al.  Electrochemical behavior of L-cysteine and its detection at carbon nanotube electrode modified with platinum. , 2005, Analytical biochemistry.

[48]  Chunwei Yu,et al.  A cyclometalated palladium-azo complex as a differential chromogenic probe for amino acids in aqueous solution. , 2005, Chemical communications.

[49]  F. Tanaka,et al.  Determination of cysteine concentration by fluorescence increase: reaction of cysteine with a fluorogenic aldehyde. , 2004, Chemical communications.