Recent progress in fluorescent and colorimetric chemosensors for detection of amino acids.

Due to the biological importance of amino acids, the development of optical probes for these molecules has been an active research area in recent years. This tutorial review focuses on recent contributions since the year 2000 concerning the fluorescent or colorimetric sensors for amino acids, and is organized according to their structural classification and reaction types. For reaction based chemosensors, the works are classified according to the mechanisms between sensors and amino acids, including imine formation, Michael addition, thiazinane or thiazolidine formation, cleavage of a sulfonate ester, cleavage of disulfide, metal complexes-displace coordination and others.

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[8]  R. Marchelli,et al.  Enantioselective sensing of amino acids by copper(II) complexes of phenylalanine-based fluorescent β-cyclodextrins , 2000 .

[9]  Xiaoling Zhang,et al.  A colorimetric and ratiometric fluorescent probe for thiols and its bioimaging applications. , 2010, Chemical communications.

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[15]  Xuesong Wang,et al.  A new squaraine and Hg2+-based chemosensor with tunable measuring range for thiol-containing amino acids , 2011 .

[16]  A. Corma,et al.  Fluorimetric detection and discrimination of α-amino acids based on tricyclic basic dyes and cucurbiturils supramolecular assembly , 2011 .

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[18]  Lin Yuan,et al.  Construction of a FRET-based ratiometric fluorescent thiol probe. , 2011, Chemical communications.

[19]  Jiangshan Shen,et al.  Specific Hg(2+)-mediated perylene bisimide aggregation for highly sensitive detection of cysteine. , 2010, Chemical communications.

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[21]  C. Girardet,et al.  Nonlinear polarization effects in superchiral nanotube sensors of amino acids , 2009 .

[22]  R. Marchelli,et al.  Enantioselective fluorescence sensing of amino acids by modified cyclodextrins: role of the cavity and sensing mechanism. , 2004, Chemistry.

[23]  J. Qin,et al.  New polyacetylene-based chemosensory materials for the “turn-on” sensing of α-amino acids , 2009 .

[24]  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.

[25]  D. Xiao,et al.  A selective optode membrane for histidine based on fluorescence enhancement of meso-meso-linked porphyrin dimer. , 2002, Analytical chemistry.

[26]  S. Joo,et al.  Hydrogen bonding-induced color recovery of gold nanoparticles upon conjugation of amino acids. , 2009, Chemical communications.

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

[28]  Jingui Qin,et al.  A new approach to fluorescence "turn-on" sensing of alpha-amino acids. , 2009, ACS applied materials & interfaces.

[29]  J. Chinta,et al.  1-(D-Glucopyranosyl-2'-deoxy-2'-iminomethyl)-2-hydroxybenzene as chemosensor for aromatic amino acids by switch-on fluorescence , 2010 .

[30]  W. Chan,et al.  An easy assembled fluorescent sensor for dicarboxylates and acidic amino acids , 2011, Beilstein journal of organic chemistry.

[31]  Wenzhu Zhang,et al.  Turn-on luminescent probe for cysteine/homocysteine based on a ruthenium(II) complex. , 2010, Inorganic chemistry.

[32]  V. Lynch,et al.  Using enantioselective indicator displacement assays to determine the enantiomeric excess of alpha-amino acids. , 2008, Journal of the American Chemical Society.

[33]  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.

[34]  V. Lynch,et al.  Colorimetric enantiodiscrimination of α-amino acids in protic media , 2005 .

[35]  He Tian,et al.  Recent progress on polymer-based fluorescent and colorimetric chemosensors. , 2011, Chemical Society reviews.

[36]  Xiaohua Li,et al.  Determination of non-protein cysteine in human serum by a designed BODIPY-based fluorescent probe. , 2011, Talanta.

[37]  Y. Nakano,et al.  Liquid Chromatographic Determination of Ornithine and Lysine Based on Intramolecular Excimer-forming Fluorescence Derivatization , 2001, Analytical sciences : the international journal of the Japan Society for Analytical Chemistry.

[38]  Jian Xu,et al.  A Bodipy-based derivative for selective fluorescence sensing of homocysteine and cysteine , 2011 .

[39]  C. Che,et al.  "Turn-on" FRET-based luminescent iridium(III) probes for the detection of cysteine and homocysteine. , 2011, Chemical communications.

[40]  W. Nau,et al.  Supramolecular tandem enzyme assays for multiparameter sensor arrays and enantiomeric excess determination of amino acids. , 2008, Chemistry.

[41]  T. Glass,et al.  Fluorescent sensors for diamines , 2005 .

[42]  E. Anslyn,et al.  Pattern-based discrimination of enantiomeric and structurally similar amino acids: an optical mimic of the mammalian taste response. , 2006, Journal of the American Chemical Society.

[43]  Ying Zhou,et al.  Fluorescent and colorimetric probes for detection of thiols. , 2010, Chemical Society reviews.

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

[45]  Yuen-Kit Cheng,et al.  Cholic-acid-based fluorescent sensor for dicarboxylates and acidic amino acids in aqueous solutions. , 2005, Organic letters.

[46]  Hyockman Kwon,et al.  Coumarin-malonitrile conjugate as a fluorescence turn-on probe for biothiols and its cellular expression. , 2011, Chemical communications.

[47]  Yongbing He,et al.  Synthesis and Chiral Recognition Properties of Novel Fluorescent Chemosensors for Amino Acid , 2008, Journal of Fluorescence.

[48]  W. Chan,et al.  Cholic acid-based fluorescent probes for enantioselective recognition of trifunctional amino acids. , 2008, Organic & biomolecular chemistry.

[49]  Kay Severin,et al.  A chemosensor array for the colorimetric identification of 20 natural amino acids. , 2005, Journal of the American Chemical Society.

[50]  S. Sasaki,et al.  Fluororeceptor for zwitterionic form amino acids in aqueous methanol solution , 2002 .

[51]  T. Stone,et al.  Tryptophan metabolism and oxidative stress in patients with chronic brain injury , 2006, European journal of neurology.

[52]  Yun‐Bao Jiang,et al.  Metal-metal-interaction-facilitated coordination polymer as a sensing ensemble: a case study for cysteine sensing. , 2011, Langmuir : the ACS journal of surfaces and colloids.

[53]  Ying Zhou,et al.  Studies leading to the development of a highly selective colorimetric and fluorescent chemosensor for lysine. , 2011, Chemical communications.

[54]  A. Taglietti,et al.  Fluorescent detection of glutamate with a dicopper(II) polyamine cage , 2004 .

[55]  V. Lynch,et al.  "Naked-eye" detection of histidine by regulation of Cu(II) coordination modes. , 2005, Chemistry.

[56]  Shaomin Ji,et al.  Styryl-BODIPY based red-emitting fluorescent OFF-ON molecular probe for specific detection of cysteine. , 2011, Biosensors & bioelectronics.

[57]  C. P. Rao,et al.  Experimental and computational studies of the recognition of amino acids by galactosyl-imine and -amine derivatives: an attempt to understand the lectin-carbohydrate interactions. , 2007, The Journal of organic chemistry.

[58]  J. Tae,et al.  Rhodamine-sugar based turn-on fluorescent probe for the detection of cysteine and homocysteine in water. , 2010, Chemical communications.

[59]  G. Patel,et al.  Recognition of lysine, arginine and histidine by novel p-sulfonatocalix[4]arene thiol functionalized gold nanoparticles in aqueous solution. , 2009, Chemical communications.

[60]  Jianbin Chao,et al.  Chromene "lock", thiol "key", and mercury(II) ion "hand": a single molecular machine recognition system. , 2010, Organic letters.

[61]  R. Marchelli,et al.  Design and synthesis of Fluorescent β-cyclodextrins for the enantioselective sensing of α-amino acids , 2003 .

[62]  X. Qu,et al.  DNA/ligand/ion-based ensemble for fluorescence turn on detection of cysteine and histidine with tunable dynamic range. , 2010, Analytical chemistry.

[63]  N. Marcotte,et al.  Designing the selectivity of the fluorescent detection of amino acids: a chemosensing ensemble for histidine. , 2003, Journal of the American Chemical Society.

[64]  Song Wang,et al.  Fluorescent chemodosimeter for Cys/Hcy with a large absorption shift and imaging in living cells. , 2011, Organic & biomolecular chemistry.

[65]  Eric V Anslyn,et al.  Differential receptor arrays and assays for solution-based molecular recognition. , 2006, Chemical Society reviews.

[66]  J. Reymond,et al.  A green fluorescent chemosensor for amino acids provides a versatile high-throughput screening (HTS) assay for proteases. , 2003, Bioorganic & medicinal chemistry letters.

[67]  Guangyan Qing,et al.  Novel chiral fluorescent chemosensors for malate and acidic amino acids based on two-arm thiourea and amide , 2008 .

[68]  Xiu‐Ping Yan,et al.  A sensitive and selective resonance light scattering bioassay for homocysteine in biological fluids based on target-involved assembly of polyethyleneimine-capped Ag-nanoclusters. , 2011, Chemical communications.

[69]  Min Ki Choi,et al.  Chiral anion recognition by color change utilizing thiourea, azophenol, and glucopyranosyl groups , 2008 .

[70]  C. P. Rao,et al.  Lower rim 1,3-diderivative of calix[4]arene-appended salicylidene imine (H(2)L): experimental and computational studies of the selective recognition of H(2)L toward Zn(2+) and sensing phosphate and amino acid by [ZnL]. , 2010, The Journal of organic chemistry.