Supramolecular assembly of a new squaraine and β-cyclodextrin for detection of thiol-containing amino acids in water

A new unsymmetrical aniline-based squaraine (SQ2) bearing binding unit of Hg2+ ion was designed and synthesised. SQ2 can form 1:2 inclusion complex with β-cyclodextrin, and the resulting complex, which undergoes absorption and fluorescence bleaching upon binding Hg2+, can serve as a turn-on colorimetric or fluorescent chemosensor in organic solvent-free aqueous solution for thiol-containing amino acids with high selectivity and tunable measuring range.

[1]  D. Ramaiah,et al.  β-Cyclodextrin as a photosensitizer carrier: effect on photophysical properties and chemical reactivity of squaraine dyes. , 2011, The journal of physical chemistry. B.

[2]  Liangqia Guo,et al.  A squaraine-based colorimetric and "turn on" fluorescent sensor for selective detection of Hg2+ in an aqueous medium. , 2011, Organic letters.

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

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

[5]  Fuyou Li,et al.  Phosphorescence imaging of homocysteine and cysteine in living cells based on a cationic iridium(III) complex. , 2010, Inorganic chemistry.

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

[7]  A. Fu,et al.  Squaraine-based colorimetric and fluorescent sensors for Cu2+-specific detection and fluorescence imaging in living cells , 2010 .

[8]  Pradipta Purkayastha.  Cu2+ induced charge transfer switch by choosing the right cyclodextrin environment , 2010 .

[9]  X. Zhong,et al.  Highly selective detection of glutathione using a quantum-dot-based OFF-ON fluorescent probe. , 2010, Chemical communications.

[10]  Juyoung Yoon,et al.  A thiol-specific fluorescent probe and its application for bioimaging. , 2010, Chemical communications.

[11]  Y. Leung,et al.  A highly selective FRET-based fluorescent probe for detection of cysteine and homocysteine. , 2010, Chemistry.

[12]  Wei Jiang,et al.  Rational design of a highly selective and sensitive fluorescent PET probe for discrimination of thiophenols and aliphatic thiols. , 2010, Chemical communications.

[13]  Weiying Lin,et al.  A highly sensitive fluorescent probe for detection of benzenethiols in environmental samples and living cells. , 2010, Chemical communications.

[14]  M. Tian,et al.  A fluorescent chemodosimeter specific for cysteine: effective discrimination of cysteine from homocysteine. , 2009, Chemical communications.

[15]  E. Anslyn,et al.  Pattern-based recognition of thiols and metals using a single squaraine indicator. , 2009, Journal of the American Chemical Society.

[16]  Long Yi,et al.  A highly sensitive fluorescence probe for fast thiol-quantification assay of glutathione reductase. , 2009, Angewandte Chemie.

[17]  Lin Yuan,et al.  A sensitive and selective fluorescent thiol probe in water based on the conjugate 1,4-addition of thiols to alpha,beta-unsaturated ketones. , 2009, Chemistry.

[18]  Kian Ping Loh,et al.  One- and two-photon turn-on fluorescent probe for cysteine and homocysteine with large emission shift. , 2009, Organic letters.

[19]  C. Rangan,et al.  Disulfide-linked, gold nanoparticle based reagent for detecting small molecular weight thiols. , 2009, Journal of the American Chemical Society.

[20]  Lin Yuan,et al.  A ratiometric fluorescent probe for cysteine and homocysteine displaying a large emission shift. , 2008, Organic letters.

[21]  A. Ajayaghosh,et al.  A near-infrared squaraine dye as a latent ratiometric fluorophore for the detection of aminothiol content in blood plasma. , 2008, Angewandte Chemie.

[22]  Fuyou Li,et al.  Selective phosphorescence chemosensor for homocysteine based on an iridium(III) complex. , 2007, Inorganic chemistry.

[23]  H. Fan,et al.  A highly selective fluorescent probe for thiophenols. , 2007, Angewandte Chemie.

[24]  B. Tang,et al.  A rhodamine-based fluorescent probe containing a Se-N bond for detecting thiols and its application in living cells. , 2007, Journal of the American Chemical Society.

[25]  Tao Yi,et al.  A highly selective fluorescence turn-on sensor for cysteine/homocysteine and its application in bioimaging. , 2007, Journal of the American Chemical Society.

[26]  D. Ramaiah,et al.  Dual-mode semisquaraine-based sensor for selective detection of Hg2+ in a micellar medium. , 2007, Organic letters.

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

[28]  B. Epe,et al.  Aggregation Behavior of Halogenated Squaraine Dyes in Buffer, Electrolytes, Organized Media, and DNA , 2002 .

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

[30]  H. Hartmann,et al.  Synthesis and characterization of a new class of unsymmetrical squaraine dyes , 2001 .

[31]  S. Vollset,et al.  Plasma Total Cysteine as a Risk Factor for Vascular Disease: The European Concerted Action Project , 2001, Circulation.

[32]  J. Szejtli.  Introduction and General Overview of Cyclodextrin Chemistry. , 1998, Chemical reviews.

[33]  Dong Liu,et al.  Aggregation Behavior of Water Soluble Bis(benzothiazolylidene)squaraine Derivatives in Aqueous Media , 1996 .

[34]  D. Whitten,et al.  Aggregation of Surfactant Squaraine Dyes in Aqueous Solution and Microheterogeneous Media: Correlation of Aggregation Behavior with Molecular Structure , 1996 .

[35]  P. Kamat,et al.  Fluorescence enhancement of bis(2,4,6-trihydroxyphenyl)squaraine anion by 2 : 1 host–guest complexation with β-cyclodextrin , 1992 .

[36]  K. Law.  Squaraine chemistry: effects of structural changes on the absorption and multiple fluorescence emission of bis[4-(dimethylamino)phenyl]squaraine and its derivatives , 1987 .

[37]  R. C. D. Selms,et al.  Reactions of squaric acid and some derivatives with thionyl chloride/,-dimethylformamide , 1970 .