Piperazine-based simple structure for selective sensing of Hg2+ and glutathione and construction of a logic circuit mimicking an INHIBIT gate

A simple chemosensor (1) has been designed and synthesized. The chemosensor selectively recognizes Hg2+ ions in THF–H2O (3 : 1, v/v) by showing a significant increase in emission and a bluish color of the solution under exposure to UV light. Change of the fluorophore unit in 1 leads to 2, which also shows selective sensing of Hg2+ under similar conditions. Furthermore, while the ensemble of 1 with Hg2+ selectively senses reduced glutathione (GSH) over cysteine and homocysteine, the ensemble of 2 with Hg2+ has been observed to be inefficient to distinguish glutathione from other biothiols. Thus probe 1 and inputs Hg2+ and GSH can be used to develop an INHIBIT logic gate.

[1]  W. Choi,et al.  Highly selective excited state intramolecular proton transfer (ESIPT)-based superoxide probing. , 2013, Organic letters.

[2]  W. Choi,et al.  Highly fluorescent and specific molecular probing of (homo)cysteine or superoxide: biothiol detection confirmed in living neuronal cells. , 2013, Organic letters.

[3]  Jian-hui Jiang,et al.  A Hg(2+)-mediated label-free fluorescent sensing strategy based on G-quadruplex formation for selective detection of glutathione and cysteine. , 2013, The Analyst.

[4]  Xiaoling Zhang,et al.  A Chloroacetate-Caged Fluorescein Chemodosimeter for Imaging Cysteine/Homocysteine in Living Cells , 2013 .

[5]  Shiguo Sun,et al.  Near-infrared fluorescent detection of glutathione via reaction-promoted assembly of squaraine-analyte adducts. , 2013, The Analyst.

[6]  Chen-Ho Tung,et al.  BODIPY-based ratiometric fluorescent sensor for highly selective detection of glutathione over cysteine and homocysteine. , 2012, Journal of the American Chemical Society.

[7]  K. Ghosh,et al.  A rhodamine appended tripodal receptor as a ratiometric probe for Hg2+ ions. , 2012, Organic & biomolecular chemistry.

[8]  T. Gunnlaugsson,et al.  Selective detection of the reduced form of glutathione (GSH) over the oxidized (GSSG) form using a combination of glutathione reductase and a Tb(III)-cyclen maleimide based lanthanide luminescent 'switch on' assay. , 2012, Journal of the American Chemical Society.

[9]  C. P. Rao,et al.  Triazole-linked-thiophene conjugate of calix[4]arene: its selective recognition of Zn2+ and as biomimetic model in supporting the events of the metal detoxification and oxidative stress involving metallothionein. , 2011, The Journal of organic chemistry.

[10]  D. Xiao,et al.  A fluorescent "turn-on" probe for the dual-channel detection of Hg(II) and Mg(II) and its application of imaging in living cells. , 2011, Talanta.

[11]  Sundargopal Ghosh,et al.  A highly selective redox, chromogenic, and fluorescent chemosensor for Hg2+ in aqueous solution based on ferrocene-glycine bioconjugates. , 2011, Inorganic chemistry.

[12]  Xiaoling Zhang,et al.  Ratiometric fluorescence chemosensors for copper(II) and mercury(II) based on FRET systems , 2010 .

[13]  Ching‐Han Hu,et al.  A pyrenyl-appended triazole-based ribose as a fluorescent sensor for Hg2+ ion. , 2010, Carbohydrate research.

[14]  Y. Ju,et al.  Synthesis and binding ability of 1,2,3-triazole-based triterpenoid receptors for recognition of Hg(2+) ion. , 2010, Bioorganic & medicinal chemistry letters.

[15]  Dan Du,et al.  Rhodamine-based ratiometric fluorescence sensing for the detection of mercury(II) in aqueous solution. , 2010, Talanta.

[16]  Tugba Ozdemir,et al.  A near IR di-styryl BODIPY-based ratiometric fluorescent chemosensor for Hg(II) , 2010 .

[17]  Hao Wang,et al.  Design of bis-spiropyran ligands as dipolar molecule receptors and application to in vivo glutathione fluorescent probes. , 2010, Journal of the American Chemical Society.

[18]  Su Yeon Lee,et al.  Hyperbranched calixarenes: synthesis and applications as fluorescent probes. , 2009, Chemical communications.

[19]  Liping Guo,et al.  Application of electrochemical properties of ordered mesoporous carbon to the determination of glutathione and cysteine. , 2009, Analytical biochemistry.

[20]  Stephen J Lippard,et al.  Small-molecule fluorescent sensors for investigating zinc metalloneurochemistry. , 2009, Accounts of chemical research.

[21]  Bin Liu,et al.  Highly sensitive and selective detection of Hg(2+) in aqueous solution with mercury-specific DNA and Sybr Green I. , 2008, Chemical communications.

[22]  Juyoung Yoon,et al.  A new trend in rhodamine-based chemosensors: application of spirolactam ring-opening to sensing ions. , 2008, Chemical Society reviews.

[23]  P. Molina,et al.  Ferrocene-based small molecules for dual-channel sensing of heavy- and transition-metal cations. , 2008, The Journal of organic chemistry.

[24]  Chunying Duan,et al.  "Turn-on" fluorescent sensor for Hg2+ via displacement approach. , 2008, Inorganic chemistry.

[25]  Mei Chen,et al.  A Novel Hg2+ Selective Ratiometric Fluorescent Chemodosimeter Based on an Intramolecular FRET Mechanism , 2008, Journal of Fluorescence.

[26]  Dylan W Domaille,et al.  Metals in neurobiology: probing their chemistry and biology with molecular imaging. , 2008, Chemical reviews.

[27]  Suna Timur,et al.  Biosensing approach for glutathione detection using glutathione reductase and sulfhydryl oxidase bienzymatic system. , 2008, Talanta.

[28]  V. Yam,et al.  Nonionic surfactant-capped gold nanoparticles as postcolumn reagents for high-performance liquid chromatography assay of low-molecular-mass biothiols. , 2007, Journal of chromatography. A.

[29]  Duong Tuan Quang,et al.  Calixarene-derived fluorescent probes. , 2007, Chemical reviews.

[30]  H. Tian,et al.  Tracking of mercury ions in living cells with a fluorescent chemodosimeter under single- or two-photon excitation. , 2007, Analytica chimica acta.

[31]  Han Zhang,et al.  8-Methoxyquinoline based turn-on metal fluoroionophores , 2007 .

[32]  Daoben Zhu,et al.  A colorimetric and fluorometric dual-model assay for mercury ion by a molecule. , 2007, Organic letters.

[33]  Stephen J Lippard,et al.  Turn-on and ratiometric mercury sensing in water with a red-emitting probe. , 2007, Journal of the American Chemical Society.

[34]  X. Qian,et al.  Two regioisomeric and exclusively selective Hg(II) sensor molecules composed of a naphthalimide fluorophore and an o-phenylenediamine derived triamide receptor. , 2006, Chemical communications.

[35]  D. Churchill.  Chemical Structure and Accidental Explosion Risk in the Research Laboratory. , 2006 .

[36]  A. Coskun,et al.  Signal ratio amplification via modulation of resonance energy transfer: proof of principle in an emission ratiometric Hg(II) sensor. , 2006, Journal of the American Chemical Society.

[37]  J. Vacek,et al.  A hydrophilic interaction chromatography coupled to a mass spectrometry for the determination of glutathione in plant somatic embryos. , 2006, The Analyst.

[38]  W. Chan,et al.  Hg2+ sensing in aqueous solutions: an intramolecular charge transfer emission quenching fluorescent chemosensors , 2006 .

[39]  R. Ito,et al.  Analysis of glutathione and glutathione disulfide in human saliva using hydrophilic interaction chromatography with mass spectrometry. , 2006, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[40]  X. Qian,et al.  Detecting Hg2+ ions with an ICT fluorescent sensor molecule: remarkable emission spectra shift and unique selectivity. , 2006, The Journal of organic chemistry.

[41]  Y. Li,et al.  Gold Nanoparticle‐Based Fluorometric and Colorimetric Sensing of Copper(II) Ions , 2005 .

[42]  Zhe Lu,et al.  Visible study of mercuric ion and its conjugate in living cells of mammals and plants. , 2005, Chemical research in toxicology.

[43]  K. Zachariasse,et al.  8-Hydroxyquinoline benzoates as highly sensitive fluorescent chemosensors for transition metal ions. , 2005, Organic letters.

[44]  He Tian,et al.  A selective fluorescent ratiometric chemodosimeter for mercury ion. , 2005, Chemical communications.

[45]  R. Løvstad.  A kinetic study on the distribution of Cu(II)-ions between albumin and transferrin , 2004, Biometals.

[46]  Hironobu Hashimoto,et al.  Hinge sugar as a movable component of an excimer fluorescence sensor. , 2004, Organic letters.

[47]  X. Qian,et al.  A highly selective and sensitive fluorescent chemosensor for Hg2+ in neutral buffer aqueous solution. , 2004, Journal of the American Chemical Society.

[48]  M. Cynader,et al.  Pyruvate Released by Astrocytes Protects Neurons from Copper-Catalyzed Cysteine Neurotoxicity , 2001, The Journal of Neuroscience.

[49]  P. Pallavicini,et al.  Molecular machines based on metal ion translocation. , 2001, Accounts of chemical research.

[50]  A. P. Silva,et al.  Combining luminescence, coordination and electron transfer for signalling purposes , 2000 .

[51]  Pi-Tai Chou,et al.  Excited-State Amine−Imine Double Proton Transfer in 7-Azaindoline , 2000 .

[52]  B. Ames,et al.  Chronically and acutely exercised rats: biomarkers of oxidative stress and endogenous antioxidants. , 2000, Journal of applied physiology.

[53]  W. MacNee,et al.  Regulation of redox glutathione levels and gene transcription in lung inflammation: therapeutic approaches. , 2000, Free radical biology & medicine.

[54]  Roberta F. White,et al.  Cognitive performance of children prenatally exposed to "safe" levels of methylmercury. , 1998, Environmental research.

[55]  Terence E. Rice,et al.  Signaling Recognition Events with Fluorescent Sensors and Switches. , 1997, Chemical reviews.

[56]  C. Masters,et al.  The Amyloid Precursor Protein of Alzheimer's Disease in the Reduction of Copper(II) to Copper(I) , 1996, Science.

[57]  Anthony W. Czarnik,et al.  Chemical Communication in Water Using Fluorescent Chemosensors , 1994 .

[58]  N. Ernsting,et al.  Tuning of photoinduced energy transfer in a bichromophoric coumarin supermolecule by cation binding , 1992 .

[59]  T. Mosmann.  Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. , 1983, Journal of immunological methods.

[60]  J. Ruedy,et al.  Methyl mercury exposure in northern Quebec. II. Neurologic findings in children. , 1983, American journal of epidemiology.

[61]  D. McClure,et al.  Spin‐Orbit Interaction in Aromatic Molecules , 1952 .

[62]  C Cox,et al.  Longitudinal neurodevelopmental study of Seychellois children following in utero exposure to methylmercury from maternal fish ingestion: outcomes at 19 and 29 months. , 1995, Neurotoxicology.