An Organic/Inorganic Hybrid Membrane as a Solid “Turn-On” Fluorescent Chemosensor for Coenzyme A (CoA), Cysteine (Cys), and Glutathione (GSH) in Aqueous Media

The preparation of a fluorogenic sensory material for the detection of biomolecules is described. Strategic functionalisation and copolymerisation of a water insoluble organic sensory molecule with hydrophilic comonomers yielded a crosslinked, water-swellable, easy-to-manipulate solid system for water “dip-in” fluorogenic coenzyme A, cysteine, and glutathione detection by means of host-guest interactions. The sensory material was a membrane with gel-like behaviour, which exhibits a change in fluorescence behaviour upon swelling with a water solution of the target molecules. The membrane follows a “turn-on” pattern, which permits the titration of the abovementioned biomolecules. In this way, the water insoluble sensing motif can be exploited in aqueous media. The sensory motif within the membrane is a chemically anchored piperazinedione-derivative with a weakly bound Hg(II). The response is caused by the displacement of the cation from the membrane due to a stronger complexation with the biomolecules, thus releasing the fluorescent sensory moieties within the membrane.

[1]  S. Ibeas,et al.  A selective and highly sensitive fluorescent probe of Hg2+ in organic and aqueous media: The role of a polymer network in extending the sensing phenomena to water environments , 2011 .

[2]  D. Spring,et al.  Fluorescent chemosensors for Zn(2+). , 2010, Chemical Society reviews.

[3]  Hae-Jo Kim,et al.  Highly selective fluorescent sensor for homocysteine and cysteine , 2008 .

[4]  Xiaoxia Ge,et al.  A New Spectrofluorometric Probe for the Determination of Trace Amounts of CoA in Injection, Human Serum and Pig Livers , 2007, Analytical sciences : the international journal of the Japan Society for Analytical Chemistry.

[5]  Ying Zhou,et al.  Fluorescent and colorimetric chemosensors for detection of nucleotides, FAD and NADH: highlighted research during 2004-2010. , 2011, Chemical Society reviews.

[6]  Yufang Xu,et al.  Highly selective fluorescent chemosensor with red shift for cysteine in buffer solution and its bioimage: symmetrical naphthalimide aldehyde , 2008 .

[7]  Juyoung Yoon,et al.  Recent progress on fluorescent chemosensors for metal ions , 2012 .

[8]  J. Hill,et al.  Thermal analysis of mercury(I) sulfate and mercury(II) sulfate , 1981 .

[9]  Wei-ping Liu,et al.  Enoxacin-Tb3+ complex as an environmentally friendly fluorescence probe for DNA and its application. , 2007, Talanta.

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

[11]  Xiaoling Zhang,et al.  A colorimetric and ratiometric fluorescent probe for quantitative detection of GSH at physiologically relevant levels , 2011 .

[12]  J. Raoof,et al.  Voltammetric sensor for glutathione determination based on ferrocene-modified carbon paste electrode , 2009 .

[13]  Gang Liu,et al.  A Highly Sensitive and Selective Competition Assay for the Detection of Cysteine Using Mercury-Specific DNA, Hg2+ and Sybr Green I , 2011, Sensors.

[14]  Fuyi Wang,et al.  A colorimetric sensor for determination of cysteine by carboxymethyl cellulose-functionalized gold nanoparticles. , 2010, Analytica chimica acta.

[15]  Chun Xing Li,et al.  Colorimetric and fluorescent dual probe based on a polythiophene derivative for the detection of cysteine and homocysteine. , 2011, Chemical communications.

[16]  Ana B. Descalzo,et al.  The supramolecular chemistry of organic-inorganic hybrid materials. , 2006, Angewandte Chemie.

[17]  Xiaoxia Ge,et al.  Spectrofluorimetric determination of trace amounts of coenzyme A using a terbium ion–ciprofloxacin complex probe in the presence of periodic acid , 2007, Analytical and bioanalytical chemistry.

[18]  F. García,et al.  Fluorogenic and Chromogenic Polymer Chemosensors , 2011 .

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

[20]  Minglei Zhao,et al.  A Chemosensing Ensemble for the Detection of Cysteine Based on the Inner Filter Effect Using a Rhodamine B Spirolactam , 2008, Journal of Fluorescence.

[21]  Tao Yi,et al.  Highly selective colorimetric sensor for cysteine and homocysteine based on azo derivatives , 2006 .

[22]  W. Chan,et al.  Ratiometric fluorescent probe for enantioselective detection of D-cysteine in aqueous solution , 2011, Beilstein journal of organic chemistry.

[23]  Jong Seung Kim,et al.  A cysteine-selective fluorescent probe for the cellular detection of cysteine. , 2012, Biomaterials.

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

[25]  Sujuan Wang,et al.  Tunable fluorescent sensing of cysteine and homocysteine by intramolecular charge transfer , 2010 .

[26]  Fengshan Yu,et al.  Enoxacin—Tb3+ Complex as an Environmentally Friendly Fluorescence Probe for Coenzyme A and Its Application , 2009 .

[27]  Sergey Vyazovkin,et al.  Isoconversional kinetics of degradation of polyvinylpyrrolidone used as a matrix for ammonium nitrate stabilization , 2008 .

[28]  N. Chandrasekaran,et al.  Selective colorimetric sensing of cysteine in aqueous solutions using silver nanoparticles in the presence of Cr³+. , 2011, Talanta.

[29]  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.

[30]  Soo-Yeon Lim,et al.  Ratiometric detection of cysteine by a ferrocenyl Michael acceptor , 2011 .

[31]  Félix Sancenón,et al.  Fluorogenic and chromogenic chemosensors and reagents for anions. , 2003, Chemical reviews.

[32]  D. H. Burns.  Anion Receptor Chemistry , 2006 .

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