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Synthetic Fluorescent Indicators for Low Molecular Weight Organic Metabolites
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Synthetic Fluorescent Indicators for Low Molecular Weight Organic Metabolites

A special issue of Sensors (ISSN 1424-8220). This special issue belongs to the section "Chemical Sensors".

Deadline for manuscript submissions: closed (30 April 2013) | Viewed by 90310

Special Issue Editor

Prof. Dr. Robert Michael Strongin

E-Mail Website
Guest Editor
Department of Chemistry, Portland State University, Portland, OR 97207, USA
Interests: biosensors; chemosensors; diagnostics; molecular probes; fluorophores; tobacco control; electronic cigarettes; cannabis chemistry; redox chemistry; fullerenes; molecular basis of disease; drug design; public health

Special Issue Information

Dear Colleagues,

As our understanding of the metabolome grows it becomes increasingly important to develop simple, robust and reliable tools for the determination of small molecule biomarkers. Moreover, there is a growing need for materials useful in emerging nations, where relatively limited access to refrigeration and electricity demands robust, user friendly and inexpensive diagnostics. In developed nations rising health care expenses, as well as demand for point-of-care and home testing kits, drive the development of efficient and user friendly diagnostics. Fully synthetic and highly selective fluorescent indicators for small organic biomarkers are potential alternatives to relatively complex instrumentation such as NMR and mass spectrometers. In general, sensors composed of fully synthetic materials are more stable and less costly than their counterparts composed of antibodies, enzymes and related biorecognition elements. The creation of fully synthetic indicators comprising components that rival nature’s selectivity embodies an ongoing fundamental challenge to chemists and is a major focus of this special issue. The topics covered will represent recent innovations in fluorescent indicators for organic compounds of interest to the sensor and diagnostics community. They will include the selective detection of sugars, amino acids, lipids and other natural products. The issue will also cover the utility of a range of materials including dyes, polymers, sensor arrays and quantum dots and nanomaterials. Both original and topical review articles may be submitted.

Prof. Dr. Robert M. Strongin
Guest Editor

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Keywords

  • fluorescent indicators for organic compounds
  • fluorescent indicators for natural products
  • fluorescent indicators for amino acids
  • fluorescent indicators for sugars
  • fluorescent indicators for saccharides
  • fluorescent indicators for lipids
  • fluorescent indicators for metabolites
  • fluorescent indicators for organic biomarkers

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Published Papers (8 papers)

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Research

Jump to: Review

307 KiB  
Article
Detection of miRNA in Cell Cultures by Using Microchip Electrophoresis with a Fluorescence-Labeled Riboprobe
by Shohei Yamamura, Shouki Yatsushiro, Yuka Yamaguchi, Kaori Abe, Yasuo Shinohara and Masatoshi Kataoka
Sensors 2012, 12(6), 7576-7586; https://doi.org/10.3390/s120607576 - 7 Jun 2012
Cited by 8 | Viewed by 7637
Abstract
The analysis of a microRNA (miRNA), miR-222 isolated from the PC12 cell line, was performed by use of the ribonuclease (RNase) protection assay, cyanine 5 (Cy5)-labeled miR-222 riboprobe, and a Hitachi SV1210 microchip electrophoresis system, which can be used to evaluate the integrity [...] Read more.
The analysis of a microRNA (miRNA), miR-222 isolated from the PC12 cell line, was performed by use of the ribonuclease (RNase) protection assay, cyanine 5 (Cy5)-labeled miR-222 riboprobe, and a Hitachi SV1210 microchip electrophoresis system, which can be used to evaluate the integrity of total RNA. The fluorescence intensity corresponding to the protected RNA fragment increased in a dose-dependent manner with respect to the complementary-strand RNA. More highly sensitive detection of miRNA by microchip electrophoresis than by conventional method using fluorescence-labeled riboprobe could be obtained in 180 s. An obvious increase in miR-222 expression induced by nerve growth factor in PC12 cells could be observed. These results clearly indicate the potential of microchip electrophoresis for the analysis of miRNA using RNase protection assay with a fluorescence-labeled riboprobe. Full article
(This article belongs to the Special Issue Synthetic Fluorescent Indicators for Low Molecular Weight Organic Metabolites)
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532 KiB  
Communication
A Fast Response Highly Selective Probe for the Detection of Glutathione in Human Blood Plasma
by Yixing Guo, Xiaofeng Yang, Lovemore Hakuna, Aabha Barve, Jorge O. Escobedo, Mark Lowry and Robert M. Strongin
Sensors 2012, 12(5), 5940-5950; https://doi.org/10.3390/s120505940 - 8 May 2012
Cited by 80 | Viewed by 12353
Abstract
A fluorescent probe for glutathione (GSH) detection was developed. Our study indicates a possible mechanism which couples a conjugate addition and micelle-catalyzed large membered ring formation/elimination sequence. This method enables excellent selectivity towards GSH over other biological thiols such as cysteine (Cys) and [...] Read more.
A fluorescent probe for glutathione (GSH) detection was developed. Our study indicates a possible mechanism which couples a conjugate addition and micelle-catalyzed large membered ring formation/elimination sequence. This method enables excellent selectivity towards GSH over other biological thiols such as cysteine (Cys) and homocysteine (Hcy). The proposed method is precise with a relative standard deviation (R.S.D) lower than 6% (n = 3) and has been successfully applied to determine GSH in human plasma with recoveries between 99.2% and 102.3%. Full article
(This article belongs to the Special Issue Synthetic Fluorescent Indicators for Low Molecular Weight Organic Metabolites)
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373 KiB  
Article
A Long-Wavelength Fluorescent Squarylium Cyanine Dye Possessing Boronic Acid for Sensing Monosaccharides and Glycoproteins with High Enhancement in Aqueous Solution
by Shingo Saito, Tara L. Massie, Takeshi Maeda, Hiroyuki Nakazumi and Christa L. Colyer
Sensors 2012, 12(5), 5420-5431; https://doi.org/10.3390/s120505420 - 27 Apr 2012
Cited by 29 | Viewed by 8549
Abstract
Fluorescence sensing of saccharides and glycoproteins using a boronic acid functionalized squarylium cyanine dye (“SQ-BA”) is characterized in terms of synthetic, fluorometric, thermodynamic and kinetic parameters. In our previous work, this newly synthesized dye was successfully applied to the separation and [...] Read more.
Fluorescence sensing of saccharides and glycoproteins using a boronic acid functionalized squarylium cyanine dye (“SQ-BA”) is characterized in terms of synthetic, fluorometric, thermodynamic and kinetic parameters. In our previous work, this newly synthesized dye was successfully applied to the separation and quantification of Gram-positive bacteria by capillary electrophoresis with laser-induced fluorescence detection (CE-LIF); however, the fundamental properties of the dye and its saccharide complexes still required elucidation, as presented in this paper. The dye itself forms nonemissive, soluble aggregates in aqueous solution. With the addition of a monosaccharide, the dye aggregate dissociates to form an emissive monomer accompanied by the formation of a cyclic cis-diol ester with long-wavelength emission (lex = 630 nm, lem = 660 nm). A very large fluorescence enhancement factor of 18× was observed for the sensing dye as a fructose complex at pH 10, yielding a limit of detection of 10 mM fructose. The relative order of fluorescence enhancement of SQ-BA with other monosaccharides was found to be: fructose > ribose > arabinose ≈ galactose > xylose > mannose > rhamnose > fucose ≈ glucose; and apparent affinity constants of 102.80, 102.08 and 100.86 M−1 were determined for fructose, ribose and glucose, respectively. Formation of the emissive complexes occurred within minutes, proving the kinetics of the sugar-dye interactions to be suitable for on-column labeling methods in CE-LIF. Furthermore, the sensing dye was successfully applied to glycoproteins, mucin type I–S and type III, which were detected with high sensitivity in batch aqueous solution as a result of the sugar-selective boronic acid-diol esterification as well as hydrophobic interactions. Full article
(This article belongs to the Special Issue Synthetic Fluorescent Indicators for Low Molecular Weight Organic Metabolites)
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Graphical abstract

586 KiB  
Article
An Organic/Inorganic Hybrid Membrane as a Solid “Turn-On” Fluorescent Chemosensor for Coenzyme A (CoA), Cysteine (Cys), and Glutathione (GSH) in Aqueous Media
by Saúl Vallejos, Pedro Estévez, Saturnino Ibeas, Félix C. García, Felipe Serna and José M. García
Sensors 2012, 12(3), 2969-2982; https://doi.org/10.3390/s120302969 - 2 Mar 2012
Cited by 14 | Viewed by 8744
Abstract
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Synthetic Fluorescent Indicators for Low Molecular Weight Organic Metabolites)
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566 KiB  
Article
A Platform for Combined DNA and Protein Microarrays Based on Total Internal Reflection Fluorescence
by Alexander Asanov, Angélica Zepeda and Luis Vaca
Sensors 2012, 12(2), 1800-1815; https://doi.org/10.3390/s120201800 - 9 Feb 2012
Cited by 22 | Viewed by 9670
Abstract
We have developed a novel microarray technology based on total internal reflection fluorescence (TIRF) in combination with DNA and protein bioassays immobilized at the TIRF surface. Unlike conventional microarrays that exhibit reduced signal-to-background ratio, require several stages of incubation, rinsing and stringency control, [...] Read more.
We have developed a novel microarray technology based on total internal reflection fluorescence (TIRF) in combination with DNA and protein bioassays immobilized at the TIRF surface. Unlike conventional microarrays that exhibit reduced signal-to-background ratio, require several stages of incubation, rinsing and stringency control, and measure only end-point results, our TIRF microarray technology provides several orders of magnitude better signal-to-background ratio, performs analysis rapidly in one step, and measures the entire course of association and dissociation kinetics between target DNA and protein molecules and the bioassays. In many practical cases detection of only DNA or protein markers alone does not provide the necessary accuracy for diagnosing a disease or detecting a pathogen. Here we describe TIRF microarrays that detect DNA and protein markers simultaneously, which reduces the probabilities of false responses. Supersensitive and multiplexed TIRF DNA and protein microarray technology may provide a platform for accurate diagnosis or enhanced research studies. Our TIRF microarray system can be mounted on upright or inverted microscopes or interfaced directly with CCD cameras equipped with a single objective, facilitating the development of portable devices. As proof-of-concept we applied TIRF microarrays for detecting molecular markers from Bacillus anthracis, the pathogen responsible for anthrax. Full article
(This article belongs to the Special Issue Synthetic Fluorescent Indicators for Low Molecular Weight Organic Metabolites)
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Review

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703 KiB  
Review
Fluorosomes: Fluorescent Virus-Like Nanoparticles that Represent a Convenient Tool to Visualize Receptor-Ligand Interactions
by Daniela Wojta-Stremayr and Winfried F. Pickl
Sensors 2013, 13(7), 8722-8749; https://doi.org/10.3390/s130708722 - 8 Jul 2013
Cited by 13 | Viewed by 9227
Abstract
Viruses are the smallest life forms and parasitize on many eukaryotic organisms, including humans. Consequently, the study of viruses and viral diseases has had an enormous impact on diverse fields of biology and medicine. Due to their often pathogenic properties, viruses have not [...] Read more.
Viruses are the smallest life forms and parasitize on many eukaryotic organisms, including humans. Consequently, the study of viruses and viral diseases has had an enormous impact on diverse fields of biology and medicine. Due to their often pathogenic properties, viruses have not only had a strong impact on the development of immune cells but also on shaping entire immune mechanisms in their hosts. In order to better characterize virus-specific surface receptors, pathways of virus entry and the mechanisms of virus assembly, diverse methods to visualize virus particles themselves have been developed in the past decades. Apart from characterization of virus-specific mechanisms, fluorescent virus particles also serve as valuable platforms to study receptor-ligand interactions. Along those lines the authors have developed non-infectious virus-like nanoparticles (VNP), which can be decorated with immune receptors of choice and used for probing receptor-ligand interactions, an especially interesting application in the field of basic but also applied immunology research. To be able to better trace receptor-decorated VNP the authors have developed technology to introduce fluorescent proteins into such particles and henceforth termed them fluorosomes (FS). Since VNP are assembled in a simple expression system relying on HEK-293 cells, gene-products of interest can be assembled in a simple and straightforward fashion—one of the reasons why the authors like to call fluorosomes ‘the poor-man’s staining tool’. Within this review article an overview on virus particle assembly, chemical and recombinant methods of virus particle labeling and examples on how FS can be applied as sensors to monitor receptor-ligand interactions on leukocytes are given. Full article
(This article belongs to the Special Issue Synthetic Fluorescent Indicators for Low Molecular Weight Organic Metabolites)
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1451 KiB  
Review
Thiol Reactive Probes and Chemosensors
by Hanjing Peng, Weixuan Chen, Yunfeng Cheng, Lovemore Hakuna, Robert Strongin and Binghe Wang
Sensors 2012, 12(11), 15907-15946; https://doi.org/10.3390/s121115907 - 19 Nov 2012
Cited by 245 | Viewed by 20590
Abstract
Thiols are important molecules in the environment and in biological processes. Cysteine (Cys), homocysteine (Hcy), glutathione (GSH) and hydrogen sulfide (H2S) play critical roles in a variety of physiological and pathological processes. The selective detection of thiols using reaction-based probes and [...] Read more.
Thiols are important molecules in the environment and in biological processes. Cysteine (Cys), homocysteine (Hcy), glutathione (GSH) and hydrogen sulfide (H2S) play critical roles in a variety of physiological and pathological processes. The selective detection of thiols using reaction-based probes and sensors is very important in basic research and in disease diagnosis. This review focuses on the design of fluorescent and colorimetric probes and sensors for thiol detection. Thiol detection methods include probes and labeling agents based on nucleophilic addition and substitution, Michael addition, disulfide bond or Se-N bond cleavage, metal-sulfur interactions and more. Probes for H2S are based on nucleophilic cyclization, reduction and metal sulfide formation. Thiol probe and chemosensor design strategies and mechanism of action are discussed in this review. Full article
(This article belongs to the Special Issue Synthetic Fluorescent Indicators for Low Molecular Weight Organic Metabolites)
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581 KiB  
Review
Visualizing Sweetness: Increasingly Diverse Applications for Fluorescent-Tagged Glucose Bioprobes and Their Recent Structural Modifications
by Woong Hee Kim, Jinho Lee, Da-Woon Jung and Darren R. Williams
Sensors 2012, 12(4), 5005-5027; https://doi.org/10.3390/s120405005 - 18 Apr 2012
Cited by 73 | Viewed by 12710
Abstract
Glucose homeostasis is a fundamental aspect of life and its dysregulation is associated with important diseases, such as cancer and diabetes. Traditionally, glucose radioisotopes have been used to monitor glucose utilization in biological systems. Fluorescent-tagged glucose analogues were initially developed in the 1980s, [...] Read more.
Glucose homeostasis is a fundamental aspect of life and its dysregulation is associated with important diseases, such as cancer and diabetes. Traditionally, glucose radioisotopes have been used to monitor glucose utilization in biological systems. Fluorescent-tagged glucose analogues were initially developed in the 1980s, but it is only in the past decade that their use as a glucose sensor has increased significantly. These analogues were developed for monitoring glucose uptake in blood cells, but their recent applications include tracking glucose uptake by tumor cells and imaging brain cell metabolism. This review outlines the development of fluorescent-tagged glucose analogues, describes their recent structural modifications and discusses their increasingly diverse biological applications. Full article
(This article belongs to the Special Issue Synthetic Fluorescent Indicators for Low Molecular Weight Organic Metabolites)
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