Ebselen-Agents for Sensing, Imaging and Labeling: Facile and Full-Featured Application in Biochemical Analysis.

Phenyl-1,2-benzoselenazol-3(2H)-one (ebselen) is a classical mimic of glutathione peroxidase (GPx). Thioredoxin interaction endows ebselen attractive biological functions, such as antioxidation and...

[1]  Yanlong Xing,et al.  Analysis of extracellular vesicles as emerging theranostic nanoplatforms , 2020 .

[2]  M. Parnham,et al.  Potential therapeutic use of ebselen for COVID-19 and other respiratory viral infections , 2020, Free Radical Biology and Medicine.

[3]  Hualiang Jiang,et al.  Structure of Mpro from SARS-CoV-2 and discovery of its inhibitors , 2020, Nature.

[4]  D. Vuckovic,et al.  Comparison of N-ethyl maleimide and N-(1-phenylethyl) maleimide for derivatization of biological thiols using liquid chromatography-mass spectrometry , 2020, Analytical and Bioanalytical Chemistry.

[5]  M. Kühl,et al.  Evaluation of Ebselen-azadioxatriangulenium as redox-sensitive fluorescent intracellular probe and as indicator within a planar redox optode , 2020 .

[6]  Tianfeng Chen,et al.  Rational design and action mechanisms of chemically innovative organoselenium in cancer therapy. , 2019, Chemical communications.

[7]  J. Fei,et al.  A hepatocyte-targeting near-infrared ratiometric fluorescent probe for monitoring peroxynitrite during drug-induced hepatotoxicity and its remediation. , 2019, Chemical communications.

[8]  C. Schofield,et al.  A Fluorescence‐Based Assay for Screening β‐Lactams Targeting the Mycobacterium tuberculosis Transpeptidase LdtMt2 , 2019, Chembiochem : a European journal of chemical biology.

[9]  B. Ruan,et al.  Design and synthesis of biotinylated Hexylselen as a probe to identify KGA allosteric inhibitors by a convenient biomolecular interaction assay. , 2019, Bioorganic & medicinal chemistry letters.

[10]  H. Ju,et al.  Selenium-isotopic signature toward mass spectrometric identification and enzyme activity assay. , 2019, Analytica chimica acta.

[11]  C. Schofield,et al.  Targeting the Mycobacterium tuberculosis transpeptidase LdtMt2 with cysteine-reactive inhibitors including ebselen , 2019, Chemical communications.

[12]  J. Fei,et al.  In-situ imaging of azoreductase activity in the acute and chronic ulcerative colitis mice by a near-infrared fluorescent probe. , 2019, Analytical chemistry.

[13]  I. Ivanović‐Burmazović,et al.  Synthesis of a Hybrid between SOD Mimetic and Ebselen to Target Oxidative Stress , 2019, European Journal of Inorganic Chemistry.

[14]  G. Mugesh,et al.  Probing the Formation of a Seleninic Acid in Living Cells by the Fluorescence Switching of a Glutathione Peroxidase Mimetic. , 2019, Angewandte Chemie.

[15]  Qianqian Sun,et al.  Dynamic fluorescent imaging analysis of mitochondrial redox in single cells with a microfluidic device. , 2019, Biosensors & bioelectronics.

[16]  Megan C. Garland,et al.  Covalent Modifiers of Botulinum Neurotoxin Counteract Toxin Persistence. , 2019, ACS chemical biology.

[17]  Xi Zhang In My Element : Selenium , 2018, Chemistry – A European Journal.

[18]  A. Holmgren,et al.  Selenocysteine in mammalian thioredoxin reductase and application of ebselen as a therapeutic. , 2018, Free radical biology & medicine.

[19]  A. Fernandes,et al.  Organic selenium compounds as potential chemotherapeutic agents for improved cancer treatment , 2018, Free radical biology & medicine.

[20]  Yue Wang,et al.  A naphthalimide based fast and selective fluorescent probe for hypochlorous acid/hypochlorite and its application for bioimaging , 2018 .

[21]  Chusen Huang,et al.  ESIPT-based ratiometric fluorescence probe for the intracellular imaging of peroxynitrite. , 2018, Chemical communications.

[22]  B. Tang,et al.  Target discovery of ebselen with a biotinylated probe. , 2018, Chemical communications.

[23]  W. Hamama,et al.  An Easy Synthetic Approach to Construct Some Ebselen Analogues and Benzo[b]selenophene Derivatives: Their Antioxidant and Cytotoxic Assessment , 2018, Journal of Heterocyclic Chemistry.

[24]  J. Rocha,et al.  Diselenoamino acid derivatives as GPx mimics and as substrates of TrxR: in vitro and in silico studies. , 2018, Organic & biomolecular chemistry.

[25]  Y. Ge,et al.  A protein structure-guided covalent scaffold selectively targets the B1 and B2 subclass metallo-β-lactamases. , 2018, Chemical communications.

[26]  Long Yi,et al.  A highly sensitive and selective fluorescent probe for fast sensing of endogenous HClO in living cells. , 2018, Chemical communications.

[27]  J. Szpunar,et al.  Advances in electrospray mass spectrometry for the selenium speciation: Focus on Se-rich yeast , 2017, TrAC Trends in Analytical Chemistry.

[28]  D. Hare,et al.  Applications of liquid chromatography-inductively coupled plasma-mass spectrometry in the biosciences: A tutorial review and recent developments , 2017, TrAC Trends in Analytical Chemistry.

[29]  F. Vanhaecke,et al.  High-performance liquid chromatography coupled to inductively coupled plasma – Mass spectrometry (HPLC-ICP-MS) for quantitative metabolite profiling of non-metal drugs , 2017, TrAC Trends in Analytical Chemistry.

[30]  B. Ruan,et al.  Ebselen: Mechanisms of Glutamate Dehydrogenase and Glutaminase Enzyme Inhibition. , 2017, ACS chemical biology.

[31]  W. Dehaen,et al.  Selenium containing macrocycles: transformation between Se–N/Se–S/Se–Se bonds , 2017, Science China Chemistry.

[32]  Christian G Elowsky,et al.  Chemoselective Alteration of Fluorophore Scaffolds as a Strategy for the Development of Ratiometric Chemodosimeters. , 2017, Angewandte Chemie.

[33]  Z. Diwu,et al.  Fluorescent real-time quantitative measurements of intracellular peroxynitrite generation and inhibition. , 2017, Analytical biochemistry.

[34]  M. Bellanda,et al.  Mechanistic Insight into the Oxidation of Organic Phenylselenides by H2 O2. , 2017, Chemistry.

[35]  B. Ruan,et al.  Biomolecular Interaction Assays Identified Dual Inhibitors of Glutaminase and Glutamate Dehydrogenase That Disrupt Mitochondrial Function and Prevent Growth of Cancer Cells. , 2017, Analytical chemistry.

[36]  T. Hazbun,et al.  Ebselen exerts antifungal activity by regulating glutathione (GSH) and reactive oxygen species (ROS) production in fungal cells. , 2017, Biochimica et biophysica acta. General subjects.

[37]  J. Ścianowski,et al.  New glutathione peroxidase mimetics-Insights into antioxidant and cytotoxic activity. , 2017, Bioorganic & medicinal chemistry.

[38]  Juyoung Yoon,et al.  Boronate based fluorescence (ESIPT) probe for peroxynitrite. , 2016, Chemical communications.

[39]  Hong Chen,et al.  Synthesis and evaluation of 8-hydroxyquinolin derivatives substituted with (benzo[d][1,2]selenazol-3(2H)-one) as effective inhibitor of metal-induced Aβ aggregation and antioxidant. , 2016, Bioorganic & medicinal chemistry.

[40]  J. Brodbelt,et al.  Cysteine-Selective Peptide Identification: Selenium-Based Chromophore for Selective S-Se Bond Cleavage with 266 nm Ultraviolet Photodissociation. , 2016, Analytical chemistry.

[41]  J. Brodbelt,et al.  Characterization of the Cysteine Content in Proteins Utilizing Cysteine Selenylation with 266 nm Ultraviolet Photodissociation (UVPD) , 2016, Journal of The American Society for Mass Spectrometry.

[42]  M. Karlsson Ott,et al.  Multifunctional Antioxidants: Regenerable Radical-Trapping and Hydroperoxide-Decomposing Ebselenols. , 2016, Angewandte Chemie.

[43]  S. Vichi,et al.  Thiols in brewed coffee: Assessment by fast derivatization and liquid chromatography–high resolution mass spectrometry , 2015 .

[44]  A. Sanz-Medel,et al.  Determination of reduced homocysteine in human serum by elemental labelling and liquid chromatography with ICP-MS and ESI-MS detection , 2015, Analytical and Bioanalytical Chemistry.

[45]  T. Wirth Small Organoselenium Compounds: More than just Glutathione Peroxidase Mimics. , 2015, Angewandte Chemie.

[46]  Pengyuan Liu,et al.  An accurate mass spectrometric approach for the simultaneous comparison of GSH, Cys, and Hcy in L02 cells and HepG2 cells using new NPSP isotope probes. , 2015, Chemical communications.

[47]  W. Liu,et al.  Reversible two-photon fluorescent probe for imaging of hypochlorous acid in live cells and in vivo. , 2015, Chemical communications.

[48]  Kwok‐yin Wong,et al.  Ebselen as a potent covalent inhibitor of New Delhi metallo-β-lactamase (NDM-1). , 2015, Chemical communications.

[49]  S. Vichi,et al.  Analysis of volatile thiols in alcoholic beverages by simultaneous derivatization/extraction and liquid chromatography-high resolution mass spectrometry. , 2015, Food chemistry.

[50]  Xingshu Li,et al.  Design, synthesis, and biological evaluation of benzoselenazole-stilbene hybrids as multi-target-directed anti-cancer agents. , 2015, European journal of medicinal chemistry.

[51]  W. Hamama,et al.  Synthesis and Antioxidant Activities of Novel Chiral Ebselen Analogues , 2014 .

[52]  J. Ścianowski,et al.  Highly efficient synthesis and antioxidant capacity of N-substituted benzisoselenazol-3(2H)-ones , 2014 .

[53]  S. Vichi,et al.  Determination of volatile thiols in roasted coffee by derivatization and liquid chromatography-high resolution mass spectrometric analysis. , 2014, Food research international.

[54]  Chad E. Schroeder,et al.  Ebselen Inhibits Hepatitis C Virus NS3 Helicase Binding to Nucleic Acid and Prevents Viral Replication , 2014, ACS chemical biology.

[55]  L. Sancineto,et al.  “The green side of the moon: ecofriendly aspects of organoselenium chemistry” , 2014 .

[56]  P. Schieberle,et al.  Characterization of the major aroma-active compounds in mango (Mangifera indica L.) cultivars Haden, White Alfonso, Praya Sowoy, Royal Special, and Malindi by application of a comparative aroma extract dilution analysis. , 2014, Journal of agricultural and food chemistry.

[57]  Tong Wu,et al.  A selenium-contained aggregation-induced "turn-on" fluorescent probe for hydrogen peroxide. , 2014, Organic & biomolecular chemistry.

[58]  S. Vichi,et al.  Determination of volatile thiols in virgin olive oil by derivatisation and LC-HRMS, and relation with sensory attributes. , 2014, Food chemistry.

[59]  Sangit Kumar,et al.  Sensitive and regenerable organochalcogen probes for the colorimetric detection of thiols , 2014 .

[60]  N. Ahalawat,et al.  An ebselen like catalyst with enhanced GPx activity via a selenol intermediate. , 2014, Organic & biomolecular chemistry.

[61]  Jiangli Fan,et al.  A near-infrared fluorescent probe for selective detection of HClO based on Se-sensitized aggregation of heptamethine cyanine dye. , 2014, Chemical communications.

[62]  Ori J. Lieberman,et al.  High-throughput screening using the differential radial capillary action of ligand assay identifies ebselen as an inhibitor of diguanylate cyclases. , 2014, ACS chemical biology.

[63]  S. Vichi,et al.  Determination of volatile thiols in lipid matrix by simultaneous derivatization/extraction and liquid chromatography-high resolution mass spectrometric analysis. Application to virgin olive oil. , 2013, Journal of chromatography. A.

[64]  Yang Sun,et al.  Synthesis and evaluation of multi-target-directed ligands against Alzheimer's disease based on the fusion of donepezil and ebselen. , 2013, Journal of medicinal chemistry.

[65]  Peng Li,et al.  A near-infrared reversible and ratiometric fluorescent probe based on Se-BODIPY for the redox cycle mediated by hypobromous acid and hydrogen sulfide in living cells. , 2013, Chemical communications.

[66]  Peng Li,et al.  Reversible near-infrared fluorescent probe introducing tellurium to mimetic glutathione peroxidase for monitoring the redox cycles between peroxynitrite and glutathione in vivo. , 2013, Journal of the American Chemical Society.

[67]  B. Tang,et al.  A near-infrared reversible fluorescent probe for real-time imaging of redox status changes in vivo , 2013 .

[68]  P. Li,et al.  A BODIPY fluorescence probe modulated by selenoxide spirocyclization reaction for peroxynitrite detection and imaging in living cells , 2013 .

[69]  Shu-Pao Wu,et al.  Hypochlorous acid turn-on fluorescent probe based on oxidation of diphenyl selenide. , 2013, Organic letters.

[70]  P. Li,et al.  A fluorescent probe for rapid detection of thiols and imaging of thiols reducing repair and H2O2 oxidative stress cycles in living cells. , 2013, Chemical communications.

[71]  D. Siegel Applications of reversible covalent chemistry in analytical sample preparation. , 2012, The Analyst.

[72]  Lingxin Chen,et al.  Sensitive near-infrared fluorescent probes for thiols based on Se-N bond cleavage: imaging in living cells and tissues. , 2012, Chemistry.

[73]  H. Zeng,et al.  Inhibition of thioredoxin reductase by a novel series of bis-1,2-benzisoselenazol-3(2H)-ones: Organoselenium compounds for cancer therapy. , 2012, Bioorganic & medicinal chemistry.

[74]  F. Nome,et al.  GPx-Like activity of selenides and selenoxides: experimental evidence for the involvement of hydroxy perhydroxy selenane as the active species. , 2012, Journal of the American Chemical Society.

[75]  P. Harrington,et al.  Fast and Selective Modification of Thiol Proteins/Peptides by N-(Phenylseleno)phthalimide , 2012, Journal of The American Society for Mass Spectrometry.

[76]  Sangit Kumar,et al.  Copper catalyzed/mediated synthetic methodology for ebselen and related isoselenazolones , 2011 .

[77]  B. Tang,et al.  A near-infrared reversible fluorescent probe for peroxynitrite and imaging of redox cycles in living cells. , 2011, Chemical communications.

[78]  Huimin Ma,et al.  An unprecedented strategy for selective and sensitive fluorescence detection of nitric oxide based on its reaction with a selenide. , 2011, Chemical communications.

[79]  P. Li,et al.  A near-IR reversible fluorescent probe modulated by selenium for monitoring peroxynitrite and imaging in living cells. , 2011, Journal of the American Chemical Society.

[80]  K. P. Bhabak,et al.  Mechanistic investigations on the efficient catalytic decomposition of peroxynitrite by ebselen analogues. , 2011, Organic & biomolecular chemistry.

[81]  Hao Zhang,et al.  Tandem MS Analysis of Selenamide-Derivatized Peptide Ions , 2011, Journal of the American Society for Mass Spectrometry.

[82]  G. Mugesh,et al.  Synthesis and antioxidant activity of peptide-based ebselen analogues. , 2011, Chemistry.

[83]  L. Andresen,et al.  Investigation of the selenium metabolism in cancer cell lines. , 2011, Metallomics : integrated biometal science.

[84]  M. Messali,et al.  Synthesis and Characterization of a New Five and Six Membered Selenoheterocyclic Compounds Homologues of Ebselen , 2011 .

[85]  D. Chopra,et al.  Cu-catalyzed efficient synthetic methodology for ebselen and related Se-N heterocycles. , 2010, Organic letters.

[86]  B. Tang,et al.  Study of highly selective and efficient thiol derivatization using selenium reagents by mass spectrometry. , 2010, Analytical chemistry.

[87]  B. Tang,et al.  Use of selenium to detect mercury in water and cells: an enhancement of the sensitivity and specificity of a seleno fluorescent probe. , 2009, Chemistry.

[88]  Rafael Radi,et al.  Chemical biology of peroxynitrite: kinetics, diffusion, and radicals. , 2009, ACS chemical biology.

[89]  Junqiu Liu,et al.  Incorporation of tellurocysteine into glutathione transferase generates high glutathione peroxidase efficiency. , 2009, Angewandte Chemie.

[90]  E. Piasecki,et al.  New organoselenium compounds active against pathogenic bacteria, fungi and viruses. , 2008, Chemical & pharmaceutical bulletin.

[91]  Adam M. Hawkridge,et al.  Synthesis, characterization, and application of iodoacetamide derivatives utilized for the ALiPHAT strategy. , 2008, Journal of the American Chemical Society.

[92]  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.

[93]  Guo-liang Zhang,et al.  High performance liquid chromatographic determination of 1,2-[bis(1,2-benzisoselenazolone-3(2H)-ketone)]-ethane (BBSKE), a novel organoselenium compound, in dog plasma using pre-column derivatization and its application in pharmacokinetic study. , 2007, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[94]  K. P. Bhabak,et al.  Synthesis, characterization, and antioxidant activity of some ebselen analogues. , 2007, Chemistry.

[95]  T. Kálai,et al.  Combining benzo[d]isoselenazol-3-ones with sterically hindered alicyclic amines and nitroxides: enhanced activity as glutathione peroxidase mimics. , 2005, Organic & biomolecular chemistry.

[96]  S. Stürup,et al.  Quantitative determination of selenium metabolites in human urine by LC-DRC-ICP-MS , 2005 .

[97]  G. Yalcin,et al.  Determination of Ebselen by HPLC: Validation and Application of the Method , 2004 .

[98]  P. Schieberle,et al.  Quantitation of the intense aroma compound 3-mercapto-2-methylpentan-1-ol in raw and processed onions (Allium cepa) of different origins and in other Allium varieties using a stable isotope dilution assay. , 2004, Journal of agricultural and food chemistry.

[99]  W. Hsu,et al.  Synthesis and biological evaluation of ebselen and its acyclic derivatives. , 2003, Chemical & pharmaceutical bulletin.

[100]  C. Dwivedi,et al.  A simultaneous liquid chromatography/mass spectrometric assay of glutathione, cysteine, homocysteine and their disulfides in biological samples. , 2003, Journal of pharmaceutical and biomedical analysis.

[101]  J. Gutteridge,et al.  Thiols in cellular redox signalling and control. , 2001, Current medicinal chemistry.

[102]  C. Schiesser,et al.  Intramolecular Homolytic Substitution with Amidyl Radicals: A Free-Radical Synthesis of Ebselen and Related Analogues. , 1997, The Journal of organic chemistry.

[103]  L. Silks,et al.  Synthesis of 2-phenyl-1,2-benziso[77Se]selenazol-3(2H)-one : Ebselen , 1996 .

[104]  E. Piasecki,et al.  Aromatic and Azaaromatic Diselenides, Benzisoselenazolones and Related Compounds as Immunomodulators Active in Humans: Synthesis and Properties , 1993 .

[105]  N. Dereu,et al.  Ortholithiation As a Tool for the Synthesis of Ebselen Analogues , 1991 .

[106]  L. Engman,et al.  Expedient synthesis of ebselen and related compounds , 1989 .

[107]  R. D. Doworkin PVC Stabilizers of the past, present, and future , 1989 .

[108]  Michio. Kobayashi,et al.  Photochemical Reaction of 2-Aryl-1,2-benzisoselenazol-3(2H)-ones , 1986 .

[109]  A. Plenevaux,et al.  Synthesis of 75Se‐2‐phenyl‐1,2‐benzisoselenazol‐3(2H)‐one (PZ 51; ebselen. A novel biologically active organo‐selenium compound , 1986 .