ChemBioChem

Cover image for Vol. 13 Issue 11

July 23, 2012

Volume 13, Issue 11

Pages 1525–1699

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlight
    8. Communications
    9. Full Papers
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    1. Cover Picture: Novel Indanone Derivatives as Potential Imaging Probes for β-Amyloid Plaques in the Brain (ChemBioChem 11/2012) (page 1525)

      Jin-Ping Qiao, Dr. Chang-Sheng Gan, Chen-Wei Wang, Jin-Fang Ge, Dou-Dou Nan, Prof. Jian Pan and Prof. Jiang-Ning Zhou

      Version of Record online: 17 JUL 2012 | DOI: 10.1002/cbic.201290043

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      The cover picture shows fluorescent microscope images (green) of amyloid plaques stained by indanone derivatives that were designed from donepezil. Using molecular imaging probes to detect senile plaques might help the early diagnosis of Alzheimer's disease (AD). On p. 1652 ff., J.-N. Zhou et al. describe how they synthesized and characterized a novel series of indanone derivatives. The in vitro binding studies, staining of Alzheimer's disease (AD) brain sections, autoradiography, and biodistribution data all suggested that these derivatives might represent potential amyloid imaging agents for the detection of senile plaques in AD.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlight
    8. Communications
    9. Full Papers
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    1. Inside Cover: A Turn-on Fluorescent Sensor for Imaging Labile Fe3+ in Live Neuronal Cells at Subcellular Resolution (ChemBioChem 11/2012) (page 1526)

      Dr. Yibin Wei, Ziya Aydin, Yi Zhang, Zhiwei Liu and Prof. Dr. Maolin Guo

      Version of Record online: 17 JUL 2012 | DOI: 10.1002/cbic.201290044

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      The inside cover picture shows labile Fe3+ pools in live human SH-SY5Y cells imaged by a confocal microscope with a new Fe3+ sensor. This highly sensitive, selective and reversible turn-on Fe3+ sensor makes it possible to see endogenous labile Fe3+ in live cells at subcellular resolution for the first time. For further details see the communication by M. Guo et al. on p. 1569 ff.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlight
    8. Communications
    9. Full Papers
    10. Preview
  4. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlight
    8. Communications
    9. Full Papers
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  5. Review

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlight
    8. Communications
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    1. Rieske Iron–Sulfur Protein of the Cytochrome bc1 Complex: A Potential Target for Fungicide Discovery (pages 1542–1551)

      Dr. Wen-Chao Yang, Hui Li, Fu Wang, Dr. Xiao-Lei Zhu and Prof. Dr. Guang-Fu Yang

      Version of Record online: 9 JUL 2012 | DOI: 10.1002/cbic.201200295

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      Risky science: The cytochrome bc1 complex is an important target for fungicides. Unfortunately, most commercial fungicides suffer from resistance after widespread application. As one of the catalytic subunit of the cyt bc1 complex, the Rieske iron–sulfur protein (ISP) is attracting attention because of its particular role in electron transfer as well as its interaction with various inhibitors.

  6. Highlight

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlight
    8. Communications
    9. Full Papers
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    1. A Need for Speed: Genetic Encoding of Rapid Cycloaddition Chemistries for Protein Labelling in Living Cells (pages 1553–1557)

      Moritz J. Schmidt and Dr. Daniel Summerer

      Version of Record online: 29 JUN 2012 | DOI: 10.1002/cbic.201200321

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      Rapid reactions: Several reactants for strain-promoted cycloaddition reactions (see picture) have been genetically encoded as the side chains of noncanonical amino acids. This results in decisive improvements for the fluorescent labelling of intracellular proteins such as quantitative turnover, completion of labelling reactions within minutes, fluorogenic effects and even partial orthogonality for multicolour labelling.

  7. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlight
    8. Communications
    9. Full Papers
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    1. Development and Application of a Fluoride-Detection-Based Fluorescence Assay for γ-Butyrobetaine Hydroxylase (pages 1559–1563)

      Anna M. Rydzik, Ivanhoe K. H. Leung, Dr. Grazyna T. Kochan, Armin Thalhammer, Prof. Udo Oppermann, Dr. Timothy D. W. Claridge and Prof. Christopher J. Schofield

      Version of Record online: 22 JUN 2012 | DOI: 10.1002/cbic.201200256

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      Fluoride assays for oxygenases: The 2-oxoglutarate-dependent oxygenase BBOX catalyses the final step in carnitine biosynthesis and is a medicinal chemistry target. We report that BBOX can hydroxylate fluorinated substrates analogues with subsequent release of a fluoride ion, thereby enabling an efficient fluorescence-based assay.

    2. Genetically Targetable and Color-Switching Fluorescent Probe (pages 1564–1568)

      Dr. Dmytro A. Yushchenko, Ming Zhang, Qi Yan, Prof. Dr. Alan S. Waggoner and Prof. Dr. Marcel P. Bruchez

      Version of Record online: 6 JUL 2012 | DOI: 10.1002/cbic.201200334

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      Color bind: We have developed a probe TMR-para-MG that switches its fluorescence emission upon binding to a fluorogen-activating protein (FAP). In cells that express FAP, this dye labels target sites in one color and mitochondria in another color, thus it might be a suitable tool for monitoring changes in mitochondrial membrane potential.

    3. A Turn-on Fluorescent Sensor for Imaging Labile Fe3+ in Live Neuronal Cells at Subcellular Resolution (pages 1569–1573)

      Dr. Yibin Wei, Ziya Aydin, Yi Zhang, Zhiwei Liu and Prof. Dr. Maolin Guo

      Version of Record online: 26 JUN 2012 | DOI: 10.1002/cbic.201200202

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      An eye for an iron: A highly sensitive, selective and reversible turn-on Fe3+ sensor for imaging labile Fe3+ in live cells at subcellular resolution is reported. The sensor can respond to changes in intracellular Fe3+ levels and was used to image endogenous chelatable Fe3+ in live human neuroblastoma SH-SY5Y cells, with two Fe3+ pools being identified in mitochondria and endosomes/ lysosomes for the first time.

    4. Molecular Drivers of Base Flipping During Sequence-Specific DNA Methylation (pages 1574–1577)

      Dr. Douglas M. Matje and Prof. Norbert O. Reich

      Version of Record online: 22 JUN 2012 | DOI: 10.1002/cbic.201200104

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      One step at a time: Substrates containing nucleotide analogues lacking sequence-specific contacts to the C5 methyltransferase M.HhaI were used to probe the role of individual interactions in effecting conformational transitions during base flipping. A segregation of duties, that is, specific recognition and chemomechanical force for base flipping and active site assembly, within the enzyme is confirmed.

  8. Full Papers

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlight
    8. Communications
    9. Full Papers
    10. Preview
    1. 19F MRI Monitoring of Gene Expression in Living Cells through Cell-Surface β-Lactamase Activity (pages 1579–1583)

      Hisashi Matsushita, Dr. Shin Mizukami, Dr. Yuki Mori, Dr. Fuminori Sugihara, Prof. Masashiro Shirakawa, Prof. Yoshichika Yoshioka and Prof. Kazuya Kikuchi

      Version of Record online: 6 JUL 2012 | DOI: 10.1002/cbic.201200331

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      MRI can provide information on deep tissues that cannot be visualized by other methods. A new 19F MRI monitoring system for gene expression in living cells was developed by exploiting cell-surface-displayed β-lactamase and a specific 19F MRI probe. This imaging strategy could lead to useful technologies for diagnosis and therapy.

    2. Kinetics Studies on the Inhibition Mechanism of Pancreatic α-Amylase by Glycoconjugated 1H-1,2,3-Triazoles: A New Class of Inhibitors with Hypoglycemiant Activity (pages 1584–1593)

      Prof. Dr. Mario Roberto Senger, Lucas da Costa Andrade Gomes, Prof. Dr. Sabrina Baptista Ferreira, Prof. Dr. Carlos Roland Kaiser, Prof. Dr. Vitor Francisco Ferreira and Prof. Dr. Floriano Paes Silva Jr

      Version of Record online: 29 JUN 2012 | DOI: 10.1002/cbic.201200272

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      Glycoconjugate triazoles (GCTs) have been found to be active against various α- and β-glycosidases, but there is scarce data about their inhibition mode. This study reports the kinetic analysis and inhibition mechanism of GCTs with porcine α-amylase, and shows that this enzyme is a possible molecular target in their hypoglycemiant activity.

    3. Identifying and Characterizing Binding Sites on the Irreversible Inhibition of Human Glutathione S-Transferase P1-1 by S-Thiocarbamoylation (pages 1594–1604)

      Dr. Indalecio Quesada-Soriano, Dr. Alessandra Primavera, Dr. Juan M. Casas-Solvas, Prof. Dr. Ramiro Téllez-Sanz, Prof. Dr. Carmen Barón, Prof. Dr. Antonio Vargas-Berenguel, Prof. Dr. Mario Lo Bello and Prof. Dr. Luís García-Fuentes

      Version of Record online: 27 JUN 2012 | DOI: 10.1002/cbic.201200210

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      Irreversible modification: We report the inactivation of GST P1-1 with S-(N-benzylthiocarbamoyl)glutathione through the covalent modification of two Cys47 residues per dimer and one Cys101. This covalent inhibition is revealed at physiological temperatures, at which the BITC moiety is covalently bound to these enzyme cysteines through an S-thiocarbamoylation reaction.

    4. Borononucleotides as Substrates/Binders for Human NMP Kinases: Enzymatic and Spectroscopic Evaluation (pages 1605–1612)

      Dr. Chahrazade El Amri, Dr. Anthony R. Martin, Dr. Jean-Jacques Vasseur and Dr. Michael Smietana

      Version of Record online: 25 JUN 2012 | DOI: 10.1002/cbic.201200199

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      B[BOND]O[BOND]P it! The ability of a series of 5′-boronoisosteric NMP analogues to bind the NMP site of selected human NMP kinases was evaluated. A borononucleotide thymidine analogue was shown to behave as substrate of human TMP kinase: the first example of a boronic acid phosphorylated by a kinase and leading to an unstable and reversible B[BOND]O[BOND]P connection.

    5. Analysis of the Mildiomycin Biosynthesis Gene Cluster in Streptoverticillum remofaciens ZJU5119 and Characterization of MilC, a Hydroxymethyl cytosyl-glucuronic Acid Synthase (pages 1613–1621)

      Jun Wu, Dr. Li Li, Prof. Zixin Deng, Prof. T. Mark Zabriskie and Dr. Xinyi He

      Version of Record online: 29 JUN 2012 | DOI: 10.1002/cbic.201200173

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      Sweet 16: The biosynthetic gene cluster for the peptidyl antibiotic mildiomycin was cloned and heterologously expressed in Streptomyces lividans. Sixteen ORFs were confirmed by systematic mutagenesis to be essential for its biosynthesis. The cytosylglucuronic acid synthase MilC was characterized in vivo and in vitro. Feeding experiments demonstrated that the carboxyl carbon originated from L-arginine.

    6. Antofine Analogues Can Inhibit Tobacco Mosaic Virus Assembly through Small-Molecule–RNA Interactions (pages 1622–1627)

      Shuang Gao, Dr. Ruoyu Zhang, Dr. Zhihong Yu and Prof. Dr. Zhen Xi

      Version of Record online: 29 JUN 2012 | DOI: 10.1002/cbic.201200313

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      Targeting viral RNA: Antofine analogues bind highly selectively and efficiently with TMV RNA to disrupt in vitro virus assembly. The relationship between the RNA binding ability and viral assembly inhibition of antofine analogues might imply a general antiviral strategy: the use of small molecules targeting viral RNA to inhibit viral assembly.

    7. Targeting Tumour Proliferation with a Small-Molecule Inhibitor of AICAR Transformylase Homodimerization (pages 1628–1634)

      Dr. Ian B. Spurr, Dr. Charles N. Birts, Dr. Francesco Cuda, Prof. Stephen J. Benkovic, Dr. Jeremy P. Blaydes and Dr. Ali Tavassoli

      Version of Record online: 4 JUL 2012 | DOI: 10.1002/cbic.201200279

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      Breaking up is hard to do: The development of an inhibitor of AICAR transformylase, a key enzyme in de novo purine biosynthesis is reported. The compound functions by inhibiting the protein–protein interaction of the monomers of this homodimeric enzyme. Inhibition of AICAR transformylase by this compound is demonstrated to reduce the proliferation of a breast cancer cell line.

    8. Volatile Lactones from Streptomycetes Arise via the Antimycin Biosynthetic Pathway (pages 1635–1644)

      Ramona Riclea, Dr. Bertrand Aigle, Prof. Dr. Pierre Leblond, Dr. Ilka Schoenian, Prof. Dr. Dieter Spiteller and Dr. Jeroen S. Dickschat

      Version of Record online: 29 JUN 2012 | DOI: 10.1002/cbic.201200260

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      Knock it out! Several volatile lactones have been found in streptomycetes. Their structures have been suggested based on GC–MS data and verified by comparison with synthetic standards. The origin of all lactones was shown in knockout experiments to depend on the antimycin biosynthetic gene cluster.

    9. Substrate-Induced Conformational Change and Isomerase Activity of Dienelactone Hydrolase and its Site-Specific Mutants (pages 1645–1651)

      Dr. Ian Walker, Dr. James E. Hennessy, Prof. Dr. David L. Ollis and Prof. Dr. Christopher J. Easton

      Version of Record online: 3 JUL 2012 | DOI: 10.1002/cbic.201200232

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      Greater longevity of an intermediate: Dienelactone hydrolase has been found to exhibit different substrate-induced conformational responses specific for hydrolysis of each of its E and Z substrate isomers. Its C123S mutant catalyses the isomerisation of these same substrates without hydrolysis because the acyl–enzyme intermediates are longer-lived, thus allowing for their interconversion followed by relactonisation.

    10. Novel Indanone Derivatives as Potential Imaging Probes for β-Amyloid Plaques in the Brain (pages 1652–1662)

      Jin-Ping Qiao, Dr. Chang-Sheng Gan, Chen-Wei Wang, Jin-Fang Ge, Dou-Dou Nan, Prof. Jian Pan and Prof. Jiang-Ning Zhou

      Version of Record online: 6 JUL 2012 | DOI: 10.1002/cbic.201200223

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      Amyloid senile plaque probes: A series of indanone derivatives has been synthesized and characterized. In vitro binding studies, staining of Alzheimer's disease (AD) brain sections, autoradiography, and biodistribution data all suggested that the indanone derivatives might represent potential amyloid imaging agents for the detection of senile plaques in AD.

    11. DYZ-2-90, a Novel Neo-tanshinlactone Ring-Opened Compound, Induces ERK-Mediated Mitotic Arrest and Subsequent Apoptosis by Activating JNK in Human Colorectal Cancer Cells (pages 1663–1672)

      Li-Ting Wang, Dr. Shiow-Lin Pan, Dr. Tzu-Hsuan Chen, Dr. Yizhou Dong, Prof. Kuo-Hsiung Lee and Prof. Che-Ming Teng

      Version of Record online: 3 JUL 2012 | DOI: 10.1002/cbic.201200191

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      Interfering: DYZ-2-90 is a novel ring-opened compound modified from neo-tanshinlactone isolated from the Chinese medicinal herb Tanshen. It binds directly to microtubules, inducing ERK-mediated mitotic arrest and subsequent apoptosis by JNK. This provides a new insight into the model of mitotic cell death, which was propounded to elucidate how cancer cells respond to microtubule-interfering agents.

    12. Thiogalactopyranosides are Resistant to Hydrolysis by α-Galactosidases (pages 1673–1679)

      Dr. Dietlind Adlercreutz, Dr. Yayoi Yoshimura, Dr. Karin Mannerstedt, Dr. Warren W. Wakarchuk, Dr. Eric P. Bennett, Prof. Norman J. Dovichi, Prof. Ole Hindsgaul and Prof. Monica M. Palcic

      Version of Record online: 27 JUN 2012 | DOI: 10.1002/cbic.201200155

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      Keep it sweet: Fluorescent glycosides containing either galactose or 5-thiogalactose as the terminal sugar were enzymatically synthesized, and hydrolysis was measured by capillary electrophoresis. The hydrolytic resistance of 5-thiogalactose analogues to human α-galactosidase A was demonstrated both in vitro and in vivo, suggesting that 5-thiogalactosides may be useful tools for the study of anabolic pathways in cell extracts or in single cells.

    13. Genetic and Biosynthetic Studies of the Fungal Prenylated Xanthone Shamixanthone and Related Metabolites in Aspergillus spp. Revisited (pages 1680–1688)

      Prof. Thomas J. Simpson

      Version of Record online: 22 JUN 2012 | DOI: 10.1002/cbic.201200014

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      On the right path: Biosynthetic pathways have been proposed, based on the analysis of gene clusters discovered by genome sequencing. But some, such as that for shamixanthone, have inconsistencies with existing biosynthetic and labelling studies. Shamixanthone is biosynthesised via chrysophanol and the xanthone aldehyde intermediates arugosins F and A, not via the carboxylic acid, monodictyphenone.

    14. Synthesis and Evaluation of Acyl-Chain- and Galactose-6′′-Modified Analogues of α-GalCer for NKT Cell Activation (pages 1689–1697)

      Ming-Han Hsieh, Dr. Jung-Tung Hung, Ya-Wen Liw, Yin-Jen Lu, Prof. Dr. Chi-Huey Wong, Prof. Dr. Alice L. Yu and Prof. Dr. Pi-Hui Liang

      Version of Record online: 22 JUN 2012 | DOI: 10.1002/cbic.201200004

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      Compounds with biased cytokine profiles: A selection of α-GalCer derivatives with modifications in the acyl side chain and/or at the galactose 6′-position were synthesized and assayed for NKT cell activation. Gal-6′-phenylacetamide-based derivatives substituted with p-nitro (32), p-tert-butyl (34), or o-, m-, or p-methyl groups (4042) were found to promote polarization biased towards T helper 1 (TH1) in vitro.

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    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlight
    8. Communications
    9. Full Papers
    10. Preview
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      Preview: ChemBioChem 12/2012 (page 1699)

      Version of Record online: 17 JUL 2012 | DOI: 10.1002/cbic.201290047

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