ChemBioChem

Cover image for Vol. 8 Issue 2

January 22, 2007

Volume 8, Issue 2

Pages 153–250

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. Communications
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    1. Cover Picture: A Structure–Activity Guided Strategy for Fluorescent Labeling of Annonaceous Acetogenin Mimetics and their Application in Cell Biology (ChemBioChem 2/2007) (page 153)

      Hai-Xia Liu, Guo-Rui Huang, Huan-Ming Zhang, Sheng Jiang, Jia-Rui Wu and Zhu-Jun Yao

      Version of Record online: 10 JAN 2007 | DOI: 10.1002/cbic.200790000

      The cover picture shows an imaging study of a cytotoxic small molecule AA005, which is able to recognize and enter human cancer cells selectively. Fluorescent labeling of AA005 was successfully accomplished by a bioactivity assessment-aided protocol after examining a number of potential derivative positions in parallel. AA005-flu was found to exhibit similar cell selectivity to its parent molecule AA005. Fluorescent images of AA005-flu show a significant difference in drug distribution between cancerous and normal cells, with accumulation of AA005-flu occurring in the mitochondria of cancers cells. For more information, see the article by Z.-J. Yao et al. on p. 172 ff.

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. Communications
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  3. Corrigendum

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. Communications
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    1. You have free access to this content
      Regioselective Carbon–Carbon Bond Formation in Proteins with Palladium Catalysis; New Protein Chemistry by Organometallic Chemistry (page 159)

      Koichiro Kodama, Seketsu Fukuzawa, Hiroshi Nakayama, Takanori Kigawa, Kensaku Sakamoto, Takashi Yabuki, Natsuko Matsuda, Mikako Shirouzu, Koji Takio, Kazuo Tachibana and Shigeyuki Yokoyama

      Version of Record online: 10 JAN 2007 | DOI: 10.1002/cbic.200790002

  4. Communications

    1. Top of page
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    3. Graphical Abstract
    4. Corrigendum
    5. Communications
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    1. Amyloid-Beta Peptide Forms Monomeric Complexes With CuII and ZnII Prior to Aggregation (pages 163–165)

      Christine Talmard, Luc Guilloreau, Yannick Coppel, Honore Mazarguil and Peter Faller

      Version of Record online: 29 DEC 2006 | DOI: 10.1002/cbic.200600319

      Thumbnail image of graphical abstract

      Brief encounter. ZnII- and CuII-induced aggregation of the peptide amyloid-β (Aβ) are considered to be involved in Alzheimer's disease. The present data indicate that ZnII and CuII transiently form a monomeric complex with Aβ40/42 before aggregation, which exhibits no further transiently stable intermediate up to ∼15-mer.

    2. Photogenerated Carbohydrate Microarrays (pages 166–168)

      Zhichao Pei, Hui Yu, Matthias Theurer, Annelie Waldén, Peter Nilsson, Mingdi Yan and Olof Ramström

      Version of Record online: 8 DEC 2006 | DOI: 10.1002/cbic.200600447

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      Sugars in a row. A new strategy for carbohydrate microarrays based on photochemical ligation of perfluorophenylazide-derivatized carbohydrates to PEO surfaces is presented. It constitutes a controllable and robust method of array fabrication, on the carbohydrate-chemistry and on the surface-chemistry levels, and the resulting carbohydrate arrays can be efficiently used to reveal the recognition patterns of carbohydrate-binding proteins.

    3. Detection of L-DNA-Tagged PCR Products by Surface Plasmon Resonance Imaging (pages 169–171)

      Gosuke Hayashi, Masaki Hagihara, Akio Kobori and Kazuhiko Nakatani

      Version of Record online: 29 DEC 2006 | DOI: 10.1002/cbic.200600477

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      Single strand stands out. A polymerase chain reaction (PCR) with a primer containing a mirror image DNA (L-DNA) sequence tag at the 5′-end produced an L-DNA duplex labeled with a single strand of L-DNA of defined sequence. The PCR products could be directly detected on the surface plasmon resonance (SPR) imaging array where the complementary L-DNA sequences were immobilized.

    4. A Structure–Activity Guided Strategy for Fluorescent Labeling of Annonaceous Acetogenin Mimetics and their Application in Cell Biology (pages 172–177)

      Hai-Xia Liu, Guo-Rui Huang, Huan-Ming Zhang, Sheng Jiang, Jia-Rui Wu and Zhu-Jun Yao

      Version of Record online: 20 DEC 2006 | DOI: 10.1002/cbic.200600411

      Thumbnail image of graphical abstract

      The potent anticancer agent AA005 has been successfully biolabeled with fluorescein. Of the two compounds synthesized, only AA005-flu retained the selectivity of AA005 for cancerous (e.g., BEL-7404) over normal (e.g., LO2) cells. Fluorescent-imaging studies revealed that AA005-flu's distribution in human normal cells was significantly difference from that in cancer cells, where AA005-flu accumulates in the mitochondria. This direct and visible evidence suggests that membrane recognition of AA005 is involved in its selective action.

  5. Full Papers

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    1. Cellular Inhibition of Protein Tyrosine Phosphatase 1B by Uncharged Thioxothiazolidinone Derivatives (pages 179–186)

      Matthew Stuible, Liang Zhao, Isabelle Aubry, Dirk Schmidt-Arras, Frank-D. Böhmer, Chao-Jun Li and Michel L. Tremblay

      Version of Record online: 27 DEC 2006 | DOI: 10.1002/cbic.200600287

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      Charge less. We show that a novel inhibitor (1) of PTP1B is active in cells at low micromolar concentrations and prevents PTP1B-mediated dephosphorylation of the FLT3-ITD receptor tyrosine kinase (shown). We have synthesized a series of derivatives for basic SAR analysis and have conducted computer-modeling studies to predict its binding mode. This class of uncharged inhibitors could be a starting point for the development of new drugs targeting protein tyrosine phosphatases.

    2. Hyrtiosal, a PTP1B Inhibitor from the Marine Sponge Hyrtios erectus, Shows Extensive Cellular Effects on PI3K/AKT Activation, Glucose Transport, and TGFβ/Smad2 Signaling (pages 187–193)

      Tao Sun, Qi Wang, Zhiguo Yu, Yu Zhang, Yuewei Guo, Kaixian Chen, Xu Shen and Hualiang Jiang

      Version of Record online: 20 DEC 2006 | DOI: 10.1002/cbic.200600349

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      A potential insulin mimetic. Protein tyrosine phosphatase 1B (PTP1B) negatively regulates insulin signaling, and PTP1B inhibitors have been seen as promising therapeutic agents against obesity and type 2 diabetes. Here we report that hyrtiosal, a marine natural product from the marine sponge Hyrtios erectus and newly identified as a PTP1B inhibitor, shows extensive cellular effects on PI3K/AKT activation, glucose transport, and TGFβ/Smad2 signaling.

    3. High-Throughput Substrate Specificity Studies of Sialidases by Using Chemoenzymatically Synthesized Sialoside Libraries (pages 194–201)

      Harshal A. Chokhawala, Hai Yu and Xi Chen

      Version of Record online: 29 DEC 2006 | DOI: 10.1002/cbic.200600410

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      Finding sialidase natural substrates. Sialoside libraries containing sialosides with different naturally occurring sialic acid forms α2,3- or α2,6-linked to Galβ-pNP or GalNAcβ-pNP have been chemoenzymatically prepared by using a highly efficient one-pot three-enzyme system. Colorimetric high-throughput screening assays on a 96-well plate-based format found diversity in substrate specificity of various bacterial sialidases (see scheme).

    4. Reversible Inactivation of the CG Specific SssI DNA (Cytosine-C5)-Methyltransferase with a Photocleavable Protecting Group (pages 202–207)

      Philipp Rathert, Tamás Raskó, Markus Roth, Krystyna Ślaska-Kiss, Alfred Pingoud, Antal Kiss and Albert Jeltsch

      Version of Record online: 29 DEC 2006 | DOI: 10.1002/cbic.200600358

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      Trick of the light. We describe the covalent modification of the SssI DNA methyltransferase (M.SssI) with 4,5-dimethoxy-2-nitrobenzyl-bromide (DMNBB) to obtain M.SssI with a caged active-site Cys residue (see figure). Irradiation of the caged enzyme with near-ultraviolet light restored its catalytic activity. The results indicate that caging by DMNBB can be used for the reversible inactivation of DNA methyltransferases.

    5. Rapid Enzymatic Isomerization of 12-Oxophytodienoic Acid in the Gut of Lepidopteran Larvae (pages 208–216)

      Birgit Schulze, Paulina Dąbrowska and Wilhelm Boland

      Version of Record online: 29 DEC 2006 | DOI: 10.1002/cbic.200600379

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      Oxylipins are fatty acid-derived molecules that control defense and metabolic activities in attacked plants. They are generated in areas where a leaf is damaged and are therefore ingested by the insect upon feeding. 12-Oxophytodienoic acid (OPDA) is rapidly isomerized by an enzyme in the insect's gut tissue to the planar iso-OPDA (see scheme). This reaction suggests that OPDA is also physiologically active in herbivorous insects, maybe due to its structural similarity to prostaglandins.

    6. Nitrosation of N-Terminally Blocked Tryptophan and Tryptophan-Containing Peptides by Peroxynitrite (pages 217–223)

      Fabienne Peyrot and Claire Ducrocq

      Version of Record online: 20 DEC 2006 | DOI: 10.1002/cbic.200600385

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      Stressed out. Tryptophan derivatives are a target for oxidative stress induced by reactive oxygen and nitrogen species, such as peroxynitrite (ONOO/ONOOH) produced from NO. and O2.−. Beside oxidation, N1-nitrosation is the main reaction of N-blocked Trp derivatives (melatonin, N-acetyl-L-tryptophan and Ac–Asp–Ile–Ile–Trp) with peroxynitrite at physiological pH (see scheme).

    7. Cysteine-Specific, Covalent Anchoring of Transition Organometallic Complexes to the Protein Papain from Carica papaya (pages 224–231)

      Pierre Haquette, Michèle Salmain, Karolina Svedlung, Annie Martel, Bogna Rudolf, Janusz Zakrzewski, Stéphane Cordier, Thierry Roisnel, Céline Fosse and Gérard Jaouen

      Version of Record online: 14 DEC 2006 | DOI: 10.1002/cbic.200600387

      Thumbnail image of graphical abstract

      Heavy metal fusion. An enzyme with a reactive thiol function within its catalytic cavity, namely papain, was site-specifically modified by several sandwich- or half-sandwich-type organometallic complexes. This approach should be useful for producing efficient heavy-atom derivatives for protein X-ray crystallography.

    8. Site-Specific Functionalization of Proteins by Organopalladium Reactions (pages 232–238)

      Koichiro Kodama, Seketsu Fukuzawa, Hiroshi Nakayama, Kensaku Sakamoto, Takanori Kigawa, Takashi Yabuki, Natsuko Matsuda, Mikako Shirouzu, Koji Takio, Shigeyuki Yokoyama and Kazuo Tachibana

      Version of Record online: 29 DEC 2006 | DOI: 10.1002/cbic.200600432

      Thumbnail image of graphical abstract

      Accommodating the organopalladium conditions. An aryl iodide tag on the Ras protein was chemoselectively modified by Mizoroki–Heck and Sonogashira reactions (see figure). The Ras protein retained its biological activity under organopalladium conditions. These results were confirmed by Western blot, LC-MS, and in vitro pull-down analyses.

    9. A Comparative Analysis of the Sugar Phosphate Cyclase Superfamily Involved in Primary and Secondary Metabolism (pages 239–248)

      Xiumei Wu, Patricia M. Flatt, Oliver Schlörke, Axel Zeeck, Tohru Dairi and Taifo Mahmud

      Version of Record online: 29 DEC 2006 | DOI: 10.1002/cbic.200600446

      Thumbnail image of graphical abstract

      Sugar phosphate cyclases (SPCs) catalyze the cyclization of sugar phosphates to produce a variety of cyclitol intermediates that serve as the building blocks of many primary and secondary metabolites. By using genetic and biochemical approaches, a number of new SPCs have been identified. Further phylogenetic analysis of SPC sequences revealed a new clade of SPCs that might regulate the biosynthesis of a novel set of secondary metabolites.

  6. Preview

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. Communications
    6. Full Papers
    7. Preview
    1. You have free access to this content
      Preview: ChemBioChem 3/2007 (page 250)

      Version of Record online: 10 JAN 2007 | DOI: 10.1002/cbic.200790003

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