ChemMedChem

Cover image for Vol. 2 Issue 3

March 12, 2007

Volume 2, Issue 3

Pages 249–382

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Highlight
    7. Communications
    8. Full Papers
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    1. Cover Picture: The Cytotoxicity of Saponins Correlates with Their Cellular Internalization (ChemMedChem 3/2007) (page 249)

      Yibing Wang, Yichun Zhang and Biao Yu

      Version of Record online: 1 MAR 2007 | DOI: 10.1002/cmdc.200790004

      The cover picture shows three structurally similar steroid glycosides bearing fluorescent tags. One crosses the cell membrane faster (top, straight arrow) than the other (left, curved path) to localize in the lysosome (red sphere). The third (middle), with a cholesterol aglycone moiety, does not enter into the cell at all. Steroid glycosides are abundant natural surfactants known as saponins, which have membrane-disrupting properties. However, the three saponins represented here are not found in the cell membrane, where cholesterol and carbohydrate chains are abundant. For details, see the Communication by B. Yu et al. on p. 288 ff.

  2. Graphical Abstract

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

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

    1. Top of page
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    3. Graphical Abstract
    4. News
    5. Review
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    1. Highlights on the Development of A2A Adenosine Receptor Agonists and Antagonists (pages 260–281)

      Gloria Cristalli, Barbara Cacciari, Diego Dal Ben, Catia Lambertucci, Stefano Moro, Giampiero Spalluto and Rosaria Volpini

      Version of Record online: 19 DEC 2006 | DOI: 10.1002/cmdc.200600193

      Thumbnail image of graphical abstract

      Adenosine modulates a variety of physiological and pathophysiological processes through the interaction with four subtypes of a family of cell-surface G-protein-coupled receptors. This review presents an update of medicinal chemistry and molecular recognition of A2A adenosine receptor agonists and antagonists and stresses the strong need for more selective ligands at the A2A human subtype.

  5. Highlight

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    1. Unique Composite Active Site of the Hepatitis C Virus NS2-3 Protease: a New Opportunity for Antiviral Drug Design (pages 283–284)

      Zucai Suo and Mohd Amir F. Abdullah

      Version of Record online: 1 FEB 2007 | DOI: 10.1002/cmdc.200600285

      Thumbnail image of graphical abstract

      The crystal structure of the catalytic domain of hepatitis C virus NS2-3 protease reveals a unique composite active site. Information from the structure may lead to the design of new antiviral drugs to control liver disease.

  6. Communications

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    1. Remote Modulation of Amine Basicity by a Phenylsulfone and a Phenylthio Group (pages 285–287)

      Rainer E. Martin, Baptiste Plancq, Olivier Gavelle, Björn Wagner, Holger Fischer, Stefanie Bendels and Klaus Müller

      Version of Record online: 3 JAN 2007 | DOI: 10.1002/cmdc.200600265

      Thumbnail image of graphical abstract

      Marked basicity-lowering effects by a sulfone unit are documented in a series of phenylsulfone amines in which the sulfone unit is placed at different topological distances to an aliphatic amine group. An exponential attenuation of basicity shifts by increasing distance is observed. Smaller effects are exerted by a phenylthio group, in each case corresponding to those of a phenylsulfone unit one σ-bond further away from the amino function.

    2. The Cytotoxicity of Saponins Correlates with Their Cellular Internalization (pages 288–291)

      Yibing Wang, Yichun Zhang and Biao Yu

      Version of Record online: 3 JAN 2007 | DOI: 10.1002/cmdc.200600235

      Thumbnail image of graphical abstract

      Sneaking in unexpectedly: Saponins are a broad class of plant-derived compounds that are commonly used as a tool to disrupt cell membranes. Some saponins such as that shown above, however, do not anchor themselves to the cell membrane, but are instead internalized. They localize specifically to acidic organelles such as lysosomes, and inhibit the growth of tumor cells.

    3. Dimerizable Redox-Sensitive Triazine-Based Cationic Lipids for in vitro Gene Delivery (pages 292–296)

      Gabriele Candiani, Massimo Frigerio, Fiorenza Viani, Chiara Verpelli, Carlo Sala, Luca Chiamenti, Nadia Zaffaroni, Marco Folini, Monica Sani, Walter Panzeri and Matteo Zanda

      Version of Record online: 27 DEC 2006 | DOI: 10.1002/cmdc.200600267

      Thumbnail image of graphical abstract

      The “Trojan Horse” trick works again. Conceptually new melamine-based cationic lipids show excellent transfection efficiency and low cytotoxicity in delivering a DNA plasmid payload to different types of cells, deceiving the natural mechanism of defense toward exogeneous DNA.

  7. Full Papers

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    1. Understanding Binding Selectivity toward Trypsin and Factor Xa: the Role of Aromatic Interactions (pages 297–308)

      Armida Di Fenza, Andreas Heine, Ulrich Koert and Gerhard Klebe

      Version of Record online: 27 DEC 2006 | DOI: 10.1002/cmdc.200600185

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      Changing identity: The binding site residues of trypsin were gradually substituted to match those of the factor Xa binding site. Crystallographic analysis of the resulting mutant proteins complexed with bis-benzamidine inhibitors having a dianhydrosugar isosorbide scaffold in common has shown that aromatic interactions play a key role in determining substrate selectivity in these serine proteases.

    2. Structure–Activity Study on the Spatial Arrangement of the Third Aromatic Ring of Endomorphins 1 and 2 Using an Atypical Constrained C Terminus (pages 309–317)

      Ye Yu, Xuan Shao, Yun Cui, Hong-mei Liu, Chang-ling Wang, Ying-zhe Fan, Jing Liu, Shou-liang Dong, Yu-xing Cui and Rui Wang

      Version of Record online: 7 FEB 2007 | DOI: 10.1002/cmdc.200600274

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      The C termini of endomorphin analogues, [Xaa4-R]EMs, modified by substitution of Phe4 with nonaromatic residues and terminated with benzyl groups, were designed to generate conformational constrains of the third aromatic ring by amide bond and torsion angles (ϕ4 and ψ4) of Xaa4.

    3. Derivatives of Iressa, a Specific Epidermal Growth Factor Receptor Inhibitor, are Powerful Apoptosis Inducers in PC3 Prostatic Cancer Cells (pages 318–332)

      Aurélie Telliez, Matthieu Desroses, Nicole Pommery, Olivier Briand, Amaury Farce, Guillaume Laconde, Amélie Lemoine, Patrick Depreux and Jean-Pierre Hénichart

      Version of Record online: 8 JAN 2007 | DOI: 10.1002/cmdc.200600128

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      Synthesis and analysis of the in vitro properties of 4-anilinoquinazoline derivatives of Iressa, a specific EGFR inhibitor, were carried out. Different relationships are proposed, and the main data is represented by induction of apoptosis in hormone-independent PC3 cell line.

    4. Steroid Conjugates of Dichloro(6-aminomethylnicotinate)platinum(II): Effects on DNA, Sex Hormone Binding Globulin, the Estrogen Receptor, and Various Breast Cancer Cell Lines (pages 333–342)

      Rainer Schobert, Günther Bernhardt, Bernhard Biersack, Susanne Bollwein, Magid Fallahi, Antje Grotemeier and Geoffrey L. Hammond

      Version of Record online: 1 FEB 2007 | DOI: 10.1002/cmdc.200600173

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      DNA binding isn't everything: The steroid tail of the platinum complex shown binds strongly to the carrier globulin SHBG, contrary to its isomer featuring a 17-O-linked estradiol. It also binds to the nuclear estrogen receptor, eliciting a distinct estrogenic response, and it inhibits the proliferation of MCF-7 breast cancer cells. Of all steroid conjugate complexes investigated, it interacted least with isolated plasmid DNA.

    5. Inhibition of Bcr-Abl Phosphorylation and Induction of Apoptosis by Pyrazolo[3,4-d]pyrimidines in Human Leukemia Cells (pages 343–353)

      Fabrizio Manetti, Annalisa Pucci, Matteo Magnani, Giada A. Locatelli, Chiara Brullo, Antonella Naldini, Silvia Schenone, Giovanni Maga, Fabio Carraro and Maurizio Botta

      Version of Record online: 13 FEB 2007 | DOI: 10.1002/cmdc.200600214

      Thumbnail image of graphical abstract

      Dual Src/Abl inhibition. On the basis of the experimental evidence that various Src inhibitors are also active against Bcr-Abl kinase (the so called dual Src/Abl inhibitors), a series of pyrazolo-pyrimidines previously found as Src inhibitors, were also tested toward Abl and Bcr-Abl-expressing cell lines. Results showed an activity toward the isolated enzyme in the low micromolar range and micromolar activity toward a panel of three human leukemia cell lines.

    6. The Natural Product Berberine is a Human Prolyl Oligopeptidase Inhibitor (pages 354–359)

      Teresa Tarrago, Nessim Kichik, Josep Seguí and Ernest Giralt

      Version of Record online: 13 FEB 2007 | DOI: 10.1002/cmdc.200600303

      Thumbnail image of graphical abstract

      Chinese medicinal plants, a new source of prolyl oligopeptidase inhibitors: 19F NMR spectroscopy screening was used to search for new prolyl oligopeptidase inhibitors in a library of traditional Chinese medicine plant extracts. Several extracts were identified as powerful inhibitors of this peptidase. The natural alkaloid berberine was isolated from Rhizoma coptidis extract and inhibited prolyl oligopeptidase in a dose-dependent manner.

    7. Model Systems for Fluorescence and Singlet Oxygen Quenching by Metalloporphyrins (pages 360–365)

      Jason R. McCarthy and Ralph Weissleder

      Version of Record online: 23 JAN 2007 | DOI: 10.1002/cmdc.200600244

      Thumbnail image of graphical abstract

      Next-generation photodynamic therapy (PDT) agents will minimize extraneous phototoxicity by being active only at the target site. This can only occur if suitable photosensitizer excited-state quenching moieties are identified. A series of porphyrin–metalloporphyrin dimers were therefore investigated for potential application in activatable PDT agents.

    8. Characterisation of the Binding of Cationic Amphiphilic Drugs to Phospholipid Bilayers Using Surface Plasmon Resonance (pages 366–373)

      Matthew R. Nussio, Matthew J. Sykes, John O. Miners and Joseph G. Shapter

      Version of Record online: 27 DEC 2006 | DOI: 10.1002/cmdc.200600252

      Thumbnail image of graphical abstract

      The interactions of three cationic amphiphilic drugs (CADs) with phospholipid vesicles were investigated using surface plasmon resonance (SPR). High CAD concentrations provided evidence for a nonsaturable binding process, which may arise from intercalation of the drugs within the lipid bilayer. CAD binding was additionally shown to be dependent on membrane fluidity.

    9. The Enhancement Effect of Gold Nanoparticles in Drug Delivery and as Biomarkers of Drug-Resistant Cancer Cells (pages 374–378)

      Jingyuan Li, Xuemei Wang, Chunxia Wang, Baoan Chen, Yongyuan Dai, Renyun Zhang, Min Song, Gang Lv and Degang Fu

      Version of Record online: 8 JAN 2007 | DOI: 10.1002/cmdc.200600264

      Thumbnail image of graphical abstract

      A golden opportunity: Functionalized gold nanoparticles (NPs) synergistically enhance the delivery of drugs to, and serve as biomarkers of drug-resistant leukemia cells. The combination of 3-mercaptopropionic acid capped Au NPs with anticancer drugs could be a new approach to the treatment of cancer.

  8. Preview

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Highlight
    7. Communications
    8. Full Papers
    9. Preview
    1. Preview: ChemMedChem 4/2007 (page 382)

      Version of Record online: 1 MAR 2007 | DOI: 10.1002/cmdc.200790007

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