Chemical Biology & Drug Design

Cover image for Chemical Biology & Drug Design

October 2013

Volume 82, Issue 4

Pages i–iii, 361–476

  1. Issue Information

    1. Top of page
    2. Issue Information
    3. Research Articles
    4. Research Letters
    1. Issue Information (pages i–iii)

      Article first published online: 19 SEP 2013 | DOI: 10.1111/cbdd.12032

  2. Research Articles

    1. Top of page
    2. Issue Information
    3. Research Articles
    4. Research Letters
    1. Synthesis and Antimalarial Bioassay of Quinine – Peptide Conjugates (pages 361–366)

      Siva S. Panda, Mohamed A. Ibrahim, Hasan Küçükbay, Marvin J. Meyers, Francis M. Sverdrup, Said A. El-Feky and Alan R. Katritzky

      Article first published online: 19 SEP 2013 | DOI: 10.1111/cbdd.12134

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      A series of quinine-peptide conjugates were by coupling amino acids and peptides varying polarity with quinine in good yields and the majority of these conjugates retain in vitro antimalarial activity with IC50 values below 100 nm, similar to quinine.

    2. Toward an Efficient Approach to Identify Molecular Scaffolds Possessing Selective or Promiscuous Compounds (pages 367–375)

      Austin B. Yongye and José L. Medina-Franco

      Article first published online: 10 SEP 2013 | DOI: 10.1111/cbdd.12162

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      A facile approach combining established tools to mine large data sets, leads to the identification of scaffolds containing selective or promiscuous compounds.

    3. Biotinylated Cyclen-Contained Cationic Lipids as Non-Viral Gene Delivery Vectors (pages 376–383)

      Qiang Liu, Wen-Jing Yi, Yi-Mei Zhang, Ji Zhang, Liandi Guo and Xiao-Qi Yu

      Article first published online: 28 JUN 2013 | DOI: 10.1111/cbdd.12159

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      Three novel biotinylated cyclen-contained cationic lipids were synthesized. These liposomes showed high cell viability even at high N/P ratios. The tocopherol-modified lipid showed the best transfection efficiency. In addition, higher transfection efficiency was obtained in tumor cells than those obtained in normal cells.

    4. Design, Synthesis, and Biological Evaluation of Novel 3,5-Disubstituted-1,2,6-Thiadiazine-1,1-Dione Derivatives as HIV-1 NNRTIs (pages 384–393)

      Ye Tian, Diwakar Rai, Peng Zhan, Christophe Pannecouque, Jan Balzarini, Erik De Clercq, Huiqing Liu and Xinyong Liu

      Article first published online: 10 SEP 2013 | DOI: 10.1111/cbdd.12160

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      On the basis of studies of two pyrimidine-derived non-nucleoside reverse-transcriptase inhibitors, DABOs, and diaryl pyrimidines, a novel class of 1,2,6-thiadiazine-1,1-dione derivatives were rationally designed using the strategies of bioisosterism and molecular hybridization, synthesized, and evaluated for their anti-HIV activity in MT4 cell cultures. Three compounds were found to have moderate activity against HIV-1 replication with EC50 values ranging from 23 to 32 μm. In addition, HIV-1 RT inhibitory assay, preliminary structure–activity relationship analysis, molecular docking studies were proformed.

    5. Study of Binding Thermodynamics in the Optimization of BH3 Mimetics (pages 394–400)

      Zhichao Zhang, Yan Zhao, Ting Song, Yubo Liu, Xiangqian Li, Pengchen Su and Shenghui Xie

      Article first published online: 10 SEP 2013 | DOI: 10.1111/cbdd.12161

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      Isothermal titration calorimetry was used to evaluate the optimization of B-cell lymphoma 2 homology domain 3-mimetics (compounds 16) from a thermodynamic perspective. Owing to 16 overcoming enthalpy-entropy compensation, the affinities of them improved gradually. Comparing 2 with 1, the enthalpy gain indicated the formation of an additional hydrogen bond to myeloid cell leukemia sequence 1 protein.

    6. Synthesis and Cytotoxicity Studies of Novel Triazolo-Benzoxazepine as New Anticancer Agents (pages 401–409)

      Biswadip Banerji, Sumit Kumar Pramanik, Priyankar Sanphui, Sameer Nikhar and Subhas C. Biswas

      Article first published online: 26 AUG 2013 | DOI: 10.1111/cbdd.12164

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      The one pot procedure for the efficient synthesis of a small library of novel triazolo-benzoxazepine. These compounds were evaluated for anticancer activity against three different cancer lines (Neura 2a, Hek 293, Hep G2). The phase-contrast images, fluorescent microscope images and confocal images unambiguously confirm the cell-death.

    7. Synthesis, Anti-MRSA, and Anti-VRE Activity of Hemin Conjugates with Amino Acids and Branched Peptides (pages 410–417)

      Sergei A. Okorochenkov, Galina A. Zheltukhina, Elena P. Mirchink, Elena B. Isakova, Alexey V. Feofanov and Vladimir E. Nebolsin

      Article first published online: 10 SEP 2013 | DOI: 10.1111/cbdd.12163

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      The number of hemin conjugates with amino acids and branched peptides were synthesized. High antibacterial activity of synthesized compounds against Gram positive bacteria including methicillin – and vancomycin-resistant strains was shown. Hemolytic and cytotoxic assays indicated that majority of synthesized conjugates possess lower toxicity and hemolytic activity than hemin.

    8. You have full text access to this OnlineOpen article
      Discovery of Staphylococcus aureus Sortase A Inhibitors Using Virtual Screening and the Relaxed Complex Scheme (pages 418–428)

      Albert H. Chan, Jeff Wereszczynski, Brendan R. Amer, Sung Wook Yi, Michael E. Jung, J. Andrew McCammon and Robert T. Clubb

      Article first published online: 19 SEP 2013 | DOI: 10.1111/cbdd.12167

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      Compounds that inhibit the Staphylococcus aureus sortase A transpeptidase enzyme could function as anti-infective agents. Here we report the identification of several inhibitors of sortase A using virtual screening methods that employ the relaxed complex scheme. The binding mechanism of the best inhibitor was investigated using molecular dynamics simulations and by performing a preliminary structure-activity relationship analysis.

    9. Preptin Analogues: Chemical Synthesis, Secondary Structure and Biological Studies (pages 429–437)

      Christina M. Buchanan, Zhenzhen Peng, Aiko Cefre and Vijayalekshmi Sarojini

      Article first published online: 19 SEP 2013 | DOI: 10.1111/cbdd.12168

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      Preptin analogues with non-protein amino acids have been chemically synthesized, characterized and analysed for their ability to augment insulin secretion from βTC6-F7 β-cells.

    10. Evaluation of the Efficiency of Synthesized Efflux Pump Inhibitors on Salmonella enterica ser. Typhimurium Cells (pages 438–445)

      Simona Sutkuvienė, Valeryia Mikalayeva, Silvia Pavan, Federico Berti and Rimantas Daugelavičius

      Article first published online: 19 SEP 2013 | DOI: 10.1111/cbdd.12173

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      This study was focused on the evaluation of efficiency of synthesized resistance-nodulation-division (RND) family efflux pump inhibitors. Efficiency of the synthesized compounds was investigated on Salmonella enterica ser. typhimurium cells using electrochemical and spectrofluorimetric methods. The results obtained showed that the registered efficiency of inhibitors depends on the permeability of cell outer membrane and the method of assay used.

  3. Research Letters

    1. Top of page
    2. Issue Information
    3. Research Articles
    4. Research Letters
    1. Pinpointing Proline Substitution to be Responsible for the Loss of Amyloidogenesis in IAPP (pages 446–452)

      Sandipan Chakraborty, Barnali Mukherjee and Soumalee Basu

      Article first published online: 17 JUL 2013 | DOI: 10.1111/cbdd.12172

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      Molecular dynamics simulation reveals that wild type hIAPP 22-28 fibril fluctuates between different β-sheet topology during the simulation. A25P Substitution is primarily accountable for the loss of amyloidogenecity of the hIAPP peptide. A25P, I26V double mutation also exhibit high fibril destabilization ability. S28P mutation has the least ability to disrupt the amyloid fibril.

    2. Bioactivities of Jc-SCRIP, a Type 1 Ribosome-Inactivating Protein from Jatropha curcas Seed Coat (pages 453–462)

      Chanthakan Nuchsuk, Nuanchawee Wetprasit, Sittiruk Roytrakul, Kiattawee Choowongkomon, Nattanan T-Thienprasert, Chotika Yokthongwattana, Theerakul Arpornsuwan and Sunanta Ratanapo

      Article first published online: 19 SEP 2013 | DOI: 10.1111/cbdd.12175

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      A new plant toxic protein with N-glycosidase activity, designated Jc-SCRIP was firstly discovered from the mature seed coat of physic nut, Jatropha curcas. Its in vitro cytotoxicity against human carcinoma cell lines and antibacterial activity suggested the highly potential use of Jc-SCRIP for medical applications.

    3. Synthesis of 1,4-Anthracene-9,10-dione Derivatives and Their Regulation of Nitric Oxide, IL-1β and TNF-α in Activated RAW264.7 Cells (pages 463–467)

      Taís Arthur Corrêa, Caio C. S. Alves, Sandra B. R. Castro, Erick E. Oliveira, Lucas S. Franco, Ana P. Ferreira and Mauro V. de Almeida

      Article first published online: 10 AUG 2013 | DOI: 10.1111/cbdd.12183

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      Mono- and disubstituted anthraquinone derivatives were synthesized through the addition of lipophilic amino alcohols. The disubstituted 1,4-anthracene-9,10-dione 10 showed significant inhibition of nitric oxide, TNF-α and IL-1β production, and the monosubstituted derivative 13 displayed a moderate to good inhibitory capacity on IL-1β and nitric oxide production, suggesting better inhibitory capacity of the inflammatory mediators by these compounds.

    4. Synthesis, Biological Evaluation and Molecular Docking Studies of High-Affinity Bone Targeting N,N'-Bis (alendronate) Diethylenetriamene-N,N'-Triacetic Acid: A Bifunctional Bone Scintigraphy Agent (pages 468–476)

      Nidhi Chadha, Deepa Sinha, Anjani K. Tiwari, Krishna Chuttani and Anil K. Mishra

      Article first published online: 26 AUG 2013 | DOI: 10.1111/cbdd.12194

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      A novel 99mTc-conjugated bisphosphonate, 99mTc- DTPA-bis(alendronate), with high affinity for bone, has been designed and synthesized . In vivo biodistribution experiments, alendronate has shown high bone-to-blood accumulation ratio of DTPA-bis(alendronate) radioactivity at early time after injection than 99mTc-MDP and 99mTc-alendronate. Docking analysis with molecular targets, Farnesyl diphosphate synthase, Geranylgeranyl pyrophosphate and Osteocalcin revealed the high affinity (−17.419) and thus confirms its efficacy as bone imaging agent.