Literature DB >> 25824229

Encoded library technology screening of hepatitis C virus NS4B yields a small-molecule compound series with in vitro replicon activity.

Christopher Arico-Muendel1, Zhengrong Zhu1, Hamilton Dickson2, Derek Parks2, Jesse Keicher2, Jianghe Deng3, Leah Aquilani3, Frank Coppo3, Todd Graybill3, Kenneth Lind1, Andrew Peat2, Michael Thomson4.   

Abstract

To identify novel antivirals to the hepatitis C virus (HCV) NS4B protein, we utilized encoded library technology (ELT), which enables purified proteins not amenable to standard biochemical screening methods to be tested against large combinatorial libraries in a short period of time. We tested NS4B against several DNA-encoded combinatorial libraries (DEL) and identified a single DEL feature that was subsequently progressed to off-DNA synthesis. The most active of the initial synthesized compounds had 50% inhibitory concentrations (IC50s) of 50 to 130 nM in a NS4B radioligand binding assay and 300 to 500 nM in an HCV replicon assay. Chemical optimization yielded compounds with potencies as low as 20 nM in an HCV genotype 1b replicon assay, 500 nM against genotype 1a, and 5 μM against genotype 2a. Through testing against other genotypes and genotype 2a-1b chimeric replicons and from resistance passage using the genotype 1b replicon, we confirmed that these compounds were acting on the proposed first transmembrane region of NS4B. A single sequence change (F98L) was identified as responsible for resistance, and it was thought to largely explain the relative lack of potency of this series against genotype 2a. Unlike other published series that appear to interact with this region, we did not observe sensitivity to amino acid substitutions at positions 94 and 105. The discovery of this novel compound series highlights ELT as a valuable approach for identifying direct-acting antivirals to nonenzymatic targets.
Copyright © 2015, American Society for Microbiology. All Rights Reserved.

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Year:  2015        PMID: 25824229      PMCID: PMC4432136          DOI: 10.1128/AAC.00070-15

Source DB:  PubMed          Journal:  Antimicrob Agents Chemother        ISSN: 0066-4804            Impact factor:   5.191


  42 in total

1.  A membranotropic region in the C-terminal domain of hepatitis C virus protein NS4B interaction with membranes.

Authors:  Jaime Guillén; Alejandro González-Alvarez; José Villalaín
Journal:  Biochim Biophys Acta       Date:  2009-07-22

2.  Palmitoylation and polymerization of hepatitis C virus NS4B protein.

Authors:  Guann-Yi Yu; Ki-Jeong Lee; Lu Gao; Michael M C Lai
Journal:  J Virol       Date:  2006-06       Impact factor: 5.103

3.  N-terminal AH2 segment of protein NS4B from hepatitis C virus. Binding to and interaction with model biomembranes.

Authors:  M Francisca Palomares-Jerez; Henrique Nemesio; Henri G Franquelim; Miguel A R B Castanho; José Villalaín
Journal:  Biochim Biophys Acta       Date:  2013-04-29

4.  Biochemical characterization of recombinant hepatitis C virus nonstructural protein 4B: evidence for ATP/GTP hydrolysis and adenylate kinase activity.

Authors:  Aaron A Thompson; Aihua Zou; Jiangli Yan; Rohit Duggal; Weidong Hao; David Molina; Ciarán N Cronin; Peter A Wells
Journal:  Biochemistry       Date:  2009-02-10       Impact factor: 3.162

5.  An amphipathic alpha-helix at the C terminus of hepatitis C virus nonstructural protein 4B mediates membrane association.

Authors:  Jérôme Gouttenoire; Roland Montserret; Audrey Kennel; François Penin; Darius Moradpour
Journal:  J Virol       Date:  2009-08-19       Impact factor: 5.103

6.  Discovery of a novel class of potent HCV NS4B inhibitors: SAR studies on piperazinone derivatives.

Authors:  Ramesh Kakarla; Jian Liu; Devan Naduthambi; Wonsuk Chang; Ralph T Mosley; Donghui Bao; Holly M Micolochick Steuer; Meg Keilman; Shalini Bansal; Angela M Lam; William Seibel; Sandra Neilson; Phillip A Furman; Michael J Sofia
Journal:  J Med Chem       Date:  2014-01-29       Impact factor: 7.446

7.  Design and synthesis of spirocyclic compounds as HCV replication inhibitors by targeting viral NS4B protein.

Authors:  Vincent W-F Tai; Dulce Garrido; Daniel J Price; Andrew Maynard; Jeffrey J Pouliot; Zhiping Xiong; John W Seal; Katrina L Creech; Luz H Kryn; Todd M Baughman; Andrew J Peat
Journal:  Bioorg Med Chem Lett       Date:  2014-04-03       Impact factor: 2.823

Review 8.  Hepatitis C virus proteins: from structure to function.

Authors:  Darius Moradpour; François Penin
Journal:  Curr Top Microbiol Immunol       Date:  2013       Impact factor: 4.291

Review 9.  The molecular and structural basis of advanced antiviral therapy for hepatitis C virus infection.

Authors:  Ralf Bartenschlager; Volker Lohmann; Francois Penin
Journal:  Nat Rev Microbiol       Date:  2013-06-10       Impact factor: 60.633

10.  A hepatitis C virus NS4B inhibitor suppresses viral genome replication by disrupting NS4B's dimerization/multimerization as well as its interaction with NS5A.

Authors:  Moonju Choi; Sungjin Lee; Taekyu Choi; Choongho Lee
Journal:  Virus Genes       Date:  2013-07-19       Impact factor: 2.198

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  9 in total

Review 1.  DNA-encoded chemistry: enabling the deeper sampling of chemical space.

Authors:  Robert A Goodnow; Christoph E Dumelin; Anthony D Keefe
Journal:  Nat Rev Drug Discov       Date:  2016-12-09       Impact factor: 84.694

2.  Comparative evaluation of DNA-encoded chemical selections performed using DNA in single-stranded or double-stranded format.

Authors:  Gabriele Bassi; Nicholas Favalli; Sebastian Oehler; Adriano Martinelli; Marco Catalano; Jörg Scheuermann; Dario Neri
Journal:  Biochem Biophys Res Commun       Date:  2020-05-05       Impact factor: 3.575

3.  Preclinical Characterization and In Vivo Efficacy of GSK8853, a Small-Molecule Inhibitor of the Hepatitis C Virus NS4B Protein.

Authors:  Jeffrey J Pouliot; Michael Thomson; Mi Xie; Joseph Horton; John Johnson; David Krull; Amanda Mathis; Yoshio Morikawa; Derek Parks; Richard Peterson; Takashi Shimada; Elizabeth Thomas; Jessica Vamathevan; Stephanie Van Horn; Zhiping Xiong; Robert Hamatake; Andrew J Peat
Journal:  Antimicrob Agents Chemother       Date:  2015-08-10       Impact factor: 5.191

4.  Off-DNA DNA-Encoded Library Affinity Screening.

Authors:  Amber L Hackler; Forrest G FitzGerald; Vuong Q Dang; Alexander L Satz; Brian M Paegel
Journal:  ACS Comb Sci       Date:  2019-12-31       Impact factor: 3.784

5.  A DNA-Encoded Library of Chemical Compounds Based on Common Scaffolding Structures Reveals the Impact of Ligand Geometry on Protein Recognition.

Authors:  Nicholas Favalli; Stefan Biendl; Marco Hartmann; Jacopo Piazzi; Filippo Sladojevich; Susanne Gräslund; Peter J Brown; Katja Näreoja; Herwig Schüler; Jörg Scheuermann; Raphael Franzini; Dario Neri
Journal:  ChemMedChem       Date:  2018-06-01       Impact factor: 3.466

Review 6.  DNA-encoded chemical libraries: foundations and applications in lead discovery.

Authors:  Gunther Zimmermann; Dario Neri
Journal:  Drug Discov Today       Date:  2016-07-28       Impact factor: 7.851

7.  Human Transbodies to HCV NS3/4A Protease Inhibit Viral Replication and Restore Host Innate Immunity.

Authors:  Surasak Jittavisutthikul; Watee Seesuay; Jeeraphong Thanongsaksrikul; Kanyarat Thueng-In; Potjanee Srimanote; Rolf G Werner; Wanpen Chaicumpa
Journal:  Front Immunol       Date:  2016-08-26       Impact factor: 7.561

8.  PTC725, an NS4B-Targeting Compound, Inhibits a Hepatitis C Virus Genotype 3 Replicon, as Predicted by Genome Sequence Analysis and Determined Experimentally.

Authors:  Jason D Graci; Stephen P Jung; John Pichardo; Frederick Lahser; Xiao Tong; Zhengxian Gu; Joseph M Colacino
Journal:  Antimicrob Agents Chemother       Date:  2016-11-21       Impact factor: 5.191

9.  Directed Chemical Evolution with an Outsized Genetic Code.

Authors:  Casey J Krusemark; Nicolas P Tilmans; Patrick O Brown; Pehr B Harbury
Journal:  PLoS One       Date:  2016-08-10       Impact factor: 3.240

  9 in total

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