Literature DB >> 27645237

Antiviral Nucleotide Incorporation by Recombinant Human Mitochondrial RNA Polymerase Is Predictive of Increased In Vivo Mitochondrial Toxicity Risk.

Martijn Fenaux1, Xiaodong Lin2, Fumiaki Yokokawa3, Zachary Sweeney2, Oliver Saunders2, Lili Xie2, Siew Pheng Lim3, Marianne Uteng4, Kyoko Uehara2, Robert Warne2, Wang Gang3, Christopher Jones2, Satya Yendluri2, Helen Gu5, Keith Mansfield6, Julie Boisclair4, Tycho Heimbach5, Alexandre Catoire5, Kathryn Bracken6, Margaret Weaver6, Heinz Moser2, Weidong Zhong2.   

Abstract

Nucleoside or nucleotide inhibitors are a highly successful class of antivirals due to selectivity, potency, broad coverage, and high barrier to resistance. Nucleosides are the backbone of combination treatments for HIV, hepatitis B virus, and, since the FDA approval of sofosbuvir in 2013, also for hepatitis C virus (HCV). However, many promising nucleotide inhibitors have advanced to clinical trials only to be terminated due to unexpected toxicity. Here we describe the in vitro pharmacology of compound 1, a monophosphate prodrug of a 2'-ethynyluridine developed for the treatment of HCV. Compound 1 inhibits multiple HCV genotypes in vitro (50% effective concentration [EC50], 0.05 to 0.1 μM) with a selectivity index of >300 (50% cytotoxic concentration [CC50], 30 μM in MT-4 cells). The active triphosphate metabolite of compound 1, compound 2, does not inhibit human α, β, or γ DNA polymerases but was a substrate for incorporation by the human mitochondrial RNA polymerase (POLRMT). In dog, the oral administration of compound 1 resulted in elevated serum liver enzymes and microscopic changes in the liver. Transmission electron microscopy showed significant mitochondrial swelling and lipid accumulation in hepatocytes. Gene expression analysis revealed dose-proportional gene signature changes linked to loss of hepatic function and increased mitochondrial dysfunction. The potential of in vivo toxicity through mitochondrial polymerase incorporation by nucleoside analogs has been previously shown. This study shows that even moderate levels of nucleotide analog incorporation by POLRMT increase the risk of in vivo mitochondrial dysfunction. Based on these results, further development of compound 1 as an anti-HCV compound was terminated.
Copyright © 2016, American Society for Microbiology. All Rights Reserved.

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Year:  2016        PMID: 27645237      PMCID: PMC5118986          DOI: 10.1128/AAC.01253-16

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


  28 in total

1.  Efficient replication of genotype 3a and 4a hepatitis C virus replicons in human hepatoma cells.

Authors:  Mohsan Saeed; Troels K H Scheel; Judith M Gottwein; Svetlana Marukian; Lynn B Dustin; Jens Bukh; Charles M Rice
Journal:  Antimicrob Agents Chemother       Date:  2012-08-06       Impact factor: 5.191

2.  Cardiac dysfunction associated with a nucleotide polymerase inhibitor for treatment of hepatitis C.

Authors:  Tariq Ahmad; Philip Yin; Jeffrey Saffitz; Paul J Pockros; Jacob Lalezari; Mitchell Shiffman; Bradley Freilich; Joann Zamparo; Kyle Brown; Dessislava Dimitrova; Monica Kumar; Doug Manion; Margo Heath-Chiozzi; Robert Wolf; Eric Hughes; Andrew J Muir; Adrian F Hernandez
Journal:  Hepatology       Date:  2015-05-26       Impact factor: 17.425

3.  Toxicity of antiviral nucleoside analogs and the human mitochondrial DNA polymerase.

Authors:  A A Johnson; A S Ray; J Hanes; Z Suo; J M Colacino; K S Anderson; K A Johnson
Journal:  J Biol Chem       Date:  2001-08-28       Impact factor: 5.157

Review 4.  Drug-induced toxicity on mitochondria and lipid metabolism: mechanistic diversity and deleterious consequences for the liver.

Authors:  Karima Begriche; Julie Massart; Marie-Anne Robin; Annie Borgne-Sanchez; Bernard Fromenty
Journal:  J Hepatol       Date:  2010-11-17       Impact factor: 25.083

5.  Adaptive mutations producing efficient replication of genotype 1a hepatitis C virus RNA in normal Huh7 cells.

Authors:  MinKyung Yi; Stanley M Lemon
Journal:  J Virol       Date:  2004-08       Impact factor: 5.103

6.  Class III phosphatidylinositol 4-kinase alpha and beta are novel host factor regulators of hepatitis C virus replication.

Authors:  Jason Borawski; Philip Troke; Xiaoling Puyang; Veronica Gibaja; Shanchaun Zhao; Craig Mickanin; Juliet Leighton-Davies; Christopher J Wilson; Vic Myer; Ivan Cornellataracido; Jeremy Baryza; John Tallarico; Gerard Joberty; Marcus Bantscheff; Markus Schirle; Tewis Bouwmeester; Joanna E Mathy; Kai Lin; Teresa Compton; Mark Labow; Brigitte Wiedmann; L Alex Gaither
Journal:  J Virol       Date:  2009-07-15       Impact factor: 5.103

7.  Circumventing the Crabtree effect: replacing media glucose with galactose increases susceptibility of HepG2 cells to mitochondrial toxicants.

Authors:  Lisa D Marroquin; James Hynes; James A Dykens; Joseph D Jamieson; Yvonne Will
Journal:  Toxicol Sci       Date:  2007-03-14       Impact factor: 4.849

8.  Replication of subgenomic hepatitis C virus RNAs in a hepatoma cell line.

Authors:  V Lohmann; F Körner; J Koch; U Herian; L Theilmann; R Bartenschlager
Journal:  Science       Date:  1999-07-02       Impact factor: 47.728

9.  Discovery of the first C-nucleoside HCV polymerase inhibitor (GS-6620) with demonstrated antiviral response in HCV infected patients.

Authors:  Aesop Cho; Lijun Zhang; Jie Xu; Rick Lee; Thomas Butler; Sammy Metobo; Vangelis Aktoudianakis; Willard Lew; Hong Ye; Michael Clarke; Edward Doerffler; Daniel Byun; Ting Wang; Darius Babusis; Anne C Carey; Polina German; Dorothea Sauer; Weidong Zhong; Stephen Rossi; Martijn Fenaux; John G McHutchison; Jason Perry; Joy Feng; Adrian S Ray; Choung U Kim
Journal:  J Med Chem       Date:  2013-05-01       Impact factor: 7.446

Review 10.  Investigational direct-acting antivirals in hepatitis C treatment: the latest drugs in clinical development.

Authors:  Ivan Gentile; Riccardo Scotto; Emanuela Zappulo; Antonio Riccardo Buonomo; Biagio Pinchera; Guglielmo Borgia
Journal:  Expert Opin Investig Drugs       Date:  2016-03-21       Impact factor: 6.498

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  8 in total

1.  Nucleotide Substrate Specificity of Anti-Hepatitis C Virus Nucleoside Analogs for Human Mitochondrial RNA Polymerase.

Authors:  Maryam Ehteshami; Longhu Zhou; Sheida Amiralaei; Jadd R Shelton; Jong Hyun Cho; Hongwang Zhang; Hao Li; Xiao Lu; Tugba Ozturk; Richard Stanton; Franck Amblard; Tamara R McBrayer; Steven J Coats; Raymond F Schinazi
Journal:  Antimicrob Agents Chemother       Date:  2017-07-25       Impact factor: 5.191

2.  A Cyclic Phosphoramidate Prodrug of 2'-Deoxy-2'-Fluoro-2'-C-Methylguanosine for the Treatment of Dengue Virus Infection.

Authors:  Ratna Karuna; Fumiaki Yokokawa; Keshi Wang; Jin Zhang; Haoying Xu; Gang Wang; Mei Ding; Wai Ling Chan; Nahdiyah Abdul Ghafar; Andrea Leonardi; Cheah Chen Seh; Peck Gee Seah; Wei Liu; Rao P S Srinivasa; Siew Pheng Lim; Suresh B Lakshminarayana; Ellie Growcott; Sreehari Babu; Martijn Fenaux; Weidong Zhong; Feng Gu; Pei-Yong Shi; Francesca Blasco; Yen-Liang Chen
Journal:  Antimicrob Agents Chemother       Date:  2020-11-17       Impact factor: 5.191

3.  Simple In Vitro Assay To Evaluate the Incorporation Efficiency of Ribonucleotide Analog 5'-Triphosphates into RNA by Human Mitochondrial DNA-Dependent RNA Polymerase.

Authors:  Gaofei Lu; Gregory R Bluemling; Shuli Mao; Michael Hager; Bharat P Gurale; Paul Collop; Damien Kuiper; Kasinath Sana; George R Painter; Abel De La Rosa; Alexander A Kolykhalov
Journal:  Antimicrob Agents Chemother       Date:  2018-01-25       Impact factor: 5.191

Review 4.  Addressing the selectivity and toxicity of antiviral nucleosides.

Authors:  Joy Y Feng
Journal:  Antivir Chem Chemother       Date:  2018 Jan-Dec

5.  Incidence and risk factors of early HCC occurrence in HCV patients treated with direct acting antivirals: a prospective multicentre study.

Authors:  Luca Rinaldi; Alessandro Perrella; Maria Guarino; Massimo De Luca; Guido Piai; Nicola Coppola; Pia Clara Pafundi; Fortunato Ciardiello; Morena Fasano; Erika Martinelli; Giovanna Valente; Riccardo Nevola; Caterina Monari; Lucia Miglioresi; Barbara Guerrera; Massimiliano Berretta; Ferdinando Carlo Sasso; Filomena Morisco; Antonio Izzi; Luigi Elio Adinolfi
Journal:  J Transl Med       Date:  2019-08-28       Impact factor: 5.531

Review 6.  In vitro methods for testing antiviral drugs.

Authors:  Michaela Rumlová; Tomáš Ruml
Journal:  Biotechnol Adv       Date:  2017-12-29       Impact factor: 14.227

7.  Efficacy and safety of sofosbuvir/ ledipasvir in treatment of patients with COVID-19; A randomized clinical trial.

Authors:  Hossein Khalili; Anahid Nourian; Zahra Ahmadinejad; Hamid Emadi Kouchak; Sirous Jafari; Sayed Ali Dehghan Manshadi; Mehrnaz Rasolinejad; Abbas Kebriaeezadeh
Journal:  Acta Biomed       Date:  2020-11-10

Review 8.  Targeting Mitochondrial Metabolism and RNA Polymerase POLRMT to Overcome Multidrug Resistance in Cancer.

Authors:  Hui-Jing Yu; Guan-Li Xiao; Yu-Ying Zhao; Xin-Xin Wang; Rongfeng Lan
Journal:  Front Chem       Date:  2021-12-16       Impact factor: 5.221

  8 in total

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