Literature DB >> 34147908

Metal binding 6-arylthio-3-hydroxypyrimidine-2,4-diones inhibited human cytomegalovirus by targeting the pUL89 endonuclease of the terminase complex.

Lei Wang1, Tiffany C Edwards2, Rajkumar Lalji Sahani2, Jiashu Xie2, Hideki Aihara3, Robert J Geraghty2, Zhengqiang Wang4.   

Abstract

The genome packaging of human cytomegalovirus (HCMV) requires a divalent metal-dependent endonuclease activity localized to the C-terminus of pUL89 (pUL89-C), which is reminiscent of RNase H-like enzymes in active site structure and catalytic mechanism. Our previous work has shown that metal-binding small molecules can effectively inhibit pUL89-C while conferring significant antiviral activities. In this report we generated a collection of 43 metal-binding small molecules by repurposing analogs of the 6-arylthio-3-hydroxypyrimidine-2,4-dione chemotype previously synthesized for targeting HIV-1 RNase H, and by chemically synthesizing new N-1 analogs. The analogs were subjected to two parallel screening assays: the pUL89-C biochemical assay and the HCMV antiviral assay. Compounds with significant inhibition from each assay were further tested in a dose-response fashion. Single dose cell viability and PAMPA cell permeability were also conducted and considered in selecting compounds for the dose-response antiviral testing. These assays identified a few analogs displaying low μM inhibition against pUL89-C in the biochemical assay and HCMV replication in the antiviral assay. The target engagement was further evaluated via a thermal shift assay using recombinant pUL89-C and molecular docking. Overall, our current work identified novel inhibitors of pUL89-C with significant antiviral activities and further supports targeting pUL89-C with metal-binding small molecules as an antiviral approach against HCMV.
Copyright © 2021 Elsevier Masson SAS. All rights reserved.

Entities:  

Keywords:  Human cytomegalovirus; Metal-binding compounds; Terminase complex; pUL89-C; thermal shift assay

Mesh:

Substances:

Year:  2021        PMID: 34147908      PMCID: PMC8373693          DOI: 10.1016/j.ejmech.2021.113640

Source DB:  PubMed          Journal:  Eur J Med Chem        ISSN: 0223-5234            Impact factor:   7.088


  63 in total

1.  Structure and inhibition of herpesvirus DNA packaging terminase nuclease domain.

Authors:  Marta Nadal; Philippe J Mas; Phillipe J Mas; Alexandre G Blanco; Carme Arnan; Maria Solà; Darren J Hart; Miquel Coll
Journal:  Proc Natl Acad Sci U S A       Date:  2010-08-30       Impact factor: 11.205

2.  Pharmacophore-based design of HIV-1 integrase strand-transfer inhibitors.

Authors:  Maria Letizia Barreca; Stefania Ferro; Angela Rao; Laura De Luca; Maria Zappalà; Anna-Maria Monforte; Zeger Debyser; Myriam Witvrouw; Alba Chimirri
Journal:  J Med Chem       Date:  2005-11-03       Impact factor: 7.446

3.  Rationally designed dual inhibitors of HIV reverse transcriptase and integrase.

Authors:  Zhengqiang Wang; Eric M Bennett; Daniel J Wilson; Christine Salomon; Robert Vince
Journal:  J Med Chem       Date:  2007-07-04       Impact factor: 7.446

Review 4.  Integrase inhibitors to treat HIV/AIDS.

Authors:  Yves Pommier; Allison A Johnson; Christophe Marchand
Journal:  Nat Rev Drug Discov       Date:  2005-03       Impact factor: 84.694

Review 5.  Targeting the terminase: An important step forward in the treatment and prophylaxis of human cytomegalovirus infections.

Authors:  Brian G Gentry; Elke Bogner; John C Drach
Journal:  Antiviral Res       Date:  2018-11-23       Impact factor: 5.970

Review 6.  Elvitegravir: a new HIV integrase inhibitor.

Authors:  Kazuya Shimura; Eiichi N Kodama
Journal:  Antivir Chem Chemother       Date:  2009-10-19

7.  Design, synthesis, and antiviral activity of certain 2,5,6-trihalo-1-(beta-D-ribofuranosyl)benzimidazoles.

Authors:  L B Townsend; R V Devivar; S R Turk; M R Nassiri; J C Drach
Journal:  J Med Chem       Date:  1995-09-29       Impact factor: 7.446

8.  Hydroxypyridonecarboxylic Acids as Inhibitors of Human Cytomegalovirus pUL89 Endonuclease.

Authors:  Jayakanth Kankanala; Yan Wang; Robert J Geraghty; Zhengqiang Wang
Journal:  ChemMedChem       Date:  2018-07-20       Impact factor: 3.466

Review 9.  Nucleoside, nucleotide, and non-nucleoside inhibitors of hepatitis C virus NS5B RNA-dependent RNA-polymerase.

Authors:  Michael J Sofia; Wonsuk Chang; Phillip A Furman; Ralph T Mosley; Bruce S Ross
Journal:  J Med Chem       Date:  2012-01-23       Impact factor: 7.446

10.  The RNase H-like superfamily: new members, comparative structural analysis and evolutionary classification.

Authors:  Karolina A Majorek; Stanislaw Dunin-Horkawicz; Kamil Steczkiewicz; Anna Muszewska; Marcin Nowotny; Krzysztof Ginalski; Janusz M Bujnicki
Journal:  Nucleic Acids Res       Date:  2014-01-23       Impact factor: 16.971

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  2 in total

1.  4,5-Dihydroxypyrimidine Methyl Carboxylates, Carboxylic Acids, and Carboxamides as Inhibitors of Human Cytomegalovirus pUL89 Endonuclease.

Authors:  Tianyu He; Tiffany C Edwards; Jiashu Xie; Hideki Aihara; Robert J Geraghty; Zhengqiang Wang
Journal:  J Med Chem       Date:  2022-04-04       Impact factor: 8.039

2.  8-Hydroxy-1,6-naphthyridine-7-carboxamides as Inhibitors of Human Cytomegalovirus pUL89 Endonuclease.

Authors:  Eunkyung Jung; Ryuichi Majima; Tiffany C Edwards; Ruben Soto-Acosta; Robert J Geraghty; Zhengqiang Wang
Journal:  ChemMedChem       Date:  2022-08-10       Impact factor: 3.540

  2 in total

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