Discovery of GS-7682, a Novel 4′-Cyano-Modified C-Nucleoside Prodrug with Broad Activity against Pneumo- and Picornaviruses and Efficacy in RSV-Infected African Green Monkeys Article Swipe
Dustin S. Siegel
,
Hon C. Hui
,
Jared Pitts
,
Meghan S. Vermillion
,
Kazuya Ishida
,
Davin Rautiola
,
Michael Keeney
,
Hammad Irshad
,
Lijun Zhang
,
Kwon Soo Chun
,
Gregory Chin
,
Bindu Goyal
,
Edward Doerffler
,
Hai Yang
,
Michael O. Clarke
,
Chris Palmiotti
,
Arya Vijjapurapu
,
Nicholas C. Riola
,
Kirsten M. Stray
,
Eisuke Murakami
,
Bin Ma
,
Ting Wang
,
Xiaofeng Zhao
,
Yili Xu
,
Gary Lee
,
Bruno Marchand
,
Minji Seung
,
Arabinda Nayak
,
Adrian Tomkinson
,
Nani Kadrichu
,
Scott Ellis
,
Ona Barauskas
,
Joy Y. Feng
,
Jason K. Perry
,
Michel Perron
,
John P. Bilello
,
Philip J. Kuehl
,
Raju Subramanian
,
Tomáš Cihlář
,
Richard L. Mackman
·
YOU?
·
· 2024
· Open Access
·
· DOI: https://doi.org/10.1021/acs.jmedchem.4c00899
YOU?
·
· 2024
· Open Access
·
· DOI: https://doi.org/10.1021/acs.jmedchem.4c00899
Acute respiratory viral infections, such as pneumovirus and respiratory picornavirus infections, exacerbate disease in COPD and asthma patients. A research program targeting respiratory syncytial virus (RSV) led to the discovery of GS-7682 (1), a novel phosphoramidate prodrug of a 4'-CN-4-aza-7,9-dideazaadenosine C-nucleoside GS-646089 (2) with broad antiviral activity against RSV (EC50 = 3-46 nM), human metapneumovirus (EC50 = 210 nM), human rhinovirus (EC50 = 54-61 nM), and enterovirus (EC50 = 83-90 nM). Prodrug optimization for cellular potency and lung cell metabolism identified 5'-methyl [(S)-hydroxy(phenoxy)phosphoryl]-l-alaninate in combination with 2',3'-diisobutyrate promoieties as being optimal for high levels of intracellular triphosphate formation in vitro and in vivo. 1 demonstrated significant reductions of viral loads in the lower respiratory tract of RSV-infected African green monkeys when administered once daily via intratracheal nebulized aerosol. Together, these findings support additional evaluation of 1 and its analogues as potential therapeutics for pneumo- and picornaviruses.
Related Topics
Concepts
Picornavirus
Rhinovirus
Virology
Prodrug
Pneumovirus
Respiratory system
Virus
Paramyxoviridae
Pneumovirinae
Nucleoside
Respiratory disease
Viral disease
Chemistry
Medicine
Lung
Pharmacology
RNA
Gene
Stereochemistry
Biochemistry
Internal medicine
Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1021/acs.jmedchem.4c00899
- OA Status
- green
- Cited By
- 8
- References
- 58
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W4400723589
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W4400723589Canonical identifier for this work in OpenAlex
- DOI
-
https://doi.org/10.1021/acs.jmedchem.4c00899Digital Object Identifier
- Title
-
Discovery of GS-7682, a Novel 4′-Cyano-Modified C-Nucleoside Prodrug with Broad Activity against Pneumo- and Picornaviruses and Efficacy in RSV-Infected African Green MonkeysWork title
- Type
-
articleOpenAlex work type
- Language
-
enPrimary language
- Publication year
-
2024Year of publication
- Publication date
-
2024-07-17Full publication date if available
- Authors
-
Dustin S. Siegel, Hon C. Hui, Jared Pitts, Meghan S. Vermillion, Kazuya Ishida, Davin Rautiola, Michael Keeney, Hammad Irshad, Lijun Zhang, Kwon Soo Chun, Gregory Chin, Bindu Goyal, Edward Doerffler, Hai Yang, Michael O. Clarke, Chris Palmiotti, Arya Vijjapurapu, Nicholas C. Riola, Kirsten M. Stray, Eisuke Murakami, Bin Ma, Ting Wang, Xiaofeng Zhao, Yili Xu, Gary Lee, Bruno Marchand, Minji Seung, Arabinda Nayak, Adrian Tomkinson, Nani Kadrichu, Scott Ellis, Ona Barauskas, Joy Y. Feng, Jason K. Perry, Michel Perron, John P. Bilello, Philip J. Kuehl, Raju Subramanian, Tomáš Cihlář, Richard L. MackmanList of authors in order
- Landing page
-
https://doi.org/10.1021/acs.jmedchem.4c00899Publisher landing page
- Open access
-
YesWhether a free full text is available
- OA status
-
greenOpen access status per OpenAlex
- OA URL
-
https://doi.org/10.7270/q2pg1xc4Direct OA link when available
- Concepts
-
Picornavirus, Rhinovirus, Virology, Prodrug, Pneumovirus, Respiratory system, Virus, Paramyxoviridae, Pneumovirinae, Nucleoside, Respiratory disease, Viral disease, Chemistry, Medicine, Lung, Pharmacology, RNA, Gene, Stereochemistry, Biochemistry, Internal medicineTop concepts (fields/topics) attached by OpenAlex
- Cited by
-
8Total citation count in OpenAlex
- Citations by year (recent)
-
2025: 7, 2024: 1Per-year citation counts (last 5 years)
- References (count)
-
58Number of works referenced by this work
- Related works (count)
-
10Other works algorithmically related by OpenAlex
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