Targeting Chikungunya Virus Replication by Benzoannulene Inhibitors Article Swipe
Shadab Ahmed
,
Nicole N. Haese
,
Jaden T. Cowan
,
Vibha Pathak
,
Omar Moukha‐Chafiq
,
Valerie J. Smith
,
Kevin J. Rodzinak
,
Fahim Ahmad
,
Sixue Zhang
,
Kiley Bonin
,
Aaron D. Streblow
,
Cassilyn E. Streblow
,
Craig N. Kreklywich
,
Clayton R. Morrison
,
Sanjay Sarkar
,
Nathaniel J. Moorman
,
Wes Sander
,
Robbie Allen
,
Victor R. DeFilippis
,
Babu L. Tekwani
,
Mousheng Wu
,
Alec J. Hirsch
,
Jessica L. Smith
,
Nichole A. Tower
,
Lynn Rasmussen
,
Robert Bostwick
,
Joseph A. Maddry
,
Subramaniam Ananthan
,
John M. Gerdes
,
Corinne E. Augelli‐Szafran
,
Mark J. Suto
,
Thomas E. Morrison
,
Mark T. Heise
,
Daniel N. Streblow
,
Ashish K. Pathak
·
YOU?
·
· 2021
· Open Access
·
· DOI: https://doi.org/10.1021/acs.jmedchem.0c02183
YOU?
·
· 2021
· Open Access
·
· DOI: https://doi.org/10.1021/acs.jmedchem.0c02183
A benzo[6]annulene, 4-(tert-butyl)-N-(3-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl) benzamide (1a), was identified as an inhibitor against Chikungunya virus (CHIKV) with antiviral activity EC90 = 1.45 μM and viral titer reduction (VTR) of 2.5 log at 10 μM with no observed cytotoxicity (CC50 = 169 μM) in normal human dermal fibroblast cells. Chemistry efforts to improve potency, efficacy, and drug-like properties of 1a resulted in a novel lead compound 8q, which possessed excellent cellular antiviral activity (EC90 = 270 nM and VTR of 4.5 log at 10 μM) and improved liver microsomal stability. CHIKV resistance to an analog of 1a, compound 1c, tracked to a mutation in the nsP3 macrodomain. Further mechanism of action studies showed compounds working through inhibition of human dihydroorotate dehydrogenase in addition to CHIKV nsP3 macrodomain. Moderate efficacy was observed in an in vivo CHIKV challenge mouse model for compound 8q as viral replication was rescued from the pyrimidine salvage pathway.
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Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1021/acs.jmedchem.0c02183
- OA Status
- green
- Cited By
- 22
- References
- 61
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W3144994887
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W3144994887Canonical identifier for this work in OpenAlex
- DOI
-
https://doi.org/10.1021/acs.jmedchem.0c02183Digital Object Identifier
- Title
-
Targeting Chikungunya Virus Replication by Benzoannulene InhibitorsWork title
- Type
-
articleOpenAlex work type
- Language
-
enPrimary language
- Publication year
-
2021Year of publication
- Publication date
-
2021-04-09Full publication date if available
- Authors
-
Shadab Ahmed, Nicole N. Haese, Jaden T. Cowan, Vibha Pathak, Omar Moukha‐Chafiq, Valerie J. Smith, Kevin J. Rodzinak, Fahim Ahmad, Sixue Zhang, Kiley Bonin, Aaron D. Streblow, Cassilyn E. Streblow, Craig N. Kreklywich, Clayton R. Morrison, Sanjay Sarkar, Nathaniel J. Moorman, Wes Sander, Robbie Allen, Victor R. DeFilippis, Babu L. Tekwani, Mousheng Wu, Alec J. Hirsch, Jessica L. Smith, Nichole A. Tower, Lynn Rasmussen, Robert Bostwick, Joseph A. Maddry, Subramaniam Ananthan, John M. Gerdes, Corinne E. Augelli‐Szafran, Mark J. Suto, Thomas E. Morrison, Mark T. Heise, Daniel N. Streblow, Ashish K. PathakList of authors in order
- Landing page
-
https://doi.org/10.1021/acs.jmedchem.0c02183Publisher landing page
- Open access
-
YesWhether a free full text is available
- OA status
-
greenOpen access status per OpenAlex
- OA URL
-
https://www.ncbi.nlm.nih.gov/pmc/articles/9774970Direct OA link when available
- Concepts
-
Dihydroorotate dehydrogenase, Chemistry, Viral replication, Virus, Benzamide, Chikungunya, Cytotoxicity, In vivo, Potency, Virology, Titer, IC50, Mechanism of action, Cell culture, Stereochemistry, Pyrimidine, In vitro, Biochemistry, Biology, Biotechnology, GeneticsTop concepts (fields/topics) attached by OpenAlex
- Cited by
-
22Total citation count in OpenAlex
- Citations by year (recent)
-
2025: 8, 2024: 7, 2023: 4, 2022: 1, 2021: 2Per-year citation counts (last 5 years)
- References (count)
-
61Number of works referenced by this work
- Related works (count)
-
10Other works algorithmically related by OpenAlex
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