Identification of SARS-CoV-2 Mpro inhibitors containing P1’ 4-fluorobenzothiazole moiety highly active against SARS-CoV-2

COVID-19 caused by SARS-CoV-2 has continually been serious threat to public health worldwide. While a few anti-SARS-CoV-2 therapeutics are currently available, their antiviral potency is not sufficient. Here, we identify two orally available 4-fluoro-benzothiazole-containing small molecules, TKB245...

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Published inNature communications Vol. 14; no. 1; pp. 1076 - 13
Main Authors Higashi-Kuwata, Nobuyo, Tsuji, Kohei, Hayashi, Hironori, Bulut, Haydar, Kiso, Maki, Imai, Masaki, Ogata-Aoki, Hiromi, Ishii, Takahiro, Kobayakawa, Takuya, Nakano, Kenta, Takamune, Nobutoki, Kishimoto, Naoki, Hattori, Shin-ichiro, Das, Debananda, Uemura, Yukari, Shimizu, Yosuke, Aoki, Manabu, Hasegawa, Kazuya, Suzuki, Satoshi, Nishiyama, Akie, Saruwatari, Junji, Shimizu, Yukiko, Sukenaga, Yoshikazu, Takamatsu, Yuki, Tsuchiya, Kiyoto, Maeda, Kenji, Yoshimura, Kazuhisa, Iida, Shun, Ozono, Seiya, Suzuki, Tadaki, Okamura, Tadashi, Misumi, Shogo, Kawaoka, Yoshihiro, Tamamura, Hirokazu, Mitsuya, Hiroaki
Format Journal Article
LanguageEnglish
Published London Nature Publishing Group UK 25.02.2023
Nature Publishing Group
Nature Portfolio
Subjects
13
14
631/154/309
631/326/22/1295
631/326/596/4130
631/45/468
ACE2
Amino acids
Angiotensin-converting enzyme 2
Antiviral agents
Antiviral drugs
Benzothiazole
Coronaviruses
Covalent bonds
COVID-19
Crystallography
Dimerization
Enzymatic activity
Fluorine
Humanities and Social Sciences
Infectivity
multidisciplinary
Optimization
Protease
Public health
Replication
Science
Science (multidisciplinary)
Severe acute respiratory syndrome coronavirus 2
Spectrometry
Online AccessGet full text

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Abstract COVID-19 caused by SARS-CoV-2 has continually been serious threat to public health worldwide. While a few anti-SARS-CoV-2 therapeutics are currently available, their antiviral potency is not sufficient. Here, we identify two orally available 4-fluoro-benzothiazole-containing small molecules, TKB245 and TKB248, which specifically inhibit the enzymatic activity of main protease (M pro ) of SARS-CoV-2 and significantly more potently block the infectivity and replication of various SARS-CoV-2 strains than nirmatrelvir, molnupiravir, and ensitrelvir in cell-based assays employing various target cells. Both compounds also block the replication of Delta and Omicron variants in human-ACE2-knocked-in mice. Native mass spectrometric analysis reveals that both compounds bind to dimer M pro , apparently promoting M pro dimerization. X-ray crystallographic analysis shows that both compounds bind to M pro ’s active-site cavity, forming a covalent bond with the catalytic amino acid Cys-145 with the 4-fluorine of the benzothiazole moiety pointed to solvent. The data suggest that TKB245 and TKB248 might serve as potential therapeutics for COVID-19 and shed light upon further optimization to develop more potent and safer anti-SARS-CoV-2 therapeutics. Effective antivirals are critical for combatting SARS-CoV-2 infections. Here, the authors develop two orally available small molecules, which specifically inhibit the activity of the SARS-CoV-2 main protease and potently block the infectivity and replication of various SARS-CoV-2 strains in cells and mice.
AbstractList COVID-19 caused by SARS-CoV-2 has continually been serious threat to public health worldwide. While a few anti-SARS-CoV-2 therapeutics are currently available, their antiviral potency is not sufficient. Here, we identify two orally available 4-fluoro-benzothiazole-containing small molecules, TKB245 and TKB248, which specifically inhibit the enzymatic activity of main protease (Mpro) of SARS-CoV-2 and significantly more potently block the infectivity and replication of various SARS-CoV-2 strains than nirmatrelvir, molnupiravir, and ensitrelvir in cell-based assays employing various target cells. Both compounds also block the replication of Delta and Omicron variants in human-ACE2-knocked-in mice. Native mass spectrometric analysis reveals that both compounds bind to dimer Mpro, apparently promoting Mpro dimerization. X-ray crystallographic analysis shows that both compounds bind to Mpro's active-site cavity, forming a covalent bond with the catalytic amino acid Cys-145 with the 4-fluorine of the benzothiazole moiety pointed to solvent. The data suggest that TKB245 and TKB248 might serve as potential therapeutics for COVID-19 and shed light upon further optimization to develop more potent and safer anti-SARS-CoV-2 therapeutics.COVID-19 caused by SARS-CoV-2 has continually been serious threat to public health worldwide. While a few anti-SARS-CoV-2 therapeutics are currently available, their antiviral potency is not sufficient. Here, we identify two orally available 4-fluoro-benzothiazole-containing small molecules, TKB245 and TKB248, which specifically inhibit the enzymatic activity of main protease (Mpro) of SARS-CoV-2 and significantly more potently block the infectivity and replication of various SARS-CoV-2 strains than nirmatrelvir, molnupiravir, and ensitrelvir in cell-based assays employing various target cells. Both compounds also block the replication of Delta and Omicron variants in human-ACE2-knocked-in mice. Native mass spectrometric analysis reveals that both compounds bind to dimer Mpro, apparently promoting Mpro dimerization. X-ray crystallographic analysis shows that both compounds bind to Mpro's active-site cavity, forming a covalent bond with the catalytic amino acid Cys-145 with the 4-fluorine of the benzothiazole moiety pointed to solvent. The data suggest that TKB245 and TKB248 might serve as potential therapeutics for COVID-19 and shed light upon further optimization to develop more potent and safer anti-SARS-CoV-2 therapeutics.
COVID-19 caused by SARS-CoV-2 has continually been serious threat to public health worldwide. While a few anti-SARS-CoV-2 therapeutics are currently available, their antiviral potency is not sufficient. Here, we identify two orally available 4-fluoro-benzothiazole-containing small molecules, TKB245 and TKB248, which specifically inhibit the enzymatic activity of main protease (M pro ) of SARS-CoV-2 and significantly more potently block the infectivity and replication of various SARS-CoV-2 strains than nirmatrelvir, molnupiravir, and ensitrelvir in cell-based assays employing various target cells. Both compounds also block the replication of Delta and Omicron variants in human-ACE2-knocked-in mice. Native mass spectrometric analysis reveals that both compounds bind to dimer M pro , apparently promoting M pro dimerization. X-ray crystallographic analysis shows that both compounds bind to M pro ’s active-site cavity, forming a covalent bond with the catalytic amino acid Cys-145 with the 4-fluorine of the benzothiazole moiety pointed to solvent. The data suggest that TKB245 and TKB248 might serve as potential therapeutics for COVID-19 and shed light upon further optimization to develop more potent and safer anti-SARS-CoV-2 therapeutics.
COVID-19 caused by SARS-CoV-2 has continually been serious threat to public health worldwide. While a few anti-SARS-CoV-2 therapeutics are currently available, their antiviral potency is not sufficient. Here, we identify two orally available 4-fluoro-benzothiazole-containing small molecules, TKB245 and TKB248, which specifically inhibit the enzymatic activity of main protease (M pro ) of SARS-CoV-2 and significantly more potently block the infectivity and replication of various SARS-CoV-2 strains than nirmatrelvir, molnupiravir, and ensitrelvir in cell-based assays employing various target cells. Both compounds also block the replication of Delta and Omicron variants in human-ACE2-knocked-in mice. Native mass spectrometric analysis reveals that both compounds bind to dimer M pro , apparently promoting M pro dimerization. X-ray crystallographic analysis shows that both compounds bind to M pro ’s active-site cavity, forming a covalent bond with the catalytic amino acid Cys-145 with the 4-fluorine of the benzothiazole moiety pointed to solvent. The data suggest that TKB245 and TKB248 might serve as potential therapeutics for COVID-19 and shed light upon further optimization to develop more potent and safer anti-SARS-CoV-2 therapeutics. Effective antivirals are critical for combatting SARS-CoV-2 infections. Here, the authors develop two orally available small molecules, which specifically inhibit the activity of the SARS-CoV-2 main protease and potently block the infectivity and replication of various SARS-CoV-2 strains in cells and mice.
AbstractCOVID-19 caused by SARS-CoV-2 has continually been serious threat to public health worldwide. While a few anti-SARS-CoV-2 therapeutics are currently available, their antiviral potency is not sufficient. Here, we identify two orally available 4-fluoro-benzothiazole-containing small molecules, TKB245 and TKB248, which specifically inhibit the enzymatic activity of main protease (Mpro) of SARS-CoV-2 and significantly more potently block the infectivity and replication of various SARS-CoV-2 strains than nirmatrelvir, molnupiravir, and ensitrelvir in cell-based assays employing various target cells. Both compounds also block the replication of Delta and Omicron variants in human-ACE2-knocked-in mice. Native mass spectrometric analysis reveals that both compounds bind to dimer Mpro, apparently promoting Mpro dimerization. X-ray crystallographic analysis shows that both compounds bind to Mpro’s active-site cavity, forming a covalent bond with the catalytic amino acid Cys-145 with the 4-fluorine of the benzothiazole moiety pointed to solvent. The data suggest that TKB245 and TKB248 might serve as potential therapeutics for COVID-19 and shed light upon further optimization to develop more potent and safer anti-SARS-CoV-2 therapeutics.Effective antivirals are critical for combatting SARS-CoV-2 infections. Here, the authors develop two orally available small molecules, which specifically inhibit the activity of the SARS-CoV-2 main protease and potently block the infectivity and replication of various SARS-CoV-2 strains in cells and mice.
Effective antivirals are critical for combatting SARS-CoV-2 infections. Here, the authors develop two orally available small molecules, which specifically inhibit the activity of the SARS-CoV-2 main protease and potently block the infectivity and replication of various SARS-CoV-2 strains in cells and mice.
ArticleNumber 1076
Author Sukenaga, Yoshikazu
Kishimoto, Naoki
Hasegawa, Kazuya
Maeda, Kenji
Iida, Shun
Ogata-Aoki, Hiromi
Saruwatari, Junji
Hattori, Shin-ichiro
Shimizu, Yosuke
Tamamura, Hirokazu
Das, Debananda
Higashi-Kuwata, Nobuyo
Ishii, Takahiro
Misumi, Shogo
Hayashi, Hironori
Imai, Masaki
Uemura, Yukari
Yoshimura, Kazuhisa
Suzuki, Tadaki
Aoki, Manabu
Okamura, Tadashi
Mitsuya, Hiroaki
Kiso, Maki
Nakano, Kenta
Bulut, Haydar
Nishiyama, Akie
Shimizu, Yukiko
Kobayakawa, Takuya
Tsuchiya, Kiyoto
Kawaoka, Yoshihiro
Tsuji, Kohei
Takamune, Nobutoki
Takamatsu, Yuki
Ozono, Seiya
Suzuki, Satoshi
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2023. This is a U.S. Government work and not under copyright protection in the US; foreign copyright protection may apply.
Copyright_xml – notice: This is a U.S. Government work and not under copyright protection in the US; foreign copyright protection may apply 2023
– notice: This is a U.S. Government work and not under copyright protection in the US; foreign copyright protection may apply 2023. This work is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.
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Snippet COVID-19 caused by SARS-CoV-2 has continually been serious threat to public health worldwide. While a few anti-SARS-CoV-2 therapeutics are currently available,...
AbstractCOVID-19 caused by SARS-CoV-2 has continually been serious threat to public health worldwide. While a few anti-SARS-CoV-2 therapeutics are currently...
Effective antivirals are critical for combatting SARS-CoV-2 infections. Here, the authors develop two orally available small molecules, which specifically...
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SubjectTerms 13
14
631/154/309
631/326/22/1295
631/326/596/4130
631/45/468
ACE2
Amino acids
Angiotensin-converting enzyme 2
Antiviral agents
Antiviral drugs
Benzothiazole
Coronaviruses
Covalent bonds
COVID-19
Crystallography
Dimerization
Enzymatic activity
Fluorine
Humanities and Social Sciences
Infectivity
multidisciplinary
Optimization
Protease
Public health
Replication
Science
Science (multidisciplinary)
Severe acute respiratory syndrome coronavirus 2
Spectrometry
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Title Identification of SARS-CoV-2 Mpro inhibitors containing P1’ 4-fluorobenzothiazole moiety highly active against SARS-CoV-2
URI https://link.springer.com/article/10.1038/s41467-023-36729-0
https://www.proquest.com/docview/2779807377
https://www.proquest.com/docview/2780081536
https://pubmed.ncbi.nlm.nih.gov/PMC9958325
https://doaj.org/article/0a9319e808d143a0af10cb89193b1a4f
Volume 14
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