Design, Synthesis, and Anti-RNA Virus Activity of 6′-Fluorinated-Aristeromycin Analogues
Identifieur interne : 000630 ( Main/Exploration ); précédent : 000629; suivant : 000631Design, Synthesis, and Anti-RNA Virus Activity of 6′-Fluorinated-Aristeromycin Analogues
Auteurs : Ji-Seong Yoon [Corée du Sud] ; Gyudong Kim [Corée du Sud] ; Dnyandev B. Jarhad [Corée du Sud] ; Hong-Rae Kim [Corée du Sud] ; Young-Sup Shin [Corée du Sud] ; Shuhao Qu [Corée du Sud, République populaire de Chine] ; Pramod K. Sahu [Corée du Sud] ; Hea Ok Kim [Corée du Sud] ; Hyuk Woo Lee [Corée du Sud] ; Su Bin Wang [Corée du Sud] ; Yun Jeong Kong [Corée du Sud] ; Tong-Shin Chang [Corée du Sud] ; Natacha S. Ogando [Pays-Bas] ; Kristina Kovacikova [Pays-Bas] ; Eric J. Snijder [Pays-Bas] ; Clara C. Posthuma [Pays-Bas] ; Martijn J. Van Hemert [Pays-Bas] ; Lak Shin Jeong [Corée du Sud]Source :
- Journal of Medicinal Chemistry [ 0022-2623 ] ; 2019.
Abstract
The
6′-fluorinated aristeromycins were designed as dual-target
antiviral compounds aimed at inhibiting both the viral RNA-dependent
RNA polymerase (RdRp) and the host cell
Url:
DOI: 10.1021/acs.jmedchem.9b00781
PubMed: 31244113
PubMed Central: 7075649
Affiliations:
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Sahu</name><affiliation wicri:level="1"><nlm:aff id="aff3"><institution>Future Medicine Co., Ltd.</institution>, Seoul 06665,<country>Korea</country></nlm:aff><country xml:lang="fr">Corée du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Kim, Hea Ok" sort="Kim, Hea Ok" uniqKey="Kim H" first="Hea Ok" last="Kim">Hea Ok Kim</name><affiliation wicri:level="1"><nlm:aff id="aff3"><institution>Future Medicine Co., Ltd.</institution>, Seoul 06665,<country>Korea</country></nlm:aff><country xml:lang="fr">Corée du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Lee, Hyuk Woo" sort="Lee, Hyuk Woo" uniqKey="Lee H" first="Hyuk Woo" last="Lee">Hyuk Woo Lee</name><affiliation wicri:level="1"><nlm:aff id="aff3"><institution>Future Medicine Co., Ltd.</institution>, Seoul 06665,<country>Korea</country></nlm:aff><country xml:lang="fr">Corée du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Wang, Su Bin" sort="Wang, Su Bin" uniqKey="Wang S" first="Su Bin" last="Wang">Su Bin Wang</name><affiliation wicri:level="1"><nlm:aff id="aff4">College of Pharmacy,<institution>Ewha Womans University</institution>, Seoul 120-750,<country>Korea</country></nlm:aff><country xml:lang="fr">Corée du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Kong, Yun Jeong" sort="Kong, Yun Jeong" uniqKey="Kong Y" first="Yun Jeong" last="Kong">Yun Jeong Kong</name><affiliation wicri:level="1"><nlm:aff id="aff4">College of Pharmacy,<institution>Ewha Womans University</institution>, Seoul 120-750,<country>Korea</country></nlm:aff><country xml:lang="fr">Corée du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Chang, Tong Shin" sort="Chang, Tong Shin" uniqKey="Chang T" first="Tong-Shin" last="Chang">Tong-Shin Chang</name><affiliation wicri:level="1"><nlm:aff id="aff1">Research Institute of Pharmaceutical Sciences, College of Pharmacy,<institution>Seoul National University</institution>, Seoul 151-742,<country>Korea</country></nlm:aff><country xml:lang="fr">Corée du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="aff4">College of Pharmacy,<institution>Ewha Womans University</institution>, Seoul 120-750,<country>Korea</country></nlm:aff><country xml:lang="fr">Corée du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Ogando, Natacha S" sort="Ogando, Natacha S" uniqKey="Ogando N" first="Natacha S." last="Ogando">Natacha S. Ogando</name><affiliation wicri:level="1"><nlm:aff id="aff5">Department of Medical Microbiology,<institution>Leiden University Medical Center</institution>, Albinusdreef 2, 2333ZA Leiden,<country>The Netherlands</country></nlm:aff><country xml:lang="fr">Pays-Bas</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Kovacikova, Kristina" sort="Kovacikova, Kristina" uniqKey="Kovacikova K" first="Kristina" last="Kovacikova">Kristina Kovacikova</name><affiliation wicri:level="1"><nlm:aff id="aff5">Department of Medical Microbiology,<institution>Leiden University Medical Center</institution>, Albinusdreef 2, 2333ZA Leiden,<country>The Netherlands</country></nlm:aff><country xml:lang="fr">Pays-Bas</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Snijder, Eric J" sort="Snijder, Eric J" uniqKey="Snijder E" first="Eric J." last="Snijder">Eric J. 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and Anti-RNA Virus Activity of
6′-Fluorinated-Aristeromycin Analogues</title><author><name sortKey="Yoon, Ji Seong" sort="Yoon, Ji Seong" uniqKey="Yoon J" first="Ji-Seong" last="Yoon">Ji-Seong Yoon</name><affiliation wicri:level="1"><nlm:aff id="aff1">Research Institute of Pharmaceutical Sciences, College of Pharmacy,<institution>Seoul National University</institution>, Seoul 151-742,<country>Korea</country></nlm:aff><country xml:lang="fr">Corée du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Kim, Gyudong" sort="Kim, Gyudong" uniqKey="Kim G" first="Gyudong" last="Kim">Gyudong Kim</name><affiliation wicri:level="1"><nlm:aff id="aff1">Research Institute of Pharmaceutical Sciences, College of Pharmacy,<institution>Seoul National University</institution>, Seoul 151-742,<country>Korea</country></nlm:aff><country xml:lang="fr">Corée du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="aff2">College of Pharmacy and Research Institute of Drug Development,<institution>Chonnam National University</institution>, Gwangju 500-757,<country>Korea</country></nlm:aff><country xml:lang="fr">Corée du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Jarhad, Dnyandev B" sort="Jarhad, Dnyandev B" uniqKey="Jarhad D" first="Dnyandev B." last="Jarhad">Dnyandev B. Jarhad</name><affiliation wicri:level="1"><nlm:aff id="aff1">Research Institute of Pharmaceutical Sciences, College of Pharmacy,<institution>Seoul National University</institution>, Seoul 151-742,<country>Korea</country></nlm:aff><country xml:lang="fr">Corée du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Kim, Hong Rae" sort="Kim, Hong Rae" uniqKey="Kim H" first="Hong-Rae" last="Kim">Hong-Rae Kim</name><affiliation wicri:level="1"><nlm:aff id="aff1">Research Institute of Pharmaceutical Sciences, College of Pharmacy,<institution>Seoul National University</institution>, Seoul 151-742,<country>Korea</country></nlm:aff><country xml:lang="fr">Corée du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Shin, Young Sup" sort="Shin, Young Sup" uniqKey="Shin Y" first="Young-Sup" last="Shin">Young-Sup Shin</name><affiliation wicri:level="1"><nlm:aff id="aff1">Research Institute of Pharmaceutical Sciences, College of Pharmacy,<institution>Seoul National University</institution>, Seoul 151-742,<country>Korea</country></nlm:aff><country xml:lang="fr">Corée du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Qu, Shuhao" sort="Qu, Shuhao" uniqKey="Qu S" first="Shuhao" last="Qu">Shuhao Qu</name><affiliation wicri:level="1"><nlm:aff id="aff1">Research Institute of Pharmaceutical Sciences, College of Pharmacy,<institution>Seoul National University</institution>, Seoul 151-742,<country>Korea</country></nlm:aff><country xml:lang="fr">Corée du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="aff6">College of Pharmaceutical Engineering,<institution>Henan University of Animal Husbandry and Economy</institution>, Zhengzhou, 450046,<country>China</country></nlm:aff><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Sahu, Pramod K" sort="Sahu, Pramod K" uniqKey="Sahu P" first="Pramod K." last="Sahu">Pramod K. Sahu</name><affiliation wicri:level="1"><nlm:aff id="aff3"><institution>Future Medicine Co., Ltd.</institution>, Seoul 06665,<country>Korea</country></nlm:aff><country xml:lang="fr">Corée du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Kim, Hea Ok" sort="Kim, Hea Ok" uniqKey="Kim H" first="Hea Ok" last="Kim">Hea Ok Kim</name><affiliation wicri:level="1"><nlm:aff id="aff3"><institution>Future Medicine Co., Ltd.</institution>, Seoul 06665,<country>Korea</country></nlm:aff><country xml:lang="fr">Corée du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Lee, Hyuk Woo" sort="Lee, Hyuk Woo" uniqKey="Lee H" first="Hyuk Woo" last="Lee">Hyuk Woo Lee</name><affiliation wicri:level="1"><nlm:aff id="aff3"><institution>Future Medicine Co., Ltd.</institution>, Seoul 06665,<country>Korea</country></nlm:aff><country xml:lang="fr">Corée du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Wang, Su Bin" sort="Wang, Su Bin" uniqKey="Wang S" first="Su Bin" last="Wang">Su Bin Wang</name><affiliation wicri:level="1"><nlm:aff id="aff4">College of Pharmacy,<institution>Ewha Womans University</institution>, Seoul 120-750,<country>Korea</country></nlm:aff><country xml:lang="fr">Corée du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Kong, Yun Jeong" sort="Kong, Yun Jeong" uniqKey="Kong Y" first="Yun Jeong" last="Kong">Yun Jeong Kong</name><affiliation wicri:level="1"><nlm:aff id="aff4">College of Pharmacy,<institution>Ewha Womans University</institution>, Seoul 120-750,<country>Korea</country></nlm:aff><country xml:lang="fr">Corée du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Chang, Tong Shin" sort="Chang, Tong Shin" uniqKey="Chang T" first="Tong-Shin" last="Chang">Tong-Shin Chang</name><affiliation wicri:level="1"><nlm:aff id="aff1">Research Institute of Pharmaceutical Sciences, College of Pharmacy,<institution>Seoul National University</institution>, Seoul 151-742,<country>Korea</country></nlm:aff><country xml:lang="fr">Corée du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="aff4">College of Pharmacy,<institution>Ewha Womans University</institution>, Seoul 120-750,<country>Korea</country></nlm:aff><country xml:lang="fr">Corée du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Ogando, Natacha S" sort="Ogando, Natacha S" uniqKey="Ogando N" first="Natacha S." last="Ogando">Natacha S. Ogando</name><affiliation wicri:level="1"><nlm:aff id="aff5">Department of Medical Microbiology,<institution>Leiden University Medical Center</institution>, Albinusdreef 2, 2333ZA Leiden,<country>The Netherlands</country></nlm:aff><country xml:lang="fr">Pays-Bas</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Kovacikova, Kristina" sort="Kovacikova, Kristina" uniqKey="Kovacikova K" first="Kristina" last="Kovacikova">Kristina Kovacikova</name><affiliation wicri:level="1"><nlm:aff id="aff5">Department of Medical Microbiology,<institution>Leiden University Medical Center</institution>, Albinusdreef 2, 2333ZA Leiden,<country>The Netherlands</country></nlm:aff><country xml:lang="fr">Pays-Bas</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Snijder, Eric J" sort="Snijder, Eric J" uniqKey="Snijder E" first="Eric J." last="Snijder">Eric J. Snijder</name><affiliation wicri:level="1"><nlm:aff id="aff5">Department of Medical Microbiology,<institution>Leiden University Medical Center</institution>, Albinusdreef 2, 2333ZA Leiden,<country>The Netherlands</country></nlm:aff><country xml:lang="fr">Pays-Bas</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Posthuma, Clara C" sort="Posthuma, Clara C" uniqKey="Posthuma C" first="Clara C." last="Posthuma">Clara C. Posthuma</name><affiliation wicri:level="1"><nlm:aff id="aff5">Department of Medical Microbiology,<institution>Leiden University Medical Center</institution>, Albinusdreef 2, 2333ZA Leiden,<country>The Netherlands</country></nlm:aff><country xml:lang="fr">Pays-Bas</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Van Hemert, Martijn J" sort="Van Hemert, Martijn J" uniqKey="Van Hemert M" first="Martijn J." last="Van Hemert">Martijn J. Van Hemert</name><affiliation wicri:level="1"><nlm:aff id="aff5">Department of Medical Microbiology,<institution>Leiden University Medical Center</institution>, Albinusdreef 2, 2333ZA Leiden,<country>The Netherlands</country></nlm:aff><country xml:lang="fr">Pays-Bas</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Jeong, Lak Shin" sort="Jeong, Lak Shin" uniqKey="Jeong L" first="Lak Shin" last="Jeong">Lak Shin Jeong</name><affiliation wicri:level="1"><nlm:aff id="aff1">Research Institute of Pharmaceutical Sciences, College of Pharmacy,<institution>Seoul National University</institution>, Seoul 151-742,<country>Korea</country></nlm:aff><country xml:lang="fr">Corée du Sud</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author></analytic><series><title level="j">Journal of Medicinal Chemistry</title><idno type="ISSN">0022-2623</idno><idno type="eISSN">1520-4804</idno><imprint><date when="2019">2019</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p content-type="toc-graphic"><graphic xlink:href="jm9b00781_0010" id="ab-tgr1"></graphic></p><p>The
6′-fluorinated aristeromycins were designed as dual-target
antiviral compounds aimed at inhibiting both the viral RNA-dependent
RNA polymerase (RdRp) and the host cell <italic>S</italic>-adenosyl-<sc>l</sc>-homocysteine (SAH) hydrolase, which would indirectly target
capping of viral RNA. The introduction of a fluorine at the 6′-position
enhanced the inhibition of SAH hydrolase and the activity against
RNA viruses. The adenosine and <italic>N</italic><sup>6</sup>-methyladenosine
analogues <bold>2a–e</bold> showed potent inhibition against
SAH hydrolase, while only the adenosine derivatives <bold>2a–c</bold> exhibited potent antiviral activity against all tested RNA viruses
such as Middle East respiratory syndrome-coronavirus (MERS-CoV), severe
acute respiratory syndrome-coronavirus, chikungunya virus, and/or
Zika virus. 6′,6′-Difluoroaristeromycin (<bold>2c</bold>) showed the strongest antiviral effect for MERS-CoV, with a ∼2.5
log reduction in infectious progeny titer in viral load reduction
assay. The phosphoramidate prodrug <bold>3a</bold> also demonstrated
potent broad-spectrum antiviral activity, possibly by inhibiting the
viral RdRp. This study shows that 6′-fluorinated aristeromycins
can serve as starting points for the development of broad-spectrum
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