Chikungunya virus inhibition by synthetic coumarin–guanosine conjugates

Hwu, Jih Ru; Huang, Wen; Lin, Shu Yu; Tan, Kui‐Thong; Hu, Yu; Shieh, Fa Kuen; Бачурин, С. О.; Ustyugov, A. A.; Tsay, Shwu‐Chen

doi:10.1016/j.ejmech.2019.01.037

Cited by 29 publications

(12 citation statements)

References 51 publications

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“…The replacement of the coumarinyl (21) by naphthyl group (23) resulted in no significant influence in the EC 50 value, probably because of the similar size and planarity of the two substituents. In contrast, substitution of the naphthyl to benzyl (not shown) considerably decreased the EC 50 values [54], confirming the importance of the size and planarity of the substituents for proper antiviral activity [54].…”

Section: Nitrogen Heterocycle-coumarin Hybrid Compoundsmentioning

confidence: 80%

“…A series of thioguanine-coumarins derivatives were studied, and the methoxylated coumarins [54] (21, 22 and 23) exhibited the best activities against CHIKV compared to the benzouracil coumarins (9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19). EC 50 values were below 13.9 µM with a significant selectivity window covering SI values between 9.37 and 21.7, whereas the molecular lipophilicity of 20, 21, 22 and 23 were between 2.97 and 3.77.…”

Section: Nitrogen Heterocycle-coumarin Hybrid Compoundsmentioning

confidence: 99%

“…The piperazinyl-pyrimidine derivatives (52)(53)(54)(55)(56)(57)(58)(59)(60)(61)(62) were planned by optimization of the compound 51, which was identified by high-throughput screening by the Center for Innovation and Stimulation of Drug Discovery and by the University of Leuven [9]. To optimize compound 51, systematic structural variations (shown in Figure 5) were performed in its structure, which was divided into five parts to achieve an increase in antiviral activity and a decrease in cytotoxicity.…”

Section: Piperazinyl-pyrimidine Derivativesmentioning

confidence: 99%

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Nitrogen-Based Heterocyclic Compounds: A Promising Class of Antiviral Agents against Chikungunya Virus

Santana

Filho

Menezes

et al. 2020

Life

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Arboviruses, in general, are a global threat due to their morbidity and mortality, which results in an important social and economic impact. Chikungunya virus (CHIKV), one of the most relevant arbovirus currently known, is a re-emergent virus that causes a disease named chikungunya fever, characterized by a severe arthralgia (joint pains) that can persist for several months or years in some individuals. Until now, no vaccine or specific antiviral drug is commercially available. Nitrogen heterocyclic scaffolds are found in medications, such as aristeromycin, favipiravir, fluorouracil, 6-azauridine, thioguanine, pyrimethamine, among others. New families of natural and synthetic nitrogen analogous compounds are reported to have significant anti-CHIKV effects. In the present work, we focus on these nitrogen-based heterocyclic compounds as an important class with CHIKV antiviral activity. We summarize the present understanding on this class of compounds against CHIKV and also present their possible mechanism of action.

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Section: Nitrogen Heterocycle-coumarin Hybrid Compoundsmentioning

confidence: 80%

Section: Nitrogen Heterocycle-coumarin Hybrid Compoundsmentioning

confidence: 99%

Section: Piperazinyl-pyrimidine Derivativesmentioning

confidence: 99%

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Nitrogen-Based Heterocyclic Compounds: A Promising Class of Antiviral Agents against Chikungunya Virus

Santana

Filho

Menezes

et al. 2020

Life

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“…160 Research on the possible uses and characteristics of coumarins are still valid. In fact, there are a large number of reports aimed at alternative uses of coumarins; more than 1300 coumarins have been isolated from plants, bacteria and fungi, [14][15][16] with antioxidant, 161 anti-HIV, 162 anticancer, 163 antiviral, 164 antituberculosis, 165 insecticide and fungicide properties, 166 among others.…”

Section: Development and Employment Of Coumarinsmentioning

confidence: 99%

Background on the control of the cattle tick R. (B.) microplus and the use of coumarin substances as an alternative

Molano¹,

Torres²,

Monrroy³

2020

PPIJ

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“…Compounds derived from coumarins and quinoline have been tested against various viruses (McKee et al, 2020;Mishra et al, 2020). Quinolines have recently been used in experimental treatments for SARS-CoV-2 infected persons in several countries (Arshad et al, 2020;Lopez et al, 2020;Mori et al, 2020) and it has been proposed that coumarins inhibit the replication of several viruses including influenza (Pavurala et al, 2018), HIV (Jesumoroti et al, 2019), Dengue (Coulerie et al, 2013), Chikungunya (Hwu et al, 2019), hepatitis (Hwu et al, 2008) and filoviruses (EBOLA, Marburgvirus (MARV) and Cuevavirus) (Liu et al, 2019).…”

Section: Introductionmentioning

confidence: 99%

In Silico Study of Coumarins and Quinolines Derivatives as Potent Inhibitors of SARS-CoV-2 Main Protease

et al. 2021

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The pandemic that started in Wuhan (China) in 2019 has caused a large number of deaths, and infected people around the world due to the absence of effective therapy against coronavirus 2 of the severe acute respiratory syndrome (SARS-CoV-2). Viral maturation requires the activity of the main viral protease (Mpro), so its inhibition stops the progress of the disease. To evaluate possible inhibitors, a computational model of the SARS-CoV-2 enzyme Mpro was constructed in complex with 26 synthetic ligands derived from coumarins and quinolines. Analysis of simulations of molecular dynamics and molecular docking of the models show a high affinity for the enzyme (∆Ebinding between −5.1 and 7.1 kcal mol−1). The six compounds with the highest affinity show Kd between 6.26 × 10–6 and 17.2 × 10–6, with binding affinity between −20 and −25 kcal mol−1, with ligand efficiency less than 0.3 associated with possible inhibitory candidates. In addition to the high affinity of these compounds for SARS-CoV-2 Mpro, low toxicity is expected considering the Lipinski, Veber and Pfizer rules. Therefore, this novel study provides candidate inhibitors that would allow experimental studies which can lead to the development of new treatments for SARS-CoV-2.

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Chikungunya virus inhibition by synthetic coumarin–guanosine conjugates

Cited by 29 publications

References 51 publications

Nitrogen-Based Heterocyclic Compounds: A Promising Class of Antiviral Agents against Chikungunya Virus

Nitrogen-Based Heterocyclic Compounds: A Promising Class of Antiviral Agents against Chikungunya Virus

Background on the control of the cattle tick R. (B.) microplus and the use of coumarin substances as an alternative

In Silico Study of Coumarins and Quinolines Derivatives as Potent Inhibitors of SARS-CoV-2 Main Protease

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