Discovery of Metal Ions Chelator Quercetin Derivatives with Potent Anti-HCV Activities

Zhong, Dongwei; Liu, Mingming; Cao, Yang; Zhu, Yelin; Bian, Shi‐Hui; Zhou, Jiayi; Wu, Feng-Jie; Ryu, Kum-Chol; Zhou, Lu; Ye, Deyong

doi:10.3390/molecules20046978

Cited by 19 publications

(12 citation statements)

References 24 publications

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“…There are few reports on the inhibition of viral infection by compounds with similar structures. For example, derivatives of the metal ion chelator, quercetin, are reported to show potent anti-HCV activities [29]. Therefore, our research provides new information applicable to the development of active aromatic ester compounds.…”

Section: Discussionmentioning

confidence: 89%

Antiviral Effects of Novel 2-Benzoxyl-Phenylpyridine Derivatives

Wang

et al. 2020

Molecules

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Coxsackievirus B3 (CVB3) is the most common cause of acute and chronic viral myocarditis, primarily in children, while human adenovirus infections represent a significant cause of morbidity and mortality worldwide, in people of all ages. A series of novel 2-benzoxyl-phenylpyridine derivatives were evaluated for their potential antiviral activities against CVB3 and adenovirus type 7 (ADV7). Preliminary assays indicated that some of these compounds exhibited excellent antiviral effects on both CVB3 and ADV7 viruses; they could effectively inhibit virus-induced cytopathic effects, reduce viral progeny yields, and had similar or superior antiviral activities compared with the control drug, ribavirin. Further, these compounds targeted the early stages of CVB3 replication in cells, including viral RNA replication and protein synthesis, rather than inactivating the virus directly, inhibiting virus adsorption/entry, or affecting viral release from cells. Our data demonstrate that the tested 2-benzoxyl-phenylpyridine derivatives are effective inhibitors of CVB3 and ADV7, raising the possibility that these compounds might be feasible candidates for anti-viral agents.

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Section: Discussionmentioning

confidence: 89%

Antiviral Effects of Novel 2-Benzoxyl-Phenylpyridine Derivatives

Wang

et al. 2020

Molecules

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“…Finally, 7-O-arylquercetins 5 and 6 were purified by RP-18 RPC using water: methanol (30:70) as solvent. [ 10 ]…”

Section: Resultsmentioning

confidence: 99%

“…; 13 C-NMR (DMSO-D6) δ: 175.9, 163.9, 160.3, 155.9, 147.8, 147.3, 145.04, 137.4, 136, 133.1, 129.06, 127.9, 121.8, 120, 115.5, 115.2, 104.03, 97.99, 92.7, 69.8, and 20.75; IR (KBr); ν max : 3253, 2922, 1655, 1589, 1498, 1350,1323, and 1165 cm −1 ; and ESI-MS ( m /z): 405 [M-H] − . [ 10 ]…”

Section: Methodsmentioning

confidence: 99%

Synthesis and In vitro Leishmanicidal Activities of Six Quercetin Derivatives

et al. 2018

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Background:Today, leishmaniasis is a widespread, infectious parasitic disease caused by Leishmania spp. Natural-derived compounds are likely to provide a valuable source of new pharmaceuticals, and among them, quercetin derivatives may have antileishmanial effects. The antileishmanial activity of 3,5,7,3’,4’-pentahydroxyflavonol (quercetin) derivatives is partly attributed to the position and pKa of phenolic or catechol hydroxyl groups. Therefore, to optimize their leishmanicidal effect, the structural features of quercetin and its derivatives were improved by acylation or alkylation of hydroxyl groups and changing their pKa and consequently their activities.Materials and Methods:In this study, during a regioselective method, quercetin derivatives were synthesized. The structures of synthesized compounds were confirmed by mass, IR, 1H-, and 13C-NMR spectral data. The antileishmanial activities of compounds 1–6 were compared with glucantime as the standard drug against promastigotes of Leishmania major using standard cell-based leishmanicidal assay.Results:In this study, during a regioselective method, two 7-O-quercetin derivatives (5 and 6), and three quercetin acetate derivatives (2, 3, and 4) were synthesized. In detail, the IC50 values found against L. major were (1) 2.5 ± 0.92; (2) 2.85 ± 0.99; (3) 15.5 ± 1.95; (4) 13.5 ± 3.5; (5) 2.6 ± 0.57; and (6) 1.3 ± 0.35 μM while IC50 value of glucantime as the standard drug was 88.5 ± 9.47 μM.Conclusions:The present study showed an effective antileishmanial activity of quercetin semisynthetic compounds (1–6) against in vitro promastigotes of L. major. Among them, quercetin analogs with more lipophilic and iron-chelating activity showed more antiparasite activity.

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“…Compound 3i, which has a 3-chlorobenzyl substitution in 7-O-arylmethylquercetin, showed stronger activity (IC 50 : 3.8 µM) than that with substitution of carboxyl groups at quercetin-3-O (IC 50 : 9.0 µM). This quercetin analog exerted potent inhibition of HCV NS5B RdRp activity through chelation of magnesium ions at the active site [59]. Other derivatives such as imidazo derivatives were also potent inhibitors of HCV [60,61].…”

Section: Anti-hcv Compounds From Natural Resourcesmentioning

confidence: 99%

Promising Anti-Hepatitis C Virus Compounds from Natural Resources

Wahyuni

Utsubo

Hotta

2016

Natural Product Communications

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Hepatitis C virus (HCV) infection is a major worldwide problem, which involves approximately 170 million people. High morbidity of patients is caused by chronic infection, which leads to liver cirrhosis, hepatocellular carcinoma and other HCV-related diseases. The sustained virological response (SVR) has been markedly improved to be >90% by the current standard interferon (IFN)-free treatment regimens with a combination of direct-acting antiviral agents (DAAs) targeting the viral NS3 protease, NS5A multi-function protein and NS5B RNA-dependent RNA polymerase, compared with 50–70% of SVR rates achieved by the previous standard IFN-based treatment regimens with or without an NS3 protease inhibitor. However, the emergence of DAA-resistant HCV strains and the limited access to the DAAs due to their high cost could be major concerns. Also, the long-term prognosis of patients treated with DAAs, such as the possible development of hepatocellular carcinoma, still needs to be further evaluated. Natural resources are considered to be good candidates to develop anti-HCV agents. Here, we summarize anti-HCV compounds obtained from natural resources, including medicinal plant extracts, their isolated compounds and some of their derivatives that possess high antiviral potency against HCV.

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Discovery of Metal Ions Chelator Quercetin Derivatives with Potent Anti-HCV Activities

Cited by 19 publications

References 24 publications

Antiviral Effects of Novel 2-Benzoxyl-Phenylpyridine Derivatives

Antiviral Effects of Novel 2-Benzoxyl-Phenylpyridine Derivatives

Synthesis and In vitro Leishmanicidal Activities of Six Quercetin Derivatives

Promising Anti-Hepatitis C Virus Compounds from Natural Resources

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