Synthesis of a carbocyclic sialic acid analogue for the inhibition of influenza virus neuraminidase

Bianco, Armandodoriano; Brufani, M.; Manna, Fedele; Melchioni, Cristiana

doi:10.1016/s0008-6215(01)00079-9

Cited by 27 publications

(18 citation statements)

References 16 publications

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“…Taxodione and taxodone are two potent antitumor agents3536. Shikimic acid is one component of the T. distichum extract and is classified as a carbocyclic sialic acid analogue3738 that is potentially able to inhibit NA function38. Among the variety of compounds that are present in T. distichum , quercetin has been reported to inhibit replication of hepatitis C virus, herpesvirus 1, rhinovirus, Japanese encephalitis virus, Mayaro virus, dengue virus type-2 and influenza virus (including H1N1 and H5N1)3940414243444546.…”

Section: Discussionmentioning

confidence: 99%

An extract from Taxodium distichum targets hemagglutinin- and neuraminidase-related activities of influenza virus in vitro

Hsieh

Chen

Lin

et al. 2016

Sci Rep

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Influenza virus remains an emerging virus and causes pandemics with high levels of fatality. After screening different plant extracts with potential anti-influenza activity, a water extract of Taxodium distichum stems (TDSWex) showed excellent activity against influenza viruses. The EC50 of TDSWex was 0.051 ± 0.024 mg/mL against influenza virus A/WSN/33. TDSWex had excellent antiviral efficacy against various strains of human influenza A and B viruses, particularly oseltamivir-resistant clinical isolates and a swine-origin influenza strain. We observed that the synthesis of viral RNA and protein were inhibited in the presence of TDSWex. The results of the time-of-addition assay suggested that TDSWex inhibited viral entry and budding. In the hemagglutination inhibition assay, TDSWex inhibited the hemagglutination of red blood cells, implying that the extract targeted hemagglutin-related functions such as viral entry. In the attachment and penetration assay, TDSWex showed antiviral activity with EC50s of 0.045 ± 0.026 and 0.012 ± 0.003 mg/mL, respectively. In addition, TDSWex blocked neuraminidase activity. We conclude that TDSWex has bimodal activities against both hemagglutinin and neuraminidase during viral replication.

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Section: Discussionmentioning

confidence: 99%

An extract from Taxodium distichum targets hemagglutinin- and neuraminidase-related activities of influenza virus in vitro

Hsieh

Chen

Lin

et al. 2016

Sci Rep

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“…EBN from Gua Madai contained 6.7 mg/g of Neu5Ac, which is higher than EBN collected from Teluk Intan which contained 3.2 mg/g of Neu5Ac (Haghani et al, 2017). SA residues could interact with the neuraminidase, and prevent this enzyme from cleaving the SA receptor present on the host cell surface hence halting the viral spread and release (Bianco et al, 2001;Haghani et al, 2016;Benton et al, 2017). Treatment with EBN for 24 h after the MDCK cells were inoculated with IAV for 1 h had the highest antiviral activity and percentage of protection against IAV when compared to EBN pre-treatment (MDCK cells treated with EBN for 1 h before IAV inoculation) and cotreatment (MDCK cells treated with EBN and IAV at the same time for 1 h) groups.…”

Section: Antiviral Immunomodulatory and Antimicrobial Actionsmentioning

confidence: 90%

Edible Bird’s Nest: Recent Updates and Industry Insights Based On Laboratory Findings

Chok

et al. 2021

Front. Pharmacol.

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Edible bird’s nest (EBN) is a traditional Chinese delicacy made of the saliva of swiftlets found in Southeast Asia. With increasing demands for EBN, quality control of EBN products is important for safe consumption. The processing steps are particularly important for efficient extraction of bioactive compounds. Geographical location, collection place, and harvesting season contribute to differences in nutritional contents in EBN. Concerns regarding presence of adulterant, chemical, and microbial contaminants in EBN as well as authentication and chemical composition measuring methods are discussed in this review. Recent discoveries of beneficial health functions of EBN in antimicrobial and antiviral actions, immunomodulation, cancer prevention and treatment, tissue regeneration, cardiometabolic maintenance, antioxidant action and neuroprotection are also reviewed. Our review provides an update on the recent research on EBN.

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“…Subsequently, the structures of the planar sialic acid transition state during the neuraminidase reaction became available. The analogous compounds of sialic acid’s transition state based on benzoic and shikimic acids, and subsequently the drug Oseltamivir [76,77,78,79], benefit from the increased affinity to neuraminidase compared to the native Neu5Ac structure [80,81]. Unfortunately, the family of compounds related to Zanamivir or Oseltamivir do not act against viruses that do not possess neuraminidase activity but instead engage undistorted sialic acids via a hemagglutinin (e.g., many non-enveloped viruses discussed in chapter 2 of this review).…”

Section: Sialic Acid-based Design Of Anti-viral Compoundsmentioning

confidence: 99%

The Symmetry of Viral Sialic Acid Binding Sites–Implications for Antiviral Strategies

Rustmeier

Strebl

Stehle

2019

Viruses

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Virus infections are initiated by the attachment of the viral particle to protein or carbohydrate receptors on the host cell. Sialic acid-bearing glycan structures are prominently displayed at the cell surface, and, consequently, these structures can function as receptors for a large number of diverse viruses. Structural biology research has helped to establish the molecular bases for many virus–sialic acid interactions. Due to the icosahedral 532 point group symmetry that underlies many viral capsids, the receptor binding sites are frequently arranged in a highly symmetric fashion and linked by five-fold, three-fold, or two-fold rotation axes. For the inhibition of viral attachment, one emerging strategy is based on developing multivalent sialic acid-based inhibitors that can simultaneously engage several of these binding sites, thus binding viral capsids with high avidity. In this review, we will evaluate the structures of non-enveloped virus capsid proteins bound to sialylated glycan receptors and discuss the potential of these structures for the development of potent antiviral attachment inhibitors.

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Synthesis of a carbocyclic sialic acid analogue for the inhibition of influenza virus neuraminidase

Cited by 27 publications

References 16 publications

An extract from Taxodium distichum targets hemagglutinin- and neuraminidase-related activities of influenza virus in vitro

An extract from Taxodium distichum targets hemagglutinin- and neuraminidase-related activities of influenza virus in vitro

Edible Bird’s Nest: Recent Updates and Industry Insights Based On Laboratory Findings

The Symmetry of Viral Sialic Acid Binding Sites–Implications for Antiviral Strategies

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