Syntheses and biological evaluations of carbosilane dendrimers uniformly functionalized with sialyl α(2→3) lactose moieties as inhibitors for human influenza viruses

Oka, Hiroyuki; Onaga, Tomotsune; Koyama, Tetsuo; Guo, Can; Suzuki, Yasuo; Esumi, Yasuaki; Hatano, Ken; Terunuma, Daiyo; Matsuoka, Koji

doi:10.1016/j.bmc.2009.06.035

Cited by 44 publications

(23 citation statements)

References 36 publications

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“…In one clinical trial the function of carbosilane dendrimers as a hemagglutinin-inhibitor against human influenza viruses was investigated (Oka et al, 2008, 2009). In its actual research agenda the World Health Organization (WHO) called up to optimize the effectiveness of current and novel antiviral treatments through development of new formulations, delivery routes, or novel defense mechanisms including natural products.…”

Section: Introductionmentioning

confidence: 99%

Antiviral activity of Ladania067, an extract from wild black currant leaves against influenza A virus in vitro and in vivo

et al. 2014

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Influenza, a respiratory disease caused by influenza viruses, still represents a major threat to humans and several animal species. Besides vaccination, only two classes of drugs are available for antiviral treatment against this pathogen. Thus, there is a strong need for new effective antivirals against influenza viruses. Here, we tested Ladania067, an extract from the leaves of the wild black currant (Ribes nigrum folium) for potential antiviral activity against influenza A virus in vitro and in vivo. In the range of 0–1 mg/ml the extract showed no cytotoxic effect on three cell lines and a CC50 of 0.5 ± 0.3 mg/ml, on peripheral blood mononuclear cells. Furthermore, the extract did not influence the proliferative status of human lymphocytes. In contrast, Ladania067 was highly effective (EC50 value: 49.3 ± 1.1 ng/ml) against the human pandemic influenza virus strain A/Regensburg/D6/09 (H1N1). The extract exhibited an antiviral effect when the virus was pre-incubated prior to infection or when added directly after infection. No antiviral effect was found when infected cells were treated 2, 4, or 8 h after infection, indicating that Ladania067 blocks a very early step in the virus infection cycle. In the mouse infection model we were able to demonstrate that an intranasal application of 500 μg Ladania067 inhibits progeny virus titers in the lung up to 85% after 24 h. We conclude that the extract from the leaves of the wild black currant may be a promising source for the identification of new molecules with antiviral functions against influenza virus.

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Section: Introductionmentioning

confidence: 99%

Antiviral activity of Ladania067, an extract from wild black currant leaves against influenza A virus in vitro and in vivo

et al. 2014

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“…Matsuoka and co‐workers constructed a library of carbosilane‐based synthetic dendrimer scaffolds to decorate Sia ligands . They employed different types of linker between the dendron scaffold and the Sia moiety to study the structure–activity relationships (Figure ).…”

Section: Sialo‐dendrimersmentioning

confidence: 99%

“…Matsuoka and co-workers constructedalibrary of carbosilane-based synthetic dendrimers caffolds to decorate Sia ligands. [49][50][51][52] They employed different types of linker between the dendron scaffold and the Sia moiety to study the structure-activity relationships( Figure 6). As ialidase-inhibition assay showedt hat the ether-and amide-linkers were more active than an aliphatic linker.M oreover,t he sialyl a(2-3) lactose moietyd isplayed strong antiviral activity.…”

Section: Sialo-dendrimersmentioning

confidence: 99%

Multivalent Sialosides: A Tool to Explore the Role of Sialic Acids in Biological Processes

Chaudhary

Toraskar

Yadav

et al. 2019

Chemistry An Asian Journal

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Sialic acids (Sias) are fascinating nine‐carbon monosaccharides that are primarily found on the terminus of the oligosaccharide chains of glycoproteins and glycolipids on cell surfaces. These Sias undergo a variety of structural modifications at their hydroxy and amine positions, thereby resulting in structural diversity and, hence, coordinating a variety of biological processes. However, deciphering the structural functions of such interactions is highly challenging, because the monovalent binding of Sias is extremely weak. Over the last decade, several multivalent Sia ligands have been synthesized to modulate their binding affinity with proteins/lectins. In this Minireview, we highlight recent developments in the synthesis of multivalent Sia probes and their potential applications. We will discuss four key multivalent families, that is, polymers, dendrimers, liposomes, and nanoparticles, and will emphasize the major parameters that are essential for the specific interactions of these molecules with proteins in biological systems.

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“…In this section, we report a synthetic assembly of sialyl Our synthetic target compounds having unique shapes, generations, and different numbers of saccharide residues are shown in Fig. (3) [15,17]. A monomeric compound 6 having a 4-pentenyl moiety as the aglycon was quantitatively prepared from a known compound 13 [13] by a combination of transesterification and saponification to remove all protections (Scheme 2).…”

Section: Use Of Sialyl Lactose As a Receptor For Hemagglutinin Of Infmentioning

confidence: 99%

“…We call a series of carbosilanes having carbohydrate moieties "Glyco-silicon Functional Materials". In this review, we describe results of synthetic studies on carbosilane compounds uniformly functionalized with sialyl carbohydrate moieties through covalent bonds and biological evaluations as inhibitors for influenza viruses [13][14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Glyco-silicon Functional Materials as Anti-influenza Virus Agents

Matsuoka¹

2012

TOGLYJ

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This review shows introduction of glycoclusters using carbosilanes as core scaffolds, preparations of glycoclusters and their excellent properties as well as functions. Since a dendrimer has unique advantages such as single molecular weight, regularity of structure and easy control of shape and size, dendrimers are utilized in various research areas. Results of syntheses and biological evaluations of the carbosilane dendrimers having carbohydrate moieties for influenza viruses are presented.

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Syntheses and biological evaluations of carbosilane dendrimers uniformly functionalized with sialyl α(2→3) lactose moieties as inhibitors for human influenza viruses

Cited by 44 publications

References 36 publications

Antiviral activity of Ladania067, an extract from wild black currant leaves against influenza A virus in vitro and in vivo

Antiviral activity of Ladania067, an extract from wild black currant leaves against influenza A virus in vitro and in vivo

Multivalent Sialosides: A Tool to Explore the Role of Sialic Acids in Biological Processes

Glyco-silicon Functional Materials as Anti-influenza Virus Agents

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