Multivalent neuraminidase hydrolysis resistant triazole-sialoside protein conjugates as influenza-adsorbents

Meng, Xin; Yang, Mei-Bing; Li, Yang; Li, Xiaobin; Jia, Tianwei; He, Hao-Jie; Yu, Qun; Guo, Na; He, Yan; Yu, Peng; Yang, Yang

doi:10.1016/j.cclet.2017.10.032

Cited by 23 publications

(17 citation statements)

References 42 publications

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“…Mass analysis of BF and BSA revealed that on average one FITC was conjugated to one BSA molecule (Table ). Coupling of mannosyl moiety to BF was carried out by the squaric acid diethyl esters method as described previously. − Briefly, fully protected mannosyl azide 1 was synthesized in good yield using trichloroacetimidate method. , After deacylation with NaOCH 3 in CH 3 OH and hydrogenation with Pd(OH) 2 /C under 1 atm of hydrogen gas, the amine 2 was reacted with one of squaric acid diethyl esters in potassium phosphate buffer (pH 7.0) to give 3 (Scheme ). The ester group of 3 was conjugated to the amines present on the side chains of lysine in borate buffer (pH 9.0) to obtain the fluorescent neomannosyl protein BFM .…”

Section: Resultsmentioning

confidence: 99%

Fluorescent Neomannosyl Bovine Serum Albumin as Efficient Probe for Mannose Receptor Imaging and MCF-7 Cancer Cell Targeting

Yang

Jia

et al. 2018

ACS Appl. Nano Mater.

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Robust carbohydrate conjugated fluorescent bovine serum albumin (BSA) as useful tool to study carbohydrate− receptor interactions and in vivo targeting is reported. Amine terminated α-mannoside was attached to fluorescein labeled BSA via diethyl squarate strategy. The surface functionalization and lectin binding specific to fluorescent neomannosyl glycoprotein were confirmed using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS), surface plasmon resonance (SPR), and microarray imaging. The glycoconjugate was further used to image concanavalin A (ConA), pili of E. coli K12, and lysosomes in MCF-7 cancerous cells successfully, suggesting that this neomannosyl glycoprotein can be used as suitable probe to elucidate carbohydrate−protein interactions, image cancers, and target drug specifically toward tumors.

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Section: Resultsmentioning

confidence: 99%

Fluorescent Neomannosyl Bovine Serum Albumin as Efficient Probe for Mannose Receptor Imaging and MCF-7 Cancer Cell Targeting

Yang

Jia

et al. 2018

ACS Appl. Nano Mater.

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“…Yan and co-workers synthesized a series of divalent oseltamivir 306 – 313 and guanidino oseltamivir 314 – 321 derivatives with esterification on the carboxyl acid group as powerful inhibitors of influenza virus neuraminidase. In this synthesis, oseltamivir 306 – 313 were synthesized by click cycloaddition reaction of the azide moiety 297 – 304 102 103 104 105 106 with propargylated ethylene glycol 305 in the presence of CuSO 4 ·5H 2 O, sodium ascorbate, THF/H 2 O, followed by the deprotection of the Boc group with trifluoroacetic acid (TFA); guanidino oseltamivir derivatives 314 – 321 were synthesized by the reaction of oseltamivir 306 – 313 with MeSC(=NBoc)NHBoc in the presence of HgCl 2 , Et 3 N, CH 2 Cl 2 at room temperature (Scheme 32 ). 107 108…”

Section: Cuaac Click Chemistry Mediated Synthesis Of Triazole-based G...mentioning

confidence: 99%

Recent Advances in the Synthesis of Bioactive Glycohybrids via Click-Chemistry

Singh

Tyagi

Mishra

et al. 2023

SynOpen

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Carbohydrates, traditionally known for their energy-providing role, have gained significant attention in drug discovery due to their diverse bioactivities and stereodiversity. However, pure carbohydrate molecules often exhibit limited bioactivity and suboptimal chemical and physical characteristics. To address these challenges, functional groups with bioactive scaffolds have been incorporated into carbohydrate to enhance their bioactivity and improve their overall properties. Among the various synthetic methods available, click chemistry has emerged as a powerful tool for the synthesis of carbohydrate-containing bioactive scaffolds, known as glycohybrids. Click chemistry offers several advantages, including high chemo- and regioselectivity, mild reaction conditions, easy purification and compatibility with multiple functional groups. In the present review, we have emphasized the recent advances and most pertinent research on the development of 1,2,3-triazole-containing glycohybrids using click reaction, their biological evaluations and the structure-activity relationship during 2017-2023. These newly synthesised glycohybrids could potentially be developed as new chemical entities (NCE) in pharmaceutical chemistry and may encourage the use of carbohydrates in drug discovery processes. 1 Introduction 2 CuAAC click chemistry mediated synthesis of triazole based glycohybrids and their biological activities 3 Conclusions and perspective

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“…α-O-Linkages are cleaved by NA. This NA-catalyzed hydrolysis is a common problem in glycochemistry and can be circumvented by replacing the susceptible O-α-linkage with a noncleavable C-, , , S-, , or N-α-linkage. − Synthetic approaches to such modifications of SA have been well reviewed elsewhere. , These substitutions produce stability against NA while maintaining the correct conformation for interaction with HA. Other more sterically bulky linkages have also been synthesized (e.g., triazoles , ), but these have not been extensively investigated in the context of anti-influenza polymers.…”

Section: Influenzamentioning

confidence: 99%

Antiviral Polymers: Past Approaches and Future Possibilities

2020

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Treating a viral disease is no simple feat. Drug resistance, latent reservoirs in the body, emerging novel viruses, and a frequent lack of specific treatments all complicate antiviral therapy. For decades, antiviral polymers have been studied for a range of infectious diseases. The field has emerged, expanded, and adapted over the past 70 years, producing unique classes of materials that hold promise for overcoming these obstacles. Antiviral polymers can directly inhibit viral replication and infection, usually by binding to the virus and preventing it from invading a host cell. They can also serve as microbicides or antiviral drug-delivery vehicles. This Perspective outlines the significant advances and challenges in the field. We discuss polymers with activity against viruses with limited treatment options (hepatitis C), ubiquitous presence (influenza, norovirus), or long-term complications (HIV). We also explore insights into different mechanisms of action, and we offer ideas on how the field of antiviral polymers might advance in the future.

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Multivalent neuraminidase hydrolysis resistant triazole-sialoside protein conjugates as influenza-adsorbents

Cited by 23 publications

References 42 publications

Fluorescent Neomannosyl Bovine Serum Albumin as Efficient Probe for Mannose Receptor Imaging and MCF-7 Cancer Cell Targeting

Fluorescent Neomannosyl Bovine Serum Albumin as Efficient Probe for Mannose Receptor Imaging and MCF-7 Cancer Cell Targeting

Recent Advances in the Synthesis of Bioactive Glycohybrids via Click-Chemistry

Antiviral Polymers: Past Approaches and Future Possibilities

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