Sialic Acid Derivative Synthesis and Inhibitory Activities against Human Parainfluenza Virus Type 1

Ikeda, Kiyoshi

doi:10.4052/tigg.23.14

Cited by 2 publications

(1 citation statement)

References 29 publications

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“…Recently, glycosidase inhibitors have gained considerable clinical relevance [18][19][20][21] and several glycomimetics such as zanamivir ® , miglustat ® , migalastat ® , voglibose ® , and acarbose ® reached the market. The selective hydrolysis of glycosidic bonds in carbohydrates and glycoconjugates is indeed involved in a plethora of key cellular processes in biological systems [22][23][24][25], and thus targeting glycosidases holds great potential for the treatment of many diseases such as type 2 diabetes [25][26][27], viral infection [21,[27][28][29][30][31], tumor metastasis [21,27,32,33], or medical diagnosis [34].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Glycosidase Inhibition Properties of Calix[8]arene-Based Iminosugar Click Clusters

et al. 2020

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A set of 6- to 24-valent clusters was constructed with terminal deoxynojirimycin (DNJ) inhibitory heads through C6 or C9 linkers by way of Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions between mono- or trivalent azido-armed iminosugars and calix[8]arene scaffolds differing in their valency and their rigidity but not in their size. The power of multivalency to upgrade the inhibition potency of the weak DNJ inhibitor (monovalent DNJ Ki being at 322 and 188 µM for C6 or C9 linkers, respectively) was evaluated on the model glycosidase Jack Bean α-mannosidase (JBα-man). Although for the clusters with the shorter C6 linker the rigidity of the scaffold was essential, these parameters had no influence for clusters with C9 chains: all of them showed rather good relative affinity enhancements per inhibitory epitopes between 70 and 160 highlighting the sound combination of the calix[8]arene core and the long alkyl arms. Preliminary docking studies were performed to get insights into the preferred binding modes.

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