Novel β -Cyclodextrin-Based Heptavalent Glycyrrhetinic Acid Conjugates: Synthesis, Characterization, and Anti-Influenza Activity

In our continuing efforts toward the design of novel pentacyclic triterpene derivatives as potential anti-influenza virus entry inhibitors, a series of homogeneous heptavalent glycyrrhetinic acid derivatives based on -cyclodextrin scaffold were designed and synthesized by click chemistry. The struct...

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Published inFrontiers in chemistry Vol. 10; p. 836955
Main Authors Liang, Shuobin, Ma, Xinyuan, Li, Man, Yi, Yanliang, Gao, Qianqian, Zhang, Yongmin, Zhang, Lihe, Zhou, Demin, Xiao, Sulong
Format Journal Article
LanguageEnglish
Published Switzerland Frontiers Media 12.04.2022
Frontiers Media S.A
Subjects
Chemical Sciences
Chemistry
glycyrrhetinic acid
hemagglutinin
influenza virus
Life Sciences
Medicinal Chemistry
Microbiology and Parasitology
multivalency
Virology
β-cyclodextrin
influenza virus
glycyrrhetinic acid
β-cyclodextrin
hemagglutinin
multivalency
Glycyrrhetinic acid
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Summary:In our continuing efforts toward the design of novel pentacyclic triterpene derivatives as potential anti-influenza virus entry inhibitors, a series of homogeneous heptavalent glycyrrhetinic acid derivatives based on -cyclodextrin scaffold were designed and synthesized by click chemistry. The structure was unambiguously characterized by NMR, IR, and MALDI-TOF-MS measurements. Seven conjugates showed sufficient inhibitory activity against influenza virus infection based on the cytopathic effect reduction assay with IC values in the micromolar range. The interactions of conjugate , the most potent compound (IC = 2.86 M, CC > 100  M), with the influenza virus were investigated using the hemagglutination inhibition assay. Moreover, the surface plasmon resonance assay further confirmed that compound bound to the influenza HA protein specifically with a dissociation constant of 5.15 × 10  M. Our results suggest the promising role of -cyclodextrin as a scaffold for preparing a variety of multivalent compounds as influenza entry inhibitors.
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Edited by: Na’il Saleh, United Arab Emirates University, United Arab Emirates
This article was submitted to Supramolecular Chemistry, a section of the journal Frontiers in Chemistry
Apurba Lal Koner, Indian Institute of Science Education and Research, Bhopal, India
These authors have contributed equally to this work
Reviewed by: Dong-Sheng Guo, Nankai University, China
ISSN:2296-2646
2296-2646
DOI:10.3389/fchem.2022.836955