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Antiviral potency of lupane and oleanane alkynyl-derivatives against human cytomegalovirus and papillomavirus

The Journal of Antibiotics volume 77, pages 50–56 (2024)Cite this article

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Abstract

A library of 18 structurally diverse semisynthetic lupane, oleanane, and ursane types triterpenoids, including C19- or C28-(1,2,3-triazolyl)- and aminomethylated derivatives obtained by the «click» reaction with various aromatic and sugar azides or by Mannich reaction with secondary amines, were tested for antiviral activity against HCMV, HSV-1, and HPV-11 types. C28-Triazolyl-derivative with a benzyl substituent of 2,3-indolo-oleanolic acid was the most active against the HCMV virus with EC50 < 0.05 (SI > 81). Lupane 3,28-diacetoxy-triazolyl derivatives with phenyl- and fluorophenyl-fragments possess the highest activity among all screened compounds toward HPV-11 type virus with EC50 values of 2.97 µM and 1.20 μM, SI90 values of 28 and >125, respectively. One can see that modification of triterpenic alkynes to Mannich bases was more efficient in increasing an activity against HSV-1 than their conversion to triazoles.

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Acknowledgements

This work was supported by the Federal program No. 1021062311392-9-1.4.1. The study of antiviral activity was funded in whole or in part with Federal funds from the National Institutes of Allergy and Infectious Diseases, National Institutes of Health, Department of Health and Human Services, under contract HHSN272201100016I (MNP).

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  1. Ufa Institute of Chemistry of the Ufa Federal Research Centre of the Russian Academy of Sciences, 71 Prospect Oktyabrya, 450054, Ufa, Russian Federation

    Elmira F. Khusnutdinova, Anastasiya V. Petrova & Oxana B. Kazakova

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  1. Elmira F. Khusnutdinova
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Khusnutdinova, E.F., Petrova, A.V. & Kazakova, O.B. Antiviral potency of lupane and oleanane alkynyl-derivatives against human cytomegalovirus and papillomavirus. J Antibiot 77, 50–56 (2024). https://doi.org/10.1038/s41429-023-00672-5

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