Betulin derivatives inhibit Alphavirus replication

L. Pohjala (Corresponding Author), Sami Alakurtti, Jari Yli-Kauhaluoma, T. Ahola, P. Tammela

Research output: Contribution to journalArticle in a proceedings journalScientificpeer-review

Abstract

Betulin is a widespread naturally occurring triterpenene, found in large quantities in birch bark. Despite the knowledge on betulin-derived compounds as anti-HIV agents, their wider antiviral spectrum remains poorly studied. In this study, a set of 68 betulin derivatives was screened against Semliki Forest virus (SFV), a member of Alphavirus genus and a commonly used model for replication of positive-stranded RNA viruses. The basic structure of betulin was moderately active against SFV (IC50 45 μM), but antiviral potency was enhanced particularly by certain cyclic ether or ester substituents, as demonstrated by 28-O-tetrahydropyranylbetulin and 3,28-betulinyl di(2-sulfobenzoate) (IC50 values 17 and 11 μM, respectively). Even though some derivatives raised also toxic responses in Huh-7 cells, therapeutic indices higher than 50 were obtained for many of the tested compounds. Due to their non-nucleoside structure and relatively low toxicity, betulin-derived compounds make a competitive contribution to the few inhibitors of these pathogens.
Original languageEnglish
Pages (from-to)S40
JournalEuropean Journal of Pharmaceutical Sciences
Volume34
Issue number1
DOIs
Publication statusPublished - 2008
MoE publication typeA4 Article in a conference publication
Event19th Helsinki Drug Research 2008 - Helsinki, Finland
Duration: 9 Jun 200811 Jun 2008

Fingerprint

Alphavirus
Semliki forest virus
Inhibitory Concentration 50
Antiviral Agents
Cyclic Ethers
Anti-HIV Agents
Betula
Poisons
RNA Viruses
Esters
betulin

Keywords

  • betulin
  • betulin derivatives
  • betulinic acid
  • cytotoxic
  • birch bark
  • antiviral spectrum
  • alphavirus

Cite this

Pohjala, L., Alakurtti, S., Yli-Kauhaluoma, J., Ahola, T., & Tammela, P. (2008). Betulin derivatives inhibit Alphavirus replication. European Journal of Pharmaceutical Sciences, 34(1), S40. https://doi.org/10.1016/j.ejps.2008.02.116
Pohjala, L. ; Alakurtti, Sami ; Yli-Kauhaluoma, Jari ; Ahola, T. ; Tammela, P. / Betulin derivatives inhibit Alphavirus replication. In: European Journal of Pharmaceutical Sciences. 2008 ; Vol. 34, No. 1. pp. S40.
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Pohjala, L, Alakurtti, S, Yli-Kauhaluoma, J, Ahola, T & Tammela, P 2008, 'Betulin derivatives inhibit Alphavirus replication', European Journal of Pharmaceutical Sciences, vol. 34, no. 1, pp. S40. https://doi.org/10.1016/j.ejps.2008.02.116

Betulin derivatives inhibit Alphavirus replication. / Pohjala, L. (Corresponding Author); Alakurtti, Sami; Yli-Kauhaluoma, Jari; Ahola, T.; Tammela, P.

In: European Journal of Pharmaceutical Sciences, Vol. 34, No. 1, 2008, p. S40.

Research output: Contribution to journalArticle in a proceedings journalScientificpeer-review

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