Synthesis and Application of Hydroquinone with Heptadecatrienyl Side Chain for Inhibition of SARS-CoV-2
Journal
IFMBE Proceedings
Journal Volume
118 IFMBE
Start Page
243
End Page
254
ISSN
16800737
ISBN
[9783031863226]
Date Issued
2025-01-01
Author(s)
Wang, Mei-Hui
Lin, Kun-Liang
Yu, Hung-Wen
Kuo, Ching-Liang
Li, Wan-Chi
Lin, Shwu-Bin
DOI
10.1007/978-3-031-86323-3_29
Abstract
Background The hydroquinone with heptadecatrienyl side chain, referred to as HQ17(3), can inhibit topoisomerase 2, which is required for proliferation of tumor cells and virus. Because HQ17(3) is mainly extracted from Rhus succedanea, which is deficient in resources and its low extraction yield limited further development in pharmaceutical industry. Aim: In this study, we aim to develop a new chemical synthesis method for HQ17(3) to explore its potential in inhibiting SARS-CoV-2. Material and Method: HQ17(3) was synthesized starting from hydroquinone to create oxynonyl-acetoxyl benzene. This intermediate was then subjected to a Wittig reaction with heptadien-triphenylphosphine, producing heptadecatrienyl alkyl acetoxybenzene. The final solid pure heptadecatrienyl hydroquinone was obtained using sodium methoxide in methanol. Additionally, the final deacetylation step of HQ17(3) utilized sodium methoxide, replacing the previously used LiAlH4 deacetylation method. The antiviral activity of HQ17(3) was evaluated to have anti-SARS-CoV-2 potential by the viral plaque reduction assay. Results: The synthesized HQ17(3) presents as a non-oily, solid pure substance. The plaque reduction assay results showed that HQ17(3) can inhibit 60% of SARS-CoV-2 replication in VeroE6 cells at approximately 10 µM. Conclusion and Discussion: A high-purity, solid HQ17(3) product was successfully synthesized through deacetylation with sodium methoxide, demonstrating effective inhibition of SARS-CoV-2 proliferation. This non-oily, chemically synthesized solid substance overcomes the limitations of natural product scarcity and fulfills pharmaceutical requirements.
Publisher
Springer Science and Business Media Deutschland GmbH
Type
conference paper