Neutralizing activity of Usnic acid and β-cyclodextrins complex against SARS-CoV-2 spike pseudovirus

References

• Araujo AA, de Melo MG, Rabelo TK, Nunes PS, Santos SL, Serafini MR, Santos MR, Quintans-Junior LJ, Gelain DP. 2015. Review of the biological properties and toxicity of usnic acid. Nat Prod Res. 29(23):2167–2180. doi:10.1080/14786419.2015.1007455.
   PubMed Web of Science ®Google Scholar
• Arima H, Motoyama K, Irie T. 2011. Recent findings on safety profiles of cyclodextrins, cyclodextrin conjugates, and polypseudorotaxanes. In Cyclodextrins in pharmaceutics, cosmetics, and biomedicine: current and future industrial applications, E.Bilensoy editor. p. 91–122. doi:10.1002/9780470926819.ch5.
   Google Scholar
• Calcott MJ, Ackerley DF, Knight A, Keyzers RA, Owen JG. 2018. Secondary metabolism in the lichen symbiosis. Chem Soc Rev. 47(5):1730–1760. doi:10.1039/c7cs00431a.
   PubMed Web of Science ®Google Scholar
• Cannella V, Altomare R, Chiaramonte G, Di Bella S, Mira F, Russotto L, Pisano P, Guercio A. 2019. Cytotoxicity evaluation of endodontic pins on L929 cell line. Biomed Res Int. 2019:3469525. doi:10.1155/2019/3469525.
   PubMed Web of Science ®Google Scholar
• Chen S, Zhang Z, Qing T, Ren Z, Yu D, Couch L, Ning B, Mei N, Shi L, Tolleson WH, et al. 2017. Activation of the Nrf2 signaling pathway in usnic acid- induced toxicity in HepG2 cells. Arch Toxicol. 91(3):1293–1307. doi:10.1007/s00204-016-1775-y.
   PubMed Web of Science ®Google Scholar
• Cutone A, Rosa L, Bonaccorsi di Patti MC, Iacovelli F, Conte MP, Ianiro G, Romeo A, Campione E, Bianchi L, Valenti P, et al. 2022. Lactoferrin binding to SARS-CoV-2 spike glycoprotein blocks pseudoviral entry and relieves iron protein dysregulation in several in vitro models. Pharmaceutics. 14(10):2111. doi:10.3390/pharmaceutics14102111.
   PubMed Web of Science ®Google Scholar
• Filimonov AS, Yarovaya OI, Zaykovskaya AV, Rudometova NB, Shcherbakov DN, Chirkova VY, Baev DS, Borisevich SS, Luzina OA, Pyankov OV, et al. 2022. (+)-Usnic acid and its derivatives as inhibitors of a wide spectrum of SARS-CoV-2 viruses. Viruses. 14(10):2154. doi:10.3390/v14102154.
   PubMed Web of Science ®Google Scholar
• Galla R, Ferrari S, Ruga S, Mantuano B, Rosso G, Tonello S, Rosa L, Valenti P, Uberti F. 2023. Effects of usnic acid to prevent infections by creating a protective barrier in an in vitro study. IJMS. 24(4):3695. doi:10.3390/ijms24043695.
   Google Scholar
• Guthappa R. 2020. Docking studies of usnic acid and sodium usnate on SARS cov-2 main protease and spike protein RBD. ChemRxiv. Cambridge: Cambridge Open Engage.
   Google Scholar
• Harrison AG, Lin T, Wang P. 2020. Mechanisms of SARS-CoV-2 transmission and pathogenesis. Trends Immunol. 41(12):1100–1115. doi:10.1016/j.it.2020.10.004.
   PubMed Web of Science ®Google Scholar
• Hu Y, Meng X, Zhang F, Xiang Y, Wang J. 2021. The in vitro antiviral activity of lactoferrin against common human coronaviruses and SARS-CoV-2 is mediated by targeting the heparan sulfate co-receptor. Emerg Microbes Infect. 10(1):317–330. doi:10.1080/22221751.2021.1888660.
   PubMed Web of Science ®Google Scholar
• Ingólfsdóttir K. 2002. Usnic acid. Phytochemistry. 61(7):729–736. doi:10.1016/s0031-9422(02)00383-7.
   PubMed Web of Science ®Google Scholar
• Jin J, Rao Y, Bian X, Zeng A, Yang G. 2013. Solubility of (+)-usnic acid in water, ethanol, acetone, ethyl acetate and n-hexane. J Solution Chem. 42(5):1018–1027. doi:10.1007/s10953-013-0010-1.
   Web of Science ®Google Scholar
• Kristmundsdóttir T, Jónsdóttir E, Ogmundsdóttir HM, Ingólfsdóttir K. 2005. Solubilization of poorly soluble lichen metabolites for biological testing on cell lines. Eur J Pharm Sci. 24(5):539–543. doi:10.1016/j.ejps.2005.01.011.
   PubMed Web of Science ®Google Scholar
• Lira MC, Siqueira-Moura MP, Rolim-Santos HM, Galetti FC, Simioni AR, Santos NP, Tabosa Do Egito ES, Silva CL, Tedesco AC, Santos-Magalhães NS. 2009. In vitro uptake and antimycobacterial activity of liposomal usnic acid formulation. J Liposome Res. 19(1):49–58. doi:10.1080/08982100802564628.
   PubMed Web of Science ®Google Scholar
• Luzina OA, Salakhutdinov NF. 2018. Usnic acid and its derivatives for pharmaceutical use: a patent review (2000-2017). Expert Opin Ther Pat. 28(6):477–491. doi:10.1080/13543776.2018.1472239.
   PubMed Web of Science ®Google Scholar
• Nikolić V, Stanković M, Nikolić L, Nikolić G, Ilić-Stojanović S, Popsavin M, Zlatković S, Kundaković T. 2013. Inclusion complexes with cyclodextrin and usnic acid. J Incl Phenom Macrocycl Chem. 76(1-2):173–182. doi:10.1007/s10847-012-0187-8.
   Web of Science ®Google Scholar
• Oh E, Wang W, Park KH, Park C, Cho Y, Lee J, Kang E, Kang H. 2022. (+)-Usnic acid and its salts, inhibitors of SARS-CoV-2, identified by using in silico methods and in vitro assay. Sci Rep. 12(1):13118. doi:10.1038/s41598-022-17506-3.
   PubMed Web of Science ®Google Scholar
• Perry NB, Benn MH, Brennan NJ, Burgess EJ, Ellis G, Galloway DJ, Lorimer SD, Tangney RS. 1999. Antimicrobial, antiviral and cytotoxic activity of New Zealand lichens. Lichenologist. 31(6):627–636. doi:10.1017/S002428299900081X.
   Google Scholar
• Rosa L, Cutone A, Conte MP, Campione E, Bianchi L, Valenti P. 2023. An overview on in vitro and in vivo antiviral activity of lactoferrin: its efficacy against SARS-CoV-2 infection. Biometals. 36(3):417–436. doi:10.1007/s10534-022-00427-z.
   PubMed Web of Science ®Google Scholar
• Santos NP, Nascimento SC, Silva JF, Pereira ECG, Silva NH, Honda NK, Santos-Magalhães NS. 2005. Usnic acid-loaded nanocapsules: an evaluation of cytotoxicity. J Drug Del Sci Tech. 15(5):355–361. doi:10.1016/S1773-2247(05)50065-0.
   Web of Science ®Google Scholar
• Scirpa P, Scambia G, Masciullo V, Battaglia F, Foti E, Lopez R, Villa P, Malecore M, Mancuso S. 1999. A zinc sulphate and usnic acid preparation used as post-surgical adjuvant therapy in genital lesion by human papillomavirus. Minerva Ginecol. 51(6):255–260. 260.
   PubMedGoogle Scholar
• Sokolov DN, Zarubaev VV, Shtro AA, Polovinka MP, Luzina OA, Komarova NI, Salakhutdinov NF, Kiselev OI. 2012. Anti-viral activity of (-)/(+) usnic acids and their derivatives against influenza virus A(H1N1) 2009. Bioorg Med Chem Lett. 22(23):7060–7064. doi:10.1016/j.bmcl.2012.09.084.
   PubMed Web of Science ®Google Scholar
• Wang Q, Zhang Y, Wu L, Niu S, Song C, Zhang Z, Lu G, Qiao C, Hu Y, Yuen K-Y, et al. 2020. Structural and functional basis of SARS-CoV-2 entry by using human ACE2. Cell. 181(4):894–904.e9. doi:10.1016/j.cell.2020.03.045.
   PubMed Web of Science ®Google Scholar
• Wang H, Xuan M, Huang C, Wang C. 2022. Advances in research on bioactivity, toxicity, metabolism, and pharmacokinetics of usnic acid in vitro and in vivo. Molecules. 27(21):7469. doi:10.3390/molecules27217469.
   PubMed Web of Science ®Google Scholar