The evaluation of in vitro antichagasic and anti-SARS-CoV-2 potential of inclusion complexes of β- and methyl-β-cyclodextrin with naphthoquinone

Verônica da Silva Oliveira, Cláudia Cândida Silva, Johny Wysllas de Freitas Oliveira, Marcelo de Sousa da Silva, Patricia Garcia Ferreira, Fernando de Carvalho da Siva, Vitor Francisco Ferreira, Euzébio Guimarães Barbosa, Cecília Gomes Barbosa, Carolina Borsoi Moraes, Lucio Holanda Gondim de Freitas-Junior, Attilio Converti, Ádley Antonini Neves de Lima

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Abstract

The compound 3a,10b-dihydro-1H-cyclopenta[b]naphtho[2,3-d]furan-5,10-dione (IVS320) is a naphthoquinone with antifungal and antichagasic potential, which however has low aqueous solubility. To increase bioavailability, inclusion complexes with β-cyclodextrin (βCD) and methyl-β-cyclodextrin (MβCD) were prepared by physical mixture (PM), kneading (KN) and rotary evaporation (RE), and their in vitro anti-SARS-CoV-2 and antichagasic potential was assessed. The formation of inclusion complexes led to a change in the physicochemical characteristics compared to IVS320 alone as well as a decrease in crystallinity degree that reached 74.44% for the IVS320-MβCD one prepared by RE. The IVS320 and IVS320-MβCD/RE system exhibited anti-SARS-CoV-2 activity, showing half maximal effective concentrations (EC50) of 0.47 and 1.22 μg/mL, respectively. Molecular docking simulation suggested IVS320 ability to interact with the SARS-CoV-2 viral protein. Finally, the highest antichagasic activity, expressed as percentage of Tripanosoma cruzi growth inhibition, was observed with IVS320-βCD/KN (70%) and IVS320-MβCD/PM (72%), while IVS320 alone exhibited only approximately 48% inhibition at the highest concentration (100 μg/mL).

Original languageEnglish
Article number104229
Number of pages12
JournalJournal of Drug Delivery Science and Technology
Volume81
DOIs
Publication statusPublished - Mar 2023

Keywords

  • Anti-SARS-CoV-2
  • Antichagasic activity
  • Inclusion complexes
  • Naphthoquinone

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