TY - JOUR
T1 - The evaluation of in vitro antichagasic and anti-SARS-CoV-2 potential of inclusion complexes of β- and methyl-β-cyclodextrin with naphthoquinone
AU - Oliveira, Verônica da Silva
AU - Silva, Cláudia Cândida
AU - de Freitas Oliveira, Johny Wysllas
AU - da Silva, Marcelo de Sousa
AU - Ferreira, Patricia Garcia
AU - da Siva, Fernando de Carvalho
AU - Ferreira, Vitor Francisco
AU - Barbosa, Euzébio Guimarães
AU - Barbosa, Cecília Gomes
AU - Moraes, Carolina Borsoi
AU - Freitas-Junior, Lucio Holanda Gondim de
AU - Converti, Attilio
AU - Lima, Ádley Antonini Neves de
N1 - Funding Information:
The authors thank the Coordination for the Improvement of Higher Education Personnel (CAPES) and the National Council for Scientific and Technological Development (CNPq) for their financial support. This study was supported by the CAPES — number 88887.505029/2020–00 . Cecilia Gomes Barbosa receives a scholarship funded by CAPES — number 88887.643352/2021–00 .
Publisher Copyright:
© 2023 Elsevier B.V.
PY - 2023/3
Y1 - 2023/3
N2 - 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).
AB - 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).
KW - Anti-SARS-CoV-2
KW - Antichagasic activity
KW - Inclusion complexes
KW - Naphthoquinone
UR - http://www.scopus.com/inward/record.url?scp=85148381514&partnerID=8YFLogxK
U2 - 10.1016/j.jddst.2023.104229
DO - 10.1016/j.jddst.2023.104229
M3 - Article
C2 - 36776572
AN - SCOPUS:85148381514
SN - 1773-2247
VL - 81
JO - Journal of Drug Delivery Science and Technology
JF - Journal of Drug Delivery Science and Technology
M1 - 104229
ER -
