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Structural Design, Synthesis and Antioxidant, Antileishmania, Anti-Inflammatory and Anticancer Activities of a Novel Quercetin Acetylated Derivative
| Content Provider | MDPI |
|---|---|
| Author | Tatiana, Barbosa dos Santos Magalhães Elisalva, Teixeira Guimarães An, íbal De Freitas Santos Júnior Silva, Saul Vislei Simões da Barboza, Orlando Maia Souza, Jéssica Teles Soares, Érica Novaes Santos, Cleonice Creusa dos Pacheco, Luciano Vasconcellos Santos, Ivanilson Pimenta Soares, Milena Botelho Pereira Meira, Cássio Santana Costa, Silvia Lima Silva, Victor Diógenes Amaral da de Santana, Lourenço Luís Botelho |
| Copyright Year | 2021 |
| Description | Quercetin (Q) is a bioflavonoid with biological potential; however, poor solubility in water, extensive enzymatic metabolism and a reduced bioavailability limit its biopharmacological use. The aim of this study was to perform structural modification in Q by acetylation, thus, obtaining the quercetin pentaacetate (Q5) analogue, in order to investigate the biological potentials (antioxidant, antileishmania, anti-inflammatory and cytotoxicity activities) in cell cultures. Q5 was characterized by FTIR,$ ^{1}$H and$ ^{13}$C NMR spectra. The antioxidant potential was evaluated against the radical $ABTS^{•+}$. The anti-inflammatory potential was evaluated by measuring the pro-inflammatory cytokine tumor necrosis factor (TNF) and the production of nitric oxide (NO) in peritoneal macrophages from BALB/c mice. Cytotoxicity tests were performed using the AlamarBlue method in cancer cells HepG2 (human hepatocarcinoma), HL-60 (promyelocytic leukemia) and MCR-5 (healthy human lung fibroblasts) as well as the MTT method for C6 cell cultures (rat glioma). Q and Q5 showed antioxidant activity of 29% and 18%, respectively, which is justified by the replacement of hydroxyls by acetyl groups. Q and Q5 showed concentration-dependent reductions in NO and TNF production (p < 0.05); Q and Q5 showed higher activity at concentrations > 40µM when compared to dexamethasone (20 µM). For the HL-60 lineage, Q5 demonstrated selectivity, inducing death in cancer cells, when compared to the healthy cell line MRC-5 $(IC_{50}$ > 80 µM). Finally, the cytotoxic superiority of Q5 was verified $(IC_{50}$ = 11 µM), which, at 50 µM for 24 h, induced changes in the morphology of C6 glioma cells characterized by a round body shape (not yet reported in the literature). The analogue Q5 had potential biological effects and may be promising for further investigations against other cell cultures, particularly neural ones. |
| Starting Page | 6923 |
| e-ISSN | 14203049 |
| DOI | 10.3390/molecules26226923 |
| Journal | Molecules |
| Issue Number | 22 |
| Volume Number | 26 |
| Language | English |
| Publisher | MDPI |
| Publisher Date | 2021-11-17 |
| Access Restriction | Open |
| Subject Keyword | Molecules Integrative and Complementary Medicine Quercetin Synthesis Quercetin Pentaacetate Antioxidant Antileishmania Anti-inflammatory Cytotoxicity Activity |
| Content Type | Text |
| Resource Type | Article |
