Structural Design, Synthesis and Antioxidant, Antileishmania, Anti-Inflammatory and Anticancer Activities of a Novel Quercetin Acetylated Derivative
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...
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oai:doaj.org-article:00138d6cee3c4b6e81565a22ed606e542021-11-25T18:28:29ZStructural Design, Synthesis and Antioxidant, Antileishmania, Anti-Inflammatory and Anticancer Activities of a Novel Quercetin Acetylated Derivative10.3390/molecules262269231420-3049https://doaj.org/article/00138d6cee3c4b6e81565a22ed606e542021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/22/6923https://doaj.org/toc/1420-3049Quercetin (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, <sup>1</sup>H and <sup>13</sup>C NMR spectra. The antioxidant potential was evaluated against the radical ABTS<sup>•+</sup>. 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 (<i>p</i> < 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<sub>50</sub> > 80 µM). Finally, the cytotoxic superiority of Q5 was verified (IC<sub>50</sub> = 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.Saul Vislei Simões da SilvaOrlando Maia BarbozaJéssica Teles SouzaÉrica Novaes SoaresCleonice Creusa dos SantosLuciano Vasconcellos PachecoIvanilson Pimenta SantosTatiana Barbosa dos Santos MagalhãesMilena Botelho Pereira SoaresElisalva Teixeira GuimarãesCássio Santana MeiraSilvia Lima CostaVictor Diógenes Amaral da SilvaLourenço Luís Botelho de SantanaAníbal de Freitas Santos JúniorMDPI AGarticlequercetinsynthesisquercetin pentaacetateantioxidantantileishmaniaanti-inflammatoryOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6923, p 6923 (2021) |
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quercetin synthesis quercetin pentaacetate antioxidant antileishmania anti-inflammatory Organic chemistry QD241-441 |
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quercetin synthesis quercetin pentaacetate antioxidant antileishmania anti-inflammatory Organic chemistry QD241-441 Saul Vislei Simões da Silva Orlando Maia Barboza Jéssica Teles Souza Érica Novaes Soares Cleonice Creusa dos Santos Luciano Vasconcellos Pacheco Ivanilson Pimenta Santos Tatiana Barbosa dos Santos Magalhães Milena Botelho Pereira Soares Elisalva Teixeira Guimarães Cássio Santana Meira Silvia Lima Costa Victor Diógenes Amaral da Silva Lourenço Luís Botelho de Santana Aníbal de Freitas Santos Júnior Structural Design, Synthesis and Antioxidant, Antileishmania, Anti-Inflammatory and Anticancer Activities of a Novel Quercetin Acetylated Derivative |
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, <sup>1</sup>H and <sup>13</sup>C NMR spectra. The antioxidant potential was evaluated against the radical ABTS<sup>•+</sup>. 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 (<i>p</i> < 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<sub>50</sub> > 80 µM). Finally, the cytotoxic superiority of Q5 was verified (IC<sub>50</sub> = 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. |
format |
article |
author |
Saul Vislei Simões da Silva Orlando Maia Barboza Jéssica Teles Souza Érica Novaes Soares Cleonice Creusa dos Santos Luciano Vasconcellos Pacheco Ivanilson Pimenta Santos Tatiana Barbosa dos Santos Magalhães Milena Botelho Pereira Soares Elisalva Teixeira Guimarães Cássio Santana Meira Silvia Lima Costa Victor Diógenes Amaral da Silva Lourenço Luís Botelho de Santana Aníbal de Freitas Santos Júnior |
author_facet |
Saul Vislei Simões da Silva Orlando Maia Barboza Jéssica Teles Souza Érica Novaes Soares Cleonice Creusa dos Santos Luciano Vasconcellos Pacheco Ivanilson Pimenta Santos Tatiana Barbosa dos Santos Magalhães Milena Botelho Pereira Soares Elisalva Teixeira Guimarães Cássio Santana Meira Silvia Lima Costa Victor Diógenes Amaral da Silva Lourenço Luís Botelho de Santana Aníbal de Freitas Santos Júnior |
author_sort |
Saul Vislei Simões da Silva |
title |
Structural Design, Synthesis and Antioxidant, Antileishmania, Anti-Inflammatory and Anticancer Activities of a Novel Quercetin Acetylated Derivative |
title_short |
Structural Design, Synthesis and Antioxidant, Antileishmania, Anti-Inflammatory and Anticancer Activities of a Novel Quercetin Acetylated Derivative |
title_full |
Structural Design, Synthesis and Antioxidant, Antileishmania, Anti-Inflammatory and Anticancer Activities of a Novel Quercetin Acetylated Derivative |
title_fullStr |
Structural Design, Synthesis and Antioxidant, Antileishmania, Anti-Inflammatory and Anticancer Activities of a Novel Quercetin Acetylated Derivative |
title_full_unstemmed |
Structural Design, Synthesis and Antioxidant, Antileishmania, Anti-Inflammatory and Anticancer Activities of a Novel Quercetin Acetylated Derivative |
title_sort |
structural design, synthesis and antioxidant, antileishmania, anti-inflammatory and anticancer activities of a novel quercetin acetylated derivative |
publisher |
MDPI AG |
publishDate |
2021 |
url |
https://doaj.org/article/00138d6cee3c4b6e81565a22ed606e54 |
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