Synthesis and in vitro Antiproliferative Activity of Flavone and 6‑Hydroxyflavone Oxime Ethers Derivatives

Díaz, John E.; Martinez, Diana C.; Lopez, Lina; Mendez, Gina M.; Vera, Ricardo; Loaiza, Alix E.

doi:10.21577/0103-5053.20170128

Cited by 7 publications

(5 citation statements)

References 7 publications

(8 reference statements)

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“…These contradictory results may be due to the dependence of cytotoxic potency on the tested cell lines or to the higher concentrations in their study because they used 200-400 µM, while in our research the maximum concentration was 50µM [114]. Our results agree with the results of Diaz et al (2017) on the impacts of their synthesized flavone oxime ethers against MDA-MB-231 with a value of IC50 (28.7 µM), which was close to the effects of our potent compound against the same cells [96].…”

Section: Preparation Of Naringenin Oximes and Oxime Etherssupporting

confidence: 91%

Investigation of antitumor properties of semi-synthetic flavonoid derivatives on gynecological cancer cell lines

Latif¹

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Section: Preparation Of Naringenin Oximes and Oxime Etherssupporting

confidence: 91%

Investigation of antitumor properties of semi-synthetic flavonoid derivatives on gynecological cancer cell lines

Latif¹

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“…6-Hydroxyflavanone has previously been shown to to exhibit no cytotoxic effects towards MRC-5 cells at 50 μM, as well as some of its derivatives, although these were oxime derivatives and not O-alkylated such as the ones presented herein [29]…”

Section: Resultsmentioning

confidence: 99%

Structural modification of naturally-occurring phenolics as a strategy for developing cytotoxic molecules towards cancer cells

Olim

Pereira

Fernandes

et al. 2023

Preprint

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Natural products belonging to different chemical classes have been established as a promising source of novel anticancer drugs. Several low molecular weight compounds from the classes of monoterpenes, phenylpropanoids and flavonoids were shown to possess anticancer activities in previous studies. In this work, over 20 semisynthetic derivatives of molecules belonging to these classes, namely thymol, eugenol and 6-hydroxyflavanone were synthesized and tested for their cytotoxicity against two human cancer cell lines, namely gastric adenocarcinoma (AGS cells) and human lung carcinoma (A549 cells). An initial screening based on viability assessment was performed in order to identify the most cytotoxic compounds at 100 μM. The results evidenced that two 6-hydroxyflavanone derivatives were the most cytotoxic among the compounds tested, being selected for further studies. Noteworthy, in a general way some of the derivatives synthesized displayed enhanced toxicity when compared with their natural counterparts. Moreover, LDH assay showed that the loss of cell viability was not accompanied by a loss of membrane integrity, thus ruling out a necrotic process. Morphological studies with AGS cells demonstrated chromatin condensation compatible with apoptosis, confirmed by the activation of caspase 3/7. Furthermore, a viability assay on non-cancer human embryonic lung fibroblast cell line (MRC-5) confirmed these two derivatives possess selective anticancer activity.

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“…6‐Hydroxyflavanone has previously been shown to exhibit no cytotoxic effects toward MRC‐5 cells at 50 µM, as well as some of its derivatives, although these were oxime derivatives and not O ‐alkylated such as the ones presented herein. [ 24 ]…”

Section: Resultsmentioning

confidence: 99%

Structural modification of naturally occurring phenolics as a strategy for developing cytotoxic molecules towards cancer cells

Olim,

Pereira,

Fernandes

et al. 2023

Archiv der Pharmazie

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Natural products belonging to different chemical classes have been established as a promising source of novel anticancer drugs. Several low‐molecular‐weight compounds from the classes of monoterpenes, phenylpropanoids, and flavonoids were shown to possess anticancer activities in previous studies. In this work, over 20 semisynthetic derivatives of molecules belonging to these classes, namely thymol, eugenol, and 6‐hydroxyflavanone were synthesized and tested for their cytotoxicity against two human cancer cell lines, namely AGS cells (gastric adenocarcinoma) and A549 cells (human lung carcinoma). An initial screening based on viability assessment was performed to identify the most cytotoxic compounds at 100 μM. The results evidenced that two 6‐hydroxyflavanone derivatives were the most cytotoxic among the compounds tested, being selected for further studies. These derivatives displayed enhanced toxicity when compared with their natural counterparts. Moreover, the lactate dehydrogenase (LDH) assay showed that the loss of cell viability was not accompanied by a loss of membrane integrity, thus ruling out a necrotic process. Morphological studies with AGS cells demonstrated chromatin condensation compatible with apoptosis, confirmed by the activation of caspase 3/7. Furthermore, a viability assay on a noncancer human embryonic lung fibroblast cell line (MRC‐5) confirmed that these two derivatives possess selective anticancer activity.

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Synthesis and in vitro Antiproliferative Activity of Flavone and 6‑Hydroxyflavone Oxime Ethers Derivatives

Cited by 7 publications

References 7 publications

Investigation of antitumor properties of semi-synthetic flavonoid derivatives on gynecological cancer cell lines

Investigation of antitumor properties of semi-synthetic flavonoid derivatives on gynecological cancer cell lines

Structural modification of naturally-occurring phenolics as a strategy for developing cytotoxic molecules towards cancer cells

Structural modification of naturally occurring phenolics as a strategy for developing cytotoxic molecules towards cancer cells

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