Kaurenoic acid nanocarriers regulates cytokine production and inhibit breast cancer cell migration

Ferreira, Kézia Cristine Barbosa; Valle, Ana Beatriz Caribé dos Santos; Gualberto, Ana Cristina Moura; Aleixo, Davi Trombini; Silva, Lívia Mara; Santos, Milena Maciel; Costa, Danilo de Souza; Oliveira, Letícia Ludmilla; Gameiro, Jacy; Tavares, Guilherme Diniz; Filho, Ademar Alves da Silva; Corrêa, José Otávio do Amaral; Pittella, Frederico

doi:10.1016/j.jconrel.2022.10.048

Cited by 6 publications

(9 citation statements)

References 64 publications

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“…Consequently, compound 19 is consistent with the structure of the di-oxo derivative of atractyligenin amide 5. The other di-oxo amides (20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31)(32) obtained by the same oxidative treatment showed NMR data very similar to those observed for 19, allowing us to determine their structures and, therefore, to completely assign all the proton and carbon signals, as reported in the Section 3.…”

Section: Synthesis and Spectroscopical Characterizationsupporting

confidence: 53%

“…In order to evaluate the importance of the oxidation states of C-2 and C-15 in terms of biological activity, it was planned to transform the two hydroxyl groups into the corresponding ketones (Scheme 2). All NMR and mass spectra of di-oxo-atractyligenin amides (19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31)(32) are included in the Supplementary Materials (Figures S48-S89). Also for the case of oxidations, only the model characterization of the modified amide 5 is reported.…”

Section: Synthesis and Spectroscopical Characterizationmentioning

confidence: 99%

“…Both the di-hydroxy amides (5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18) and the related di-oxo amides (19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31)(32) obtained from the diterpene atractyligenin were tested on HCT116 colon cancer cells by MTT assays using a wide range concentration of all compounds (10-300 µM). Interestingly, although 1 used at high concentrations did not cause significant changes in colon cancer cell viability after 48 h of treatment, amide derivatives showed remarkable cytotoxic effects only at the highest doses used (200 and 300 µM) (Figure 2).…”

Section: Investigation Of the Cytotoxic Activity Of Compounds 1 And 5...mentioning

confidence: 99%

“…Structure-activity relationship studies have demonstrated that the double bond on C-16 is responsible for its genotoxicity [25]. Considering these aspects, it was also highlighted that this compound shows important cytotoxic effects on several cell lines, such as HeLa, A-549, HEp-2, PC-3, and MCF-7, acting in a dose-dependent manner [26], and many of its derivatives have shown antitumor activity against several cancer cell lines, like MCF-7 [27], 4T1 [28], and U87 [29], as well as other tumor lines [30].…”

Section: Introductionmentioning

confidence: 99%

“…NaHCO 3 (1:1 mixture, 8 mL) brine (8 mL), then dried with Na 2 SO 4 . Removal of the solvent under vacuum afforded the di-oxidates of atractyligenin amides (19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31)(32), which were purified by silica gel column chromatography. (19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31)(32) The amides (5-18) (1.0 equiv.)…”

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confidence: 99%

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Synthetic Derivatives of Natural ent-Kaurane Atractyligenin Disclose Anticancer Properties in Colon Cancer Cells, Triggering Apoptotic Cell Demise

Badalamenti,

Maggio,

Fontana

et al. 2024

IJMS

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The antitumor activity of different ent-kaurane diterpenes has been extensively studied. Several investigations have demonstrated the excellent antitumor activity of synthetic derivatives of the diterpene atractyligenin. In this research, a series of new synthetic amides and their 15,19-di-oxo analogues obtained from atractyligenin by modifying the C-2, C-15, and C-19 positions were designed in order to dispose of a set of derivatives with different substitutions at the amidic nitrogen. Using different concentrations of the obtained compounds (10–300 μM) a reduction in cell viability of HCT116 colon cancer cells was observed at 48 h of treatment. All the di-oxidized compounds were more effective than their alcoholic precursors. The di-oxidized compounds had already reduced the viability of two colon cancer cells (HCT116 and Caco-2) at 24 h when used at low doses (2.5–15 μM), while they turned out to be poorly effective in differentiated Caco-2 cells, a model of polarized enterocytes. The data reported here provide evidence that di-oxidized compounds induced apoptotic cell death, as demonstrated by the appearance of condensed and fragmented DNA in treated cells, as well as the activation of caspase-3 and fragmentation of its target PARP-1.

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Section: Synthesis and Spectroscopical Characterizationsupporting

confidence: 53%

Section: Synthesis and Spectroscopical Characterizationmentioning

confidence: 99%

Section: Investigation Of the Cytotoxic Activity Of Compounds 1 And 5...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Synthetic Derivatives of Natural ent-Kaurane Atractyligenin Disclose Anticancer Properties in Colon Cancer Cells, Triggering Apoptotic Cell Demise

Badalamenti,

Maggio,

Fontana

et al. 2024

IJMS

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Aromatase inhibition using Juniperus procera phytochemical constituents: molecular docking study

Al-Zahrani

2024

J.Umm Al-Qura Univ. Appll. Sci.

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The key step in the biosynthesis of estrogen is the enzyme activity of aromatase. Several malignancies, including breast cancer, have been linked to the initiation and progression of estrogen overexpression. Exemestane, Arimidex and Femara are the most common aromatase inhibitors used to treat hormone-dependent breast cancers. Drug resistance and side effects are commonly associated with these treatments. The purpose of this in silico study was to list the chemical compounds of Juniperus procera that have been published in scientific papers. The second goal was to evaluate the inhibitory activity of 124 phytochemicals of Juniperus procera compared to known aromatase inhibitors such as Exemestane, Arimidex and Femara. The 3D structure of aromatase (PDB id: 3s7s) employed for docking studies using AutoDock Tools as well as normal mode analysis studies utilizing the NMSim web server. Juniperolide, Kaurenoic acid and Isocupressic acid were identified as competitive aromatase inhibitors compared to FDA approved anti-cancer drugs, specifically Exemestane, Arimidex and Femara. The stability of the ligand–protein interface was studied to support the docking findings. To our knowledge, this is the first study that investigates the possible inhibition roles of some compounds of Juniperus procera on the aromatase enzyme.

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Uncovering the effect and mechanism of Jiawei Xiaoyao Wan in treating breast cancer complicated with depression based on network pharmacology and experimental analysis

Bai,

Niu,

Song

et al. 2024

Phytomedicine

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Kaurenoic acid nanocarriers regulates cytokine production and inhibit breast cancer cell migration

Cited by 6 publications

References 64 publications

Synthetic Derivatives of Natural ent-Kaurane Atractyligenin Disclose Anticancer Properties in Colon Cancer Cells, Triggering Apoptotic Cell Demise

Synthetic Derivatives of Natural ent-Kaurane Atractyligenin Disclose Anticancer Properties in Colon Cancer Cells, Triggering Apoptotic Cell Demise

Aromatase inhibition using Juniperus procera phytochemical constituents: molecular docking study

Uncovering the effect and mechanism of Jiawei Xiaoyao Wan in treating breast cancer complicated with depression based on network pharmacology and experimental analysis

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