l-carvone decreases breast cancer cells adhesion, migration, and invasion by suppressing FAK activation

Lima, Lorena; Ganzella, Fernando Augusto de Oliveira; Cardoso, Gabriela Casani; Pires, Verônica dos Santos; Chequin, Andressa; Santos, Giulia Luiza; Braun-Prado, Karin; Galindo, Claudia; Braz, Odair; Molento, Marcelo Beltrão; Acco, Alexandra; Adami, Eliana Rezende; Costa, Érico T.; Franco, Célia Regina Cavichiolo; Klassen, Giseli; Ramos, Edneia Amancio de Souza

doi:10.1016/j.cbi.2023.110480

Cited by 7 publications

(3 citation statements)

References 49 publications

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“…The biological activity of members of this class is widely considered in the literature, where the multifaceted action mechanisms in the chemoprophylaxis of oncological diseases is described. In particular, the success of the clinical use of carvone-a cyclic saturated monoterpenoid-has been confirmed in the treatment of colorectal carcinoma [29], breast adenocarcinoma [30,31], stomach cancer [32], melanoma [33], neuroblastoma [34] and leukemia [35]. An improvement in the pathophysiological state was shown in rats with colon cancer [36] and bladder cancer [37] in the case of the use of a bicyclic monoterpenoid myrtenal.…”

Section: Introductionmentioning

confidence: 94%

Hydroxamic Acids Containing a Bicyclic Pinane Backbone as Epigenetic and Metabolic Regulators: Synergizing Agents to Overcome Cisplatin Resistance

Aleksandrova,

Munkuev,

Mozhaitsev

et al. 2023

Cancers

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Multidrug resistance is the dominant obstacle to effective chemotherapy for malignant neoplasms. It is well known that neoplastic cells use a wide range of adaptive mechanisms to form and maintain resistance against antitumor agents, which makes it urgent to identify promising therapies to solve this problem. Hydroxamic acids are biologically active compounds and in recent years have been actively considered to be potentially promising drugs of various pharmacological applications. In this paper, we synthesized a number of hydroxamic acids containing a p-substituted cinnamic acid core and bearing bicyclic pinane fragments, including derivatives of (−)-myrtenol, (+)-myrtenol and (−)-nopol, as a Cap-group. Among the synthesized compounds, the most promising hydroxamic acid was identified, containing a fragment of (−)-nopol in the Cap group 18c. This compound synergizes with cisplatin to increase its anticancer effect and overcomes cisplatin resistance, which may be associated with the inhibition of histone deacetylase 1 and glycolytic function. Taken together, our results demonstrate that the use of hydroxamic acids with a bicyclic pinane backbone can be considered to be an effective approach to the eradication of tumor cells and overcoming drug resistance in the treatment of malignant neoplasms.

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Section: Introductionmentioning

confidence: 94%

Hydroxamic Acids Containing a Bicyclic Pinane Backbone as Epigenetic and Metabolic Regulators: Synergizing Agents to Overcome Cisplatin Resistance

Aleksandrova,

Munkuev,

Mozhaitsev

et al. 2023

Cancers

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“…As a natural and sustainable forest product-bearing carbonyl, carvone has been found in the seed essential oils of Anethum graveolens [9], Mentha spicata [10,11], and Carum 2 of 12 carvi [12], and its diverse pharmacological activities have been reported [13], such as antifungal [14][15][16][17], antioxidant [18], anti-inflammatory [19], and anticancer activities [20,21]. Moreover, it was discovered that the original skeleton of carvone could serve as an available pharmacophore for bioactive compounds [22][23][24][25][26].…”

Section: Introductionmentioning

confidence: 99%

An Effective and Promising Strategy for Plant Protection: Synthesis of L-Carvone-Based Thiazolinone–Hydrazone/Nanochitosan Complexes with Antifungal Activity and Sustained Releasing Performance

Li,

Duan,

Lin

et al. 2024

IJMS

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The development of novel natural product-derived nano-pesticide systems with loading capacity and sustained releasing performance of bioactive compounds is considered an effective and promising plant protection strategy. In this work, 25 L-carvone-based thiazolinone–hydrazone compounds 4a~4y were synthesized by the multi-step modification of L-carvone and structurally confirmed. Compound 4h was found to show favorable and broad-spectrum antifungal activity through the in vitro antifungal activity evaluation of compounds 4a~4y against eight phytopathogenic fungi. Thus, it could serve as a leading compound for new antifungal agents in agriculture. Moreover, the L-carvone-based nanochitosan carrier 7 bearing the 1,3,4-thiadiazole-amide group was rationally designed for the loading and sustained releasing applications of compound 4h, synthesized, and characterized. It was proven that carrier 7 had good thermal stability below 200 °C, dispersed well in the aqueous phase to form numerous nanoparticles with a size of~20 nm, and exhibited an unconsolidated and multi-aperture micro-structure. Finally, L-carvone-based thiazolinone–hydrazone/nanochitosan complexes were fabricated and investigated for their sustained releasing behaviors. Among them, complex 7/4h-2 with a well-distributed, compact, and columnar micro-structure displayed the highest encapsulation efficiency and desirable sustained releasing property for compound 4h and thus showed great potential as an antifungal nano-pesticide for further studies.

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“…Carvone, a forest biomass resource containing the chemical structure of monocyclic monoterpenoid, is naturally found in a variety of plant essential oils [2], such as Carum carvi L. [3,4], Anethum graveolens L. [4], and Mentha spicata L., [5,6] and has been reported to show a wide range of pharmacological activities, including anti-oxidative [6,7], anti-manic[8], anti-in ammatory [9,10], antifungal [11,12], repellent [13], and anticancer [4,14,15] activities. Moreover, the molecular skeleton of carvone has been developed into an important building block for discovering leading compounds with anticancer activity [16][17][18][19].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antiproliferative activity, 3D-QSAR and molecular docking studies of novel L-carvone-derived pyrimidine-urea compounds

Meng

Zhang

Duan

et al. 2023

Preprint

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In order to explore novel antiproliferative compounds, twenty L-carvone-derived pyrimidine-urea compounds 4a – 4t were synthesized through the multi-step reaction of L-carvone, and structurally characterized by FT-IR, 1H-NMR, 13C-NMR, and HRMS. Besides, the in vitro antiproliferative activities of the target compounds against HepG2, Hela, and MCF-7 cells were evaluated by MTT assay. According to the results, the target compounds showed certain inhibitory activities against the tested cancer cell lines, and five compounds (4b, 4h, 4k, 4l, and 4t) exhibited better inhibition activities against Hela cell than the positive control (5-FU). Among them, compound 4b held significant antiproliferative activities against Hela and HepG2 cells, and thus deserved further study as a leading compound of new anticancer drugs. In addition, an effective and reasonable 3D-QSAR model was built by CoMFA method to analyze the relationship between the structures of the target compounds and their antiproliferative activities (expressed as pIC50) against Hela cell, and proven to have good predictive ability. Molecular docking was carried out to study the binding modes of compound 4b and Survivin which can enter the butt pocket like potential Survivin inhibitor GDP366, forming hydrogen bonding and hydrophobic interactions similar to each other.

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l-carvone decreases breast cancer cells adhesion, migration, and invasion by suppressing FAK activation

Cited by 7 publications

References 49 publications

Hydroxamic Acids Containing a Bicyclic Pinane Backbone as Epigenetic and Metabolic Regulators: Synergizing Agents to Overcome Cisplatin Resistance

Hydroxamic Acids Containing a Bicyclic Pinane Backbone as Epigenetic and Metabolic Regulators: Synergizing Agents to Overcome Cisplatin Resistance

An Effective and Promising Strategy for Plant Protection: Synthesis of L-Carvone-Based Thiazolinone–Hydrazone/Nanochitosan Complexes with Antifungal Activity and Sustained Releasing Performance

Synthesis, antiproliferative activity, 3D-QSAR and molecular docking studies of novel L-carvone-derived pyrimidine-urea compounds

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