Synthesis and in vitro anticancer activity of new 2-thioxo-oxazolidin-4-one derivatives

Campos, Júlia Furtado; Pereira, Michelly Cristiny; Sena, Wanessa Layssa Batista de; Martins, Caio; Oliveira, Jamerson Ferreira de; Amorim, Cézar Augusto da Cruz; Rêgo, Moacyr Jesus Barreto de Melo; Pitta, Marina Galdino da Rocha; Lima, Maria do Carmo Alves de; Pitta, Ivan da Rocha

doi:10.1016/j.pharep.2017.03.005

Cited by 10 publications

(7 citation statements)

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“…Scientific literature data reported that different oxazolidin-2-one derivatives could inhibit cell proliferation and promote apoptosis in a variety of cancer cell lines [18,23,24]. On this basis, we explored OI ability to induce apoptosis in MCF-7 and HeLa cells.…”

Section: Discussionmentioning

confidence: 99%

“…Since several reports evidenced that oxazolidinones were able to induce apoptosis [18,23,24], we next tested whether also OI exposure could induce cell death by triggering apoptosis, in both our tested cell lines. The impact of this oxazolidin-2-one derivative on apoptosis was assessed by using two different approaches.…”

Section: Oi Triggers Apoptotic Cell Death In Mcf-7 and Hela Cellsmentioning

confidence: 99%

“…Moreover, further literature data indicate that different oxazolidinone derivatives are endowed with promising antineoplastic activity, in particular by acting as partial agonists of peroxisome proliferator-activated receptor-gamma (PPAR-γ) [22]. Other oxazolidinones, derived from linezolid 3, inhibit cell proliferation inducing apoptosis by caspase-3 and -9 activation in DU145 prostate cancer cells [18], while different 2-thioxo-oxazolidin-4-one derivatives exhibited anticancer activity on hematopoietic cancer cells, and significantly increased the expression of genes involved in inflammation and apoptosis in acute leukemia cells [23]. Very recently, dehydroabietic acid oxazolidinone hybrids have shown to exert a promising antiproliferative activity on several human cancer cell lines, and a particular compound is able to induce apoptosis by causing an arrest of the cell cycle in the G1 phase [24].…”

Section: Introductionmentioning

confidence: 99%

“…Very recently, dehydroabietic acid oxazolidinone hybrids have shown to exert a promising antiproliferative activity on several human cancer cell lines, and a particular compound is able to induce apoptosis by causing an arrest of the cell cycle in the G1 phase [24]. Thus, development and evaluation of new oxazolidinones as possible anticancer agents is a very interesting ongoing research topic [23,25,26].…”

Section: Introductionmentioning

confidence: 99%

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5-(Carbamoylmethylene)-oxazolidin-2-ones as a Promising Class of Heterocycles Inducing Apoptosis Triggered by Increased ROS Levels and Mitochondrial Dysfunction in Breast and Cervical Cancer

et al. 2020

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Oxazolidinones are antibiotics that inhibit protein synthesis by binding the 50S ribosomal subunit. Recently, numerous worldwide researches focused on their properties and possible involvement in cancer therapy have been conducted. Here, we evaluated in vitro the antiproliferative activity of some 5-(carbamoylmethylene)-oxazolidin-2-ones on MCF-7 and HeLa cells. The tested compounds displayed a wide range of cytotoxicity on these cancer cell lines, measured by MTT assay, exhibiting no cytotoxicity on non-tumorigenic MCF-10A cells. Among the nine tested derivatives, four displayed a good anticancer potential. Remarkably, OI compound showed IC50 values of 17.66 and 31.10 µM for MCF-7 and HeLa cancer cells, respectively. Furthermore, we assessed OI effect on the cell cycle by FACS analysis, highlighting a G1 phase arrest after 72 h, supported by a low expression level of Cyclin D1 protein. Moreover, mitochondrial membrane potential was reduced after OI treatment driven by high levels of ROS. These findings demonstrate that OI treatment can inhibit MCF-7 and HeLa cell proliferation and induce apoptosis by caspase-9 activation and cytochrome c release in the cytosol. Hence, 5-(carbamoylmethylene)-oxazolidin-2-ones have a promising anticancer activity, in particular, OI derivative could represent a good candidate for in vivo further studies and potential clinical use.

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Section: Discussionmentioning

confidence: 99%

Section: Oi Triggers Apoptotic Cell Death In Mcf-7 and Hela Cellsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

5-(Carbamoylmethylene)-oxazolidin-2-ones as a Promising Class of Heterocycles Inducing Apoptosis Triggered by Increased ROS Levels and Mitochondrial Dysfunction in Breast and Cervical Cancer

et al. 2020

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“…Cells were reincubated (3 h), the blue formazan precipitate was dissolved in 20% SDS, SigmaAldrich) and its absorbance measured at 570 nm, using a plate reader (EL808; BIOTEK). 27…”

Section: Human Cell Culture Assaymentioning

confidence: 99%

Antioxidant Capacity and Cytotoxicity of the Aqueous Extract of Myrcia guianensis (Aubl.) DC

Bernardes¹,

Sarrazin²,

Santos³

et al. 2018

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Myrtaceae Juss. Comprises 132 genera and 5671 species of trees and shrubs, which are distributed mainly in tropical and subtropical regions of the world, parti cularly South America, Australia and Tropical Asia. 1 It is one of the most prominent families in Brazil, represented by 23 genera and 1034 species, with occurrence in all regions of the country 23 Myrcia De Candolle is one of the largest genera in the Americas, with more than 300 species distributed from Mexico to Southern Brazil, occurring in its different biomes, especially in savannas and secondary forests. 4 Myrcia guianensis (Aubl.) DC. has an extensive synonymy with species and varieties of Aulomyrcia, Eugenia, Myrcia and Myrtus. 5 It is a mediumsized shrub widely distributed in the Brazilian Amazon and included in a group of species of Myrcia, popularly known as "Pedraumecaá" or "Insulin plant". Some studies have demonstrated the widespread use of Myrcia species as hypoglycemic agents, such as M. multiflora, 67 M. bella 8 and M. splendens and M. palustris. 910 Also, the macerated leaves of M. guianensis have been used to neutralize various snake venoms effects. 11 The hydroalcoholic leaf extract of M. guianensis was analized by HPLC PDAESI/MS, showing the presence of gallic, caffeic and quinic acids, in addition to other glycosylated Antioxidant Capacity and Cytotoxicity of the Aqueous Extract of Myrcia guianensis (Aubl.) DC ABSTRACT Introduction: Ethnobotanical studies report that Myrcia guianensis (Myrtaceae), belonging to a group of plants known as pedrá-ume-caá or insulin plant, is used as a tea to treat various diseases, including diabetes, a metabolic disorder that leads to the constant production of free radicals. The objective of this work was to determine the antioxidant capacity and the cytotoxicity of the AEMg. Methods: The content of phenolic compounds in AEMg was determined by colorimetric assays. In vitro tests of the antioxidant capacity of AEMg, in the sequestration of DPPH radicals, in β-carotene bleaching, in the FRAP, as well as in human fibroblast cells of the MRC-5 lineage, were performed. The cytotoxic activity of AEMg was evaluated in assays with eukaryotic cells from yeast Saccharomyces cerevisiae and in PBMC. Results: The results showed that the AEMg is rich in phenolic compounds, presenting high antioxidant potential in all the tests carried out, including in human fibroblast cells of the MRC-5 lineage, besides not being toxic to eukaryotic cells. Conclusion: The AEMg, rich in antioxidant compounds and no toxicity, can be used as source of natural antioxidant in the treatment of metabolic diseases to combat free radicals.

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Valorization of CO₂ into N‐alkyl Oxazolidin‐2‐ones Promoted by Metal‐Free Porphyrin/TBACl System: Experimental and Computational Studies

et al. 2021

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The cycloaddition of CO 2 to N-alkyl aziridines was efficiently promoted by the convenient TPPH 2 /TBACl binary catalytic system. The metal-free procedure was effective for the synthesis of differently substituted N-alkyl oxazolidin-2-ones in yields up to 100 % and excellent regioselectivities (up to 99 %). The mechanism of the reaction was proposed based on a DFT study which indicated the formation of an adduct between TPPH 2 and TBACl as the effective catalytic active species.

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Synthesis and in vitro anticancer activity of new 2-thioxo-oxazolidin-4-one derivatives

Cited by 10 publications

References 48 publications

5-(Carbamoylmethylene)-oxazolidin-2-ones as a Promising Class of Heterocycles Inducing Apoptosis Triggered by Increased ROS Levels and Mitochondrial Dysfunction in Breast and Cervical Cancer

5-(Carbamoylmethylene)-oxazolidin-2-ones as a Promising Class of Heterocycles Inducing Apoptosis Triggered by Increased ROS Levels and Mitochondrial Dysfunction in Breast and Cervical Cancer

Antioxidant Capacity and Cytotoxicity of the Aqueous Extract of Myrcia guianensis (Aubl.) DC

Valorization of CO₂ into N‐alkyl Oxazolidin‐2‐ones Promoted by Metal‐Free Porphyrin/TBACl System: Experimental and Computational Studies

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Synthesis and in vitro anticancer activity of new 2-thioxo-oxazolidin-4-one derivatives

Cited by 10 publications

References 48 publications

5-(Carbamoylmethylene)-oxazolidin-2-ones as a Promising Class of Heterocycles Inducing Apoptosis Triggered by Increased ROS Levels and Mitochondrial Dysfunction in Breast and Cervical Cancer

5-(Carbamoylmethylene)-oxazolidin-2-ones as a Promising Class of Heterocycles Inducing Apoptosis Triggered by Increased ROS Levels and Mitochondrial Dysfunction in Breast and Cervical Cancer

Antioxidant Capacity and Cytotoxicity of the Aqueous Extract of Myrcia guianensis (Aubl.) DC

Valorization of CO2 into N‐alkyl Oxazolidin‐2‐ones Promoted by Metal‐Free Porphyrin/TBACl System: Experimental and Computational Studies

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Valorization of CO₂ into N‐alkyl Oxazolidin‐2‐ones Promoted by Metal‐Free Porphyrin/TBACl System: Experimental and Computational Studies