Phenylpropanoid-based sulfonamide promotes cyclin D1 and cyclin E down-regulation and induces cell cycle arrest at G1/S transition in estrogen positive MCF-7 cell line

Azevedo-Barbosa, Helloana; Ferreira-Silva, Guilherme Álvaro; Silva, Carolina Faria; Souza, Thiago Belarmino de; Dias, Danielle Ferreira; Paula, Alessandro Vinícius de; Ionta, Marisa; Carvalho, Diogo Teixeira

doi:10.1016/j.tiv.2019.04.023

Cited by 33 publications

(30 citation statements)

References 57 publications

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“…The substances evaluated in this study were synthesized according to the synthetic route shown in Scheme 2, and this route has previously been reported by Azevedo‐Barbosa et al [30] . In summary, the starting molecules 1 and 2 were nitrated to produce intermediate compounds 3a – 3d that were further reduced to aryl amines 4a – 4d with tin chloride.…”

Section: Resultsmentioning

confidence: 99%

“…The synthesis and characterization of the amino key intermediates 4a – 4d and the sulfonamide compounds 5a – 5d and 6a – 6d has previously been published by this research group [30] . The synthesis of the new compounds 6e and 6f were done as follows:…”

Section: Methodsmentioning

confidence: 99%

“…Pharmacological properties of eugenol have been extensively highlighted, especially involving its antibacterial and antifungal properties [17–22] . Our research group has previously demonstrated that synthetic compounds obtained from natural phenylpropanoids, such as eugenol or its analogs (dihydroeugenol and isoeugenol), have important antimicrobial activity and that hybrids obtained from phenylpropanoids and sulfonamide moieties have important antitumor activity [23–30] . Taking advantage of the molecular hybridization strategy (and the well‐established antibacterial potential of eugenol and sulfonamide‐based drugs separately) herein we present for the first time the antibacterial activity of eugenol and dihydroeugenol‐based hybrids bearing the sulfonamide functionality ( Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

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Design, Synthesis, Antimicrobial Evaluation and in Silico Studies of Eugenol‐Sulfonamide Hybrids

Azevedo-Barbosa

Vale

Rossi

et al. 2021

Chemistry & Biodiversity

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Using molecular hybridization, specific sulfonamide derivatives of eugenol were synthesized with subtle modifications in the allylic chain of the eugenol subunit (and also in the nature of the substituent group in the sulfonamide aromatic ring) which allowed us to study the influence of structural changes on the antimicrobial potential of the hybrids. Antimicrobial test results showed that most of the synthesized hybrid compounds showed good activity with better results than the parent compounds. Molecular docking studies of the hybrids with the essential bacterial enzyme DHPS showed complexes with low binding energies, suggesting that DHPS could be a possible target for the antibacterial sulfonamide‐eugenol hybrids. Furthermore, most of the final compounds presented similar docking poses to that of the crystallographic ligand sulfamethoxazole. The results obtained allow us to conclude that these are promising compounds for use as new leads in the search for new antibacterial sulfonamides.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Design, Synthesis, Antimicrobial Evaluation and in Silico Studies of Eugenol‐Sulfonamide Hybrids

Azevedo-Barbosa

Vale

Rossi

et al. 2021

Chemistry & Biodiversity

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“…Many anti-tumor drugs may inhibit the proliferation of tumor cells through cell cycle arrest [32,33]. As shown in Figure 4, PEO led to significant changes of cell cycle progression.…”

Section: Resultsmentioning

confidence: 99%

Essential Oil from Pinus Koraiensis Pinecones Inhibits Gastric Cancer Cells via the HIPPO/YAP Signaling Pathway

et al. 2019

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Pinecone is a traditional folk herb, which has been used in China for many years. In this paper, the essential oil from Pinus koraiensis pinecones (PEO) was obtained by hydrodistillation and 41 compounds were identified by gas chromatography–mass spectrometry (GC-MS), mainly including α-Pinene (40.91%), Limonene (24.82%), and β-Pinene (7.04%). The purpose of this study was to investigate the anti-tumor activity of PEO on MGC-803 cells and its mechanism. Anti-tumor experiments in vitro showed PEO could significantly inhibit the proliferation and migration of MGC-803 cells, and it also could arrest the cell cycle in the G2/M phase, decrease the mitochondrial membrane potential, and induce apoptosis. Finally, the effects of PEO on genes expression on MGC-803 cells were analyzed by RNA sequencing, and results showed that after treatment with PEO, 100 genes were up-regulated, and 57 genes were down-regulated. According to the KEGG pathway and GSEA, FAT4, STK3, LATS2, YAP1, and AJUBA were down-regulated, which were related to HIPPO signaling pathway. Real-time PCR and western blot further confirmed the results of RNA sequencing. These results indicated that PEO may exert anti-tumor activity via the HIPPO/YAP signaling pathway. The anti-tumor mechanism of this oil can be further studied, which is important for the development of anti-tumor drugs.

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“…Following 24 hours after treatment, pcDNA3.1-CTRP6 transfection rescued the phenotypes induced by miR-29b/c, including the expression levels of cell cycle genes (Cyclin B, Cyclin E) and the percentage of EdU-positive cells in the proliferation stage, as well as the expression levels of adipogenesis-related genes ( C/EBPα, PPARγ, FAS, ap2 and ATGL ) and intracellular TG content in the differentiation stage. Cyclin E is the limiting factor of G1/S transition in eukaryocytes [ 24 ]. C/EBPα and PPARγ are critical transcription factors for the differentiation of adipocytes [ 25 ].…”

Section: Discussionmentioning

confidence: 99%

MicroRNA-29b/29c targeting CTRP6 influences porcine adipogenesis via the AKT/PKA/MAPK Signalling pathway

et al. 2021

Adipocyte

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Porcine fat deposition is an important economic trait of pig breeds, and understanding the gene regulatory network in adipocytes is essential for modern pig breeding. In a previous study, we demonstrated that miR-29a negatively regulates the differentiation of porcine adipocytes. In this study, we investigated the roles of miR-29b/c in porcine adipocytes and the underlying mechanisms. Using EdU staining and the CCK-8 assay, we observed that transfection with the miR-29b/c agomir promoted the proliferation of porcine intramuscular (IM) and subcutaneous (SC) adipocytes by altering the expression of cell-cycle-related genes. According to the results of oil red O staining and western blot analysis, transfection with the miR-29b/c agomir suppressed the differentiation of porcine SC and IM adipocytes via the AKT/PKA/MAPK signalling pathway. Furthermore, we proved that miR-29b/c regulates porcine adipocytes by directly targeting the 3ʹ-untranslated region (3ʹUTR) of CTRP6 using a dual-luciferase reporter assay. Finally, co-transfection with miR-29b/c and CTRP6 partially restored the changes of phenotype and gene expression induced by miR-29b/c overexpression in 3T3-L1 adipocytes. Taken together, our data demonstrate that both miR-29b and miR-29 c negatively regulate porcine adipogenesis by targeting CTRP6, which furthers our understanding of the gene network that regulates fat deposition in pigs.

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Phenylpropanoid-based sulfonamide promotes cyclin D1 and cyclin E down-regulation and induces cell cycle arrest at G1/S transition in estrogen positive MCF-7 cell line

Cited by 33 publications

References 57 publications

Design, Synthesis, Antimicrobial Evaluation and in Silico Studies of Eugenol‐Sulfonamide Hybrids

Design, Synthesis, Antimicrobial Evaluation and in Silico Studies of Eugenol‐Sulfonamide Hybrids

Essential Oil from Pinus Koraiensis Pinecones Inhibits Gastric Cancer Cells via the HIPPO/YAP Signaling Pathway

MicroRNA-29b/29c targeting CTRP6 influences porcine adipogenesis via the AKT/PKA/MAPK Signalling pathway

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