An Updated Review on Biologically Promising Natural Oxepines

Mandal, Bhagirath; Karmakar, Indrajit; Brahmachari, Goutam

doi:10.1002/cbdv.202200484

Cited by 5 publications

(1 citation statement)

References 50 publications

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“…A variety of compounds with DO frameworks exhibit advantageous and intriguing biomedical properties, including antipsychotic, anti-inflammatory, antidepressant, insecticidal, antiepileptic, and anticancer properties [52,53]. Several of their derivatives have been documented to exhibit a promising capacity to inhibit the viability of human cancer cell lines [24].…”

Section: Discussionmentioning

confidence: 99%

A New Benzo[6,7]oxepino[3,2-b] Pyridine Derivative Induces Apoptosis in Canine Mammary Cancer Cell Lines

Jianpraphat,

Supsavhad,

Ngernmeesri

et al. 2024

Animals

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CMC is the most frequently diagnosed cancer and one of the leading causes of death in non-spayed female dogs. Exploring novel therapeutic agents is necessary to increase the survival rate of dogs with CMC. MPOBA is a BZOP derivative that has a significant anticancer effect in a human cell line. The main goal of this study was to investigate the anticancer properties of MPOBA against two CMC cell lines (REM134 and CMGT071020) using a 3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay, a wound healing assay, a transwell migration assay, an Annexin V-FITC apoptosis assay with a flow cytometry analysis, a mRNA expression analysis using quantitative real-time PCR (qRT-PCR), and an immunohistochemistry (IHC). According to the accumulated studies, MPOBA caused significant concentration- and time-dependent reductions in cell proliferation and cell migration and induced apoptosis in both CMC cell lines. In gene expression analysis, nine canine genes, including TP53, BCL-2, BAX, epidermal growth factor receptor (EGFR), snail transcription factor (SNAIL), snail-related zinc-finger transcription factor (SLUG), TWIST, E-cadherin, and N-cadherin, were investigated. The mRNA expression results revealed that MPOBA induced upregulation of TP53 and overexpression of the pro-apoptotic gene BAX, together with an inhibition of BCL-2. Moreover, MPOBA also suppressed the mRNA expression levels of SNAIL, EGFR, and N-cadherin and induced upregulation of E-cadherin, crucial genes related to the epithelial-to-mesenchymal transition (EMT). However, there was no significant difference in the IHC results of the expression patterns of vimentin (VT) and cytokeratin (CK) between MPOBA-treated and control CMC cells. In conclusion, the results of the present study suggested that MPOBA exhibited significant anticancer activity by inducing apoptosis in both CMCs via upregulation of TP53 and BAX and downregulation of BCL-2 relative mRNA expression. MPOBA may prove to be a potential candidate drug to be further investigated as a therapeutic agent for CMC.

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Section: Discussionmentioning

confidence: 99%

A New Benzo[6,7]oxepino[3,2-b] Pyridine Derivative Induces Apoptosis in Canine Mammary Cancer Cell Lines

Jianpraphat,

Supsavhad,

Ngernmeesri

et al. 2024

Animals

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A Computational Study on the Radical Cascade Cyclization Mechanism of Synthesis of Benzo[b]oxepinones and Chromanes

Fıstıkçı¹

2023

ChemistrySelect

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A computational study on the reaction mechanism of the effective synthesis of sulfonated benzo[b]oxepinones and chromanes by radical cascade cyclization is carried out employing the density functional theory (DFT). Based on our computations, the rate‐determining step is the formation of arylsulfonyl radical for the reaction scheme. Our calculations show that the reaction of 1,8‐ and 1,7‐enynes with arylsulfonyl radical proceeds by forming more thermodynamically stable intermediates. Therefore, 1,8‐enynes prefer 7‐exo‐trig cyclization, while 1,7‐enynes prefer 6‐exo‐trig cyclization. Our computations are consistent with experimental results of the radical cascade cyclization of 1,8‐ and 1,7‐enynes. Moreover, our computations show that if the reaction is carried out in a proton‐free solvent, the elimination product can be obtained from the cascade radical cyclization of the 1,7‐enyne.

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Base-promoted cyclization ofortho-hydroxyacetophenones within situgenerated cyclopropenes: diastereoselective access to spirobenzo[b]oxepines and related precursors

Samanta¹,

Prakash

2023

Org. Biomol. Chem.

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An Updated Review on Biologically Promising Natural Oxepines

Cited by 5 publications

References 50 publications

A New Benzo[6,7]oxepino[3,2-b] Pyridine Derivative Induces Apoptosis in Canine Mammary Cancer Cell Lines

A New Benzo[6,7]oxepino[3,2-b] Pyridine Derivative Induces Apoptosis in Canine Mammary Cancer Cell Lines

A Computational Study on the Radical Cascade Cyclization Mechanism of Synthesis of Benzo[b]oxepinones and Chromanes

Base-promoted cyclization ofortho-hydroxyacetophenones within situgenerated cyclopropenes: diastereoselective access to spirobenzo[b]oxepines and related precursors

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