Evaluation of Anti-cancer Activity of Stilbene and Methoxydibenzo[b,f] oxepin Derivatives

Garbicz, Damian; Mielecki, Damian; Wrzesiński, Michał; Pilżys, Tomasz; Marcinkowski, Michał; Piwowarski, Jan; Dębski, Janusz; Palak, Ewelina; Szczeciński, Przemysław; Krawczyk, Hanna; Grzesiuk, Elżbieta

doi:10.2174/1568009617666170623120742

Cited by 14 publications

(8 citation statements)

References 39 publications

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“…Continuing our study [25][26][27][28][29][30][31] of microtubule inhibitors, we analyzed the structure of active colchicine, active combretastatin A-4, and derivative dibenzo[b,f ]oxepine (Figure 1). It can be observed that the substituents and backbone arrangements were similar.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Investigations of Building Blocks with Dibenzo[b,f] Oxepine for Use in Photopharmacology

Tobiasz

Borys

Borecka

et al. 2021

IJMS

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The synthesis of photoswitchable azo-dibenzo[b,f]oxepine derivatives and microtubule inhibitors were described. Subsequently, we examined the reaction of methoxy derivative 3-nitrodibenzo[b,f]oxepine with different aldehydes and in the presence of BF3·OEt2 as a catalyst. Our study provided a very concise method for the construction of the azo-dibenzo[b,f]oxepine skeleton. The analysis of products was run using experimental and theoretical methods. Next, we evaluated the E/Z isomerization of azo-dibenzo[b,f]oxepine derivatives, which could be photochemically controlled using visible-wavelength light.

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Section: Introductionmentioning

confidence: 99%

“…It can be observed that the substituents and backbone arrangements were similar. Additionally, the dibenzo[b,f ]oxepine showed the strongest cytotoxic effect against HeLa and U87 cancerous cells [27] and had (Z)-stilbene motif in their skeleton. Additionally, their aromatic rings were connected by oxygen.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Investigations of Building Blocks with Dibenzo[b,f] Oxepine for Use in Photopharmacology

Tobiasz

Borys

Borecka

et al. 2021

IJMS

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“…[40][41][42] Newly discovered Res analogs and oligomers from diverse sources have exhibited more potent anticancer activity than Res itself. [43][44][45] Stilbenes' anticancer mechanisms result from the modulation of multiple signaling pathways, including cell cycle arrest, induction of DNA repair and stress response, apoptosis, and antiangiogenesis, [46][47][48] therefore justifying the anticancer resourcefulness of Res and its analogs and polymers. [49] Gnetin C (GnC) is a naturally occurring dimer of Res found in the melinjo plant Gnetum gnemon, which is widely farmed in Southeast Asia and used in Indonesian cuisine.…”

Section: Introductionmentioning

confidence: 99%

Molecular Efficacy of Gnetin C as Dual‐Targeted Therapy for Castrate‐Resistant Prostate Cancer

Campanelli,

Deabel,

Puaar

et al. 2023

Molecular Nutrition Food Res

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ScopeResistance of castrate‐resistant prostate cancer (CRPC) to enzalutamide (Enz) involves the expression of constitutively active androgen receptor splice variant (AR‐V7). In addition to altered AR pathways, CRPC is characterized by “non‐AR‐driven” signaling, which includes an overexpression of metastasis‐associated protein 1 (MTA1). Combining natural compounds with anticancer drugs may enhance drug effectiveness while reducing adverse effects. In this study, the in vitro and in vivo anticancer effects of Gnetin C (GnC) alone and in combination with Enz against CRPC are examined.Methods and resultsThe effects of GnC alone and in combination with Enz are assessed by cell viability, clonogenic survival, cell migration, and AR and MTA1 expression using 22Rv1 cells. The tumor growth in vivo is assessed by bioluminescent imaging, western blots, RT‐PCR, and IHC. GnC alone and in combined treatment inhibit cell viability, clonogenic survival and migration, and AR and MTA1 expression in 22Rv1 cells. The underlying AR‐ and MTA1‐targeted anticancer mechanisms of treatments in vivo involve inhibition of proliferation and angiogenesis, and induction of apoptosis.ConclusionThe findings demonstrate that GnC alone and GnC combined with Enz effectively inhibits AR‐ and MTA1‐promoted tumor‐progression in advanced CRPC, which indicates its potential as a novel therapeutic approach for CRPC.

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“…Dibenzo[b, f ]oxepine derivatives are an important scaffold in natural, medicinal chemistry, and these derivatives occur in several medicinally relevant plants [1][2][3]. The dibenzo [b, f ] oxepine system can be associated with various biological properties such as antidepressant and anti-estrogenic [4], analgesic [5], anti-inflammatory [6], antipsychotic [7], angiotensin II receptor antagonistic [8], antioxidant [9], antimycobacterial [10], antidiabetic [11], and antitumor activities [3,12], as well as anti-apoptosis [13] properties. The treatment of progressive neurodegenerative diseases [14] such as Parkinson's and Alzheimer's diseases [15] with synthetic dibenzo[b, f ]oxepine derivatives is of particular interest.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Study of Dibenzo[b, f]oxepine Combined with Fluoroazobenzenes—New Photoswitches for Application in Biological Systems

et al. 2022

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Dibenzo[b, f]oxepine derivatives are an important scaffold in natural, medicinal chemistry, and these derivatives occur in several medicinally relevant plants. Two dibenzo[b, f]oxepines were selected and connected with appropriate fluorine azobenzenes. In the next step, the geometry of E/Z isomers was analyzed using density functional theory (DFT) calculations. Then the energies of the HOMO and LUMO orbitals were calculated for the E/Z isomers to determine the HOMO-LUMO gap. Next, modeling of the interaction between the obtained isomers of the compounds and the colchicine α and β-tubulin binding site was performed. The investigated isomers interact with the colchicine binding site in tubulin with a part of the dibenzo[b, f]oxepine or in a part of the azo switch, or both at the same time. Based on the UV-VIS spectra, it was found that in the case of compounds with an azo bond in the meta position, the absorption bands n→π* for both geometric isomers and their separation from π→π* are visible. These derivatives therefore have the potential to be used in photopharmacology.

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Evaluation of Anti-cancer Activity of Stilbene and Methoxydibenzo[b,f] oxepin Derivatives

Cited by 14 publications

References 39 publications

Synthesis and Investigations of Building Blocks with Dibenzo[b,f] Oxepine for Use in Photopharmacology

Synthesis and Investigations of Building Blocks with Dibenzo[b,f] Oxepine for Use in Photopharmacology

Molecular Efficacy of Gnetin C as Dual‐Targeted Therapy for Castrate‐Resistant Prostate Cancer

Synthesis and Study of Dibenzo[b, f]oxepine Combined with Fluoroazobenzenes—New Photoswitches for Application in Biological Systems

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