Novel 3′,5′-diprenylated chalcones inhibited the proliferation of cancer cells in vitro by inducing cell apoptosis and arresting cell cycle phase

Wen, Zhonghang; Zhang, Yongqiang; Wang, Xinghui; Zeng, Xiaoping; Hu, Zhan-Xing; Liu, Yi; Xie, Yuxin; Guang-yi, Liang; Zhu, Jianguo; Luo, Heng; Xu, Bixue

doi:10.1016/j.ejmech.2017.03.077

Cited by 17 publications

(13 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We conducted a preliminary study of the growth assay, apoptosis progression of PC3 cells by C10 in our previous published paper [18]. However, this study was a research paper focusing on chemical synthesis of 3',5'-diprenylated chalcone derivatives and their primary cytotoxicity.…”

Section: C10 Inhibited the Proliferation Of Pc3 Cells By Inducing Apomentioning

confidence: 99%

“…Chalcone is an important group of flavones containing two phenyl rings (A-and B-rings) connected by a three-carbon α, β-unsaturated carbonyl bridge [17]. Given this special structure, prenylated chalcone has various pharmacological properties including anti-bacterial, anti-inflammation, and anti-cancer properties [18][19][20]. We previously designed and synthesized a series of novel 3 ,5 -diprenylated chalcones aiming to identify those having an anti-proliferative effect.…”

Section: Introductionmentioning

confidence: 99%

“…We previously designed and synthesized a series of novel 3 ,5 -diprenylated chalcones aiming to identify those having an anti-proliferative effect. We identified three compounds showing inhibitory activity on tumor cell proliferation in vitro by inducing cell apoptosis and cell cycle arrest, and (E)-1-(2-hydroxy-4-methoxy-3,5-diprenyl) phenyl-3-(3-pyridinyl)propene-1-one (C10) exhibited potent anti-cancer activity with better selectivity and lower toxicity than the other two in leukemia cells [18,21]. Our research group conducted a systematic study on anticancer drugs targeting Fli-1.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Fli-1 Activation through Targeted Promoter Activity Regulation Using a Novel 3’, 5’-diprenylated Chalcone Inhibits Growth and Metastasis of Prostate Cancer Cells

et al. 2020

IJMS

Self Cite

View full text Add to dashboard Cite

The friend leukemia integration 1 (Fli-1) gene is involved in the expression control of key genes in multiple pathogenic/physiological processes, including cell growth, differentiation, and apoptosis; this implies that Fli-1 is a strong candidate for drug development. In our previous study, a 3′,5′-diprenylated chalcone, (E)-1-(2-hydroxy-4-methoxy-3,5-diprenyl) phenyl-3-(3-pyridinyl)-propene-1-one (C10), was identified as a novel anti-prostate cancer (PCa) agent. Here, we investigated the molecular mechanisms underlying the anti-cancer effects of C10 on the growth, metastasis, and invasion of PC3 cells in vitro. Our results show that C10 exhibited a strong inhibitory effect on proliferation and metastasis of PC3 cells via several cellular and flow cytometric analyses. Further mechanism studies revealed that C10 likely serves as an Fli-1 agonist for regulating the expression of Fli-1 target genes including phosphatidylinositol 3-kinase (P110), murine double minute2 (MDM2), B-cell lymphoma-2 (Bcl-2), Src homology-2 domain-containing inositol 5-phosphatase 1 (SHIP-1), and globin transcription factor-1 (Gata-1) as well as the phosphorylation of extracellular-regulated protein kinases 1 (ERK1). Further, we confirmed that C10 can regulate the expressions of vascular endothelial growth factor 1 (VEGF-1), transforming growth factor-β2 (TGF-β2), intercellular cell adhesion molecule-1 (ICAM-1), p53, and matrix metalloproteinase 1 (MMP-1) genes associated with tumor apoptosis, migration, and invasion. Thus, C10 exhibits stronger anticancer activity with novel molecular targets and regulatory molecular mechanisms, indicating its great potency for development as a novel targeted anticancer drug.

show abstract

Section: C10 Inhibited the Proliferation Of Pc3 Cells By Inducing Apomentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Fli-1 Activation through Targeted Promoter Activity Regulation Using a Novel 3’, 5’-diprenylated Chalcone Inhibits Growth and Metastasis of Prostate Cancer Cells

et al. 2020

IJMS

Self Cite

View full text Add to dashboard Cite

show abstract

“…Similar activity was noted through fluorination at C4 ( 13e ), perhaps reflecting enhanced lipophilicity of these derivatives, while introduction of either 4-hydroxy ( 13j ) or methoxy ( 13c ) substitution reduced activity in both cell lines. Indeed, lipophilicity of chalcones has been cited as an important parameter for observed Pgp inhibitory activity [25]. Multiple ring substitution with methoxy substituents was detrimental to activity, as noted by compound ( 13i ).…”

Section: Resultsmentioning

confidence: 99%

Design, synthesis and evaluation of novel 2,2-dimethyl-2,3-dihydroquinolin-4(1H)-one based chalcones as cytotoxic agents

Jean

Farrell

Farrelly

et al. 2018

Heliyon

View full text Add to dashboard Cite

We designed and synthesised a series of novel chalcones, incorporating the heterocyclic framework of 2,2-dimethyl-2,3-dihydro-4(1H)-quinolinone, which was prepared via Sonogashira coupling of a substituted orthoaniline under aqueous conditions using Pd catalysis followed by acid-mediated cyclisation. The compounds were screened against the NCI-N87 and DLD-1 cancer cell lines, with most compounds showing low micromolar cytotoxic activity.

show abstract

“…After treatment with different concentrations of compound 11E (0 µM, 6 µM, 8µM, 10 µM) for 48 h, MGC-803 cells were stained with PI and FITC, and then analyzed by the flow cytometry [31]. As illustrated in Fig.…”

Section: Resultsmentioning

confidence: 99%

Discovery of 5,6-diaryl-1,2,4-triazines hybrids as potential apoptosis inducers

Song

Hou

et al. 2017

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

A series of 5,6-diaryl-1,2,4-triazines hybrids bearing a 1,2,3-triazole linker were synthesized by molecular hybridization strategy and evaluated for antiproliferative activity against three selected cancer cell lines (MGC-803, EC-109 and PC-3). The first structure-activity relationship (SAR) for these 5,6-diaryl-1,2,4-triazines is explored in this report with evaluation of 15 variants of the structural class. Among these chemical derivatives, 3-(((1-(4-fluorobenzyl)-1H-1,2,3-triazol-4-yl)methyl)thio)-5,6-diphenyl-1,2,4-triazine (11E) showed the more potent inhibitory effect against three cell lines than 5-Fu. Cellular mechanism studies in MGC-803 cells elucidated 11E inhibited colony formation and arrested cell cycle at G2/M phase. Furthermore, compound 11E caused morphological changes, decreased mitochondrial membrane potential, and induced apoptosis through the apoptosis-related proteins in MGC-803 cells. It was the first time, to our knowledge, that 5,6-diaryl-1,2,4-triazines bearing a 1,2,3-triazole linker were used as potential apoptosis inducers.

show abstract

Novel 3′,5′-diprenylated chalcones inhibited the proliferation of cancer cells in vitro by inducing cell apoptosis and arresting cell cycle phase

Cited by 17 publications

References 26 publications

Fli-1 Activation through Targeted Promoter Activity Regulation Using a Novel 3’, 5’-diprenylated Chalcone Inhibits Growth and Metastasis of Prostate Cancer Cells

Fli-1 Activation through Targeted Promoter Activity Regulation Using a Novel 3’, 5’-diprenylated Chalcone Inhibits Growth and Metastasis of Prostate Cancer Cells

Design, synthesis and evaluation of novel 2,2-dimethyl-2,3-dihydroquinolin-4(1H)-one based chalcones as cytotoxic agents

Discovery of 5,6-diaryl-1,2,4-triazines hybrids as potential apoptosis inducers

Contact Info

Product

Resources

About