Insights into the importance for designing curcumin-inspired anticancer agents by a prooxidant strategy: The case of diarylpentanoids

Dai, Fang; Liu, Guoyun; Li, Yan; Yan, Wenjing; Wang, Qi; Yang, Jie; Lu, Dongliang; Ding, Dejun; Dong, Lin; Zhou, Bo

doi:10.1016/j.freeradbiomed.2015.04.017

Cited by 70 publications

(55 citation statements)

References 87 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…(2) After treatment for 48 h, the curcumin analogs with the ortho-substituent on the aromatic ring(s) was more active than their corresponding meta-substituted compounds, which was more active than the para-substituted compounds, against the three cancer cells. The presence of the substituents at the ortho, but not para or meta, positions of the aromatic ring(s) significantly increase the cytotoxicity, highlighting a so-called ortho effect (Dai et al, 2015). Previously, the presence of ortho effect was also proved to significantly strengthen the cytotoxicity of cinnamaldehydes (Chew et al, 2010), chalcones (Gan et al, 2013) and mono-carbonyl curcumin analogs (Dai et al, 2015).…”

Section: Cytotoxicity and Sarmentioning

confidence: 99%

“…Then the suspension was centrifuged for 5 min (9400 g, at 4°C), and the supernatant was then scanned using a UV/Visible spectrophotometer (Dai et al, 2015).…”

Section: Uptake and Metabolic Stability Assaymentioning

confidence: 99%

“…Lipid peroxidation was measured according to the protocol as described previously (Dai et al, 2015). NCI-H460 cells were seeded at a density of 5 Â 10 5 per well in six-well plates and allowed to grow for 24 h, after exposure to 1a at the indicated concentrations (0, 5, 10, 20 and 30 μM) for 18 h, the cells were harvested.…”

Section: Determination Of Thiobarbituric Acid-reactive Substance (Tbars)mentioning

confidence: 99%

“…The presence of the substituents at the ortho, but not para or meta, positions of the aromatic ring(s) significantly increase the cytotoxicity, highlighting a so-called ortho effect (Dai et al, 2015). Previously, the presence of ortho effect was also proved to significantly strengthen the cytotoxicity of cinnamaldehydes (Chew et al, 2010), chalcones (Gan et al, 2013) and mono-carbonyl curcumin analogs (Dai et al, 2015). (3) 1a showed less active than curcumin after treatment for 24 h against NCI-H460 cells, which was apposed to the results of 48 h. The phenomenon may be due to the cellular uptake of 1a and curcumin in NCI-H460 cells.…”

Section: Cytotoxicity and Sarmentioning

confidence: 99%

“…A large amount of research work demonstrated that replace the β-diketone moiety by ketone not only enhanced stability in vitro but also greatly improved pharmacokinetic profiles in vivo (Liang et al, 2009). Our group's work was also exploiting reactive oxygen species-promoting signaling for designing curcumin-inspired anticancer agents and found that they can target TrxR (thioredoxin reductase) and convert this antioxidant enzyme into a reactive oxygen species promoter (Dai et al, 2015).…”

Section: Introductionmentioning

confidence: 98%

See 4 more Smart Citations

2,2′-Fluorine mono-carbonyl curcumin induce reactive oxygen species-Mediated apoptosis in Human lung cancer NCI-H460 cells

Liu

Zeng

Chen

et al. 2016

European Journal of Pharmacology

Self Cite

View full text Add to dashboard Cite

Section: Cytotoxicity and Sarmentioning

confidence: 99%

“…Then the suspension was centrifuged for 5 min (9400 g, at 4°C), and the supernatant was then scanned using a UV/Visible spectrophotometer (Dai et al, 2015).…”

Section: Uptake and Metabolic Stability Assaymentioning

confidence: 99%

Section: Determination Of Thiobarbituric Acid-reactive Substance (Tbars)mentioning

confidence: 99%

Section: Cytotoxicity and Sarmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

See 3 more Smart Citations

2,2′-Fluorine mono-carbonyl curcumin induce reactive oxygen species-Mediated apoptosis in Human lung cancer NCI-H460 cells

Liu

Zeng

Chen

et al. 2016

European Journal of Pharmacology

Self Cite

View full text Add to dashboard Cite

Small Molecules to Target the Selenoprotein Thioredoxin Reductase

Zhang

Liu

et al. 2018

Chemistry An Asian Journal

View full text Add to dashboard Cite

The selenoprotein thioredoxin reductase (TrxR) enzymes are the only identified proteins that maintain thioredoxin (Trx) proteins in a reduced state under physiological conditions, and consequently play a pivotal role in the regulation of various cellular redox signaling pathways involved in cell differentiation, growth, and death. The elevated expression of TrxR enzymes has been observed in different types of cancer cells, and this overexpression is of pathological significance in maintaining tumor phenotypes, such as uncontrolled proliferation and resistance to apoptosis. Herein, we discuss recent advances in the study of TrxR, including classic assays of TrxR, the emerging chemical tools of TrxR, and small molecules that target TrxR as potential anticancer agents.

show abstract

Design, Synthesis, and Anticancer Activity of Cinnamoylated Barbituric Acid Derivatives

Liu

et al. 2022

Chemistry & Biodiversity

Self Cite

View full text Add to dashboard Cite

This work deals with the design and synthesis of 18 barbituric acid derivatives bearing 1,3‐dimethylbarbituric acid and cinnamic acid scaffolds to find potent anticancer agents. The target molecules were obtained through Knoevenagel condensation and acylation reaction. The cytotoxicity was assessed by the MTT assay. Flowcytometry was performed to determine the cell cycle arrest, apoptosis, ROS levels and the loss of MMP. The ratios of GSH/GSSG and the MDA levels were determined by using UV spectrophotometry. The results revealed that introducing substitutions (CF3, OCF3, F) on the meta‐ of the benzyl ring of barbituric acid derivatives led to a considerable increase in the antiproliferative activities compared with that of corresponding ortho‐ and para‐substituted barbituric acid derivatives. Mechanism investigation implied that the 1c could increase the ROS and MDA level, decrease the ratio of GSH/GSSG and MMP, and lead to cell cycle arrest. Further research is needed for structural optimization to enhance hydrophilicity, thereby improve the biological activity of these compounds.

show abstract

Insights into the importance for designing curcumin-inspired anticancer agents by a prooxidant strategy: The case of diarylpentanoids

Cited by 70 publications

References 87 publications

2,2′-Fluorine mono-carbonyl curcumin induce reactive oxygen species-Mediated apoptosis in Human lung cancer NCI-H460 cells

2,2′-Fluorine mono-carbonyl curcumin induce reactive oxygen species-Mediated apoptosis in Human lung cancer NCI-H460 cells

Small Molecules to Target the Selenoprotein Thioredoxin Reductase

Design, Synthesis, and Anticancer Activity of Cinnamoylated Barbituric Acid Derivatives

Contact Info

Product

Resources

About