Design and synthesis of methoxyphenyl- and coumarin-based chalcone derivatives as anti-inflammatory agents by inhibition of NO production and down-regulation of NF-κB in LPS-induced RAW264.7 macrophage cells

Emam, Soha H.; Sonousi, Amr; Osman, Eman O.; Hwang, Dukhyun; Kim, Gun‐Do; Hassan, Rasha A.

doi:10.1016/j.bioorg.2021.104630

Cited by 60 publications

(42 citation statements)

References 48 publications

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“…Two chalcone derivatives as anti-inflammatory agents were developed by Emam et al They reported that compound 41 (Figure 4) exhibited the highest anti-inflammatory activity by inhibition of NO concentration in LPS-induced RAW264.7 macrophages (IC 50 ¼11.2 mM). Moreover, compound 41 decreased the expression of NF-jB and phosphorylated IjB in LPS-stimulated macrophages 56 . In a different study, Ma et al synthesised a series of novel derivatives between resveratrol and chalcone possessing piperazine moiety.…”

Section: Chalcone Derivatives As Anti-inflammatory Agentsmentioning

confidence: 96%

“…They reported that compound 41 ( Figure 4 ) exhibited the highest anti-inflammatory activity by inhibition of NO concentration in LPS-induced RAW264.7 macrophages (IC 50 =11.2 µM). Moreover, compound 41 decreased the expression of NF-κB and phosphorylated IκB in LPS-stimulated macrophages 56 . In a different study, Ma et al.…”

Section: Recent Development In Anti-inflammatory Agentsmentioning

confidence: 96%

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Small molecule compounds with good anti-inflammatory activity reported in the literature from 01/2009 to 05/2021: a review

Bian

Wu³

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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Inflammation and disease are closely related. Inflammation can induce various diseases, and diseases can promote inflammatory response, and two possibly induces each other in a bidirectional loop. Inflammation is usually treated using synthetic anti-inflammatory drugs which are associated with several adverse effects hence are not safe for long-term use. Therefore, there is need for anti-inflammatory drugs which are not only effective but also safe. Several researchers have devoted to the research and development of effective anti-inflammatory drugs with little or no side effects. In this review, we studied some small molecules with reported anti-inflammatory activities and hence potential sources of anti-inflammatory agents. The information was retrieved from relevant studies published between January 2019 and May, 2021 for review. This review study was aimed to provide relevant information towards the design and development of effective and safe anti-inflammation agents.

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Section: Chalcone Derivatives As Anti-inflammatory Agentsmentioning

confidence: 96%

Section: Recent Development In Anti-inflammatory Agentsmentioning

confidence: 96%

Small molecule compounds with good anti-inflammatory activity reported in the literature from 01/2009 to 05/2021: a review

Bian

Wu³

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…These protons present signals corresponding to two doublets with variable δ between 8.5 and 7.0 and with J ab = 16 Hz on average. this high constant corresponds to a trans isomer [ 27 , 28 , 29 ]. As for the 13 C-NMR spectrum, we will mention typical signals such as carbonyl shifts.…”

Section: Resultsmentioning

confidence: 99%

“…As for the 13 C-NMR spectrum, we will mention typical signals such as carbonyl shifts. first of all, we will detail that the carbon of the α,β-unsaturated ketone has a δ 190–180 ppm and carbonyl carbons of α-pyrone δ 165–155 pmm on average [ 27 , 28 , 29 ], the compounds were characterized by 1 H and 13 C NMR ( Supplementary Materials; Figures S1–S15 ).…”

Section: Resultsmentioning

confidence: 99%

Coumarin-Chalcone Hybrids as Inhibitors of MAO-B: Biological Activity and In Silico Studies

et al. 2021

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Fourteen coumarin-derived compounds modified at the C3 carbon of coumarin with an α,β-unsaturated ketone were synthesized. These compounds may be designated as chalcocoumarins (3-cinnamoyl-2H-chromen-2-ones). Both chalcones and coumarins are recognized scaffolds in medicinal chemistry, showing diverse biological and pharmacological properties among which neuroprotective activities and multiple enzyme inhibition, including mitochondrial enzyme systems, stand out. The evaluation of monoamine oxidase B (MAO-B) inhibitors has aroused considerable interest as therapeutic agents for neurodegenerative diseases such as Parkinson’s. Of the fourteen chalcocumarins evaluated here against MAO-B, ChC4 showed the strongest activity in vitro, with IC50 = 0.76 ± 0.08 µM. Computational docking, molecular dynamics and MM/GBSA studies, confirm that ChC4 binds very stably to the active rMAO-B site, explaining the experimental inhibition data.

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“…Meanwhile, only compound 1 can notably inhibit the protein expression of iNOS and NF-κB p65 ( Figure 9D ), while 5 exerts slight inhibition on the protein expression of COX-2 and NF-κB p65 ( Figure 9D ). NF-κB p65 is a pivotal transcriptional factor in the macrophage activation progress, which can activate and translocate into the nucleus to regulate the transcription of COX-2 and iNOS ( Emam et al, 2021 ). We also found that both 1 and 5 can inhibit the nuclear translocation of NF-κB p65 ( Figure 9C ).…”

Section: Resultsmentioning

confidence: 99%

New Polyketides With Anti-Inflammatory Activity From the Fungus Aspergillus rugulosa

Qiao

Deng

et al. 2021

Front. Pharmacol.

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Two new polyketide compounds, asperulosins A and B (1–2), and one new prenylated small molecule, asperulosin C (3), along with nine known compounds (4–12), were isolated and identified from a fungus Aspergillus rugulosa. Their structures were extensively elucidated via HRESIMS, 1D, and 2D NMR analysis. The absolute configurations of the new compounds were determined by the comparison of their electronic circular dichroism (ECD), calculated ECD spectra, and the detailed discussion with those in previous reports. Structurally, compounds 1 and 2 belonged to the polyketide family and were from different origins. Compound 2 was constructed by five continuous quaternary carbon atoms, which occur rarely in natural products. All of the isolates were evaluated for anti-inflammatory activity against the production of nitric oxide (NO) in lipopolysaccharide (LPS)-induced RAW264.7 cells. Among those, compounds 1 and 5 showed a significant inhibitory effect on NO production with IC50 values of 1.49 ± 0.31 and 3.41 ± 0.85 μM, respectively. Additionally, compounds 1 and 5 markedly increased the secretion of anti-inflammatory cytokine IL10 while suppressing the secretion of pro-inflammatory cytokines IL6, TNF-α, IFN-γ, MCP-1, and IL12. Besides, 1 and 5 inhibited the transcription level of pro-inflammatory macrophage markers IL6, IL1β, and TNF-α while remarkably elevating the anti-inflammatory factor IL10 and M2 macrophage markers ARG1 and CD206. Moreover, 1 and 5 restrained the expression and nuclear translocation of NF-κB, as well as its downstream signaling proteins COX-2 and iNOS. All these results suggest that 1 and 5 have potential as anti-inflammatory agents, with better or comparable activities than those of the positive control, dexamethasone.

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Design and synthesis of methoxyphenyl- and coumarin-based chalcone derivatives as anti-inflammatory agents by inhibition of NO production and down-regulation of NF-κB in LPS-induced RAW264.7 macrophage cells

Cited by 60 publications

References 48 publications

Small molecule compounds with good anti-inflammatory activity reported in the literature from 01/2009 to 05/2021: a review

Small molecule compounds with good anti-inflammatory activity reported in the literature from 01/2009 to 05/2021: a review

Coumarin-Chalcone Hybrids as Inhibitors of MAO-B: Biological Activity and In Silico Studies

New Polyketides With Anti-Inflammatory Activity From the Fungus Aspergillus rugulosa

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