Synthesis and Studying of the Biological Activity of Some New Coumarin-3-carboxylic Acid Heterocyclic Derivatives

Radhi, Ali Jabbar; Razaq, Alaa Fadihl; Mohammed, Majed Jari

doi:10.21608/ejchem.2021.36058.2745

Cited by 2 publications

(2 citation statements)

References 9 publications

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“…The carbon signals corresponding to the remaining atoms in 8-methoxy-5-bromocoumarin-3-carboxamide are detected within the anticipated spectral regions. The verification of the structures of coumarin-3-carboxylic acid derivatives (8 and 9) was conducted through the analysis of the signals observed in the 1 H-NMR spectra [ 71 ]. The spectrum of 8 demonstrated the lack of two proton signals attributed to the presence of the amino (NH 2 ) group.…”

Section: Resultsmentioning

confidence: 99%

Novel 8-Methoxycoumarin-3-Carboxamides with potent anticancer activity against liver cancer via targeting caspase-3/7 and β-tubulin polymerization

Alzamami,

Radwan,

Abo-Elabass

et al. 2023

BMC Chemistry

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In the present study, we explored the potential of coumarin-based compounds, known for their potent anticancer properties, by designing and synthesizing a novel category of 8-methoxycoumarin-3-carboxamides. Our aim was to investigate their antiproliferative activity against liver cancer cells. Toward this, we developed a versatile synthetic approach to produce a series of 8-methoxycoumarin-3-carboxamide analogues with meticulous structural features. Assessment of their antiproliferative activity demonstrated their significant inhibitory effects on the growth of HepG2 cells, a widely studied liver cancer cell line. Among screened compounds, compound 5 exhibited the most potent antiproliferative activity among the screened compounds (IC50 = 0.9 µM), outperforming the anticancer drug staurosporine (IC50 = 8.4 µM), while showing minimal impact on normal cells. The flow cytometric analysis revealed that compound 5 induces cell cycle arrest during the G1/S phase and triggers apoptosis in HepG2 cells by increasing the percentage of cells arrested in the G2/M and pre-G1 phases. Annexin V-FITC/PI screening further supported the induction of apoptosis without significant necrosis. Further, compound 5 exhibited the ability to activate caspase3/7 protein and substantially inhibited β-tubulin polymerization activity in HepG2 cells. Finally, molecular modelling analysis further affirmed the high binding affinity of compound 5 toward the active cavity of β-tubulin protein, suggesting its mechanistic involvement. Collectively, our findings highlight the therapeutic potential of the presented class of coumarin analogues, especially compound 5, as promising candidates for the development of effective anti-hepatocellular carcinoma agents.

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Section: Resultsmentioning

confidence: 99%

Novel 8-Methoxycoumarin-3-Carboxamides with potent anticancer activity against liver cancer via targeting caspase-3/7 and β-tubulin polymerization

Alzamami,

Radwan,

Abo-Elabass

et al. 2023

BMC Chemistry

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“…It is well known that the key element of probe design is the ability of an excellently chosen uorophore to combine with the detection group for speci c recognition. Coumarin dyes are widely used in uorescent probes because of their low biotoxicity, high uorescence sensitivity, good photostability and easy modi cation of the main chain [22][23][24][25][26][27][28][29][30] . Coumarin derivatives can also be used as uorescence markers or imaging agents to identify tumor lesions and study the subcellular localization of drugs [31][32][33][34][35][36][37][38][39][40][41][42] .…”

Section: Introductionmentioning

confidence: 99%

Two Novel coumarin-based fluorescent probes for the detection of Cu2+ and biological applications

Zhang

Huang

Wang

et al. 2023

Preprint

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Large accumulations of copper (Cu) ions in the human body may cause damage, including organ and brain damage. In recent years, studies have proven that a large accumulation of Cu ions can lead to Parkinson's disease and Alzheimer's disease, therefore it is great important to develop novel strategies for detecting trace Cu in environmental and biological samples. In this work, we designed two new coumarin-based colorimetric and fluorescent probes HQ1 and HQ2. These two probes could selectively respond to Cu2+ with obvious color and fluorescence changes, and the presence of other metal ions had no effect on these changes. The two probes also exhibited high sensitivity for Cu2+, with a detection limit as low as 1.81×10-8 M/ 1.57×10-8 M. Notably, the two probes showed potential practical applications and were successfully used for detecting Cu2+ in a test strip, A549 cells and living zebrafish larvae.

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Synthesis and Studying of the Biological Activity of Some New Coumarin-3-carboxylic Acid Heterocyclic Derivatives

Cited by 2 publications

References 9 publications

Novel 8-Methoxycoumarin-3-Carboxamides with potent anticancer activity against liver cancer via targeting caspase-3/7 and β-tubulin polymerization

Novel 8-Methoxycoumarin-3-Carboxamides with potent anticancer activity against liver cancer via targeting caspase-3/7 and β-tubulin polymerization

Two Novel coumarin-based fluorescent probes for the detection of Cu2+ and biological applications

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