Coumarin derivatives with anticancer activities: An update

Song, Xu-Feng; Fan, Jing; Liu, Lan; Liu, Xiaofeng; Gao, Feng

doi:10.1002/ardp.202000025

Cited by 92 publications

(56 citation statements)

References 93 publications

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“…Among those nucleos that have shown promising results, we can point to the bicalutamide, isoxazolones, pyrrole carboxamides, pyridines and N ‐arylpiperazine derivatives, indeno[1,2‐ d ]pyrimidine‐5‐one, imide‐based analogs, hydantoin, benzochromene, benzoquinoline, quinoline, coumarin derivatives, and organometallic‐containing derivatives. [ 9‐14 ]…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 5H‐indeno[1,2‐b]pyridine derivatives: Antiproliferative and antimetastatic activities against two human prostate cancer cell lines

Charris

Rodrígues

Ramírez

et al. 2021

Archiv der Pharmazie

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This study describes the direct synthesis of 2‐amino‐4‐(phenylsubstituted)‐5H‐indeno[1,2‐b]pyridine‐3‐carbonitrile derivatives 5–21, through sequential multicomponent reaction of aromatic aldehydes, malononitrile, and 1‐indanone in the presence of ammonium acetate and acetic acid (catalytic). The biological study showed that compound 10 significantly impeded proliferation of the cell lines PC‐3, LNCaP, and MatLyLu. The antimetastatic effects of compound 10 could be related with inhibition of MMP9 in the PC‐3 and LNCaP human cell lines. On the basis of a study of the structure–activity relationship of these compounds, we propose that the presence of two methoxy groups at positions 6 and 7 of the indeno nucleus and a 4‐hydroxy‐3‐methoxy phenyl substitution pattern at position 4 of the pyridine ring is decisive for these types of molecules to exert very good antiproliferative and antimetastatic activities.

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Section: Introductionmentioning

confidence: 99%

Synthesis of 5H‐indeno[1,2‐b]pyridine derivatives: Antiproliferative and antimetastatic activities against two human prostate cancer cell lines

Charris

Rodrígues

Ramírez

et al. 2021

Archiv der Pharmazie

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“…Our results showed that coumarin-triazole compounds 3c, d, e, and f significantly inhibited the proliferation of A549cells. Previous studies showed that coumarin-derivated compounds could cause cytotoxicity on various human cancer cell lines [4,13]. Yu et al, [14] showed that coumarin compounds bearing triazole moiety exhibited an important cytotoxic activity against human breast (MDA-MB-231), colorectal (HT-29 and HCT-116), and lung A549 cells.…”

Section: Discussionmentioning

confidence: 99%

“…Heterocyclic complexes derived from natural compounds can interact more easily with biological targets due to relatively weak binding in their structure compared to the native form [3]. More than half of the approved drugs are derived from synthetic forms of natural compounds [4]. Coumarin is an important secondary metabolite related to defense mechanisms in the plant.…”

Section: Introductionmentioning

confidence: 99%

“…Previous studies have shown that hybrid formations of coumarin with molecules such as hydrazine, pyrazole, pyridine, thiazole, and chalcone exhibit anticancer effects by inducing cell cycle arrest, pro-apoptotic gene expressions, and DNA damage [4]. Recently, specifically targeted prodrugs bearing coumarin moiety have become an attractive approach to overcome the acquired resistance of cancer cells to cisplatin, particularly through easily interacting with cellular components and promoting cellular signaling pathways [8].…”

Section: Introductionmentioning

confidence: 99%

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Novel coumarin compounds potentiate the effect of cisplatin on lung cancer cells by enhancing pro-apoptotic gene expressions, G2/M cell arrest, oxidative and antiangiogenic effects

Güner¹,

Bektaş²,

Menteşe³

2021

Preprint

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Coumarin is a functional compound with a pronounced wide range of biological activities and has recently been shown to have anticancer effects on various human cancer cells. Cisplatin is widely used in the treatment of many cancers but its effectiveness is limited due to acquired resistance and dose-related side effects. This study aimed to reveal the chemosensitizing ability of novel synthesized coumarin-triazole hybrid compounds (3a-f) alone or their combination with cisplatin in A549 cells.MTT assay was used for cytotoxic effects. Lactate dehydrogenase (LDH), antioxidant/oxidant status, DNA fragmentation were determined spectrophotometrically by using commercial kits. Muse™ Cell Analyzer was used to assess cell cycle progression. Pro/anti-apoptotic gene expressions were determined by Real-Time qPCR. The antiangiogenic activity was determined by VEGF expression and Hen's chorioallantoic membrane model. Compounds 3c, d, e, and f potentiated the cisplatin-induced cytotoxicity through the increase of LDH release and DNA fragmentation, induced G2/M cell cycle arrest, overproduction of oxidative stress, and decrease of cellular antioxidant levels. These compounds combined with cisplatin caused upregulation in the pro-apoptotic Bax, Bıd, caspase-3, caspase-8, caspase-9, Fas, and p53 gene expressions while downregulating anti-apoptotic DFFA, NFkB1, and Bcl2 gene expressions. These combinations caused vascular loss and a reduction in VEGF expression. These results suggest that a combinational regimen of coumarin compounds with cisplatin overcome the acquired resistance of cancer cells to cisplatin and, considering compounds have relatively low toxicity in normal cells, decrease the dose requirement of cisplatin in cancer treatments.

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“…For example, the insertion of a biologically active morpholine fragment into TSC backbones improved their aqueous solubility and anticancer activity in various cancer cell lines [23,26]. Herein, a biologically active coumarin (or 2H-chromen-2-one) fragment (Chart 1, right) was selected to be incorporated, due to its well-documented wide spectrum of activities, including antibacterial, antifungal, neuroprotective, antiamoebic, anti-inflammatory, and cytotoxic properties [27][28][29][30][31][32][33][34][35][36][37][38]. In addition, another biologically active piperazine fragment was included, since heteroaromatic ring systems are considered highly impactful design elements for the optimisation of key pharmacological parameters [23,39].…”

Section: Introductionmentioning

confidence: 99%

Coumarin-Based Triapine Derivatives and Their Copper(II) Complexes: Synthesis, Cytotoxicity and mR2 RNR Inhibition Activity

et al. 2021

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A series of thiosemicarbazone-coumarin hybrids (HL1-HL3 and H2L4) has been synthesised in 12 steps and used for the preparation of mono- and dinuclear copper(II) complexes, namely Cu(HL1)Cl2 (1), Cu(HL2)Cl2 (2), Cu(HL3)Cl2 (3) and Cu2(H2L4)Cl4 (4), isolated in hydrated or solvated forms. Both the organic hybrids and their copper(II) and dicopper(II) complexes were comprehensively characterised by analytical and spectroscopic techniques, i.e., elemental analysis, ESI mass spectrometry, 1D and 2D NMR, IR and UV–vis spectroscopies, cyclic voltammetry (CV) and spectroelectrochemistry (SEC). Re-crystallisation of 1 from methanol afforded single crystals of copper(II) complex with monoanionic ligand Cu(L1)Cl, which could be studied by single crystal X-ray diffraction (SC-XRD). The prepared copper(II) complexes and their metal-free ligands revealed antiproliferative activity against highly resistant cancer cell lines, including triple negative breast cancer cells MDA-MB-231, sensitive COLO-205 and multidrug resistant COLO-320 colorectal adenocarcinoma cell lines, as well as in healthy human lung fibroblasts MRC-5 and compared to those for triapine and doxorubicin. In addition, their ability to reduce the tyrosyl radical in mouse R2 protein of ribonucleotide reductase has been ascertained by EPR spectroscopy and the results were compared with those for triapine.

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Coumarin derivatives with anticancer activities: An update

Cited by 92 publications

References 93 publications

Synthesis of 5H‐indeno[1,2‐b]pyridine derivatives: Antiproliferative and antimetastatic activities against two human prostate cancer cell lines

Synthesis of 5H‐indeno[1,2‐b]pyridine derivatives: Antiproliferative and antimetastatic activities against two human prostate cancer cell lines

Novel coumarin compounds potentiate the effect of cisplatin on lung cancer cells by enhancing pro-apoptotic gene expressions, G2/M cell arrest, oxidative and antiangiogenic effects

Coumarin-Based Triapine Derivatives and Their Copper(II) Complexes: Synthesis, Cytotoxicity and mR2 RNR Inhibition Activity

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