Selective cytotoxicity and apoptosis induction in glioma cell lines by 5-oxygenated-6,7-methylenedioxycoumarins from Pterocaulon species

Vianna, Débora Renz Barreto; Hamerski, Lidilhone; Figueiró, Fabrício; Bernardi, Andressa; Visentin, Lorenzo C.; Pires, Elisa Nicoloso Simões; Teixeira, Hélder Ferreira; Salbego, Christianne Gazzana; Eifler‐Lima, Vera Lucia; Battastini, Ana Maria Oliveira; Poser, Gilsane Lino von; Pinto, Ângelo C.

doi:10.1016/j.ejmech.2012.09.007

Cited by 48 publications

(35 citation statements)

References 31 publications

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“…These compounds have become of importance in recent years due to their various biological activities. Previous biological activity studies performed on coumarin derivatives revealed that these compounds have antitumor [ 9 ], photochemotherapy, anti-HIV [ 10 , 11 ], antibacterial and antifungal [ 12 , 13 ], anti-inflammatory [ 14 , 15 , 16 ], anticoagulant [inhibitors of the enzyme VKOR (vitamin K epoxide reductase)] [ 17 , 18 ], triglycerides lowering [ 19 ] and central nervous system stimulant effects [ 20 ]. However, a strong antioxidant and protective effect against oxidative stress by scavenging the reactive oxygen species has also been reported for hydroxycoumarins [ 21 ].…”

Section: Introductionmentioning

confidence: 99%

Coumarins and Coumarin-Related Compounds in Pharmacotherapy of Cancer

Akkol

Genç

Karpuz

et al. 2020

Cancers

312

120

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Cancer is one of the most common causes of disease-related deaths worldwide. Despite the discovery of many chemotherapeutic drugs that inhibit uncontrolled cell division processes for the treatment of various cancers, serious side effects of these drugs are a crucial disadvantage. In addition, multi-drug resistance is another important problem in anticancer treatment. Due to problems such as cytotoxicity and drug resistance, many investigations are being conducted to discover and develop effective anticancer drugs. In recent years, researchers have focused on the anticancer activity coumarins, due to their high biological activity and low toxicity. Coumarins are commonly used in the treatment of prostate cancer, renal cell carcinoma and leukemia, and they also have the ability to counteract the side effects caused by radiotherapy. Both natural and synthetic coumarin derivatives draw attention due to their photochemotherapy and therapeutic applications in cancer. In this review, a compilation of various research reports on coumarins with anticancer activity and investigation and a review of structure-activity relationship studies on coumarin core are presented. Determination of important structural features around the coumarin core may help researchers to design and develop new analogues with a strong anticancer effect and reduce the potential side effects of existing therapeutics.

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Section: Introductionmentioning

confidence: 99%

Coumarins and Coumarin-Related Compounds in Pharmacotherapy of Cancer

Akkol

Genç

Karpuz

et al. 2020

Cancers

312

120

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“…5 Research has also demonstrated the selective cytotoxicity of coumarins for tumor cells as well as their influence on the regulation of immune response, cell growth and differentiation. 6,7 The physical, pharmacological and therapeutic properties of coumarins are adjusted by the substitution of a heterocyclic moiety as a substituent or as a fused component in the coumarin skeleton. 8 The investigations of metal-based drugs have become an interesting subject for bioinorganic chemists.…”

Section: Introductionmentioning

confidence: 99%

Crystal Structure, Hirshfeld Surface Analysis and Biological Activities of trans-Dipyridinebis (3-Acetyl-2-Oxo-2H-Chromen-4-Olato)Cobalt(II)

Bejaoui¹,

Rohlíček²,

Eigner³

et al. 2019

ACSi

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The novel cobalt(II) complex, trans-dipyridinebis(3-acetyl-2-oxo-2H-chromen-4-olato)cobalt(II), was synthesized in ethanol. The coordination sphere of the cobalt cation was elucidated using single-crystal X-ray diffraction analysis and spectroscopic techniques (FT-IR, UV-Visible and fluorescence). Hirshfeld surface analysis indicates that hydrogen bond interactions, such as C-H•••O hydrogen bonding between the oxygen of lactone group and the pyridine appear as a primary interaction between the complex's molecules. The presence of π-π stacking was evident by the shape index and curvature. Analysis of 2D fingerprint plots confirm that intermolecular H•••H, C•••H and H•••O interactions are well dominated and are in complement to the Hirshfeld surface. The metal-ligand coordination strongly influences the fluorescence intensity (the fluorescence quenching) and the offset of the emission wavelength. The metal complex was monitored for antimicrobial activity using the disk diffusion method and showed significant activity compared to the coumarin ligand.

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“…Coumarins are a large class of compounds that display a wide variety of interesting biological properties [2][3][4][5][6][7], being their 2H-chromen-2-one nuclei the structural feature responsible for this "privileged" pharmacological profile. This planar ring system is composed by one aromatic ring, capable of establishing hydrophobic, π-π, CH-π and cation-π interactions, and one lactone ring, which contains two oxygen atoms that may interact via hydrogen bonding with a series of amino acid residues, such as serine, threonine, cysteine, asparagine, glutamine, and tyrosine [8].…”

Section: Introductionmentioning

confidence: 99%

1-[2-(4-Methyl-7-coumarinyloxy)ethyl]-4-(5-{1-[2-(4-methyl-7-coumarinyloxy)ethyl]-1H-1,2,3-triazol-4-yl}pentyl)-1H-1,2,3-triazole

Torres

Azambuja

Gonçalves

et al. 2016

Molbank

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Nature often produces compounds with a high degree of symmetry to reduce structural information and complexity. Synthesis of identical twin drugs, through the linkage of two identical pharmacophoric entities, is a classical strategy to produce more potent and/or selective drugs. Herein, two units of the privileged core of the coumarin hymecromone were linked together using "click chemistry". Synthesis of 1-[2-(4-Methyl-7-coumarinyloxy)ethyl]-4-(5-{1-[2-(4-methyl-7-coumarinyloxy)ethyl]-1H-1,2,3-triazol-4-yl}pentyl)-1H-1,2,3-triazole was achieved by coupling of two identical units of an azido coumarin with a symmetrical alkine using copper(I)-catalyzed alkyne-azide cycloaddition reaction, in good yields and with complete regioselectivity.

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Selective cytotoxicity and apoptosis induction in glioma cell lines by 5-oxygenated-6,7-methylenedioxycoumarins from Pterocaulon species

Cited by 48 publications

References 31 publications

Coumarins and Coumarin-Related Compounds in Pharmacotherapy of Cancer

Coumarins and Coumarin-Related Compounds in Pharmacotherapy of Cancer

Crystal Structure, Hirshfeld Surface Analysis and Biological Activities of trans-Dipyridinebis (3-Acetyl-2-Oxo-2H-Chromen-4-Olato)Cobalt(II)

1-[2-(4-Methyl-7-coumarinyloxy)ethyl]-4-(5-{1-[2-(4-methyl-7-coumarinyloxy)ethyl]-1H-1,2,3-triazol-4-yl}pentyl)-1H-1,2,3-triazole

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