Cytotoxic and apoptotic potential of some coumarin and 2-amino-3-carbonitrile selenophene derivatives in prostate cancer

Yıldırım, Metin; Erşatır, Mehmet; Arslan, Badel; Giray, Elife Sultan

doi:10.3906/kim-2008-56

Cited by 5 publications

(5 citation statements)

References 29 publications

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“…In comparison to conventional chemotherapeutic agents, organoselenium compounds such as 10–14 have excellent cytotoxic properties with low side effects [ 99 , 102 , 105 , 106 , 109 ]. Recent studies have also pointed to selenium-based nanomedicines, suggesting the design of selenium nanoparticles as an efficient strategy to improve drug delivery and thus cancer treatment [ 190 ].…”

Section: Discussionmentioning

confidence: 99%

“…The coumarin ring is present in several compounds that have shown a variety of anticancer activities (e.g., inhibition of angiogenesis), kinases or enzymes (e.g., telomerase, aromatase, carbonic anhydrase or steroid sulfatase) [ 103 , 104 ]. Yildirim et al [ 105 ] described a small series (four compounds) of coumarin hybrids with 2-aminoselenophene-3-carbonitrile ( Figure 7 ). The compounds were tested against prostate cancer on DU145 cells and showed antiproliferative activity with IC 50 ranging from 20 to 44.0 µM (higher than for the corresponding coumarin analogues).…”

Section: Selenium-containing Compounds As Therapeutic Agentsmentioning

confidence: 99%

“… Structures and activity of the most potent selenium-based hybrids 10 - 14 . Data from: a [ 99 ], b [ 102 ], c [ 105 ], d [ 106 ], e [ 109 ]. …”

Section: Figurementioning

confidence: 99%

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Selenium-Containing Agents Acting on Cancer—A New Hope?

et al. 2022

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Selenium-containing agents are more and more considered as an innovative potential treatment option for cancer. Light is shed not only on the considerable advancements made in understanding the complex biology and chemistry related to selenium-containing small molecules but also on Se-nanoparticles. Numerous Se-containing agents have been widely investigated in recent years in cancer therapy in relation to tumour development and dissemination, drug delivery, multidrug resistance (MDR) and immune system-related (anti)cancer effects. Despite numerous efforts, Se-agents apart from selenocysteine and selenomethionine have not yet reached clinical trials for cancer therapy. The purpose of this review is to provide a concise critical overview of the current state of the art in the development of highly potent target-specific Se-containing agents.

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Section: Discussionmentioning

confidence: 99%

Section: Selenium-containing Compounds As Therapeutic Agentsmentioning

confidence: 99%

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Selenium-Containing Agents Acting on Cancer—A New Hope?

et al. 2022

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“…The works of Arsenyan et al [ 16 ] and Domracheva et al [ 17 ] reported on the antioxidant and anticancer activities of seleno–coumarin isomers. Most recently, Yildirim et al [ 18 ] delved into the pharmacological effects of 3-acetyl coumarin–selenophene in DU-145 tumor cells, exploring its activities during apoptosis and oxidative stress. These findings further boost the study and investigation of the pharmacological properties of 4-(Phenylselanyl)-2H-chromen-2-one (4-PSCO), an innovative and promising compound belonging to this class of compounds on the rise.…”

Section: Introductionmentioning

confidence: 99%

4-(Phenylselanyl)-2H-chromen-2-one-Loaded Nanocapsule Suspension—A Promising Breakthrough in Pain Management: Comprehensive Molecular Docking, Formulation Design, and Toxicological and Pharmacological Assessments in Mice

da Fonseca,

Prado,

Paltian

et al. 2024

Pharmaceutics

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Therapies for the treatment of pain and inflammation continue to pose a global challenge, emphasizing the significant impact of pain on patients’ quality of life. Therefore, this study aimed to investigate the effects of 4-(Phenylselanyl)-2H-chromen-2-one (4-PSCO) on pain-associated proteins through computational molecular docking tests. A new pharmaceutical formulation based on polymeric nanocapsules was developed and characterized. The potential toxicity of 4-PSCO was assessed using Caenorhabditis elegans and Swiss mice, and its pharmacological actions through acute nociception and inflammation tests were also assessed. Our results demonstrated that 4-PSCO, in its free form, exhibited high affinity for the selected receptors, including p38 MAP kinase, peptidyl arginine deiminase type 4, phosphoinositide 3-kinase, Janus kinase 2, toll-like receptor 4, and nuclear factor-kappa β. Both free and nanoencapsulated 4-PSCO showed no toxicity in nematodes and mice. Parameters related to oxidative stress and plasma markers showed no significant change. Both treatments demonstrated antinociceptive and anti-edematogenic effects in the glutamate and hot plate tests. The nanoencapsulated form exhibited a more prolonged effect, reducing mechanical hypersensitivity in an inflammatory pain model. These findings underscore the promising potential of 4-PSCO as an alternative for the development of more effective and safer drugs for the treatment of pain and inflammation.

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“…Heterocyclic rac -2-amino-3-carbonitrile derivatives have received much attention in recent years. − In medicinal applications, rac -2-amino-3-carbonitrile derivatives have been used as antioxidants, anticancer, , and antitumor agents . Their medicinal potency as anticancer and antitumor drugs is dependent on their DNA binding affinity.…”

Section: Introductionmentioning

confidence: 99%

Classical Intermolecular Hydrogen Bonding Motifs of Heterocyclic rac-2-Amino-3-carbonitrile Derivatives: Linking Hirshfeld Surface Analysis, CT-DNA Binding Affinity, and Molecular Docking

Zamisa

Ngubane

Adeleke

et al. 2022

Crystal Growth & Design

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Four 2-amino-4-(aryl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile (Series I) and three 2-amino-1phenyl-7,7-dimethyl-5-oxo-4-(aryl)-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile (Series II) derivatives were formed via multicomponent microwave reactions as racemic mixtures. The solid-state IR spectra revealed bands in the region between 3190 and 3414 cm −1 attributed to the amino functional group's asymmetric, symmetric, and bending overtone vibration modes. Furthermore, the IR spectra of some of the compounds in each series were similar and this served as an indication of similar structural features in the solid state. This was confirmed via single-crystal X-ray diffraction. A detailed survey of the related 2-amino-3-carbonitrile derivatives in the Cambridge Structural Database revealed 12 classical intermolecular hydrogen-bonding motifs involving the amino functional group. The vast variation in the hydrogen bonding motifs was found to be caused by the type of group bonded to the 4H-pyran (in Series I) or dihydropyridine (in Series II) moiety. In this work, an unprecedented hydrogen bonding motif comprising a non-classical hydrogen bond acceptor was found in one instance. For both Series I and II, the N−H•••N and N−H•••O hydrogen bonds were investigated using noncovalent interaction (NCI) plots and molecular pairwise energy calculations. The contributions of reciprocal N•••H and O•••H contacts (attributed to N−H•••N and N−H•••O, respectively) toward the Hirshfeld surface range between 9.9 and 15.3% in Series I and between 10.8 and 15.0% in Series II. In addition, the compounds showed moderate to good binding affinity to calf thymus DNA (CT-DNA) with intrinsic binding constants (K b ) between 8.00 × 10 4 and 5.00 × 10 5 M −1 for Series I compounds and between 6.60 × 10 4 and 1.45 × 10 5 M −1 for Series II. A relationship was established between the reciprocal N•••H to O•••H contributions ratio from the Hirshfeld surface analysis and K b . Molecular docking studies of each compound's respective enantiomers into DNA were done using canonical−DNA dodecamer (B-DNA) as a model for CT-DNA. The compounds were found to interact with DNA via a minor groove-binding mode. The S-enantiomer for most of the compounds bound favorably compared to their respective R-enantiomers. The ratio of calculated ΔG for the DNA binding of the Renantiomer to that of the S-enantiomer (ΔG R /ΔG S ) follows the same positive trend as the experimental K b value for each compound in Series I while a negative trend was observed for Series II. Finally, a relationship between the Hirshfeld surface analysis and calculated ΔG values was also established in this work.

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Cytotoxic and apoptotic potential of some coumarin and 2-amino-3-carbonitrile selenophene derivatives in prostate cancer

Cited by 5 publications

References 29 publications

Selenium-Containing Agents Acting on Cancer—A New Hope?

Selenium-Containing Agents Acting on Cancer—A New Hope?

4-(Phenylselanyl)-2H-chromen-2-one-Loaded Nanocapsule Suspension—A Promising Breakthrough in Pain Management: Comprehensive Molecular Docking, Formulation Design, and Toxicological and Pharmacological Assessments in Mice

Classical Intermolecular Hydrogen Bonding Motifs of Heterocyclic rac-2-Amino-3-carbonitrile Derivatives: Linking Hirshfeld Surface Analysis, CT-DNA Binding Affinity, and Molecular Docking

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