Synthesis of diaryl urea derivatives and evaluation of their antiproliferative activities in colon adenocarcinoma

GÖMEÇ, Muhammed; Yulak, Fatih; Gezegen, Hayreddin; Özkaraca, Mustafa; Sayın, Koray; Ataseven, Hilmi

doi:10.1016/j.molstruc.2021.132318

Cited by 8 publications

(6 citation statements)

References 30 publications

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“…The molecule with the highest interaction of molecules with anti‐oxidant and enzyme proteins has the most negative docking score value. Chemical interactions that occur between molecules and proteins are hydrogen bonds, polar and hydrophobic interactions, π‐π and halogen [40–44] . These interactions of molecules in RM with anti‐oxidant and enzyme proteins are given in Figures 6, 7, 8, 9, and 10.…”

Section: Resultsmentioning

confidence: 99%

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The Evaluation of Anticancer, Antioxidant, Antidiabetic and Anticholinergic Potentials of Endemic Rhabdosciadium microcalycinum Supported by Molecular Docking Study

et al. 2022

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Lung cancer is the most common cancer worldwide and the leading cause of cancer‐related death. Plant‐derived natural products and compounds are an inspiring source of chemotherapeutic agents. Alzheimer's disease (AD) is linked to the decline of acetylcholine (ACh) effects in the brain, so acetylcholinesterase (AChE) inhibitors are important in the treatment of AD. In this study, the chemical components and bioactivity of ethanolic extract of Rhabdosciadium microcalycinum (RM) was investigated by various methods. The lipophilic components of RM was determined by gas chromagraphy‐mass spectrometry (GC‐MS). Antioxidant activicty tests were evaluated with FCAP (Ferrous chelating antioxidant power assay), FRAP (Ferric reducing antioxidant power assay), ABTS (2,2′‐Azino‐bis(3‐ethylbenzothiazoline‐6‐sulfonic acid) diammonium salt assay) and DPPH (2,2‐diphenyl‐1‐picrylhydrazyl assay). The anticancer effect of RM was evaluated by WST‐1 (4‐[3‐(4‐iodophenyl)‐2‐(4‐nitrophenyl)‐2H‐5‐tetrazolio]‐1,3‐benzene disulfonate), colony formation, wound healing and CDDE (cell death detection Elisa) analysis on A549 lung cancer cells. Enzyme inhibition effects of RM was determined against AChE and α‐glycosidase (AG) enzymes. According to the results of molecular docking found in the study; With a docking score of −4.56 for HP5 protein, −6.23 for BXO protein, −5.25 for AFI protein, −3.90 for gly protein and −7.74 for AChE protein, Telecinobufagin molecule was found to have higher activity than other molecules. After docking calculations, Absorption, Distribution, Metabolism, Excretion and Toxicity (ADME/T) analysis was performed to examine the effects and reactions of molecules on human metabolism. RM inhibited the viability of A549 cells dose‐dependent manner (IC50=117.15±8.58 μg/mL), and it was also observed that RM suppressed colony formation, prevented cell migration and directed the cells to apoptosis. RM has important lipophilic components, and significant antioxidant and enzyme inhibition potential. IC50 values of RM for AChE and AG enzymes were found as 35.86 mg/mL, and 10.14 mg/mL, respectively. In conclusion, the findings of this study reveal that ethanol extract from the aerial part of Rhabdosciadium microcalycinum may be a potential therapeutic agent for the treatment of human lung cancer and Alzheimer's disease, due to its phytochemical components.

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Section: Resultsmentioning

confidence: 99%

“…Chemical interactions that occur between molecules and proteins are hydrogen bonds, polar and hydrophobic interactions, π-π and halogen. [40][41][42][43][44] These interactions of molecules in RM with anti-oxidant and enzyme proteins are given in Figures 6, 7, 8, 9, and 10.…”

Section: Chemistryselect Molecular Docking Calculationmentioning

confidence: 99%

The Evaluation of Anticancer, Antioxidant, Antidiabetic and Anticholinergic Potentials of Endemic Rhabdosciadium microcalycinum Supported by Molecular Docking Study

et al. 2022

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“…These chemical interactions between the compound and cancer proteins are hydrogen bonds, polar and hydrophobic interactions, π–π, and halogen. [ 72 ] The interactions of molecules with cancer proteins and the parameters obtained from this interaction are given in Table 3 and Figures 6–9.…”

Section: Resultsmentioning

confidence: 99%

Quinoline‐fused both non‐peripheral and peripheral Zn^IIand Mg^IIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

Yalazan

Tüzün

Akkaya

et al. 2022

Applied Organom Chemis

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Quinoline-fused Zn II (ZnPc p /ZnPc np ) and Mg II (MgPc p /MgPc np ) phthalocyanines with four 4-methylquinolin-2-ol (1) at non-peripheral or peripheral positions of the phthalocyanine core have been synthesized via cyclotetramerization of phthalonitrile derivatives (CN p /CN np ) in the presence of zinc (II) and magnesium (II) metal ions in this study. After synthesis and characterization processes, anti-cholinesterase, anti-α-glucosidase, DNA nuclease, antioxidant activities, and in silico calculations of both peripheral and non-peripheral Zn II and Mg II phthalocyanines were investigated. The inhibitory effects of metallated phthalocyanines on acetylcholinesterase, butyrylcholinesterase, and α-glucosidase enzymes were tested by spectrophotometric method. Theoretical methods are used to compare both the chemical and biological activities of the studied phthalonitrile derivatives and metallated phthalocyanine compounds.

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“…The designed compounds were predicted to target the estrogen receptor and were assessed for antiproliferative activity against the estrogen receptor (+) breast cancer cell line MCF-7. 17 was the most potent compound of the series with an estimated MCF-7 IC 50 around 20 μM, but no cytotoxicity in healthy fibroblast cells (Gömeç et al, 2022).…”

Section: Future Perspective and Outlook On Novel Compoundsmentioning

confidence: 94%

“…Briefly, 16 potentially being able to bind to Hsp90 revealed the importance of the urea moiety to effectively interact with the target. The urea forms three H-bonds with Gly97 and Lys58 involving the NH and the carbonyl, respectively ( Gömeç et al, 2022 ). In a following study, the same authors reported the anticancer investigation of another set of diphenyl ureas.…”

Section: Future Perspective and Outlook On Novel Compoundsmentioning

confidence: 99%

Urea-based anticancer agents. Exploring 100-years of research with an eye to the future

et al. 2022

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Suramin was the first urea-based drug to be approved in clinic, and in the following century a number of milestone drugs based on this scaffold were developed. Indeed, urea soon became a privileged scaffold in medicinal chemistry for its capability to establish a peculiar network of drug−target interactions, for its physicochemical properties that are useful for tuning the druggability of the new chemical entities, and for its structural and synthetic versatility that opened the door to numerous drug design possibilities. In this review, we highlight the relevance of the urea moiety in the medicinal chemistry scenario of anticancer drugs with a special focus on the kinase inhibitors for which this scaffold represented and still represents a pivotal pharmacophoric feature. A general outlook on the approved drugs, recent patents, and current research in this field is herein provided, and the role of the urea moiety in the drug discovery process is discussed form a medicinal chemistry standpoint. We believe that the present review can benefit both academia and pharmaceutical companies’ medicinal chemists to prompt research towards new urea derivatives as anticancer agents.

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Synthesis of diaryl urea derivatives and evaluation of their antiproliferative activities in colon adenocarcinoma

Cited by 8 publications

References 30 publications

The Evaluation of Anticancer, Antioxidant, Antidiabetic and Anticholinergic Potentials of Endemic Rhabdosciadium microcalycinum Supported by Molecular Docking Study

The Evaluation of Anticancer, Antioxidant, Antidiabetic and Anticholinergic Potentials of Endemic Rhabdosciadium microcalycinum Supported by Molecular Docking Study

Quinoline‐fused both non‐peripheral and peripheral Zn^IIand Mg^IIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

Urea-based anticancer agents. Exploring 100-years of research with an eye to the future

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Synthesis of diaryl urea derivatives and evaluation of their antiproliferative activities in colon adenocarcinoma

Cited by 8 publications

References 30 publications

The Evaluation of Anticancer, Antioxidant, Antidiabetic and Anticholinergic Potentials of Endemic Rhabdosciadium microcalycinum Supported by Molecular Docking Study

The Evaluation of Anticancer, Antioxidant, Antidiabetic and Anticholinergic Potentials of Endemic Rhabdosciadium microcalycinum Supported by Molecular Docking Study

Quinoline‐fused both non‐peripheral and peripheral ZnIIand MgIIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

Urea-based anticancer agents. Exploring 100-years of research with an eye to the future

Contact Info

Product

Resources

About

Quinoline‐fused both non‐peripheral and peripheral Zn^IIand Mg^IIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies