Synthesis, structural characterization, and in vitro anti-cancer activities of new phenylacrylonitrile derivatives

Amino acid conjugates are described by the reaction of amino acids with bioactive organic groups such as vitamins, hormones, flavonoids, steroids, and sugars. In this study, 12 new conjugates were synthesized by reaction of cinnamic acid derivatives with various amino acids. Cytotoxic studies against four different human cancer cells (MCF7, PC‐3, Caco‐2, and A2780) were carried out by MTT assay method at five different concentrations. The structure‐activity relationships based on the cell viability rates were evaluated. To compare the anticancer activities of the compounds using computational chemistry methods, they were docked against A2780 human ovarian cancer, Michigan Cancer Foundation‐7 (MCF7), human prostate cancer (PC‐3) and human colon epidermal adenocarcinoma (Caco‐2) cell lines and compared with the standard 5‐Fluorouracil. The results indicate that the efficacy of cinnamic acid derivatives increases with the presence of amino acids. Comet assay was conducted to understand whether the cell deaths occur through DNA damage mechanism and the results exhibit that the changes in the specified parameters were statistically significant (p<0.05). Our study demonstrated that the compounds cause cell death through the formation of DNA damage mechanism.

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“…Each data represents an average of 10 measurements. [51] All cell viability results were determined considering control cells.…”

Section: In Vitro Cytotoxic Assay (Mtt Assay)mentioning

confidence: 99%

Synthesis of New Cinnamoyl‐Amino Acid Conjugates and in Vitro Cytotoxicity and Genotoxicity Studies

Çalışkan

Öztürk

Koran

et al. 2022

Chemistry & Biodiversity

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“…Probe MCPC, 6,7-dihydroxy-3-(4-chlorophenyl)coumarin, was successfully synthesized under microwave irradiation procedure with solvent free conditions according to the reported method in the literatures [25][26][27]. The synthesis protocols and characterization data were presented in Supplementary Information file in detail.…”

Section: Fabrication Of the Probe Mcpcmentioning

confidence: 99%

Fluorescent sensing platform for low-cost detection of Cu2+by coumarin derivative: DFT calculation and practical application in herbal and black tea samples

Savran¹,

Karagöz²,

Elmas³

et al. 2020

Turk J Chem

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A fluorogenic probe based on a coumarin-derivative for Cu 2+ sensing in CH 3 CN/H 2 O media (v/v, 95/5, 5.0 µM) was developed and applied in real samples. 3-(4-chlorophenyl)-6,7-dihydroxy-coumarin (MCPC) probe was obtained by synthetic methodologies and identified by spectral techniques. The probe MCPC showed remarkable changes with a "turn-off" fluorogenic sensing approach for the monitoring of Cu 2+ at 456 nm under an excitation wavelength of 366 nm. The response time of the probe MCPC was founded as only 1 min. The detection limit of the probe MCPC was recorded to be 1.47 nM. The binding constant and possible stoichiometric ratio (1:1) values were determined by Benesi-Hildebrand and Job's plot systems, respectively. The mechanism of the probe MCPC with Cu 2+ was further confirmed by ESI-MS and FT-IR analyses, as well as supported by theoretical calculations. Furthermore, the probe MCPC was successfully employed for the practical applications to sense Cu 2+ in different herbal and black tea samples. The proposed sensing method was also verified by ICP-OES method.

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“…2-(2,3,4-trimethoxyphenyl)-1-(3-(methylphenyl))acrylonitrile (1a) was synthesized and purified according to methods in the literature [15][16][17]. Cyclotriphosphazene compounds containing dioxybiphenyl HCP-1 and HCP-3 were synthesized as defined by Carriedo et al [18,19].…”

Section: Synthesismentioning

confidence: 99%

Design and fabrication of dioxyphenylcoumarin substituted cyclotriphosphazene compounds photodiodes

Elgazzar

Dere

Özen

et al. 2017

Physica B: Condensed Matter

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Synthesis, structural characterization, and in vitro anti-cancer activities of new phenylacrylonitrile derivatives

Cited by 20 publications

References 30 publications

Synthesis of New Cinnamoyl‐Amino Acid Conjugates and in Vitro Cytotoxicity and Genotoxicity Studies

Synthesis of New Cinnamoyl‐Amino Acid Conjugates and in Vitro Cytotoxicity and Genotoxicity Studies

Fluorescent sensing platform for low-cost detection of Cu2+by coumarin derivative: DFT calculation and practical application in herbal and black tea samples

Design and fabrication of dioxyphenylcoumarin substituted cyclotriphosphazene compounds photodiodes

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