Investigation of the radical scavenging potential of vanillin-based pyrido-dipyrimidines: experimental and <i>in silico</i> approach

Janković, Nenad; Tadić, Julijana; Milović, Emilija; Marković, Zoran; Jeremić, Svetlana; Petronijević, Jelena; Joksimović, Nenad; Borović, Teona Teodora; Bukhari, Syed Nasir Abbas

doi:10.1039/d3ra02469e

Cited by 5 publications

(2 citation statements)

References 51 publications

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“…The scavenging capacity on DPPH radicals was in the order of 13/14 > 23/24 > 19/20 > 21/22 > 15/16 > 17/18 > 11/12. Additionally, the Trolox equivalent antioxidant capacity (TEAC) was calculated [31,32]. The obtained results were as follows: 0.19 (for 13/14), 0.18 (for 23/24), 0.10 (for 19/20), 0.07 (for 21/22, 15/16, and 17/18), and 0.03 for 11/12.…”

Section: Resultsmentioning

confidence: 99%

“…For this purpose, the calibration curve of inhibition ratio (%DPPH) vs. TE concentration was prepared and presented in the Supporting Information (Figure S22). Finally, the results of DPPH radical scavenging activity by β-carbonyl selenides were presented as Trolox equivalent antioxidant capacity (TEAC) and calculated as follows [31,32]:…”

Section: Dpph Radical Scavenging Assaymentioning

confidence: 99%

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Synthesis of New Chiral β-Carbonyl Selenides with Antioxidant and Anticancer Activity Evaluation—Part I

Laskowska,

Pacuła-Miszewska,

Obieziurska-Fabisiak

et al. 2024

Materials

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A series of unsymmetrical phenyl β-carbonyl selenides with o-amido function substituted on the nitrogen atom with chiral alkyl groups was obtained. The compounds form a series of enantiomeric and diastereomeric pairs and present the first examples of this type of chiral Se derivatives. All obtained selenides were further evaluated as antioxidants and anticancer agents to define the influence of the particular stereochemistry of the attached functional groups on the bioactivity of the molecules. The highest H2O2 reduction potential was observed for N-(cis-2-hydroxy-1-indanyl)-2-((2-oxopropyl)selanyl)benzamide, and the best radical scavenging properties for N-(-1-hydroxy-2-butanyl)-2-((2-oxopropyl)selanyl)benzamide. Also, both enantiomers of the N-(1-hydroxy-2-butanyl) selenide expressed the highest cytotoxic potential towards human promyelocytic leukemia HL-60 cell line with similar IC50 values 14.4 ± 0.5 and 16.2 ± 1.1 µM, respectively. On the other hand, breast cancer cell line MCF-7 was most sensitive to N-((R)-(-)-1-hydroxy-2-butanyl)- 2-((2-oxopropyl)selanyl)benzamide (IC50 of 35.7 ± 0.6 µM). The structure–activity dependence of the obtained Se derivatives was discussed, and the most potent compounds were selected.

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Section: Resultsmentioning

confidence: 99%

Section: Dpph Radical Scavenging Assaymentioning

confidence: 99%

Synthesis of New Chiral β-Carbonyl Selenides with Antioxidant and Anticancer Activity Evaluation—Part I

Laskowska,

Pacuła-Miszewska,

Obieziurska-Fabisiak

et al. 2024

Materials

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Exploring the Bioactive Potential of Pinus mugo Turra Essential Oil: Volatile Composition, Antioxidant, Antimicrobial, Antibiofilm and Insecticidal Activities

Kačániová,

Vukic,

Čmiková

et al. 2024

Flavour & Fragrance J

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Pinus represents a potential source of valuable bioactive substances. In this study, the chemical composition and biological activity of essential oils extracted from Pinus mugo Turra needles (PMEO) were investigated. GC/MS analyses were used to assess the volatile elements found in the PMEO sample. The antioxidant activity was evaluated using DPPH and ABTS techniques. Antimicrobial properties were evaluated against yeasts and bacteria (both Gram‐positive and Gram‐negative) using the disc diffusion method, minimal inhibition concentration and vapour phase on fruit and vegetable models. Mass spectrometry and the crystal violet technique were used to measure the antibiofilm activity. The contact application method was used to assess the insecticidal activity of different concentration of PMEO against Harmonia axyridis. The GC/MS analysis identified β‐phellandrene (20.5%), α‐pinene (19.4%), δ‐3‐carene (16.7%), β‐pinene (11.1%) and β‐myrcene (9.4%) as main constituents. PMEO exhibited antioxidant activity against DPPH and ABTS radical species, with IC50 values of 1.92 and 1.14 mg/mL, respectively. PMEO showed an inhibitory effect against microbial strains ranging from 6.67 to 13.33 mm. By employing the microdilution method, PMEO showed antimicrobial activity with MIC50 values ranging from 2.52 to 7.41 mg/mL and MIC90 values ranging from 2.72 to 7.7 mg/mL. The in situ antimicrobial investigations revealed that PMEO exerts the highest activity against E. aerogenes and P. putida on apple and beetroot models. Furthermore, PMEO exhibited noteworthy potential against biofilm‐forming S. enterica growing on plastic and glass surfaces. Additionally, an evaluation of the PMEO insecticidal potential was performed using H. axyridis. Insecticidal properties against H. axyridis were observed at concentrations of 50% and 100%. PMEO displayed good antioxidant, antibacterial and insecticidal properties, significant antibiofilm features and excellent preservative properties for extending the shelf life of foods.

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Investigation of the antimicrobial potential of selected pyrido-dipyrimidines: A computational approach to Gyrase inhibition

Janković,

Jeremić,

Matić

et al. 2024

Journal of Molecular Structure

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Investigation of the radical scavenging potential of vanillin-based pyrido-dipyrimidines: experimental and in silico approach

Abstract: The tested compounds showed significant antioxidant activity (ABTS and DPPH assays). Pyrido-dipyrimidine containing two aromatic OH groups has the highest TEAC values, which indicates its stronger antioxidant activity compared to trolox.

Cited by 5 publications

References 51 publications

Synthesis of New Chiral β-Carbonyl Selenides with Antioxidant and Anticancer Activity Evaluation—Part I

Synthesis of New Chiral β-Carbonyl Selenides with Antioxidant and Anticancer Activity Evaluation—Part I

Exploring the Bioactive Potential of Pinus mugo Turra Essential Oil: Volatile Composition, Antioxidant, Antimicrobial, Antibiofilm and Insecticidal Activities

Investigation of the antimicrobial potential of selected pyrido-dipyrimidines: A computational approach to Gyrase inhibition

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