Synthesis of New 1,2,3,4-Tetrahydroquinoline Hybrid of Ibuprofen and Its Biological Evaluation

Manolov, Stanimir; Ivanov, Iliyan; Bojilov, Dimitar

doi:10.3390/m1350

Cited by 6 publications

(10 citation statements)

References 36 publications

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“…However, it is essential to disturb the equilibrium of the antioxidant system and incorporate external antioxidants. This, in turn, mitigates aging processes and safeguards against the disruption of the internal antioxidant system [ 22 ]. In the current study, we explored the potential of newly synthesized flurbiprofen derivatives to function as exogenous antioxidants by neutralizing H 2 O 2 .…”

Section: Resultsmentioning

confidence: 99%

“…The Manolov et al method was used to assess the hydrogen peroxide scavenging capability [ 22 ]. A 43 mM solution of H 2 O 2 was prepared in potassium phosphate buffer solution (0.2 M, pH 7.4).…”

Section: Methodsmentioning

confidence: 99%

“…In vitro analysis of anti-inflammatory activity was assessed as inhibition of albumin denaturation (IAD). The analysis was performed according Manolov et al method [ 22 ]. The experiment was performed with human albumin.…”

Section: Methodsmentioning

confidence: 99%

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Novel Flurbiprofen Derivatives as Antioxidant and Anti-Inflammatory Agents: Synthesis, In Silico, and In Vitro Biological Evaluation

Ivanov,

Manolov,

Bojilov

et al. 2024

Molecules

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In this study, we present the synthesis of five novel compounds by combining flurbiprofen with various substituted 2-phenethylamines. The synthesized derivatives underwent comprehensive characterization using techniques such as 1H- and 13C-NMR spectroscopy, UV-Vis spectroscopy, and high-resolution mass spectrometry (HRMS). Detailed HRMS analysis was performed for each of these newly created molecules. The biological activities of these compounds were assessed through in vitro experiments to evaluate their potential as anti-inflammatory and antioxidant agents. Furthermore, the lipophilicity of these derivatives was determined, both theoretically using the cLogP method and experimentally through partition coefficient (RM) measurements. To gain insights into their binding affinity, we conducted an in silico analysis of the compounds’ interactions with human serum albumin (HSA) using molecular docking studies. Our findings reveal that all of the newly synthesized compounds exhibit significant anti-inflammatory and antioxidant activities, with results statistically comparable to the reference compounds. Molecular docking studies further explain the observed in vitro results, shedding light on the molecular mechanisms behind their biological activities. Using in silico method, toxicity was calculated, resulting in LD50 values. Depending on the administration route, the novel flurbiprofen derivatives show lower toxicity compared to the standard flurbiprofen.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Novel Flurbiprofen Derivatives as Antioxidant and Anti-Inflammatory Agents: Synthesis, In Silico, and In Vitro Biological Evaluation

Ivanov,

Manolov,

Bojilov

et al. 2024

Molecules

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“…The Manolov et al method was used to assess the hydrogen peroxide scavenging capability [17]. A 43 mM solution of H 2 O 2 was prepared in a potassium phosphate buffer solution (0.2 M, pH 7.4).…”

Section: In Vitro Analysis 241 Hydrogen Peroxide Scavenging Activity ...mentioning

confidence: 99%

Synthesis, Molecular Docking, Molecular Dynamics Studies, and In Vitro Biological Evaluation of New Biofunctional Ketoprofen Derivatives with Different N-Containing Heterocycles

Manolov,

Bojilov,

Ivanov

et al. 2023

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Herein, we report the synthesis of four new hybrid molecules between ketoprofen or 2-(3-benzoylphenyl)propanoic acid and N-containing heterocyclic compounds, such as piperidine, pyrrolidine, 1,2,3,4-tetrahydroquinoline, and 1,2,3,4-tetrahydroisoquinoline. The obtained hybrid compounds were fully characterized using 1H- and 13C-NMR, UV-Vis, and HRMS spectra. Detailed HRMS analysis is provided for all novel hybrid molecules. The compounds were assessed for their in vitro anti-inflammatory and antioxidant activity. The lipophilicity of the hybrids was determined, both theoretically (cLogP) and experimentally (RM). The affinity of the compounds to the human serum albumin was assessed in silico by molecular docking study using two software, and the stability of the predicted complexes was evaluated by molecular dynamics study. All novel hybrids have shown very good HPSA activity, statistically close when compared to the reference—quercetin. The molecular docking confirmed the obtained in vitro results. Tetrahydroquinoline derivative 3c and tetrahydroisoquinoline derivative 3d have the highest affinity for albumin. They show stronger anti-inflammatory action than their predecessor, ketoprofen and the regularly used ibuprofen.

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“…The identification of flavonoids was made on the basis of two scan events: full scan MS mode and MS/MS experiment, and by comparing the chromatographic and the mass spectral data of the investigated compounds with those of rutin, quercetin 3-β-D-glucoside, quercetin 3-β-D-galactoside, quercetin, and hispidulin. The Manolov et al approach was used to evaluate the capacity to scavenge hydrogen peroxide [54]. A 43 mM solution of H 2 O 2 was prepared in potassium phosphate buffer solution (0.2 M, pH 7.4).…”

Section: Identification Of Flavonoids By Orbitrap Uhplc-ms/msmentioning

confidence: 99%

Characterization of Polyphenols from Chenopodium botrys after Fractionation with Different Solvents and Study of Their In Vitro Biological Activity

Bojilov,

Manolov,

Nacheva

et al. 2023

Molecules

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In the present work, we have investigated the polyphenolic composition of Chenopodium botrys from Bulgaria. The polyphenols were fractionated with solvents of varying polarity (n-hexane, chloroform, ethyl acetate, and n-butanol). The fractions were analyzed by HPLC-PDA and UHPLC-MS. The ethyl acetate fraction contained mono- and di-glycosides of quercetin, di-glycosides of kaempferol, and isorhamnetin and monoglycosides of hispidulin and jaceosidine. We found quercetin triglycosides in the butanol fraction. The ethyl acetate and butanol fractions contained 168.82 mg/g Extr and 67.21 mg/g Extr of quercetin glycosides, respectively. The main components of the polyphenolic complex in C. botrys were 6-methoxyflavones (355.47 mg/g Extr), which were found in the chloroform fraction. The flavonoids pectolinarigenin, demethylnobiletin, and isosinensetin, and the glycosides of quercetin (triglycosides, acylglycosides), kaempferol, isorhamnetin, hispidiulin, and jaceosidine, were discovered and reported in Chenopodium botrys for the first time. We used in vitro methods to assess the biological activity against oxidative stress (hydrogen peroxide scavenging activity (HPSA) and hydroxyl radical scavenging activity (HRSA)), nitrosative stress (nitric oxide scavenging activity (NOSA)), anti-inflammatory activity (IAD inhibition), and anti-tryptic activity (ATA). Quercetin mono- and di-glycosides exhibited greater HPSA and HRSA (IC50 = 39.18, 105.03 µg/mL), while 6-methoxyflavones had a greater NOSA (IC50 = 146.59 µg/mL). The same components showed the highest ATA (IC50 ranging from 116.23 to 202.44 µg/mL).

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Synthesis of New 1,2,3,4-Tetrahydroquinoline Hybrid of Ibuprofen and Its Biological Evaluation

Cited by 6 publications

References 36 publications

Novel Flurbiprofen Derivatives as Antioxidant and Anti-Inflammatory Agents: Synthesis, In Silico, and In Vitro Biological Evaluation

Novel Flurbiprofen Derivatives as Antioxidant and Anti-Inflammatory Agents: Synthesis, In Silico, and In Vitro Biological Evaluation

Synthesis, Molecular Docking, Molecular Dynamics Studies, and In Vitro Biological Evaluation of New Biofunctional Ketoprofen Derivatives with Different N-Containing Heterocycles

Characterization of Polyphenols from Chenopodium botrys after Fractionation with Different Solvents and Study of Their In Vitro Biological Activity

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