Stable ester and amide conjugates of some NSAIDs as analgesic and antiinflammatory compounds with improved biological activity

Uludag, Mecit Orhan; Ergün, Burcu Çaliskan; Alkan, Duygu Aslı

doi:10.3906/kim-1010-732

Cited by 8 publications

(6 citation statements)

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“…However, long-term reception of NSAIDs weakens their activity owing to gastrointestinal and renal side effects due to a combination of local irritations produced by their free carboxyl group and by suppression of the cytoprotective prostaglandins on gastric mucosa. 2 Magnetic nanoparticles (MNPs) offer bimodal and/or multiple capabilities in clinical use 3 due to the ability to perform as contrast agents in magnetic resonance imaging and/or in magnetic hyperthermia, whereas they are proposed as drug carriers in order to surpass the limitations that drugs undergo due to poor targeting or cytotoxicity and decreased efficacy. To our knowledge, the use of MNPs as NSAIDs carriers has not been given much attention.…”

Section: Introductionmentioning

confidence: 99%

“…The main role of NSAIDs is to block the formation of prostaglandins with the inhibition of the enzymes responsible for their production (i.e., cyclooxygenases, COX). However, long-term reception of NSAIDs weakens their activity owing to gastrointestinal and renal side effects due to a combination of local irritations produced by their free carboxyl group and by suppression of the cytoprotective prostaglandins on gastric mucosa …”

Section: Introductionmentioning

confidence: 99%

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Octadecylamine-Mediated Versatile Coating of CoFe₂O₄ NPs for the Sustained Release of Anti-Inflammatory Drug Naproxen and in Vivo Target Selectivity

Georgiadou

Makris

Papagiannopoulou

et al. 2016

ACS Appl. Mater. Interfaces

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Magnetic nanoparticles (MNPs) can play a distinct role in magnetic drug delivery via their distribution to the targeted area. The preparation of such MNPs is a challenging multiplex task that requires the optimization of size, magnetic, and surface properties for the achievement of desirable target selectivity, along with the sustained drug release as a prerequisite. In that context, CoFe2O4 MNPs with a small size of ∼7 nm and moderate saturation magnetization of ∼60 emu g(-1) were solvothermally synthesized in the presence of octadecylamine (ODA) with a view to investigate the functionalization route effect on the drug release. Synthetic regulations allowed us to prepare MNPs with aminated (AmMNPs) and amine-free (FAmMNPs) surface. The addition of the nonsteroidal anti-inflammatory drug with a carboxylate donor, Naproxen (NAP), was achieved by direct coupling with the NH2 groups, rendered by ODA, through the formation of an amide bond in the case of AmMNPs. In the case of FAmMNPs, indirect coupling of NAP was performed through an intermediate linker (polyethylenimine) and on PEG-ylated MNPs. FT-IR, (1)H NMR, (13)C NMR, and UV-vis data confirmed the addition of NAP, whereas diverse drug-release behavior was observed for the different functionalization approaches. The biological behavior of the MNPs@NAP was evaluated in vitro in rat serum and in vivo in mice, after radiolabeling with a γ-emitting radionuclide, (99m)Tc. The in vivo fate of MNPs@NAP carriers was in straightforward relation with the direct or indirect coupling of NAP. Furthermore, an inflammation was induced intramuscularly, where the directly coupled (99m)Tc-MNPs@NAP carriers showed increased accumulation at the inflammation site.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Octadecylamine-Mediated Versatile Coating of CoFe₂O₄ NPs for the Sustained Release of Anti-Inflammatory Drug Naproxen and in Vivo Target Selectivity

Georgiadou

Makris

Papagiannopoulou

et al. 2016

ACS Appl. Mater. Interfaces

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“…Ning and co-workers report the synthesis and characterization of the fluorinated product of compound 3a [40]. The second reported by us, molecule 3b, partially consists of the molecule reported by a group of Turkish scientists [41]. There was no information available in chemical databases for compounds 3c and 3d.…”

Section: Synthesismentioning

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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“…1,2,5,6 In order to minimize side effects, improve analgesic/anti-inflammatory activity, a number of NSAID derivatives were prepared and some of them were reported to have better bioavailability, less gastric irritation and improved anti-oxidant property etc. [7][8][9][10][11] Naproxen, a nonselective NSAID presents the least cardiovascular risk and provides the most effective relief for arthritic patients among all NSAIDs. 12 However, arthritic doses of naproxen are significantly toxic to the GI tract resulting from COX-1 inhibition.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Naproxen Esters and Evaluation of their In vivo and In silico Analgesic and Anti-inflammatory Activities

Akter

Mahmud

Nasiruddin

et al. 2023

Dhaka Univ. J. Pharm. Sci

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Three consecutive alkyl esters methyl (1), ethyl (2) and isopropyl (3) esters were synthesized from naproxen by direct Fischer esterification reaction and were evaluated for their in vivo and in silico analgesic and antiinflammatory activities. Methyl and ethyl ester showed potent peripheral analgesia with 82.09% and 82.59% writhing inhibition, respectively compared to that of naproxen (64.68% inhibition) at equivalent dose of 25 mg/kg bw. In antiinflammatory study, all the three esters generated 96.75%, 91.54% and 90.65% inhibition of inflammation at 5th hour, similar to that obtained by naproxen (95.12% inhibition). Molecular docking study suggested that methyl ester had the highest binding energy towards COX-2 enzyme, while isopropyl ester possessed the lowest energy, and also exhibited the lower Vander Waals interaction that might affect COX inhibition. Moreover, all the compounds had satisfactory ADME profile. Again, methyl ester satisfied the safety issues, while other compounds might have cardio toxicity. Dhaka Univ. J. Pharm. Sci. 22(1): 105-114, 2023 (June)

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Stable ester and amide conjugates of some NSAIDs as analgesic and antiinflammatory compounds with improved biological activity

Cited by 8 publications

References 0 publications

Octadecylamine-Mediated Versatile Coating of CoFe₂O₄ NPs for the Sustained Release of Anti-Inflammatory Drug Naproxen and in Vivo Target Selectivity

Octadecylamine-Mediated Versatile Coating of CoFe₂O₄ NPs for the Sustained Release of Anti-Inflammatory Drug Naproxen and in Vivo Target Selectivity

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

Synthesis of Naproxen Esters and Evaluation of their In vivo and In silico Analgesic and Anti-inflammatory Activities

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Stable ester and amide conjugates of some NSAIDs as analgesic and antiinflammatory compounds with improved biological activity

Cited by 8 publications

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Octadecylamine-Mediated Versatile Coating of CoFe2O4 NPs for the Sustained Release of Anti-Inflammatory Drug Naproxen and in Vivo Target Selectivity

Octadecylamine-Mediated Versatile Coating of CoFe2O4 NPs for the Sustained Release of Anti-Inflammatory Drug Naproxen and in Vivo Target Selectivity

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

Synthesis of Naproxen Esters and Evaluation of their In vivo and In silico Analgesic and Anti-inflammatory Activities

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Octadecylamine-Mediated Versatile Coating of CoFe₂O₄ NPs for the Sustained Release of Anti-Inflammatory Drug Naproxen and in Vivo Target Selectivity

Octadecylamine-Mediated Versatile Coating of CoFe₂O₄ NPs for the Sustained Release of Anti-Inflammatory Drug Naproxen and in Vivo Target Selectivity