Antioxidant activity of dopamine and L-DOPA in lipid micelles and their cooperation with an analogue of α-tocopherol

Jodko-Piórecka, Katarzyna; Litwinienko, Grzegorz

doi:10.1016/j.freeradbiomed.2015.02.006

Cited by 64 publications

(55 citation statements)

References 74 publications

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“…This is possibly the first direct evidence that the SPLET mechanism is relevant in enhancing the reactivity of RTAs with peroxyl radicals (besides DPPH . ) during inhibited autoxidations in homogeneous systems; however, interestingly, a minor enhancement (+30 %) in the antioxidant performance of PMHC upon increasing the pH from 7 to 10 was recently reported in the autoxidation of a heterogeneous lipid system . Indeed, we were surprised by the modest magnitude of the “SPLET effect”.…”

Section: Resultsmentioning

confidence: 99%

“…This is possibly the first direct evidence that the SPLET mechanism is relevant in enhancingt he reactivity of RTAs with peroxyl radicals (besides DPPHC [32] )d uring inhibited autoxidations in homogeneouss ystems; however,i nterestingly,aminor enhancement (+ 30 %) in the antioxidant performance of PMHC upon increasing the pH from 7t o1 0w as recently reportedi nthe autoxidationo faheterogeneous lipid system. [33] Indeed, we were surprised by the modestm agnitude of the "SPLETe ffect". In our system, UV/Vis spectroscopy confirmed that around 60 %o fT rolox exists in the phenoxide form at pH 12 (see Figure 6), but nonethelesst he increasei nt he rate constant recorded under our settings is modest compared with kinetic solvent effects of up to orders of magnitude reportedi ni onisingo rganic solvents (e.g.,a lcohols) for acidic phenols reacting with DPPHC.…”

Section: Measurement Of K Inh For Phenols In Water:pha Nd Solvent Effmentioning

confidence: 99%

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Peroxyl Radical Reactions in Water Solution: A Gym for Proton‐Coupled Electron‐Transfer Theories

Amorati

Baschieri

Morroni

et al. 2016

Chemistry A European J

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The reactions of alkylperoxyl radicals with phenols have remained difficult to investigate in water. We describe herein a simple and reliable method based on the inhibited autoxidation of water/THF mixtures, which we calibrated against pulse radiolysis. With this method we measured the rate constants kinh for the reactions of 2-tetrahydrofuranylperoxyl radicals with reference compounds: urate, ascorbate, ferrocenes, 2,2,5,7,8-pentamethyl-6-chromanol, Trolox, 6-hydroxy-2,5,7,8-tetramethylchroman-2-acetic acid, 2,6-di-tert-butyl-4-methoxyphenol, 4-methoxyphenol, catechol and 3,5-di-tert-butylcatechol. The role of pH was investigated: the value of kinh for Trolox and 4-methoxyphenol increased 11- and 50-fold from pH 2.1 to 12, respectively, which indicate the occurrence of a SPLET-like mechanism. H(D) kinetic isotope effects combined with pH and solvent effects suggest that different types of proton-coupled electron transfer (PCET) mechanisms are involved in water: less electron-rich phenols react at low pH by concerted electron-proton transfer (EPT) to the peroxyl radical, whereas more electron-rich phenols and phenoxide anions react by multi-site EPT in which water acts as proton relay.

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Section: Resultsmentioning

confidence: 99%

Section: Measurement Of K Inh For Phenols In Water:pha Nd Solvent Effmentioning

confidence: 99%

Peroxyl Radical Reactions in Water Solution: A Gym for Proton‐Coupled Electron‐Transfer Theories

Amorati

Baschieri

Morroni

et al. 2016

Chemistry A European J

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“…The ability of NB-2 to trap peroxyl radicals was evaluated by monitoring the rate of peroxidation of methyl linoleate dispersed in the micellar system. The uptake of dissolved oxygen during peroxidation of micelles was carried out at 37 • C by using a RC650 Respirometer (Strathkelvin Instruments) equipped with a Clark-type electrode in the same way as described in one of our previous papers [30][31][32]. The samples were buffered at pH 7.0 with a Tris buffer and the chambers with magnetic stirring, containing 3 mL of micelles were saturated with oxygen.…”

Section: Methodology Of Autoxidation Measurementsmentioning

confidence: 99%

“…The micelles were prepared using a methodology described in our previous kinetic studies [30,31]. Glass test-tubes with 19 µL of methyl linoleate (LinMe) and 10.5 mL of 16 mM Triton X-100 were stirred using Vortex for 60 sec.…”

Section: Preparation Of Micellesmentioning

confidence: 99%

Hydroxycinnamyl Derived BODIPY as a Lipophilic Fluorescence Probe for Peroxyl Radicals

et al. 2020

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Herein, we describe the synthesis of a fluorescent probe NB-2 and its use for the detection of peroxyl radicals. This probe is composed of two receptor segments (4-hydroxycinnamyl moieties) sensitive towards peroxyl radicals that are conjugated with a fluorescent reporter, dipyrrometheneboron difluoride (BODIPY), whose emission changes depend on the oxidation state of the receptors. The measurement of the rate of peroxidation of methyl linoleate in a micellar system in the presence of 1.0 µM NB-2 confirmed its ability to trap lipid peroxyl radicals with the rate constant kinh = 1000 M−1·s−1, which is ten-fold smaller than for pentamethylchromanol (an analog of α-tocopherol). The reaction of NB-2 with peroxyl radicals was further studied via fluorescence measurements in methanol, with α,α′-azobisisobutyronitrile (AIBN) used as a source of radicals generated by photolysis or thermolysis, and in the micellar system at pH 7.4, with 2,2′-azobis(2-amidinopropane) (ABAP) used as a thermal source of the radicals. The reaction of NB-2 receptors with peroxyl radicals manifests itself by the strong increase of a fluorescence with a maximum at 612–616 nm, with a 14-fold enhancement of emission in methanol and a 4-fold enhancement in the micelles, as compared to the unoxidized probe. Our preliminary results indicate that NB-2 behaves as a “switch on” fluorescent probe that is suitable for sensing peroxyl radicals in an organic lipid environment and in bi-phasic dispersed lipid systems.

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“…With age, the accumulation of these biomolecules occurs and that becomes a significant risk factor for this disease. In accordance with the role of reactive oxygen species in the progression of PD, the antioxidants can potentially serve as a disease treatment [4].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Antioxidant Activity of Potassium Cis-Diaqua-Bis (Oxalato) Chromate (Iii) With Levodopa and Carbidopa

Rout

Pattanaik

Chandra

et al. 2018

Int J Pharm Pharm Sci

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Objective: These studies focus on the interaction between two clinically active antiparkinsonian drugs L-dopa (L) and carbidopa (C) with the cis-[Cr(C2O4)2(H2O)2] - Methods:The resulting synthesized complexes were characterized by UV-VIS and FTIR spectroscopy. Evaluation of antioxidant activities of this cis-[Cr(C and evaluation of the synthesized product from a coordination chemistry aspect with respect to the possibility of its antioxidant activity and its therapeutic application in the treatment of Parkinson disease. Results:The results of spectral analysis of the synthesized products indicate that complexes have a Cr(III) ion coordinated via the carboxylic and amino group. In the reduction of radical DPPH -carbidopa(MC) and standard butylated hydroxytoluene (BHT) were carried out by using 1,1-diphenyl-1-picrylhydrazyl free radical (DPPH), 2,2-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cations and hydrogen peroxide method.· and the formation of radical monocation ABTS ·+ the ability to scavenge radical was measured in these experiments by the discoloration of the solution. However, in hydrogen peroxide method, the increased in absorbance showing its scavenging potential. The scavenging capacity of the test compounds and standard on the DPPH, ABTS ·+ , H2O2 decreased in the order BHT>ML>MC>C>L which were 98.4, 96.4, 86.4, 68.3, 49.7% for DPPH, BHT>ML>L>MC>C which were 99.3, 96.9, 96.3,66.6, 53.4% for ABTS ·+ , BHT>ML>MC>L>C which were 68.8%, 52.4%, 49.6%, 43.1% and 37.7% for H2O2 Conclusion:The experimental findings showed that cis-[Cr(C at the concentration of 50 µg/ml, respectively.

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Antioxidant activity of dopamine and L-DOPA in lipid micelles and their cooperation with an analogue of α-tocopherol

Cited by 64 publications

References 74 publications

Peroxyl Radical Reactions in Water Solution: A Gym for Proton‐Coupled Electron‐Transfer Theories

Peroxyl Radical Reactions in Water Solution: A Gym for Proton‐Coupled Electron‐Transfer Theories

Hydroxycinnamyl Derived BODIPY as a Lipophilic Fluorescence Probe for Peroxyl Radicals

Synthesis, Characterization and Antioxidant Activity of Potassium Cis-Diaqua-Bis (Oxalato) Chromate (Iii) With Levodopa and Carbidopa

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