Antioxidant activity of highly hydroxylated fullerene C60 and its interactions with the analogue of α-tocopherol

Grebowski, Jacek; Konopko, Adrian; Krokosz, Anita; DiLabio, Gino A.; Litwinienko, Grzegorz

doi:10.1016/j.freeradbiomed.2020.08.017

Cited by 31 publications

(27 citation statements)

References 75 publications

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“…LUVs were obtained by multiple extrusions (at least 21 times) in an Avanti mini extruder (Avanti Polar Lipids Inc.). Basing on the DLS method, the size distribution of LUVs was determined, and it was 170 ± 45 nm (in agreement with previously prepared LUVs 43 ). The buffer solutions were the same as those for micellar systems.…”

Section: Methodssupporting

confidence: 83%

Unexpected Role of pH and Microenvironment on the Antioxidant and Synergistic Activity of Resveratrol in Model Micellar and Liposomal Systems

Konopko

Litwinienko

2021

J. Org. Chem.

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Experimental and theoretical studies indicate that resveratrol (RSV, dietary polyphenol that effectively reduces cellular oxidative stress) is a good scavenger of hydroxyl, alkoxyl, and peroxyl radicals in homogeneous systems. However, the role of RSV as a chain-breaking antioxidant is still questioned. Here, we describe pH dependent effectiveness of RSV as an inhibitor of peroxidation of methyl linoleate in Triton X-100 micelles and in 1,2-dimyristoyl- sn -glycero-3-phosphocholine (DMPC) liposomes, with the best effectiveness at pH 6 (stoichiometric factors, n , are 4.9 and 5.6, and the rate constants for reaction with peroxyl radicals, k inh , are 1200 and 3300 M –1 s –1 in micellar and liposomal systems, respectively). We propose the mechanism in which RSV-derived radicals are coupled to dimers with recovered ability to trap lipidperoxyl radicals. The formation of such dimers is facilitated due to increased local concentration of RSV at the lipid–water interface. Good synergy of RSV with α-tocopherol analogue in micelles and liposomes is in contrast to the previously reported lack of synergy in non-polar solvents; however, the increased persistency of tocopheroxyl radicals in dispersed lipid/water systems and proximal localization of both antioxidants greatly facilitate the possible recovery of α-TOH by RSV.

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Section: Methodssupporting

confidence: 83%

Unexpected Role of pH and Microenvironment on the Antioxidant and Synergistic Activity of Resveratrol in Model Micellar and Liposomal Systems

Konopko

Litwinienko

2021

J. Org. Chem.

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“…Different strategies have been considered to increase fullerene‐based PS’s hydrophilicity to attend a better cell membrane affinity. For instance, C 60 has been polyhydroxylated (37), attached to peptides and proteins (38), amino acids (38, 39), and functionalized with cationic groups (40). The addition of azomethine ylide to C 60 through the decarboxylation route, is an adequate methodology toward the development of substituted fullerene derivatives.…”

Section: Resultsmentioning

confidence: 99%

Tuning the Polarity of Fullerene C₆₀ Derivatives for Enhanced Photodynamic Inactivation^†

Palacios

Durantini

Heredia

et al. 2021

Photochem & Photobiology

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In this article, four novel fulleropyrrolidines derivatives were synthesized to study how the effect of polarity and positive charge distribution can influence the efficacy of photodynamic inactivation treatments to kill bacteria. The design of the photosensitizers was based on DFT calculations that allowed us to estimate the dipolar moment of the molecules. Neutral compounds bearing N-methyl bis-acetoxy-ethyl (1) and bis-hydroxyethyl (2) amine were the starting material to obtain the dicationic analogs N,N-dimethyl bis-methoxyethyl (3), and bis-acetoxy-ethyl) (4) methylammonio. As expected from fullerene C 60 derivatives, compounds 1-4 absorb in the UV region, with a peak at 430 nm, a broader range of absorption up to 710 nm, and exhibit weak fluorescence emission in toluene and reverse micelles. In the biomimetic AOT micellar system, the highest singlet oxygen photosensitization was found for compounds 1, followed by 3, 2, and 4. Whereas 4 was the most effective reducing nitro blue tetrazolium in the presence of β-NADH. The influence of type I and type II mechanism on the photodynamic activity of compounds 3 and 4 was further examined in the presence of Ltryptophan and two reactive oxygen species scavengers. In vitro experiments indicated that the compounds with the highest dipolar moments, 3 (37.19 D) and 4 (38.46 D), inactivated methicillin-resistant Staphylococcus aureus and Escherichia coli bacteria using an energy dose <2.4 J cm −2 . No inactivation was observed for the neutral analogs with the lowest dipolar moments. These findings help to optimize sensitizer structures to improve photodynamic inactivation.

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“…This equipment works best in air and in water but is incompatible with organic solvents [89,113]. A second method suitable for aqueous systems is based on a polarographic Clark electrode, that produces a current that is proportional to the amount of O 2 that reaches the electrode tip after crossing a polymeric membrane [114].…”

Section: Advantages Of Oximetrymentioning

confidence: 99%

Methods to Determine Chain-Breaking Antioxidant Activity of Nanomaterials beyond DPPH•. A Review

Baschieri

Amorati

2021

Antioxidants

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This review highlights the progress made in recent years in understanding the mechanism of action of nanomaterials with antioxidant activity and in the chemical methods used to evaluate their activity. Nanomaterials represent one of the most recent frontiers in the research for improved antioxidants, but further development is hampered by a poor characterization of the ‘‘antioxidant activity’’ property and by using oversimplified chemical methods. Inhibited autoxidation experiments provide valuable information about the interaction with the most important radicals involved in the lipid oxidation, namely alkylperoxyl and hydroperoxyl radicals, and demonstrate unambiguously the ability to stop the oxidation of organic materials. It is proposed that autoxidation methods should always complement (and possibly replace) the use of assays based on the quenching of stable radicals (such as DPPH• and ABTS•+). The mechanisms leading to the inhibition of the autoxidation (sacrificial and catalytic radical trapping antioxidant activity) are described in the context of nanoantioxidants. Guidelines for the selection of the appropriate testing conditions and of meaningful kinetic analysis are also given.

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Antioxidant activity of highly hydroxylated fullerene C60 and its interactions with the analogue of α-tocopherol

Cited by 31 publications

References 75 publications

Unexpected Role of pH and Microenvironment on the Antioxidant and Synergistic Activity of Resveratrol in Model Micellar and Liposomal Systems

Unexpected Role of pH and Microenvironment on the Antioxidant and Synergistic Activity of Resveratrol in Model Micellar and Liposomal Systems

Tuning the Polarity of Fullerene C₆₀ Derivatives for Enhanced Photodynamic Inactivation^†

Methods to Determine Chain-Breaking Antioxidant Activity of Nanomaterials beyond DPPH•. A Review

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Antioxidant activity of highly hydroxylated fullerene C60 and its interactions with the analogue of α-tocopherol

Cited by 31 publications

References 75 publications

Unexpected Role of pH and Microenvironment on the Antioxidant and Synergistic Activity of Resveratrol in Model Micellar and Liposomal Systems

Unexpected Role of pH and Microenvironment on the Antioxidant and Synergistic Activity of Resveratrol in Model Micellar and Liposomal Systems

Tuning the Polarity of Fullerene C60 Derivatives for Enhanced Photodynamic Inactivation†

Methods to Determine Chain-Breaking Antioxidant Activity of Nanomaterials beyond DPPH•. A Review

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Tuning the Polarity of Fullerene C₆₀ Derivatives for Enhanced Photodynamic Inactivation^†