Antioxidant effect of cardanol in mixed nanoformulations with pluronic

Zaccheroni, Nelsi; Amorati, Riccardo; Mezzina, Elisabetta; Baschieri, Andrea; Palomba, Francesco; Prata, Cecilia; Facchini, Carlotta; Guernelli, Susanna

doi:10.1016/j.molliq.2020.113822

Cited by 6 publications

(3 citation statements)

References 55 publications

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“…Oxygen consumption during autoxidation experiments was measured with an optical oxygen meter (Firesting O 2 , Pyro Science GmbH). 47 Typical samples consisted of ABCV 27 mM, NaOH 54 mM, THF (10 or 25% v/v), pH 7.4 0.1 M phosphate buffer, 30 °C. Using the α-tocopherol hydrosoluble analogue Trolox as a reference antioxidant (having n = 2), the rate of radical initiation was calculated as R i = 1.6 × 10 –9 M s –1 for [ABCV] = 27 mM by the relation R i = 2[Trolox]/τ, where τ is the duration of the inhibition period.…”

Section: Methodsmentioning

confidence: 99%

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Nitroxides as Building Blocks for Nanoantioxidants

Genovese

Baschieri

Vona

et al. 2021

ACS Appl. Mater. Interfaces

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Nitroxides are an important class of radical trapping antioxidants whose promising biological activities are connected to their ability to scavenge peroxyl (ROO • ) radicals. We have measured the rate constants of the reaction with ROO • ( k inh ) for a series of 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) derivatives as 5.1 × 10 6 , 1.1 × 10 6 , 5.4 × 10 5 , 3.7 × 10 5 , 1.1 × 10 5 , 1.9 × 10 5 , and 5.6 × 10 4 M –1 s –1 for −H, −OH, −NH 2 , −COOH, −NHCOCH 3 , −CONH(CH 2 ) 3 CH 3 , and =O substituents in the 4 position, with a good Marcus relationship between log ( k inh ) and E ° for the R 2 NO • /R 2 NO + couple. Newly synthesized Pluronic-silica nanoparticles (PluS) having nitroxide moieties covalently bound to the silica surface (PluS–NO) through a TEMPO–CONH–R link and coumarin dyes embedded in the silica core, has k inh = 1.5 × 10 5 M –1 s –1 . Each PluS-bound nitroxide displays an inhibition duration nearly double that of a structurally related "free" nitroxide. As each PluS–NO particle bears an average of 30 nitroxide units, this yields an overall ≈60-fold larger inhibition of the PluS–NO nanoantioxidant compared to the molecular analogue. The implications of these results for the development of novel nanoantioxidants based on nitroxide derivatives are discussed, such as the choice of the best linkage group and the importance of the regeneration cycle in determining the duration of inhibition.

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Section: Methodsmentioning

confidence: 99%

“…Oxygen consumption during autoxidation experiments was measured with an optical oxygen meter (Firesting O 2 , Pyro Science GmbH) . Typical samples consisted of ABCV 27 mM, NaOH 54 mM, THF (10 or 25% v/v), pH 7.4 0.1 M phosphate buffer, 30 °C.…”

Section: Methodsmentioning

confidence: 99%

Nitroxides as Building Blocks for Nanoantioxidants

Genovese

Baschieri

Vona

et al. 2021

ACS Appl. Mater. Interfaces

Self Cite

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“…In addition to this, the literature studies have reported the induced micellar transitions by solubilizing several drugs as effective additives. Amid the varied class of drugs, specific focus has been given to antioxidants (gallates) because of its effective degree of binding with ionic surfactants, thereby offering an insight into the operative mixed formulations for biomedical applications. − In particular, propyl gallate (PG) is widely studied due to its moderate hydrophilic nature and slow oxidation kinetics . Andrzejewska et al studied the co-adsorption of CTAB and PG on the hydrophilic silica surface and inferred the interaction of PG with hydrophobic CTAB aggregates as the main governing force .…”

Section: Introductionmentioning

confidence: 99%

Tuning Cationic Micelle Properties with an Antioxidant Additive: A Molecular Perspective

et al. 2021

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In this work, we characterize the micellization and morphology transition induced in aqueous cetyltrimethylammonium bromide (CTAB) solution by the addition of the antioxidant propyl gallate (PG) using tensiometry, rheology, and small-angle neutron scattering (SANS) techniques combined with the molecular dynamics (MD) simulation approach. The adsorption of CTAB at the air–water interface in the presence of varying [PG] revealed a progressive decrease in the critical micelle concentration (CMC), while the changes in different interfacial parameters indicated enhancement of the hydrophobicity induced by PG in the CTAB micellar system. The dynamic rheology behavior indicated an increase in the flow viscosity (η) as a function of [PG]. Moreover, the rheological components (storage modulus, G′, and loss modulus, G″) depicted the viscoelastic features. SANS measurements depicted the existence of ellipsoidal micelles with varying sizes and aggregation number (N agg) as a function of [PG] and temperature. Computational simulation performed using density functional theory (DFT) calculations and molecular dynamics (MD) provided an insight into the atomic composition of the examined system. The molecular electrostatic potential (MEP) analysis depicted a close proximity of CTAB, i.e., emphasized favorable interactions between the quaternary nitrogen of CTAB and the hydroxyl group of the PG monomer, further validated by the two-dimensional nuclear Overhauser enhancement spectroscopy (2D-NOESY), which showed the penetration of PG inside the CTAB micelles. In addition, various dynamic properties, viz., the radial distribution function (RDF), the radius of gyration (R g), and solvent-accessible surface area (SASA), showed a significant microstructural evolution of the ellipsoidal micelles in the examined CTAB–PG system, where the changes in the micellar morphology with a more elongated hydrophobic chain and the increased R g and SASA values indicated the notable intercalation of PG in the CTAB micelles.

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Recent Trends of Cashew Nutshell Liquid: Extraction, Chemistry, and Applications

Mlowe,

Mgaya

2024

Plant Biomass Derived Materials

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Antioxidant effect of cardanol in mixed nanoformulations with pluronic

Cited by 6 publications

References 55 publications

Nitroxides as Building Blocks for Nanoantioxidants

Nitroxides as Building Blocks for Nanoantioxidants

Tuning Cationic Micelle Properties with an Antioxidant Additive: A Molecular Perspective

Recent Trends of Cashew Nutshell Liquid: Extraction, Chemistry, and Applications

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