Influence of structurally related micelle forming surfactants on the antioxidant activity of natural substances

Battista, Sara; Campitelli, Patrizio; Carlone, Armando; Giansanti, Luisa

doi:10.1016/j.chemphyslip.2019.104818

Cited by 11 publications

(24 citation statements)

References 54 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Our investigation points out that, more than the charge or the chain length, the combination of both these parameters is fundamental in determining liposomes physicochemical properties and their ability of influencing the antioxidant effectiveness of UA. In particular, a synergistic effect between C14 chain length and the N-oxide moiety confirm the potentiality of N-ox in enhancing the antioxidant properties of the included solute [35]. As a consequence, this formulation shows the best potentiality as UA delivery systems, despite its relatively low stability.…”

Section: Resultsmentioning

confidence: 59%

“…DMPC, chol, UA, phosphate-buffered saline tablets (PBS, 0.01 M phosphate buffer; 0.0027 M KCl; 0.137 M NaCl; pH 7.4), dialysis tubing cellulose membrane (cut-off = 14,000), CH 3 COONa, H 2 O 2 and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS) were purchased from Sigma-Aldrich. The synthetic surfactants were prepared as previously described [35]. All reagents used for the synthesis and solvents were used without further purification.…”

Section: Methodsmentioning

confidence: 99%

“…In particular, the fact that in the case of UA the oxidation rate increases as a function of the polarity of the medium [54] could contribute to the highest antioxidant activity of UA observed in DMPC/ chol/ N-ox 14 liposomes. It is interesting that in the case of micelles of pure synthetic surfactants the nature of the polar headgroup rather than chain length seems to play a major role in affecting the antioxidant activity of UA, indicating the complex crucial effect of the incorporating aggregates [35]. To deepen our understanding of the investigated process, kinetics curves were fitted with an exponential decay by two processes (Eq.…”

Section: Evaluation Of Antioxidant Activity Of Ua By Abts˙+ Methodologymentioning

confidence: 99%

“…The variability in zeta potential values of N-ox containing liposomes demonstrates as the subtle hydrophobic/hydrophilic balance in surfactant structure can significantly influence their properties and confirms that chain length can play a crucial role in determin ing liposomes properties [40][41][42], in analogy with what observed for micelles of pure synthetic surfactants. 35 In particular, in the literature it is reported that properties of the bilayer such as thickness, surface area, trans-gauche chain isomerization and bilayer fluctuations in mixed liposomes containing N-oxide surfactants depend on chain length mismatch with the other lipid components [43]. The unexpected zeta potential of DMPC/chol/N-ox liposomes could result from the location at the same side of the pyrrolidinium ring of both the hydrophilic N-oxide and hydroxyl moieties.…”

Section: Dls and Zeta Potentialmentioning

confidence: 99%

“…This peculiar aspect, commonly neglected in the investigations on the physicochemical properties of liposomes, is particularly important because the antioxidant activity is often related to the biological properties of many active principles [28,[32][33][34]. Literature reports demonstrate that aggregates of surfactants bearing the N-oxide moiety can affect the antioxidant activity of a molecule they include (such as UA) [35] or with which they strictly interact (such as L-ascorbic acid) [1].…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Use of N-oxide and cationic surfactants to enhance antioxidant properties of (+)-usnic acid loaded liposomes

Battista

Campitelli

Galantini

et al. 2020

Colloids and Surfaces A: Physicochemical and Engineering Aspect

Self Cite

View full text Add to dashboard Cite

The influence of the presence of synthetic structurally related N-oxide and corresponding cationic surfactants with different chain lengths on the properties of 1,2-dimyristoyl-sn-glycero-3-phosphocholine liposomes was investigated. Their potentiality as delivery systems of (+)-usnic acid was also evaluated by studying its entrapment efficiency and its antioxidant activity. In fact, (+)-usnic acid has many pharmacological properties that, as many natural substances, are often strictly linked to their antioxidant power. N-oxide surfactants can enhance this property and improve the efficacy of the system. Based on this premise, we verified how and to what extent the molecular structure of liposomes components affects this effect: the best antioxidant effectiveness was observed when (+)-usnic acid was included in liposomes containing the N-oxide surfactant with C14 alkyl chain. Our results underline the importance of the hydrophilic/hydrophobic balance of the monomer in determining the properties of the aggregates in which it is included.

show abstract

Section: Resultsmentioning

confidence: 59%

Section: Methodsmentioning

confidence: 99%

Section: Evaluation Of Antioxidant Activity Of Ua By Abts˙+ Methodologymentioning

confidence: 99%

Section: Dls and Zeta Potentialmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Use of N-oxide and cationic surfactants to enhance antioxidant properties of (+)-usnic acid loaded liposomes

Battista

Campitelli

Galantini

et al. 2020

Colloids and Surfaces A: Physicochemical and Engineering Aspect

Self Cite

View full text Add to dashboard Cite

show abstract

Correlation of Physicochemical and Antimicrobial Properties of Liposomes Loaded with (+)‐Usnic Acid

et al. 2020

Self Cite

View full text Add to dashboard Cite

+)-Usnic acid (UA) is a natural substance that displays pharmacological activity, but it is barely soluble in water, so it was included in liposomes in order to study its properties. First, the effects of phospholipid structure and loading methodology on UA entrapment efficacy were evaluated. Then, the physicochemical and biological properties (UA delivery efficacy to Staphylococcus aureus bacterial cells) of different liposome formulations containing structurally related amphiphiles derived from L-prolinol were fully investigated. Entrapment efficiency of UA with passive loading by incubation was 80-100 molar percentage, which is related to lipophilicity of the drug and to the packing and fluidity of the bilayer. Some of the investigated formulations show the potential of UA in delivery systems (minimum inhibitory concentration of liposomal UA: 8 μg/mL) and even subtle variations of the molecular structure of lipids can significantly affect the liposomes' physicochemical properties and efficiency of drug release. μL of liposomes not previously incubated with bacteria (blank sample) and 2970 μL of Mueller-Hinton medium used in biological experiments.

show abstract

Synthesis of 2‐Aryl‐N‐(EWG‐methyl)‐N‐methylpyrrolidinium Salts as Precursors of Ylides Entering the [1,2] Stevens Rearrangement

et al. 2021

View full text Add to dashboard Cite

N-(EWG-CH2 )-N-methyl-2-phenylpyrrolidinium (EWG -electronwithdrawing group) salts were obtained in two different ways. N-(EWG-CH 2 )-2-phenylpyrrolidines were quaternized with iodomethane, dimethylsulfate or methyl trifluoromethanesulfonate forming pyrrolidinium iodides, methylsulfates and triflates. The counterion exchange in the methylsulfates was carried out yielding respective tetrafluoroborates. The second method was based on the quaternization of N-methyl-2-phenylpyrrolidine with methyl α-halogenoacetate or phenacyl bromide. All listed salts were oily and formed in high yields as mixtures of diastereoisomers, with cis or trans isomer predominating, depending on the method applied. The effect of the counterion present in the obtained salts was analyzed. Ylides generated from these salts in different base/solvent systems afforded products of the [1,2] Stevens rearrangement, 2-EWG-1-methyl-3-phenylpiperidines, with the trans isomers predominating, in moderate to good yields. In case of the [1,2] shift, the yields of respective products depended on EWG present in the substrate (methoxycarbonyl, acetyl, dimethylcarbamoyl and benzoyl).

show abstract

Influence of structurally related micelle forming surfactants on the antioxidant activity of natural substances

Cited by 11 publications

References 54 publications

Use of N-oxide and cationic surfactants to enhance antioxidant properties of (+)-usnic acid loaded liposomes

Use of N-oxide and cationic surfactants to enhance antioxidant properties of (+)-usnic acid loaded liposomes

Correlation of Physicochemical and Antimicrobial Properties of Liposomes Loaded with (+)‐Usnic Acid

Synthesis of 2‐Aryl‐N‐(EWG‐methyl)‐N‐methylpyrrolidinium Salts as Precursors of Ylides Entering the [1,2] Stevens Rearrangement

Contact Info

Product

Resources

About