Lipophilization of Ascorbic Acid: A Monolayer Study and Biological and Antileishmanial Activities

Kharrat, Nadia; Aissa, Imen; Sghaier, Manel; Bouaziz, Mohamed; Sellami, Mohamed; Laouini, Dhafer; Gargouri, Youssef

doi:10.1021/jf5029398

Cited by 21 publications

(19 citation statements)

References 40 publications

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“…This supports previous reports that evidence an enhanced bactericidal capacity for the ASCn compounds in comparison with the addition of soluble ASC together with the corresponding fatty acid [9].…”

Section: Discussionsupporting

confidence: 92%

“…The ASCn, used in different pharmacological preparations due to its amphiphilic nature and anti-oxidative power, have shown subtly differences on therapeutic effectiveness [7][8][9]27]. …”

Section: Discussionmentioning

confidence: 99%

“…ASC12 appeared able to partition into the liposome surface, but not deeply penetrate it. In addition, it shows considerable effects on membrane tension decrease and release of vesicular content, a capacity that may enhance hydrophobic drug delivery [7,9].…”

Section: Discussionmentioning

confidence: 99%

“…This result suggests that the ASC-containing compound should be integrated into the lipid membrane in order to be effectively able to reduce membrane components. Since the reduction power of the ASCn studied are similar [9,26] the differences in fluorescence intensity decay may be a direct measurement of the ability for membrane incorporation of the compounds. Then, ASC12…”

Section: Direct Observation Of Ascn-membrane Interactionmentioning

confidence: 99%

“…On the other hand, the ASC16 coagel acts as a good adjuvant in immunization of animal model [8], presumably because some inflammatory-cytotoxic activity. Additionally, it has been recently reported that some members of this drug family show bactericidal and antileishmanial action [9]. All these applications indirectly imply the interaction of ASCn with biological membranes that is the first cell barrier.…”

Section: _ Introductionmentioning

confidence: 98%

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The amphiphilic alkyl ester derivatives of l -ascorbic acid induce reorganization of phospholipid vesicles

Giudice

Ambroggio

Mottola

et al. 2016

Biochimica et Biophysica Acta (BBA) - Biomembranes

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l-ascorbic acid alkyl esters (ASCn) are lipophilic forms of vitamin C, which maintain some of its antioxidant power. Those properties make this drug family attractive to be used in pharmacological preparations protecting other redox-sensible drugs or designed to reduce possible toxic oxidative processes. In this work, we tested the ability of l-ascorbic acid alkyl esters (ASCn) to modulate the structure, permeability, and rheological properties of phospholipid bilayers. The ASCn studied here (ASC16, ASC14, and ASC12) alter the structural integrity as well as the rheological properties of phospholipid membranes without showing any evident detergent activity. ASC14 appeared as the most efficient drug in destabilize the membrane structure of nano- and micro-size phospholipid liposomes inducing vesicle content leakage and shape elongation on giant unilamellar vesicles. It also was the most potent enhancer of membrane microviscosity and surface water structuring. Only ASC16 induced the formation of drug-enriched condensed domains after its incorporation into the lipid bilayer, while ASC12 appeared as the less membrane-disturbing compound, likely because of its poor, and more superficial, partition into the membrane. We also found that incorporation of ASCn into the lipid bilayers enhanced the reduction of membrane components, compared with soluble vitamin C. Our study shows that ASCn compounds, which vary in the length of the acyl chain, show different effects on phospholipid vesicles used as biomembrane models. Those variances may account for subtly differences in the effectiveness on their pharmacological applications.

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Section: Discussionsupporting

confidence: 92%

“…The ASCn, used in different pharmacological preparations due to its amphiphilic nature and anti-oxidative power, have shown subtly differences on therapeutic effectiveness [7][8][9]27]. …”

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Direct Observation Of Ascn-membrane Interactionmentioning

confidence: 99%

Section: _ Introductionmentioning

confidence: 98%

See 3 more Smart Citations

The amphiphilic alkyl ester derivatives of l -ascorbic acid induce reorganization of phospholipid vesicles

Giudice

Ambroggio

Mottola

et al. 2016

Biochimica et Biophysica Acta (BBA) - Biomembranes

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show abstract

Introduction

2021

Chemo‐Enzymatic Cascade Reactions

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Valorization of antioxidants extracted from olive mill wastewater

Aissa

Kharrat

Aloui

et al. 2017

Biotech and App Biochem

Self Cite

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Antioxidants are highly important gradients used to preserve cosmetic products and reduce the effect of oxidative stress on the skin. The present work explores the possibility of using phenolic compounds of olive mill wastewater (OMW) as effective alternatives to the commercial antioxidants used in cosmetic formulations deemed by their allergic and carcinogenic effects. Esterification of tyrosol and hydroxytyrosol extracted from OMW with various fatty acids was conducted using Novozyme 435 lipase as a biocatalyst. Upon synthesis, butyrate, caprate, laurate, and palmitate tyrosyl and hydroxytyrosyl esters were isolated and evaluated for their antioxidant and antibacterial activities. Results showed that laurate derivatives are the most efficient in preventing lipid oxidation and inhibiting growth of pathogenic strains. In the prospective of industrial use, laurate tyrosyl and hydroxytyrosyl derivatives were incorporated in a formulation of moisturizer to substitute the commercial antioxidant butylated hydroxyltoluene. Oleuropein, extracted from olive leaves powder, was also tested as an antiaging ingredient in cosmetic formulations. The evaluation of physicochemical, microbiological, and sensorial properties of the new cosmetic products indicated that oleuropein and lipophilic derivatives do not affect the properties of the standard formulation. Oleuropein and lipophilic derivatives can be added as active ingredients to stabilize cosmetic preparations.

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Lipophilization of Ascorbic Acid: A Monolayer Study and Biological and Antileishmanial Activities

Cited by 21 publications

References 40 publications

The amphiphilic alkyl ester derivatives of l -ascorbic acid induce reorganization of phospholipid vesicles

The amphiphilic alkyl ester derivatives of l -ascorbic acid induce reorganization of phospholipid vesicles

Introduction

Valorization of antioxidants extracted from olive mill wastewater

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