Glycyrrhiza acid micelles loaded with licochalcone A for topical delivery: Co-penetration and anti-melanogenic effect

Wang, Zhuxian; Xue, Yi; Chen, Tingting; Du, Qizhen; Zhu, Zhaoming; Wang, Yuan; Wu, Yuh Lin; Zeng, Quanfu; Shen, Chunyan; Jiang, Cuiping; Yang, Zhijun; Zhu, Hongxia; Liu, Li; Qiang, Liu

doi:10.1016/j.ejps.2021.106029

Cited by 15 publications

(10 citation statements)

References 42 publications

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“…Licochalcone A (LicA) [18] and glabridin (Gla) [19], flavonoid compounds extracted from the roots of Glycyrrhiza glabra L., both have significant anti-melanogenic effects on cellular and animal levels as we previously revealed. However, the poor water solubility and higher log P hinders their transdermal permeation when applied alone, which further influences their practical use.…”

Section: Introductionmentioning

confidence: 78%

Quantitative Structure-Activity Relationship of Enhancers of Licochalcone A and Glabridin Release and Permeation Enhancement from Carbomer Hydrogel

et al. 2022

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This study aimed to systematically compare licochalcone A (LicA) and glabridin (Gla) (whitening agents) release and permeation from Carbomer 940 (CP) hydrogels with different enhancers, and evaluate the relationship between the quantitative enhancement efficacy and structures of the enhancers. An in vitro release study and an in vitro permeation experiment in solution and hydrogels using porcine skin were performed. We found that the Gla–CP hydrogel showed a higher drug release and skin retention amount than LicA–CP due to the higher solubility in medium and better miscibility with the skin of Gla than that of LicA. Enhancers with a higher molecular weight (MW) and lower polarizability showed a higher release enhancement effect (ERrelease) for both LicA and Gla. The Van der Waals forces in the drug–enhancers–CP system were negatively correlated with the drug release percent. Moreover, enhancers with a higher log P and polarizability displayed a higher retention enhancement effect in solution (ERsolution retention) for LicA and Gla. Enhancers decreased the whole intermolecular forces indrug–enhancers-skin system, which had a linear inhibitory effect on the drug retention. Moreover, C=O of ceramide acted asthe enhancement site for drug permeation. Consequently, Transcutol® P (TP) and propylene glycol (PG), seven enhancers showed a higher retention enhancement effect in hydrogel (ERhydrogel retention) for LicA and Gla. Taken together, the conclusions provide a strategy for reasonable utilization of enhancers and formulation optimization in topical hydrogel whitening.

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Section: Introductionmentioning

confidence: 78%

Quantitative Structure-Activity Relationship of Enhancers of Licochalcone A and Glabridin Release and Permeation Enhancement from Carbomer Hydrogel

et al. 2022

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“…Liquiritin (LiQ) [ 4 ] and isoliquiritin (IsL) [ 5 ] are effective in atopic dermatitis, while isoliquiritigenin (IsLT) [ 6 ] and licochalcone B (LB) [ 7 ] play a vital role in suppressing melanoma cells in the skin. Glabridin (Gla 1) [ 8 ] and licochalcone A (LA) [ 9 , 10 ] possess remarkable anti-melanogenic effect as we previously found, and liquiritigenin (LiQT) [ 11 ] is extensively used in anti-aging cosmetic formulations. The skin protective activities of LFs compounds provide them with great potential for application in topical formulations such as hydrogels [ 12 ].…”

Section: Introductionmentioning

confidence: 99%

Log P Determines Licorice Flavonoids Release Behaviors and Classification from CARBOMER Cross-Linked Hydrogel

Wang

Xue

et al. 2022

Pharmaceutics

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The dynamic drug release mechanisms from Carbomer 940 (CP) hydrogels have not been systematically explored elsewhere. This study aimed to investigate the quantitative structure−activity relationship of licorice flavonoids (LFs) compounds on their drug release from CP hydrogels based on LFs-CP interactions and drug solubility in the release medium. Ten LFs-CP hydrogels were formulated, and their in vitro release study was conducted. The intermolecular forces of LFs-CP systems were characterized by FTIR, molecular docking and molecular dynamic simulation. Ten LFs compounds were classified into I (high-release capability) LFs and II (low-release capability) LFs according to the different negative correlations between drug release percent at 48 h and intermolecular forces of drugs-CP, respectively. Moreover, high-release LFs possessed significantly lower log P and higher drug solubility in the release medium than low-release LFs. All I LFs release behaviors best followed the first-order equation, while II LFs release characteristics best fitted the zero-order equation except for isoliquiritigenin. Log P mainly affect the hydrogel relaxation process for I drugs release and the drug diffusion process for II drugs release. Higher log P values for LFs resulted in higher intermolecular strength for I drugs-CP systems and lower drug solubility in the release medium for II drugs, which hindered drug release. Hydrophobic association forces in drug-CP hydrogel played a more and more dominant role in hindering I LFs release with increasing release time. On the other hand, lower drug solubility in the release medium restricted II LFs release, and the dominant role of drug solubility in the release medium increased in 24 h followed by a significant decline after 36 h. Collectively, log P of LFs served as a bridge to determine LFs compound release behaviors and classification from CP hydrogels, which provided guidelines for reasonable design of LFs hydrogels in pharmaceutical topical formulations.

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“…Fortunately, its poor solubility and potential haemolytic and cytotoxic effects were overcome in a study by Silva et al [ 266 ], in which licochalcone A was incorporated into solid lipid nanoparticles. The penetration of licochalcone A into the epidermis can be increased with micellar vehicles coloaded with glycyrrhizic acid [ 267 ].…”

Section: Discussionmentioning

confidence: 99%

Prenylated Flavonoids in Topical Infections and Wound Healing

et al. 2022

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The review presents prenylated flavonoids as potential therapeutic agents for the treatment of topical skin infections and wounds, as they can restore the balance in the wound microenvironment. A thorough two-stage search of scientific papers published between 2000 and 2022 was conducted, with independent assessment of results by two reviewers. The main criteria were an MIC (minimum inhibitory concentration) of up to 32 µg/mL, a microdilution/macrodilution broth method according to CLSI (Clinical and Laboratory Standards Institute) or EUCAST (European Committee on Antimicrobial Susceptibility Testing), pathogens responsible for skin infections, and additional antioxidant, anti-inflammatory, and low cytotoxic effects. A total of 127 structurally diverse flavonoids showed promising antimicrobial activity against pathogens affecting wound healing, predominantly Staphylococcus aureus strains, but only artocarpin, diplacone, isobavachalcone, licochalcone A, sophoraflavanone G, and xanthohumol showed multiple activity, including antimicrobial, antioxidant, and anti-inflammatory along with low cytotoxicity important for wound healing. Although prenylated flavonoids appear to be promising in wound therapy of humans, and also animals, their activity was measured only in vitro and in vivo. Future studies are, therefore, needed to establish rational dosing according to MIC and MBC (minimum bactericidal concentration) values, test potential toxicity to human cells, measure healing kinetics, and consider formulation in smart drug release systems and/or delivery technologies to increase their bioavailability.

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Glycyrrhiza acid micelles loaded with licochalcone A for topical delivery: Co-penetration and anti-melanogenic effect

Cited by 15 publications

References 42 publications

Quantitative Structure-Activity Relationship of Enhancers of Licochalcone A and Glabridin Release and Permeation Enhancement from Carbomer Hydrogel

Quantitative Structure-Activity Relationship of Enhancers of Licochalcone A and Glabridin Release and Permeation Enhancement from Carbomer Hydrogel

Log P Determines Licorice Flavonoids Release Behaviors and Classification from CARBOMER Cross-Linked Hydrogel

Prenylated Flavonoids in Topical Infections and Wound Healing

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