Influence of ceramide 2 on in vitro skin permeation and retention of 5-ALA and its ester derivatives, for Photodynamic Therapy

Pierre, Maria Bernadete Riemma; Lopez, Renata Fonseca Vianna; Bentley, Maria Vitória Lopes Badra

doi:10.1590/s1984-82502009000100013

Cited by 8 publications

(6 citation statements)

References 31 publications

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“…Although proteins occupy 80% of the SC constituents, the polar pathway is not the major route for flavonoids because of the limited skin deposition enhancement after protein denaturation. A high affinity of the penetrants to the SC lipids can generate a reservoir in the skin for plentiful absorption [ 26 ]. To obtain detailed information on the absorption of flavonoids, we established the possible flavonoid-lipid interaction employing molecular docking.…”

Section: Discussionmentioning

confidence: 99%

Elucidating the Skin Delivery of Aglycone and Glycoside Flavonoids: How the Structures Affect Cutaneous Absorption

Chuang

Lin

et al. 2017

Nutrients

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Flavonoids are bioactive phytochemicals that exhibit protective potential against cutaneous inflammation and photoaging. We selected eight flavonoid aglycones or glycosides to elucidate the chemistry behind their skin absorption capability through experimental and computational approaches. The skin delivery was conducted using nude mouse and pig skins mounted on an in vitro Franz cell assembly. The anti-inflammatory activity was examined using the O2•– and elastase inhibition in activated human neutrophils. In the equivalent dose (6 mM) application on nude mouse skin, the skin deposition of naringenin and kaempferol was 0.37 and 0.11 nM/mg, respectively, which was higher than that of the other flavonoids. Both penetrants were beneficial for targeted cutaneous therapy due to their minimal diffusion across the skin. The absorption was generally greater for topically applied aglycones than glycosides. Although naringenin could be classified as a hydrophilic flavonoid, the flexibility of the chiral center in the C ring of this flavanone could lead to better skin transport than the flavonols and flavones with a planar structure. An optimized hydrophilic and lipophilic balance of the flavonoid structure was important for governing the cutaneous delivery. The hydrogen bond acceptor and stratum corneum lipid docking estimated by molecular modeling showed some relationships with the skin deposition. The interaction with cholesteryl sulfate could be a factor for predicting the cutaneous absorption of aglycone flavonoids (correlation coefficient = 0.97). Baicalin (3 µM) showed the highest activity against oxidative burst with an O2•– inhibition percentage of 77%. Although naringenin displayed an inhibition efficiency of only 20%, this compound still demonstrated an impressive therapeutic index because of the high absorption. Our data are advantageous to providing the information on the structure–permeation relationship for topically applied flavonoids.

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Section: Discussionmentioning

confidence: 99%

Elucidating the Skin Delivery of Aglycone and Glycoside Flavonoids: How the Structures Affect Cutaneous Absorption

Chuang

Lin

et al. 2017

Nutrients

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“…Samples of 0.60 mL were withdrawn from the receptor medium (with replacement of the same volume) at 30 min and 1, 2, 4, 6, 12, and 24 h. Sink conditions were maintained in all cases, and the absence of air bubbles was checked after each replacement. The MB concentration was analyzed by spectrophotometry (λ = 664 nm) and determined on the basis of the available area for skin permeation, and these values were plotted as a function of time (micrograms per square centimeter). , …”

Section: Methodsmentioning

confidence: 99%

Functional Polymeric Systems as Delivery Vehicles for Methylene Blue in Photodynamic Therapy

et al. 2015

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Antibiotic-resistant microorganisms have become a global concern, and the search for alternative therapies is very important. Photodynamic therapy (PDT) consists of the use of a nontoxic photosensitizer (PS), light, and oxygen. This combination produces reactive oxygen species and singlet oxygen, which can alter cellular structures. Methylene blue (MB) is a substance from the phenothiazine class often used as a PS. In this work, to facilitate the PS contact within the wounds, we have used Design of Experiments 2(3) plus central point to develop functional polymeric systems. The formulations were composed by poloxamer 407 [15.0, 17.5, or 20.0% (w/w)], Carbopol 934P [0.15, 0.20, or 0.25% (w/w)], and MB [0.25, 0.50, or 0.75% (w/w)]. The sol-gel transition temperature, flow rheometry, in vitro MB release, and ex vivo study of MB cutaneous permeation and retention were investigated. Moreover, the evaluation of photodynamic activity was also analyzed by in vitro degradation of tryptophan by singlet oxygen and using Artemia salina. The determination of the gelation temperature displayed values within the range of 25-37 °C, and the systems with better characteristics were subjected to rheological analysis and in vitro release profiling. The 20/0.15/0.25 formulation showed the best release profile (42.57% at 24 h). This system displayed no significant skin permeation (0.38% at 24 h), and the photooxidation of tryptophan test showed the production of reactive species of oxygen. The toxicity test using A. salina revealed that the MB associated with the light increased the mortality rate by 61.29%. Therefore, investigating the PDT efficacy of the functional polymeric system containing MB will be necessary in the future.

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“…1 mL of the formulation was placed homogeneously over the mucosa in the donor compartment. The temperature of the formulation was maintained at 37 °C by thermal exchange between the tissue and the formulation and also the temperature control provided by the equipment [103–104]. Afterwards, 500 µL of the receptor medium was collected and replaced by fresh medium to ensure sink condition at 0.5 h, 1 h, 2 h, 3 h, 4 h, 6 h, 8 h and 24 h. The samples were diluted in methanol (1:2), filtered in PTFE and quantified by the HPLC method.…”

Section: Methodsmentioning

confidence: 99%

Design of a nanostructured mucoadhesive system containing curcumin for buccal application: from physicochemical to biological aspects

Ferreira¹,

Braga²,

Oliveira³

et al. 2019

Beilstein J. Nanotechnol.

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Mucoadhesive nanostructured systems comprising poloxamer 407 and Carbopol 974P® have already demonstrated good mucoadhesion, as well as improved mechanical and rheological properties. Curcumin displays excellent biological activity, mainly in oral squamous cancer; however, its physicochemical characteristics hinder its application. Therefore, the aim of this study was to develop nanostructured formulations containing curcumin for oral cancer therapy. The photophysical interactions between curcumin and the formulations were elucidated by incorporation kinetics and location studies. They revealed that the drug was quickly incorporated and located in the hydrophobic portion of nanometer-sized polymeric micelles. Moreover, the systems displayed plastic behavior with rheopexy characteristics at 37 °C, viscoelastic properties and a gelation temperature of 36 °C, which ensures increased retention after application in the oral cavity. The mucoadhesion results confirmed the previous findings with the nanostructured systems showing a residence time of 20 min in porcine oral mucosa under flow system conditions. Curcumin was released after 8 h and could permeate through the porcine oral mucosa. Cytotoxicity testing revealed that the formulations were selective to cancer cells over healthy cells. Therefore, these systems could improve the physicochemical characteristics of curcumin by providing improved release and permeation, while selectivity targeting cancer cells.

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Influence of ceramide 2 on in vitro skin permeation and retention of 5-ALA and its ester derivatives, for Photodynamic Therapy

Cited by 8 publications

References 31 publications

Elucidating the Skin Delivery of Aglycone and Glycoside Flavonoids: How the Structures Affect Cutaneous Absorption

Elucidating the Skin Delivery of Aglycone and Glycoside Flavonoids: How the Structures Affect Cutaneous Absorption

Functional Polymeric Systems as Delivery Vehicles for Methylene Blue in Photodynamic Therapy

Design of a nanostructured mucoadhesive system containing curcumin for buccal application: from physicochemical to biological aspects

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