Galactosyl Pentadecene Reversibly Enhances Transdermal and Topical Drug Delivery

Kopečná, Monika; Macháček, Miloslav; Prchalová, Eva; Štěpánek, Petr; Drašar, Pavel; Kotora, Martin; Vávrová, Kateřina

doi:10.1007/s11095-017-2214-3

Cited by 20 publications

(41 citation statements)

References 39 publications

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“…For the measurement, the tips of measuring probes were immersed in donor and in acceptor chamber, both lled with PBS buffer pH 7.4. 36 Skin samples with determined impedance above 3 kU were used in the permeation experiments. These values were similar to the electrical resistance of human skin reported by others.…”

Section: Skin Electrical Impedancementioning

confidence: 99%

Enhancement of ibuprofen solubility and skin permeation by conjugation with l-valine alkyl esters

et al. 2020

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New ibuprofen derivatives were made via conjugation with L-valine alkyl esters (ValOR), where R was changed from an ethyl to a hexyl group. The ionic structure was confirmed using NMR and FTIR. Specific rotation, solubility in commonly used solvents, thermal properties including phase transitions temperatures, and thermal stability were also determined. The ionic structure with a protonated amine group on an L-valine ester and melting points below 100 C allowed inclusion of these ibuprofen derivatives into the pharmaceutically active protic ionic liquids. The ibuprofen salt solubility in deionised water and two buffer solutions at pH 5.4 and 7.4 were established and compared with the parent acid solubility. The octanol/water (buffer) partition coefficient, permeation through porcine skin, and accumulation in the skin were also measured. Ibuprofen pairing with L-valine alkyl esters [ValOR][IBU], caused higher solubility and a greater drug molecule absorption through biological membranes. log P was lower for ibuprofen salts than for the acid and it increased with a longer L-valine ester cation alkyl chain. In vitro porcine skin tests showed that ibuprofen salts with a propyl or isopropyl ester in L-valine are particularly relevant for topical application. They provide transport for ibuprofen through the skin at much higher rate than the unmodified acid and a higher permeated ibuprofen concentration, which can improve efficacy. Thus, synthesised ibuprofen derivatives could be used as drug carriers in transdermal systems to provide better drug bioavailability, and they can be also be the source of exogenous L-valine.

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Section: Skin Electrical Impedancementioning

confidence: 99%

Enhancement of ibuprofen solubility and skin permeation by conjugation with l-valine alkyl esters

et al. 2020

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“…Skin impedance was measured using an LCR 4080 meter (Conrad Electronic, Germany) operating in parallel mode at 120 Hz (kΩ error < 0.5%). To make the measurement, the tips of the probes were immersed in the donor and acceptor chambers lled with the PBS solution (Kopečná et al 2017). Membranes with an electrical resistance of >3 kΩ, corresponding to the resistance measured for human skin, were used in the study (Davies et al 2004).…”

Section: Skin Permeation Studies Of Eugenol and New Estersmentioning

confidence: 99%

“…All donor chambers were closed with a plastic stopper to prevent excessive evaporation of the solution. The described tests were carried out for 24 hours, while 0.3 ml of the solution located in the acceptor chamber was taken at speci ed intervals (30 min, 1 h, 2 h, 3 h, 4 h, 5 h, 8 h and 24 h), and then supplemented with a fresh portion buffer at the same pH (Kopečná et al 2017). The samples were analyzed by high-performance liquid chromatography (HPLC) with a UV spectrophotometric detector (Knauer, Berlin, Germany).…”

Section: Skin Permeation Studies Of Eugenol and New Estersmentioning

confidence: 99%

Enhancement of the Antioxidant and Skin Permeation Properties of Eugenol by the Esterification of Eugenol to New Derivatives

Makuch

Nowak

Günther

et al. 2020

Preprint

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The aim of the study was to determine the antioxidant activity and assess the lipophilicity and skin penetration of eugenyl chloroacetate (EChA), eugenyl dichloroacetate (EDChA), and eugenyl trichloroacetate (ETChA). Identification of the obtained products was based on gas chromatography (GC), infrared spectroscopy (FTIR/ATR), gas chromatography coupled with mass spectrometry (GC-MS), and the analysis of 13C-NMR and 1H-NMR spectra. The antioxidative capacity of the derivatives obtained was determined by the DPPH free radical reduction method, while the octanol/water partition coefficient (shake-flask method) was tested to determine the lipophilicity of these compounds. In the next stage of testing EDChA and ETChA–(compounds characterized by the highest degree of free radical scavenging), the penetration of DPPH through pig skin and its accumulation in the skin were evaluated. For comparison, penetration studies of eugenol alone as well as dichloroacetic acid (DChAA) and trichloroacetic acid (TChAA) were also carried out. The antioxidant activity (DPPH, ABTS, and Folin–Ciocalteu methods) of the fluid that penetrated through pig skin was also evaluated. The in vitro pig skin penetration study showed that eugenol derivatives are particularly relevant for topical application. The obtained derivatives were characterized by a high level of antioxidant activity estimated after 24 hours of conducting the experiment, which indicates long-term protection against reactive oxygen species (ROS) in the deeper layers of the skin.

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“…For this purpose skin impedance was measured using an LCR 4080 meter (Conrad Electronic, Germany) operating in parallel mode at 120 Hz (kΩ error < 0.5%). To make the measurement, the tips of the probes were immersed in the donor and acceptor chambers filled with the PBS solution [34]. Membranes with an electrical resistance of >3 kΩ, corresponding to the resistance measured for human skin, were used in the study [35].…”

Section: Measurement Of the Antioxidant Capacity Of Cosmetic Formulatmentioning

confidence: 99%

An Advanced Mode of Antioxidants Delivery System Effective in the Treatment of ROS and Skin Permeation of The Cosmetic Formulations - The Possible Application of Clove Oil, Eugenol and New Eugenol Derivative

Makuch¹,

Nowak²,

Günther³

et al. 2020

Preprint

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The main focus of this work is to extend the knowledge about the complexity of issues of oxidative stress. Natural compounds play a serious role in multiple aspects of both human, leading to clear health-promoting effects. This work is focused on the potential application cosmetic formulations containing including but not limited to of clove water and isolated clove oils on their aid in the control of the diseases. The aim of our work was to prepare to evaluate cosmetic formulations containing clove oil, eugenol or new eugenol ester derivative (eugenyl dichloroacetate - EDChA) but also cosmetic formulations containing the aqueous phase obtained after separation of essential oil following the clove buds steam distillation. To evaluate the antioxidants transdermal delivery system, in vitro permeation experiments in a Franz diffusion cell were performed using pig skin. The antioxidative capacity of the cosmetic formulations obtained was determined by the DPPH free radical reduction method. In the next stage, the antioxidant activity (DPPH, ABTS, and Folin–Ciocalteu methods) of the fluid that penetrated through pig skin and of the fluid obtained after skin extraction, were also evaluated. For comparison, studies of cosmetic formulation containing alone dichloroacetic acid (DChAA) were as well carried out. The obtained cosmetic formulations were characterized by of antioxidant activity estimated after 24 hours of conducting the experiment, which indicates long-term protection against reactive oxygen species (ROS) in the deeper layers of the skin. The results of this work contribute to the development of cosmetic formulations with antioxidant potential, emphasizing that the water phases are waste from the process of cloves steam distillation and are not used to prepare cosmetic formulations. The use of waste water from the clove buds steam distillation process is environmentally friendly and not allows us to waste, containing however valuable biologically active compounds (furfural, methyl salicylate, 4-allilofenol, eugenol, α- and β-caryophyllene, eugenyl acetate, β-caryophyllene oxide). Together, these results suggest that cosmetic formulations may be potential drug candidates for chemopreventive, antineoplastic and antimutagenic therapy.

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Galactosyl Pentadecene Reversibly Enhances Transdermal and Topical Drug Delivery

Abstract: Galactosyl pentadecene A15 is a potent enhancer with low toxicity and reversible action.

Cited by 20 publications

References 39 publications

Enhancement of ibuprofen solubility and skin permeation by conjugation with l-valine alkyl esters

Enhancement of ibuprofen solubility and skin permeation by conjugation with l-valine alkyl esters

Enhancement of the Antioxidant and Skin Permeation Properties of Eugenol by the Esterification of Eugenol to New Derivatives

An Advanced Mode of Antioxidants Delivery System Effective in the Treatment of ROS and Skin Permeation of The Cosmetic Formulations - The Possible Application of Clove Oil, Eugenol and New Eugenol Derivative

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