Epidermal permeability: Penetrant structure relationships. 2. The effect of h-bonding groups in penetrants on their diffusion through the stratum corneum

Roberts, Michael S.; Pugh, W.; Hadgraft, Jonathan

doi:10.1016/0378-5173(95)04278-4

Cited by 111 publications

(69 citation statements)

References 15 publications

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“…20,21) The non-ionic form of resveratrol shows high lipophilicity according to the partition coefficient (log P octanol/water ϭ3.32). The partition coefficient for compounds between SC and water (log P SC/water ) can be estimated as 22) : log P SC/water ϭϪ0.024ϩ0.59 log P octanol/water . This formula shows that the partitioning of the drug into the SC from an aqueous solution is directly related to its lipophilicity.…”

Section: Discussionmentioning

confidence: 99%

Delivery of Resveratrol, a Red Wine Polyphenol, from Solutions and Hydrogels <i>via</i> the Skin

Hung

Lin

Huang

et al. 2008

Biological & Pharmaceutical Bulletin

105

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Resveratrol is a naturally occurring polyphenolic compound which has received much attention in the prevention of and therapy for cardiovascular diseases and cancers ( Fig. 1).1) Red grapes and wines contain considerable amounts of resveratrol. Resveratrol has many benefits for the skin. Topically applied resveratrol has been shown to possess strong antiproliferative and chemopreventive properties against skin carcinogenesis.2-4) Resveratrol affords substantial protection against skin damage from ultraviolet B (UVB) exposure. 5,6) Resveratrol shows antimicrobial activity against dermatophytes and herpes simplex virus. 7,8) Resveratrol can also be used in the dermocosmetic field because of its role as a phytoestrogen based on its ability to activate estrogen receptors. 9)The oral bioavailability of resveratrol is poor, leading to an irrelevant in vivo effect with oral administration compared to its powerful in vitro efficacy. 10) Resveratrol also has a short initial half-life (8-14 min) and is extensively metabolized in the body.11) Several phase I clinical trials are currently underway for oral resveratrol in humans at doses of as high as 7.5 g per day. This would require 2.7 kg of resveratrol a year at a current cost of ca. US$6800. Therefore it is becoming increasingly important to find ways to improve the bioavailability of and block the metabolism of resveratrol. Delivery of resveratrol via the skin is an attractive alternative to oral dosing for both topical and transdermal applications.No evidence currently exists in the literature to support the notion that a sufficient amount of resveratrol can be delivered to produce therapeutic benefits via a skin route. Designs of optimal formulations for resveratrol permeation via the skin are also lacking. The purposes of this study were to establish basic profiles of resveratrol permeability into and across the skin. The optimal pH and co-solvent of the vehicles for resveratrol were investigated for better permeation. The present study utilized Franz cells to explore the in vitro skin permeation of resveratrol. The drug amount retained within the skin reservoir was determined by in vitro and in vivo methods. Various skin membranes, including nude mouse skin, stratum corneum (SC)-stripped skin, delipidized skin, and cellulose membranes, were used as permeation barriers to elucidate the mechanisms and pathways. One particular problem common to drug delivery systems designed for use on the skin is the poor retention at the site of application. This problem can be resolved by incorporating bioadhesive hydrogels within the system. Hence, the ability of a series of hydrogel formulations to deliver topically applied resveratrol was examined. The permeability of piceatannol (Fig. 1), a resveratrol analogue with considerably higher activity, was also evaluated in this study. Resveratrol, the main active polyphenol in red wine, has been demonstrated to show benefits against skin disorders. The bioavailability of orally administered resveratrol is insufficient to permit high...

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Section: Discussionmentioning

confidence: 99%

Delivery of Resveratrol, a Red Wine Polyphenol, from Solutions and Hydrogels <i>via</i> the Skin

Hung

Lin

Huang

et al. 2008

Biological & Pharmaceutical Bulletin

105

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“…The permeability coefficients of solutes through the stratum corneum have previously been related to the presence of H-bonding groups on the penetrant [65,66,67,68]. While lipophilicity has been determined to be highly significant in solute partitioning into the stratum corneum from aqueous solutions, Roberts et al [64] determined that the hydrogen-bonding ability of a solute was the main determinant of solute partitioning across the stratum corneum. …”

Section: John Pugh Lecturer In Pharmaceutics Welsh School Of Pharmamentioning

confidence: 99%

“…Their follow-up study focused on the effect of the hydrogen-bonding properties of potential penetrants on diffusion across the stratum corneum [64]. The permeability coefficients of solutes through the stratum corneum have previously been related to the presence of H-bonding groups on the penetrant [65,66,67,68].…”

Section: John Pugh Lecturer In Pharmaceutics Welsh School Of Pharmamentioning

confidence: 99%

The Contributions of the Celtic Masters and Their Associates

Gp¹

2013

Skin Pharmacol Physiol

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“…For instance, n-octanol and alkanes, which are the solvents traditionally used in lipophilicity measurements, cannot be employed because they are not polarizable. Nevertheless, a solvatochromic analysis of the water/DCE systems revealed [123] that this system accounts very well for the Hbonding capacity of solutes which plays a major role in membrane permeation [124,125]. As many compounds have low solubility in alkanes and as water/n-octanol partition coefficients are not always good predictors of biodistribution, the water/DCE system has become the system of reference to replace the water/alkane system and to characterise H-bonding properties of solutes [126 -131].…”

Section: Pharmacokineticsmentioning

confidence: 99%

Electrochemistry at liquid/liquid interfaces: methodology and potential applications

Reymond

Fermı́n

Lee

et al. 2000

Electrochimica Acta

285

223

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Epidermal permeability: Penetrant structure relationships. 2. The effect of h-bonding groups in penetrants on their diffusion through the stratum corneum

Cited by 111 publications

References 15 publications

Delivery of Resveratrol, a Red Wine Polyphenol, from Solutions and Hydrogels <i>via</i> the Skin

Delivery of Resveratrol, a Red Wine Polyphenol, from Solutions and Hydrogels <i>via</i> the Skin

The Contributions of the Celtic Masters and Their Associates

Electrochemistry at liquid/liquid interfaces: methodology and potential applications

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