Effects of 1,8-cineole on the dynamics of lipids and proteins of stratum corneum

Anjos, Jorge Luiz Vieira dos; Neto, Diógenes de Sousa; Alonso, Antônio

doi:10.1016/j.ijpharm.2007.05.041

Cited by 52 publications

(40 citation statements)

References 33 publications

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“…Maximum flux was obtained when menthol was used as permeation enhancer and its enhancing activity was attributed to its hydrogen bonding ability (58). However, the study conducted by Anjos and coworkers revealed that l-menthol stabilized mainly in the central region of stratum corneum membranes, which interacted with the membrane lipids and resulted in disruption of hydrogen bonds in the polar membrane interface (59). The combination of menthol and iontophoresis was suggested to enhance the in vitro permeation of methotrexate due to alteration of lipidprotein domains of mice skin (60).…”

Section: Mentholmentioning

confidence: 99%

Percutaneous Permeation Enhancement by Terpenes: Mechanistic View

Sapra

Jain

Tiwary

2008

AAPS J

145

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Abstract. A popular approach for improving transdermal drug delivery involves the use of penetration enhancers (sorption promoters or accelerants) which penetrate into skin to reversibly reduce the barrier resistance. The potential mechanisms of action of penetration enhancers include disruption of intercellular lipid and/or keratin domains and tight junctions. This results in enhanced drug partitioning into tissue, altered thermodynamic activity/solubility of drug etc. Synthetic chemicals (solvents, azones, pyrrolidones, surfactants etc.) generally used for this purpose are rapidly losing their value in transdermal patches due to reports of their absorption into the systemic circulation and subsequent possible toxic effect upon long term application. Terpenes are included in the list of Generally Recognized As Safe (GRAS) substances and have low irritancy potential. Their mechanism of percutaneous permeation enhancement involves increasing the solubility of drugs in skin lipids, disruption of lipid/protein organization and/or extraction of skin micro constituents that are responsible for maintenance of barrier status. Hence, they appear to offer great promise for use in transdermal formulations. This article is aimed at reviewing the mechanisms responsible for percutaneous permeation enhancement activity of terpenes, which shall foster their rational use in transdermal formulations.

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Section: Mentholmentioning

confidence: 99%

Percutaneous Permeation Enhancement by Terpenes: Mechanistic View

Sapra

Jain

Tiwary

2008

AAPS J

145

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“…6 In previous studies, two-component EPR spectra of several spin labels in membranes of stratum corneum, the upper skin layer, were examined using the fitting program NLLS to monitor the dynamic and fraction of probe in each component. [8][9][10] The presence of the terpenes L-menthol and 1,8-cineole, two potent skin permeation enhancers, in stratum corneum at 1% (w/w) or DPPC vesicles at a terpene:lipid molar ratio of 0.7:1 drastically increased the lipid fluidity, especially by transferring the spin probes from a more to a less motionally restricted spectral component in the membranes. 9,10 More recently, EPR spectra of spin labels in membrane were simulated using two-component models to study effects of the anti antileishmanial drug miltefosine in stratum corneum intercellular membranes 11 and trypanocidal action of elatol 12 as well as the toxicity of terpenes in cultured fibroblasts.…”

Section: Introductionmentioning

confidence: 99%

“…[8][9][10] The presence of the terpenes L-menthol and 1,8-cineole, two potent skin permeation enhancers, in stratum corneum at 1% (w/w) or DPPC vesicles at a terpene:lipid molar ratio of 0.7:1 drastically increased the lipid fluidity, especially by transferring the spin probes from a more to a less motionally restricted spectral component in the membranes. 9,10 More recently, EPR spectra of spin labels in membrane were simulated using two-component models to study effects of the anti antileishmanial drug miltefosine in stratum corneum intercellular membranes 11 and trypanocidal action of elatol 12 as well as the toxicity of terpenes in cultured fibroblasts. 13 Since the question of the spectral components in the EPR spectra of spin-labeled lipids in membrane models of simple bilayers has not been addressed in depth, we conducted an extensive experimental study with the spin probe methyl 5-doxyl-stearate (5-DMS) in vesicles of saturated phosphatidylcholines with acyl chain lengths ranging from 16 to 22 carbon atoms and temperatures in the 10 to 78 o C range.…”

Section: Introductionmentioning

confidence: 99%

Electron paramagnetic resonance (EPR) spectral components of spin-labeled lipids in saturated phospholipid bilayers: effect of cholesterol

Camargos¹,

Alonso²

2013

Quím. Nova

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Recebido em 23/9/12; aceito em 7/1/13; publicado na web em 6/5/13Electron paramagnetic resonance (EPR) spectroscopy was used to study the main structural accommodations of spin labels in bilayers of saturated phosphatidylcholines with acyl chain lengths ranging from 16 to 22 carbon atoms. EPR spectra allowed the identification of two distinct spectral components in thermodynamic equilibrium at temperatures below and above the main phase transition. An accurate analysis of EPR spectra, using two fitting programs, enabled determination of the thermodynamic profile for these major probe accommodations. Focusing the analysis on two-component EPR spectra of a spin-labeled lipid, the influence of 40 mol % cholesterol in DPPC was studied.

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“…Electron paramagnetic resonance (EPR) of spin labels has been employed to obtain information on the molecular dynamics of SC membranes [6][7][8][9][10][11][12] and SC proteins [13][14][15][16] in the intact tissue. The EPR spectra of spinlabeled stearic acids in SC membranes were able to distinguish two main environments for the probe distribution into the membranes.…”

Section: Introductionmentioning

confidence: 99%

Molecular Dynamics and Partitioning of Di‐tert‐butyl Nitroxide in Stratum Corneum Membranes: Effect of Terpenes

Camargos

Moraes

Anjos

et al. 2010

Lipids

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In this work, we have used electron paramagnetic resonance (EPR) spectroscopy of the small spin label di-tert-butyl nitroxide (DTBN), which partitions the aqueous and hydrocarbon phases, to study the interaction of the terpenes alpha-terpineol, 1,8-cineole, L(-)-carvone and (+)-limonene with the uppermost skin layer, the stratum corneum, and the membrane models of 1,2-dipalmitoyl-sn-glycero-3-phosphatidylcholine (DPPC) and 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC). The EPR spectra indicated that the terpenes increase both the partition coefficient and the rotational correlation time of the spin labels in the stratum corneum membranes, whereas similar effects were observed in the DMPC and DPPC bilayers only at temperatures below the liquid-crystalline phase. The EPR parameter associated to probe polarity inside the membranes showed thermotropically induced changes, suggesting relocations of spin probe, which were dependent on the membrane phases. While the DMPC and DPPC bilayers showed abrupt changes in the partitioning and rotational correlation time parameters in the phase transitions, the SC membranes were characterized by slight changes in the total range of measured temperatures, presenting the greatest changes or membranes reorganizations in the temperature range of approximately 50 to approximately 74 degrees C. The results suggest that terpenes act as spacers, weakening the hydrogen-bonded network at the polar interface and thus fluidizing the stratum corneum lipids.

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Effects of 1,8-cineole on the dynamics of lipids and proteins of stratum corneum

Cited by 52 publications

References 33 publications

Percutaneous Permeation Enhancement by Terpenes: Mechanistic View

Percutaneous Permeation Enhancement by Terpenes: Mechanistic View

Electron paramagnetic resonance (EPR) spectral components of spin-labeled lipids in saturated phospholipid bilayers: effect of cholesterol

Molecular Dynamics and Partitioning of Di‐tert‐butyl Nitroxide in Stratum Corneum Membranes: Effect of Terpenes

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