Ion-pair Formation as a Strategy to Enhance Topical Delivery of Salicylic Acid

Megwa, S. A.; Cross, Sheree E.; Benson, Heather A. E.; Roberts, Michael S.

doi:10.1211/0022357001774804

Cited by 58 publications

(29 citation statements)

References 26 publications

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“…These amines exist as bulk cations in near neutral pH solution and can form anionic non-covalent complexes, thus reducing the net charge and increasing lipophilicity of the complexes. Ion pair reagents are routinely used in HPLC chromatography to increase the retention time of a hydrophilic ion and have been expected to enhance the oral absorption of ionic drugs [25,26].…”

Section: Permeation Of Vanadium-dipic Complexes Across Caco-2 Cell Momentioning

confidence: 99%

The permeability and cytotoxicity of insulin-mimetic vanadium (III,IV,V)-dipicolinate complexes

Zhang

Yang

Wang

et al. 2006

Journal of Inorganic Biochemistry

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Section: Permeation Of Vanadium-dipic Complexes Across Caco-2 Cell Momentioning

confidence: 99%

The permeability and cytotoxicity of insulin-mimetic vanadium (III,IV,V)-dipicolinate complexes

Zhang

Yang

Wang

et al. 2006

Journal of Inorganic Biochemistry

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“…[5][6][7] The association with oppositely charged ions reduces or neutralizes the electrostatic charges. For salicylate, enhancement of skin permeation by ion-pair formation with alkylamines and quaternary ammonium ions in ethanol-pyopylene glycol (2 : 1 v/v) 6,7) and in aqueous medium 8) has been reported. Ion-pair absorption of lidocaine-n-alkanoate from ethanolic medium 9) and ion-pair complex of cromolyn from isopropyl myristate (IPM) has also been reported.…”

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confidence: 99%

Enhanced Skin Permeation of Salicylate by Ion-Pair Formation in Non-aqueous Vehicle and Further Enhancement by Ethanol and l-Menthol

et al. 2006

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“…12) To examine the possibility of the involvement of the ion-pair formation between salicylate and the cationic surfactants such as 2C10, we next examined the effects of ndimethyldialkylammoniums on the permeation of silicon rubber membrane; Since permeation of drugs through silicon rubber membrane follows the pH-partition hypothethis, 13) and the membrane has been used to study the possibility of the contribution of the ion-pair formation on the enhancement effects of various skin permeation enhancers. 14) Undissociated forms of salicylic acid rapidly permeated through the silicon rubber membrane, which was shown as a large permeability coefficient value at acidic pH (pH 2.6) in Table 2.…”

Section: Resultsmentioning

confidence: 99%

Enhancement Effects of Double-Chained Cationic Surfactants of n-Dimethyldialkylammoniums on Permeability of Salicylate through Guinea Pig Dorsal Skin.

Kitagawa

Kasamaki

2002

Chem. Pharm. Bull.

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It has been demonstrated that various kinds of surfactants disrupt the barrier function of skin and increase transdermal drug permeability.1) Among them, long-chain cationic surfactants such as n-dodecyltrimethylammonium (1C12) are known to have marked enhancement effects on the transdermal permeation of hydrophilic drugs.2,3) These cationic surfactants seem to interact with proteins in the stratum corneum as well as the lipid lamella, improve the hydrophilic property of the skin and enhance the skin permeation of relatively hydrophilic drugs. 3)Different from the single-chained cationic surfactants, some of the double-chained cationic surfactants form bilayer vesicles just like phospholipids. [4][5][6] We recently examined the effects of double-chained cationic surfactants of n-dimethyldialkylammoniums (CH 3 ) 2 N ϩ (C n H 2nϩ1 ) 2 on skin permeation of undissociated form of benzoic acid through excised guinea pig dorsal skin at acidic donor pH conditions. 6)n-Dimethyldialkylammoniums with relatively shorter alkyl chains such as dimethyldidecylammonium (2C10) seem to form micelles instead of vesicles. The findings on the five double-chained cationic surfactants tested (nϭ10-18) revealed the marked enhancement effects of the surfactants with relatively shorter alkyl chains, whose enhancement mechanism is possibly similar to that of single-chained cationic surfactants.The enhancement effects of the cationic surfactants may be different depending on the electric charge of the drugs. Therefore, in this study we examined the effects of five n-dimethyl-and n-dimethyldistearylammonium (2C18) on in vitro skin permeation of anionic drugs using salicylate, whose pK a value is 3.0, 7) as a model drug. We compared their enhancement effects with those on undissociated forms of drugs we previously reported.6) We also compared their enhancement effects on the permeation of salicylate with those of singlechained cationic surfactants of n-alkyltrimethylammoniums and those of the vesicles consisting of n-dimethyldialkylammoniums and egg yolk phosphatidylcholine (egg yolk PC). In order to clarify the mechanism of the enhancement, we furthermore examined the effects of n-dimethyldialkylammoniums on the permeation of salicylate though silicon rubber membrane. We also examined their effects on the skin content of salicylate.Experimental Materials Bromide salts of n-dimethyldialkylammoniums and nalkyltrimethylammoniums were purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). Sodium salicylate, egg yolk phosphatidylcholine (egg yolk PC) and all other reagents were from Wako Pure Chemical Industries. Silicon rubber sheet was purchased from GE Toshiba Silicones Co., Ltd. (Ota, Japan).Preparation of Surfactant Solutions and Sonicated Dispersions nDimethyldialkylammoniums were used after preparing the sonicated dispersions as described previously.6) Bromide salts of n-dimethyldialkylammoniums were dissolved in chloroform, and the solvent was evaporated. Dried surfactant films were prepared by removing the solvent under vacuum...

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Ion-pair Formation as a Strategy to Enhance Topical Delivery of Salicylic Acid

Cited by 58 publications

References 26 publications

The permeability and cytotoxicity of insulin-mimetic vanadium (III,IV,V)-dipicolinate complexes

The permeability and cytotoxicity of insulin-mimetic vanadium (III,IV,V)-dipicolinate complexes

Enhanced Skin Permeation of Salicylate by Ion-Pair Formation in Non-aqueous Vehicle and Further Enhancement by Ethanol and l-Menthol

Enhancement Effects of Double-Chained Cationic Surfactants of n-Dimethyldialkylammoniums on Permeability of Salicylate through Guinea Pig Dorsal Skin.

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