Effect of 1-alkyl- or 1-alkenylazacycloalkanone derivatives on penetration of mitomycin C through rat skin.

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Abstract
The effects of five new compounds containing an azacyclo ring and a terpene or an alkyl chain, i.e., 1-geranylazacyclohexan-2-one (6Gu), 1-(3,7-dimethyloctyl)azacycloheptan-2-one (7GS), 1-(3,7,11-trimethyldodecyl)azacycloheptan-2-one (7FS), 1-geranylgeranylazacycloheptan-2-one (7GGU), and 1-geranylgeranylazacyclohexan-2-one (6GGU), on percutaneous penetration of mitomycin C (MMC) through rat skin in vitro were investigated in comparison with those of 1-farnesylazacycloheptan-2-one (7FU) and 1-dodecylazacycloheptan-2-one (Azone). In an in vitro diffusion experiment, 6GU, 7GS, 7FU, 7FS, 7GGU, 6GGU, and Azone significantly enhanced MMC penetration through rat skin compared with the controls. The size of the azacyclo ring had little effect on the potency of these penetration enhancers. On the other hand, the changes in the length of the hydrophobic chain resulted in some variation in the activity of these compounds. Azone and 7FU, which have a hydrophobic chain of length of twelve carbons, were the most effective among enhancers with an azacycloheptanone ring, and 7GGU, with the longest hydrophobic chain, showed the weakest MMC penetration-enhancing activity. Among the compounds with an azacyclohexanone ring. 6GGU (with a longer hydrophobic chain) was more effective than 6Gu (with a shorter hydrophobic chain). Saturation of the double bonds of the farnesyl group of 7FU decreased the enhancing ability.

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