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Molecules 2011, 16(8), 6778-6790; doi:10.3390/molecules16086778
Article

A Biomimetic Chitosan Derivates: Preparation, Characterization and Transdermal Enhancement Studies of N-Arginine Chitosan

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Received: 11 July 2011 / Revised: 25 July 2011 / Accepted: 1 August 2011 / Published: 9 August 2011
(This article belongs to the Section Medicinal Chemistry)
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Abstract

A novel arginine-rich chitosan (CS) derivates mimicked cell penetration peptides; N-Arginine chitosan (N-Arg-CS) was prepared by two reaction methods involving activated L-arginine and the amine group on the chitosan. FTIR spectra showed that arginine was chemically coupled with CS. Elemental analysis estimated that the degrees of substitution (DS) of arginine in CS were 6%, 31.3% and 61.5%, respectively. The drug adefovir was chosen as model and its permeation flux across excised mice skin was investigated using a Franz diffusion cell. The results showed that the most effective enhancer was 2% (w/v) concentration of 10 kDa N-Arg-CS with 6% DS. At neutral pH, the cumulative amount of adefovir permeated after 12 hours was 2.63 ± 0.19 mg cm−2 which was 5.83-fold more than adefovir aqueous solution. Meanwhile N-Arg-CS was 1.83, 2.22, and 2.45 times more effective than Azone, eucalyptus and peppermint, respectively. The obtained results suggest that N-Arg-CS could be a promising transdermal enhancer.
Keywords: biomimetic chitosan derivates; arginine-rich; cell penetration peptides; N-arginine chitosan; transdermal enhancer; adefovir biomimetic chitosan derivates; arginine-rich; cell penetration peptides; N-arginine chitosan; transdermal enhancer; adefovir
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Lv, H.-X.; Zhang, Z.-H.; Wang, X.-P.; Cheng, Q.-Q.; Wang, W.; Huang, X.-H.; Zhou, J.-P.; Zhang, Q.; Hou, L.-L.; Huo, W. A Biomimetic Chitosan Derivates: Preparation, Characterization and Transdermal Enhancement Studies of N-Arginine Chitosan. Molecules 2011, 16, 6778-6790.

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