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Synthesis of N, N-dimethyl N-ethyl Chitosan as a Carrier for Oral Delivery of Peptide Drugs

Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran, Cosar Pharmaceutical Co., Tehran, Iran

A. M.M. Sadeghi

Department of Pharmaceutical Technology, Leiden/Amsterdam Center for Drug Research, Leiden, The Netherlands

M. R. Avadi

Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran

M. Amini

Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran

M. Rafiee-Tehrani

Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran

A. Shafiee

Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran, ashafiee{at}ams.ac.ir

R. Majlesi

Cosar Pharmaceutical Co., Tehran, Iran

H. E. Junginger

Department of Pharmaceutical Technology, Leiden/Amsterdam Center for Drug Research, Leiden, The Netherlands, Pharmaceutical Sciences, Naresuan University, Phitsanulok, Thailand

N, N-dimethyl N-ethyl chitosan (DMEC), a quanternized derivative of chitosan was synthesized based on a modified two-step method via a 2² factorial design to optimize the preparative conditions. The degree of deacetylation of the starting chitosan was determined by FTIR and NMR methods and was 95%. In the first step of the synthesis, mono-ethyl chitosan was prepared by introducing an ethyl group onto the amine group of chitosan via a Schiff base and in the next step methyl iodide was added to produce DMEC which was water soluble in a pH range of 4-8. The DMEC polymers with different degrees of quaternization were obtained and fully characterized using FTIR and 1H-NMR spectroscopic methods. Based on 1H-NMR calculations, the degree of quaternization was 52% by optimizing the two-step process.

Key Words: chitosan • quaternized chitosan • drug absorption enhancer • degree of quaternization

Journal of Bioactive and Compatible Polymers, Vol. 21, No. 5, 433-444 (2006)
DOI: 10.1177/0883911506068679


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