Applied Vol. 12, No. I , May ;rna, 29-32 Methoxy poly(ethylene glyco l) OI Preparation and spectroscopic characterization of methoxy poly(ethylene glycon-grafted low molecular weight water-soluble chitosan Don-Gon KimI. Joong-Kuen Kwon l . Young-II Jeong l . Mi-Kyeong Jang l . Jaw-Woon Nah l ' JDepartment of Polymer Science and Engineering. Sunchon National University. Suncheon. Jeonnam 540-742. Korea 2Department of Bioenvironmental and Chemical Engineering. Chosun College of Science & Technology. Gwang-ju 501-744. Korea Abstract The object of this study is to test solubility of methoxy poly (ethylene glycol) (MPEG) -grafted chitosan copolymer in the organic solvents and aqueous solution. Water-soluble chitosan with low molecular weight (LMWSC) was used to synthesis of PEG-graft copolymerization. MPEG was conjugated to the water soluble chitosan using 4-dicyclohexylcarbodimide (DCC). and N-hydroxysuccimide (NHS ), Introduction of PEG was confirmed by JH NMR spectroscopy. Degree of substitution (DS) of MPEG into chitosan was calculated from JH NMR results. From these results. Furthermore. introduction of PEG into chitosan increases the solubility in aqueous solution with various organic solvent such as DMF. DMSO. ethanol. and acetone. 1. Introduction To overcome drawbacks of chitosan , various kind of derivatives of chitosan have been developed [1, 2]. Among them , PEGylation of chitosan was reported by several authors to increase aqueous solubility of chitosan [1 -5]. Ouchi et a l. reported that PEGylation of chitosan bring out increased solubility to aqueous solution or organic solvent , and self-aggregation properties in aqueous solution. PEGylaion of chitosan derivatives is favorable to biocompatibility improvementand increase cell viability compared to trimethyl chitosan [4 J. Other candidates for modification of chitosan is to graft poly (L-lactide) or polycaprolactone to give a amphiphilic properties , i.e. chitosan consisted of hydrophilic domain and polyester composed of hydrophobic domain [6 , 71. Resultantly , nanoparticles of chitosan-g-polyester has reduced particle size with sub-lOO nm and they showed self-assembling properties of copolymed6 ,7 J. In previous report , we showed that water-soluble chitosan with low molecular weight (M.W.) (abbreviated as LMWSC) is a distinguished candidates as a drug or DNA carriers due to their good aqueous-solubility and elevated free-amine group in chitosan. Since LMWSC has high content of free amine group in chitosan chain , it is distinguished from other kind of chitosan in the increased affinity to DNA or anionic drug. Furthermore , PEG-graft LMWSC can be used as a excellent drug or 29
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Applied Chemisσy ,
Vol. 12, No. I, May ;rna, 29-32
Methoxy poly(ethylene glycol)OI 수식흰 저톨짜량 수용성 키톨싼의
체죠및특성
깊호쿄 J 권중근 l 정영일 J 장미경 J 나재운 J.
l순천대학교 공과대학 고분자공학과
2조선이공대학 생명환경화꽁과
Preparation and spectroscopic characterization of methoxypoly(ethylene glycon-grafted low molecular weight
water-soluble chitosan
Don-Gon KimI. Joong-Kuen Kwon l. Young-II Jeong l
. Mi-Kyeong Jang l.
Jaw-Woon Nah l'
JDepartment of Polymer Science and Engineering. Sunchon National University. Suncheon. Jeonnam540-742. Korea
2Department of Bioenvironmental and Chemical Engineering. Chosun Collegeof Science & Technology. Gwang-ju 501-744. Korea
Abstract
The object of this study is to test solubility of methoxy poly (ethylene glycol)
(MPEG) -grafted chitosan copolymer in the organic solvents and aqueous solution.
Water-soluble chitosan with low molecular weight (LMWSC) was used to synthesis of
PEG-graft copolymerization. MPEG was conjugated to the water soluble chitosan using
4-dicyclohexylcarbodimide (DCC). and N-hydroxysuccimide (NHS), Introduction of
PEG was confirmed by JH NMR spectroscopy. Degree of substitution (DS) of MPEG into
chitosan was calculated from JH NMR results. From these results. Furthermore.
introduction of PEG into chitosan increases the solubility in aqueous solution with variousorganic solvent such as DMF. DMSO. ethanol. and acetone.
1. Introduction
To overcome drawbacks of chitosan , various kind of derivatives of chitosan have been
developed [1, 2]. Among them , PEGylation of chitosan was reported by several authors to
increase aqueous solubility of chitosan [1 -5]. Ouchi et a l. reported that PEGylation of
chitosan bring out increased solubility to aqueous solution or organic solvent, and
self-aggregation properties in aqueous solution. PEGylaion of chitosan derivatives is
favorable to biocompatibility improvementand increase cell viability compared to trimethyl
chitosan [4 J. Other candidates for modification of chitosan is to graft poly (L-lactide) or
polycaprolactone to give a amphiphilic properties, i.e. chitosan consisted of hydrophilic
domain and polyester composed of hydrophobic domain [6 ,71. Resultantly , nanoparticles of
chitosan-g-polyester has reduced particle size with sub-lOO nm and they showed
self-assembling properties of copolymed6,7J. In previous report , we showed that
water-soluble chitosan with low molecular weight (M.W.) (abbreviated as LMWSC) is a
distinguished candidates as a drug or DNA carriers due to their good aqueous-solubility and
elevated free-amine group in chitosan. Since LMWSC has high content of free amine group
in chitosan chain , it is distinguished from other kind of chitosan in the increased affinity to
DNA or anionic drug. Furthermore , PEG-graft LMWSC can be used as a excellent drug or
29
30 김동곤·권중근·정영일·장미경·나재운
gene carrier. Hu et a l. reported that PEG-grafted chitosan has increased solubility in
aqueous solution and organic solvent such as dimethylformamide (DMF) and
dimethylsulfoxide (DMSO). However , they did not showed aqueous solubility at various pH
and various kind of organic solven t. Increased solubility in aqueous solution with various pH
and organic solvent will give advantages to application of chitosan derivatives in biomedical
field.
In this study , we synthesized methoxy PEG-grafted LMWSC (abbreviated as ChitoPEG)
and characterized with I H- NMR. Furthermore , solubility potential of ChitoPEG was
investigated at organic solvent such as DMF , DMSO , acetone , acetonitrile , and ethano l.
Introduction of PEG to chitosan will increase processibility and application area by increase
solubility parameters.
2. Experimental
2. 1. MaterialsWater-soluble chitosan with low molecular weight (M.W. = 10,000 Da , deacetylation
degree = 97.0 %, abbreviated as LMWSC) was gift from Chittolife Co. Ltd. Seoul ,
Korea.Water-insoluble chitosan was purchased from Wako Pure Chemical , Co. Ltd. Japan
Cchitosan 10 , abbreviated as IS-chitosan). Methoxy poly(ethylene glyco l) (MPEG) (M.W. =2 ,000 g/mo l) was purchased from SunBio Co. Korea. , N,N’-dicyclohexy1carbodiimide