키토산과 모노(2-메타크릴로일 옥시에틸)산 포스페이트 그라프트공중합과 그의 항균효과

정병옥; 정석진; 정택상; 이영무; 최규석; 김재진; 한승희

Journal of the Korean Industrial and Engineering Chemistry, Vol.9, No.6, 935-941, November, 1998

Export Citation

키토산과 모노(2-메타크릴로일 옥시에틸)산 포스페이트 그라프트공중합과 그의 항균효과

Graft Copolymerization of Chitosan and Mono(2-methacryloyl oxyethyl) Acid Phosphate and Its Antifungal Effect

정병옥, 정석진, 정택상, 이영무, 최규석, 김재진, 한승희

초록

키토산에 음이온계 수용성의 함인계 모노머인 mono(2-methacryloy1 oxyethyl) acid phosphate를 그라프트공중합시켜 새로운 유도체를 합성하였다. 그라프트공중합의 최적 그라프트율은 개시제농도 3.5x10^-3M, 모노머농도 0.19 M, 반응온도 40℃에서 가장 높은 값을 나타내었고, 반응시간 4시간 이후로는 거의 같은 값을 나타내었다. 그라프트공중합체와 chitosan의 유리아민의 함량에 따른 항균성을 Candida albicans, Trichophyton rubrum 및 Trichophyton violaceum에 대하여 shake flask법으로 조사한 결과, pH 5.75에서 가장 우수한 항균성능이 발현되고, 곰팡이 균류에 대한 선택성이 나타남을 확인할 수 있었다.

New type of chitosan deriertives was synthesised by graft copolymerization of mono(2-methacryloyl oxyethyl) acid phosphate into chitosan. The reaction conditions showing the highest percentage of grafting were an initiator concentration of 3.5 x 10^-3 M, monomer concentration of 0.19 M, and reaction temperature of 40℃, while rate of grafting showed same value after elapsing 4hours of reaction time. The antifungal activity of chitosan depending on content of free amine and kind of monomer was examined against Candida albicans, Trichophyton rubrum and Trichophyton uiolaceum by shake flask method. The pH value of buffer solution to show the highest antifungal activity was 5.75, and the selectivity of mold strain was observed.

Keywords:Chitosan;Graft Copolymerization;Antifungal Effect;Mono(2-methacryloyl oxyethyl) Acid

[References]

Muzzarelli RAA, "Chitin," Pergamon Press, Oxford (1977)
Muzzarelli RAA, Pariser ER, Proc. 1st Conf. Chitin/Chitosan, MIT Cambridge (1987)
Hirano S, Tokura S, Proc. 2nd Conf. Chitin/Chitosan, The Japanese Society Chitin and Chitosan (1982)
Zikakis JP, Chitin, Chitosan and Related Enzyme, Academic Press, New York (1984)
Hou WM, Miyazari S, Takoda M, Chem. Pharm. Bull., 33, 3986 (1985)
Hirano S, Noisiki Y, J. Biomed. Mater. Res., 19, 413 (1985)
Kojima K, Yoshikuni M, Suzuki T, J. Appl. Polym. Sci., 24, 1587 (1979)
Bough MA, Food Product Development, 11, 90 (1977)
Li W, Li Z, Liao W, Feng XD, J. Biomater. Sci.-Polym. Ed., 4, 557 (1993)
Allan CR, Hadwiger LA, Exp. Mycol., 3, 285 (1979)
Kendra DF, Hadwiger LA, Exp. Mycol., 8, 276 (1984)
Uchida Y, Food Chem., 2, 22 (1988)
Kim CH, Kim SY, Choi KS, Polym. Adv. Technol., 8, 319 (1997)
Kim CH, Choi JW, Chun HJ, Choi KS, Polym. Bull., 38(4), 387 (1997)
Song JY, Kim IH, Chung DH, J. Food Hygiene Safety, 10, 199 (1995)
Mima S, Miya M, Iwamoto R, Yoshikawa S, J. Appl. Polym. Sci., 28, 1909 (1983)
Goni I, Gurruchaga M, Valeru M, Guzman GM, J. Polym. Sci., 21, 2573 (1983)
Fang SW, Li CF, Shin DYC, J. Food Protection, 57, 136 (1994)
Ide H, Graft Polymerization and Its Application, Chater 2, Polymer-Publication Conference, Kyoto, Japan (1977)
Post FJ, Krihnmurty GB, Flanagan MD, Appl. Microbial., 11, 430 (1963)
Shepherd MG, Microbial Cell Wall Synthesis and Autolysis, ed. by C. Nombela, Elsevier Science Publishers, Amsterdam, 73 (1984)
Creager JG, Black JG, Davison VE, Microbiology Principles and Application, Prentice-Hall, Inc., New Jersey, U.S.A., 75 (1990)

[1] Muzzarelli RAA, "Chitin," Pergamon Press, Oxford (1977)

[2] Muzzarelli RAA, Pariser ER, Proc. 1st Conf. Chitin/Chitosan, MIT Cambridge (1987)

[3] Hirano S, Tokura S, Proc. 2nd Conf. Chitin/Chitosan, The Japanese Society Chitin and Chitosan (1982)

[4] Zikakis JP, Chitin, Chitosan and Related Enzyme, Academic Press, New York (1984)

[5] Hou WM, Miyazari S, Takoda M, Chem. Pharm. Bull., 33, 3986 (1985)

[6] Hirano S, Noisiki Y, J. Biomed. Mater. Res., 19, 413 (1985)

[7] Kojima K, Yoshikuni M, Suzuki T, J. Appl. Polym. Sci., 24, 1587 (1979)

[8] Bough MA, Food Product Development, 11, 90 (1977)

[9] Li W, Li Z, Liao W, Feng XD, J. Biomater. Sci.-Polym. Ed., 4, 557 (1993)

[10] Allan CR, Hadwiger LA, Exp. Mycol., 3, 285 (1979)

[11] Kendra DF, Hadwiger LA, Exp. Mycol., 8, 276 (1984)

[12] Uchida Y, Food Chem., 2, 22 (1988)

[13] Kim CH, Kim SY, Choi KS, Polym. Adv. Technol., 8, 319 (1997)

[14] Kim CH, Choi JW, Chun HJ, Choi KS, Polym. Bull., 38(4), 387 (1997)

[15] Song JY, Kim IH, Chung DH, J. Food Hygiene Safety, 10, 199 (1995)

[16] Mima S, Miya M, Iwamoto R, Yoshikawa S, J. Appl. Polym. Sci., 28, 1909 (1983)

[17] Goni I, Gurruchaga M, Valeru M, Guzman GM, J. Polym. Sci., 21, 2573 (1983)

[18] Fang SW, Li CF, Shin DYC, J. Food Protection, 57, 136 (1994)

[19] Ide H, Graft Polymerization and Its Application, Chater 2, Polymer-Publication Conference, Kyoto, Japan (1977)

[20] Post FJ, Krihnmurty GB, Flanagan MD, Appl. Microbial., 11, 430 (1963)

[21] Shepherd MG, Microbial Cell Wall Synthesis and Autolysis, ed. by C. Nombela, Elsevier Science Publishers, Amsterdam, 73 (1984)

[22] Creager JG, Black JG, Davison VE, Microbiology Principles and Application, Prentice-Hall, Inc., New Jersey, U.S.A., 75 (1990)