항바이러스 활성을 갖는 Trifluoroacetyl Chitosan 유도체의 제조

김천호; 신차균; 신계숙; 손태일

Journal of the Korean Industrial and Engineering Chemistry, Vol.10, No.4, 599-602, June, 1999

Export Citation

항바이러스 활성을 갖는 Trifluoroacetyl Chitosan 유도체의 제조

Preparation of Trifluoroacetyl Chitosan Derivatives with Antiviral Activity

김천호, 신차균, 신계숙, 손태일

초록

Chitosan을 아질산부해법을 이용하여 저분자화시킨 다음, 저분자량 chitosan의 유리 아민기와 trifluoroacetic anhydride를 반응시켜 새로운 함불소 chitosan 올리고머 유도체(FCO)를 합성하였다. 이들 반응의 진행은 FT-IR, ¹H, NMR, ¹³C NMR 및 ¹⁹F{¹H}NMR 등을 통해 확인하였다. FCO의 항바이러스 효과는 바이러스 감염용액에 다양한 농도의 FCO를 첨가하고 세포를 감염시킨 후, 36시간 후에 복제되고 있는 바이러스 DNA 양을 측정하여 조사하였다. 바이러스 복제는 FCO를 첨가하여 바이러스를 감염시킨 세포들에서, FCO를 첨가하지 않은 대조군에 비하여 첨가한 FCO의 농도에 비례하여 감소하여, FCO가 바이러스 감염을 효과적으로 억제함을 제시한다. 특히, 1 % FCO의 감염용액으로 처리된 세포에서는 바이러스의 복제가 대조군에 비하여 40 %로 감소하였다.

Chitosan was depolymerized by using nitrous acid. In order to synthesize new fluorinated chitosan oligomer(FCO) derivative, free amine groups of resulting low molucular weight chitosan oligomers were reacted with trifluoroacetic anhydride. The structure changes in the samples were conformed by using FT-IR, ¹H, NMR, ¹³C NMR and ¹⁹F{¹H}NMR. Antiviral activity of FCO was studied by measuring DAN amounts of the replication viruses at 36 hr after the cells were infected with the viral solution containing FCO of various concentrations. The viral replications in the cells infected with the viral solution containing FCO were proportionally decreased with the FCO does, compared to those of the control groups, indicating that FCO efficiently inhibits viral infection. In particular, viral replication was decreased to 40 % in the 1 % FCO-treated cells.

Keywords:Chitosan derivatives;Antiviral activity

[References]

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Abeles RH, Maycock AL, Acc. Chem. Res., 9, 313 (1976)
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Muzzarelli RAA, Chitin, Pergamon Press, New York (1977)
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Hirano S, Tokura S, Proc. 2nd. Conf. Chitin/Chitosan, The Japanese Society of Chitin and Chitosan (1982)
Zikakis JP, Chitin, Chitosan and Related Enzyme, Academic Press, New York (1984)
Muzzarelli RAA, Jeuniaux C, Gooday GW, Chitin in Nature and Technology, Plenum Press, New York (1986)
Rupley JA, Biochim. Biophys. Acta, 83, 245 (1964)
Horowitz ST, Roseman S, Blumenthal HJ, J. Am. Chem. Soc., 79, 5046 (1957)
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戶倉淸一, 最後のバイオマスキチン, キトサン, キチン, キトサン硏究會編, 技報堂出版, p. 51 (1988)
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內田泰, キチン, キトサンの應用, キチン, キトサン硏究會編, 技報堂出版, p. 71 (1990)
Suzuki S, Okawa Y, Okura Y, Hashimoto K, Suzuki M, Proc. of the 2nd Int. Conf. on Chitin and Chitosan (1989)
田口鐵男, 金子有太郞, 千原吳郞, Biotherapy, 2, 509 (1988)
古江尙, Biotherapy, 2, 543 (1988)
Kim CH, Lee ES, Hahm YT, Kim BY, Sohn TI, J. Korean Ind. Eng. Chem., in press (1999)
Snapka RM, Mol. Cell. Biol., 6, 4221 (1986)
Hirt B, J. Mol. Biol., 26, 365 (1967)
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Toei K, Kohata T, Anal. Chem. Acta, 83, 59 (1976)

[Referenced By]

[1] Peters R, Proc. Roy. Soc. Ser., B139, 143 (1952)

[2] Fried J, Sabo EF, J. Am. Chem. Soc., 75, 2273 (1953)

[3] Heidelberger C, Dushinsky R, Nature, 179, 663 (1957)

[4] Abeles RH, Maycock AL, Acc. Chem. Res., 9, 313 (1976)

[5] Kollonisch J, Patchett AA, Marburg S, Maycock AL, Perkins LM, Doldouras GA, Duggan DE, Aster SD, AAPG Bull., 274, 906 (1978)

[6] Muzzarelli RAA, Chitin, Pergamon Press, New York (1977)

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

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

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

[10] Muzzarelli RAA, Jeuniaux C, Gooday GW, Chitin in Nature and Technology, Plenum Press, New York (1986)

[11] Rupley JA, Biochim. Biophys. Acta, 83, 245 (1964)

[12] Horowitz ST, Roseman S, Blumenthal HJ, J. Am. Chem. Soc., 79, 5046 (1957)

[13] Bosso C, Defaye J, Domard A, Gadelle A, Carbohydr. Res., 156, 57 (1986)

[14] 戶倉淸一, 最後のバイオマスキチン, キトサン, キチン, キトサン硏究會編, 技報堂出版, p. 51 (1988)

[15] 東市郞, キチン, キトサンの應用, キチン, キトサン硏究會編, 技報堂出版, p. 195 (1990)

[16] 內田泰, キチン, キトサンの應用, キチン, キトサン硏究會編, 技報堂出版, p. 71 (1990)

[17] Suzuki S, Okawa Y, Okura Y, Hashimoto K, Suzuki M, Proc. of the 2nd Int. Conf. on Chitin and Chitosan (1989)

[18] 田口鐵男, 金子有太郞, 千原吳郞, Biotherapy, 2, 509 (1988)

[19] 古江尙, Biotherapy, 2, 543 (1988)

[20] Kim CH, Lee ES, Hahm YT, Kim BY, Sohn TI, J. Korean Ind. Eng. Chem., in press (1999)

[21] Snapka RM, Mol. Cell. Biol., 6, 4221 (1986)

[22] Hirt B, J. Mol. Biol., 26, 365 (1967)

[23] Shin CG, Strayer JM, Wani MA, Snapka RH, Ter. Car. Mutagen, 10, 41 (1990)

[24] Toei K, Kohata T, Anal. Chem. Acta, 83, 59 (1976)