Synthesis of Polymeric Drugs Containing D-Glucosamine as a Spacer

Kim KS; Lim DS; Cho SH

Korea Polymer Journal, Vol.4, No.1, 16-22, April, 1996

5-FU-1-acetic acid, which is a dervative of 5-FU known to have remarkable antitumor activity, was synthesized. Glc-5-FU was synthesized by the reaction of D-glucosamine with 5-FU-1-acetic acid forming amide bond and MNGLc, as a new vinyl monomer, was synthesized by the reaction of D-glucosamine with methacryloyl-type monomr. For the purpose of providing the polymeric drugs such as poly(MNGF-co-MNG), poly (MNGF-co-MA), and poly(MNGF-co-AAm), the polymeriztion of MNGLc with MA and with AAm as well as the esterification of poly (MNGLc), poly (MNG-co-MA), and poly (MNG-co-AAm) with 5-FU-1-acetic acid were performed. In addition, poly(MAGF-co-MA) prodrung was synthesized by the reaction of GLc-5-FU with poly(methacrylic acid) homopolymer.

[References]

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[Referenced By]

[1] Gebelin CG, Baig W, Morgan RM, Glovwacky R, Polym. Prepr., 20, 600 (1979)

[2] Ouchi T, Yuyama H, Vogl O, Makromol. Chem. Rapid Commun., 6, 815 (1985)

[3] Ouchi T, Hagita K, Kawashima M, Inoi T, J. Bioact. Compat. Polym., 3, 53 (1988)

[4] Zhuo RX, Liao J, Fan CL, Chem. J. Chin. Univ. Eng., 6(3), 244 (1990)

[5] Young FS, Zhuo RX, Polym. J., 22, 592 (1990)

[6] Ozaki S, Ike Y, Mizuno H, Ishikawa K, Hori M, Bull. Chem. Soc. Jpn., 50, 2406 (1977)

[7] Ozaki S, Watanabe Y, Hoshiko T, Mizuno H, Ishikawa K, Hori M, Chem. Pharm. Bull., 32, 733 (1984)

[8] Ozaki S, Watanabe Y, Ogasawara T, Yamauchi Y, Fujiwara K, Hoshi A, Iigo M, Chem. Pharm. Bull., 33, 2832 (1985)

[9] Ozaki S, Watanabe Y, Hoshiko T, Nagase T, Ogasawara T, Furukawa H, Uemura A, Ishikawa K, Mori M, Iigo M, Tokuzen R, Chem. Pharm. Bull., 34, 150 (1986)

[10] Ouchi T, Fujie H, Jokei S, Sakamoto Y, Chikashita H, Inoi T, Vogl O, J. Polym. Sci. A: Polym. Chem., 24, 2059 (1986)

[11] Ouchi T, Yuyama H, Vogl O, J. Polym. Sci. C: Polym. Lett., 25, 279 (1987)

[12] Ouchi T, Yuyama H, Vogl O, J. Macromol. Sci.-Chem., A24, 1011 (1987)

[13] Ouchi T, Hagita K, Kawashima M, Inoi T, Tashiro T, J. Control. Release, 8, 141 (1988)

[14] Ohnishi S, Polym. J., 21, 955 (1989)

[15] Yang T, Zhno R, Polym. J., 22, 572 (1990)

[16] Akashi M, Miyauchi N, Morita N, Minota T, J. Bioactive Compatible Polym., 2, 232 (1987)

[17] Akashi M, Iwasaki H, Miyauchi N, Sato T, Sunamoto J, Takemoto K, J. Bioactive Compatible Polym., 4, 126 (1989)

[18] Sirca AE, Woodman RJ, J. Natl. Cancer Inst., 47, 377 (1971)

[19] Susuki K, Tokoro A, Okawa Y, Susuki S, Macrobiol. Immunol. Chem., 30, 777 (1986)

[20] Tada M, Bull. Chem. Soc. Jpn., 48, 3427 (1975)