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Synthesis and antitumour and antiangiogenesis activity of polymers containing methacryloyl‐2‐oxy‐1,2,3‐propane tricarboxylic acid
Author(s) -
Lee SunMi,
Chung IlDoo,
Lee NeungJu,
Ha ChangSik,
Lee ChiHo,
Cho WonJei
Publication year - 2001
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/1097-0126(200101)50:1<119::aid-pi597>3.0.co;2-i
Subject(s) - tricarboxylic acid , maleic anhydride , chemistry , propane , monomer , dichloroacetic acid , polymer chemistry , nuclear chemistry , organic chemistry , citric acid cycle , polymer , biochemistry , copolymer , metabolism
A new monomer, methacryloyl‐2‐oxy‐1,2,3‐propane tricarboxylic acid (MTCA), was synthesized from citric acid and methacrylic anhydride. Poly(methacryloyl‐2‐oxy‐1,2,3‐propane tricarboxylic acid) and poly(methacryloyl‐2‐oxy‐1,2,3‐propane tricarboxylic acid)‐ co ‐(maleic anhydride) were prepared by radical polymerizations. Terpoly(methacryloyl‐2‐oxy‐1,2,3‐propane tricarboxylic acid–maleic anhydride–furan) was obtained by in situ terpolymerization of MTCA and exo ‐3,6‐epoxy‐1,2,3,6‐tetrahydrophthalic anhydride. The synthesized samples were identified by FTIR, 1 H NMR and 13 C NMR spectroscopies. The number‐average molecular weights of the fractionated polymers determined by GPC were in the range 14 900–16 600 and polydispersity indices were less than 1.14. The in vitro IC 50 values of the monomer and polymers against cancer and normal cell lines were much higher than those of 5‐fluorouracil (5‐FU). The in vivo antitumour activities of the synthesized samples at a dosage of 0.8 mg kg −1 against mice bearing the sarcoma 180 tumour cell line decreased in the order terpoly(MTCA‐MAH‐FUR) > poly(MTCA‐ co ‐MAH) > poly(MTCA) > MTCA > 5‐FU. The synthesized samples inhibited DNA replication and angiogenetic activity more than did 5‐FU. © 2001 Society of Chemical Industry