The Nature of Hydrolysis of Novel Methacryloyl Polymeric Prodrugs Prepared by Mechanochemical Solid State Polymerization
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概要
- 論文の詳細を見る
The alkaline hydrolysis of several powdered methacryloyl polymeric prodrugs (1P-3P) prepared by mechanochemical polymerization, each of which contains acetaminophen (1), 7-theophyllineacetic acid (2) and 5-fluorouracil (3) as a pendant drug group has been examined in a heterogeneous system on its comparison with that of the corresponding polymeric prodrugs prepared by conventional radial-initiated polymerizations. The rate of hydrolysis depended largely on the structural features of the polymer hydrolyzates; carboxyl groups are formed with the progress of hydrolysis of 1P and 3P so that the rate of hydrolysis is markedly lowered due to suppression of a subsequent nucleophilic attack of hydroxyl anions, and the reaction ceased before its completion. In contrast, the hydrolysis of 2P was completed within several hours and finally the suspended powders had been completely solubilized, since non-acidic hydroxylethyl groups are formed as a polymer hydrolyzate. Thus, the kinetics for hydrolysis of 2P was shown to be well correlated with the powder dissolution rate, which is known as the Hixson-Crowell cube root law. It has also been observed that the rate of hydrolysis of 1Pm was higher than that of 1Pr. This fact has been ascribed to the difference in the stereochemical configuration (tacticity) of the polymer main chain between 1Pm and 1Pr, where m and r denote mechanochemical and radical-initiated, respectively.
- 公益社団法人日本薬学会の論文
- 1991-11-25
著者
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葛谷 昌之
Matsuyama Univ. Ehime Jpn
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葛谷 昌之
Laboratory of Pharmaceutical Physical Chemistry
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近藤 伸一
Laboratory of Pharmaceutical Physical Chemistry, Gifu Pharmaceutical University
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