120th General Meeting of the KCS

Type Poster Presentation
Area Life Chemistry
Room No. Exhibition Hall 2+3
Time 10월 19일 (목요일) 11:00~12:30
Code BIO.P-284
Subject Maleic acid amide derivatives for potential pH-sensitive drug release
Authors Taeyang An, Yan Lee*
Division of Chemistry, Seoul National University, Korea
Abstract In drug delivery system, a variety of external stimuli, such as pH, redox potential, light, temperature, are exploited for controlled release of drug molecules. Among them, pH is one of the most frequently used signals because pH varies widely at the organ, tissue, and even subcellular levels. In our group, pH-sensitivity of maleic acid amide derivatives has been studied. Maleic acid amide moieties contain cis double bond and it was shown that pH-sensitive degradability of maleic acid amide derivatives can be tuned by adjusting α, β-substituents. Also, pH and light dual sensitivity was achieved by introducing fumaric acid amide derivatives, trans isomers of maleic acid amide derivatives. Fumaric acid amide derivatives themselves are not degradable at acidic pH. However, they can be converted into corresponding cis isomer maleic acid amide derivatives under UV irradiation. Furthermore, a pH-sensitive drug carrier based on β-cyclodextrin (β-CD) and 1-methyl-2-(2’-carboxyethyl) maleic anhydrides (MCM) was developed. β-CD-MCM was conjugated with cephradine (CP) with high efficiency and more than 80% of conjugated CP molecules could be released again at pH 5.5 within 30 minutes. In 2013, Radosz group reported that succinic acid amide bond, which is known to be stable under acidic condition, with adjacent guanidine groups can be decomposed at pH 5.0. Inspired by this report, effect of nearby guanidine groups on pH-sensitive degradability of succinic- or maleic acid amide bond is being studied in our lab.
E-mail suns2000@snu.ac.kr