title: Comparison of pH-sensitive degradability of maleic acid amide derivatives.
abstract: We synthesized five maleic acid amide derivatives (maleic, citraconic, cis-aconitic, 2-(2'-carboxyethyl) maleic, 1-methyl-2-(2'-carboxyethyl) maleic acid amide), and compared their degradability for the future development of pH-sensitive biomaterials with tailored kinetics of the release of drugs, the change of charge density, and the degradation of scaffolds. The degradation kinetics was highly dependent upon the substituents on the cis-double bond. Among the maleic acid amide derivatives, 2-(2'-carboxyethyl) maleic acid amide with one carboxyethyl and one hydrogen substituent showed appropriate degradability at weakly acidic pH, and the additional carboxyl group can be used as a pH-sensitive linker.
authors.affiliation: Department of Chemistry, College of Natural Sciences, Seoul National University, Gwanak-ro 1, Gwanak-gu, Seoul 151-747, Republic of Korea.
authors.forename: Sunyoung
authors.initials: S
authors.lastname: Kang
authors.affiliation: Department of Chemistry, College of Natural Sciences, Seoul National University, Gwanak-ro 1, Gwanak-gu, Seoul 151-747, Republic of Korea.
authors.forename: Youngeun
authors.initials: Y
authors.lastname: Kim
authors.affiliation: Department of Chemistry, College of Natural Sciences, Seoul National University, Gwanak-ro 1, Gwanak-gu, Seoul 151-747, Republic of Korea.
authors.forename: Youngjun
authors.initials: Y
authors.lastname: Song
authors.affiliation: Department of Chemistry, College of Natural Sciences, Seoul National University, Gwanak-ro 1, Gwanak-gu, Seoul 151-747, Republic of Korea.
authors.forename: Jin Uk
authors.initials: JU
authors.lastname: Choi
authors.affiliation: Department of Chemistry, College of Natural Sciences, Seoul National University, Gwanak-ro 1, Gwanak-gu, Seoul 151-747, Republic of Korea.
authors.forename: Euddeum
authors.initials: E
authors.lastname: Park
authors.affiliation: Department of Chemistry, College of Natural Sciences, Seoul National University, Gwanak-ro 1, Gwanak-gu, Seoul 151-747, Republic of Korea.
authors.forename: Wonmin
authors.initials: W
authors.lastname: Choi
authors.affiliation: Department of Chemistry, College of Natural Sciences, Seoul National University, Gwanak-ro 1, Gwanak-gu, Seoul 151-747, Republic of Korea.
authors.forename: Jeongseon
authors.initials: J
authors.lastname: Park
authors.affiliation: Department of Chemistry, College of Natural Sciences, Seoul National University, Gwanak-ro 1, Gwanak-gu, Seoul 151-747, Republic of Korea. Electronic address: gacn@snu.ac.kr.
authors.forename: Yan
authors.initials: Y
authors.lastname: Lee
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry*; D016503:Drug Delivery Systems; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D008298:Maleates / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000577:Amides; D008298:Maleates
keywords: Degradability; Drug delivery; Maleic acid amide; pH-sensitivity