Comparison of pH-sensitive degradability of maleic acid amide derivatives

Sunyoung Kang; Youngeun Kim; Youngjun Song; Jin Uk Choi; Euddeum Park; Wonmin Choi; Jeongseon Park; Yan Lee

doi:10.1016/j.bmcl.2014.03.057

Comparison of pH-sensitive degradability of maleic acid amide derivatives

Bioorg Med Chem Lett. 2014 May 15;24(10):2364-7. doi: 10.1016/j.bmcl.2014.03.057. Epub 2014 Mar 26.

Authors

Sunyoung Kang¹, Youngeun Kim¹, Youngjun Song¹, Jin Uk Choi¹, Euddeum Park¹, Wonmin Choi¹, Jeongseon Park¹, Yan Lee²

Affiliations

¹ Department of Chemistry, College of Natural Sciences, Seoul National University, Gwanak-ro 1, Gwanak-gu, Seoul 151-747, Republic of Korea.
² 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.

PMID: 24731272
DOI: 10.1016/j.bmcl.2014.03.057

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.

Keywords: Degradability; Drug delivery; Maleic acid amide; pH-sensitivity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amides / chemical synthesis
Amides / chemistry*
Drug Delivery Systems
Hydrogen-Ion Concentration
Kinetics
Maleates / chemical synthesis
Maleates / chemistry*

Substances

Amides
Maleates