Comparison of pH-sensitive degradability of maleic acid amide derivatives

被引：48
|
作者：
Kang, Sunyoung [1 ]
Kim, Youngeun [1 ]
Song, Youngjun [1 ]
Choi, Jin Uk [1 ]
Park, Euddeum [1 ]
Choi, Wonmin [1 ]
Park, Jeongseon [1 ]
Lee, Yan [1 ]
机构：
[1] Seoul Natl Univ, Dept Chem, Coll Nat Sci, Seoul 151747, South Korea
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2014年 / 24卷 / 10期
关键词：
Maleic acid amide; pH-sensitivity; Degradability; Drug delivery; DRUG-DELIVERY; GENE DELIVERY; COMPLEX MICELLES; NANOCARRIERS; EFFICIENT; SIRNA; HYDROLYSIS; STABILITY; CYTOPLASM; CATALYSIS;
D O I：
10.1016/j.bmcl.2014.03.057
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
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. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2364 / 2367
页数：4
相关论文
共 50 条
  • [1] pH-sensitive multilayers based on maleic acid terpolymers with weak and strong acid moieties
    Suflet, Dana Mihaela
    Pelin, Irina Mihaela
    Timpu, Daniel
    Popescu, Irina
    COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS, 2013, 436 : 113 - 122
  • [2] A pH-SENSITIVE DRUG CARRIER BASED ON MALEIC ACID-SUBSTITUTED CYCLOTRIPHOSPHAZENE
    Qiu, Jinjun
    Wang, Yu
    Liu, Yuanyuan
    Zhang, Min
    Wu, Zhangxin
    Liu, Chengmei
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2015, 190 (09) : 1551 - 1561
  • [3] Radioiodinated phenylalkyl malonic acid derivatives as pH-sensitive apoptosis tracers
    Bauwens, Matthias
    De Saint-Hubert, Marijke
    Cleynhens, Jan
    Li Junjie
    Ni Yicheng
    Mottaghy, Felix M.
    Verbruggen, Alfons
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2011, 54 : S189 - S189
  • [4] Thermo- and pH-sensitive polymers containing cholic acid derivatives
    Benrebouh, A
    Avoce, D
    Zhu, XX
    POLYMER, 2001, 42 (09) : 4031 - 4038
  • [5] Radioiodinated Phenylalkyl Malonic Acid Derivatives as pH-Sensitive SPECT Tracers
    Bauwens, Matthias
    De Saint-Hubert, Marijke
    Cleynhens, Jan
    Brams, Laura
    Devos, Ellen
    Mottaghy, Felix M.
    Verbruggen, Alfons
    PLOS ONE, 2012, 7 (06):
  • [6] Thermosensitive and pH-sensitive polymers based on maleic anhydride copolymers
    Yin, XC
    Stöver, HDH
    MACROMOLECULES, 2002, 35 (27) : 10178 - 10181
  • [7] Novel pH-sensitive zwitterionic poly(amino acid) derivatives for drug delivery
    Wang, Xiaojuan
    Wu, Guolin
    He, Tao
    Wang, Yong
    Wang, Yinong
    Fan, Yunge
    Gao, Hui
    Ma, Jianbiao
    JOURNAL OF CONTROLLED RELEASE, 2011, 152 : E93 - E94
  • [8] Zwitterionic Chitosan Derivatives for pH-Sensitive Stealth Coating
    Xu, Peisheng
    Bajaj, Gaurav
    Shugg, Tyler
    Van Alstine, William G.
    Yeo, Yoon
    BIOMACROMOLECULES, 2010, 11 (09) : 2352 - 2358
  • [9] pH-Sensitive microgels functionalized with folic acid
    Saez-Martinez, V.
    Alvarez, L. Perez
    Merrero, M. T.
    Hernaez, E.
    Katime, I.
    EUROPEAN POLYMER JOURNAL, 2008, 44 (05) : 1309 - 1322
  • [10] pH-Sensitive liposomes with embedded ampholytic derivatives of cholan-24-oic acid
    Popov, Anton S.
    Efimova, Anna A.
    Kazantsev, Alexey, V
    Erzunov, Dmitry A.
    Lukashev, Nikolay, V
    Grozdova, Irina D.
    Melik-Nubarov, Nikolay S.
    Yaroslavov, Alexander A.
    MENDELEEV COMMUNICATIONS, 2021, 31 (06) : 827 - 829
12345