PEGylated Polyurea Bearing Hindered Urea Bond for Drug Delivery

Meishan Chen; Xiangru Feng; Weiguo Xu; Yanqiao Wang; Yanan Yang; Zhongyu Jiang; Jianxun Ding

doi:10.3390/molecules24081538

PEGylated Polyurea Bearing Hindered Urea Bond for Drug Delivery

Molecules. 2019 Apr 18;24(8):1538. doi: 10.3390/molecules24081538.

Authors

Meishan Chen^{1

2}, Xiangru Feng^{3

4}, Weiguo Xu^{5

6}, Yanqiao Wang^{7

8}, Yanan Yang⁹, Zhongyu Jiang^{10

11}, Jianxun Ding^{12

13}

Affiliations

¹ Chemical Engineering Institute, Changchun University of Technology, 2055 Yan'an Street, Changchun 130012, China. mschen@ciac.ac.cn.
² Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun 130022, China. mschen@ciac.ac.cn.
³ Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun 130022, China. xrfeng@ciac.ac.cn.
⁴ Jilin Biomedical Polymers Engineering Laboratory, 5625 Renmin Street, Changchun 130022, China. xrfeng@ciac.ac.cn.
⁵ Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun 130022, China. wgxu@caic.ac.cn.
⁶ Jilin Biomedical Polymers Engineering Laboratory, 5625 Renmin Street, Changchun 130022, China. wgxu@caic.ac.cn.
⁷ Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun 130022, China. candyqiao77@jlu.edu.cn.
⁸ Jilin Biomedical Polymers Engineering Laboratory, 5625 Renmin Street, Changchun 130022, China. candyqiao77@jlu.edu.cn.
⁹ Chemical Engineering Institute, Changchun University of Technology, 2055 Yan'an Street, Changchun 130012, China. yangyanan@ccut.edu.cn.
¹⁰ Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun 130022, China. zyjiang@ciac.ac.cn.
¹¹ Jilin Biomedical Polymers Engineering Laboratory, 5625 Renmin Street, Changchun 130022, China. zyjiang@ciac.ac.cn.
¹² Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun 130022, China. jxding@ciac.ac.cn.
¹³ Jilin Biomedical Polymers Engineering Laboratory, 5625 Renmin Street, Changchun 130022, China. jxding@ciac.ac.cn.

Abstract

In recent years, polyureas with dynamic hindered urea bonds (HUBs), a class of promising biomedical polymers, have attracted wide attention as a result of their controlled hydrolytic properties. The effect of the chemical structures on the properties of polyureas and their assemblies has rarely been reported. In this study, four kinds of polyureas with different chemical groups have been synthesized, and the polyureas from cyclohexyl diisocyanate and tert-butyl diamine showed the fastest hydrolytic rate. The amphiphilic polyurea composed of hydrophobic cyclohexyl-tert-butyl polyurea and hydrophilic poly(ethylene glycol) (PEG) was synthesized for the controlled delivery of the antitumor drug paclitaxel (PTX). The PTX-loaded PEGylated polyurea micelle more effectively entered into the murine breast cancer 4T1 cells and inhibited the corresponding tumor growth in vitro and in vivo. Therefore, the PEGylated polyurea with adjustable degradation might be a promising polymer matrix for drug delivery.

Keywords: amphiphilic copolymer; cancer chemotherapy; controlled drug delivery; hydrolyzable polyurea; micelle.

MeSH terms

Animals
Cell Death / drug effects
Cell Line, Tumor
Cell Proliferation / drug effects
Drug Delivery Systems*
Female
Mice, Inbred BALB C
Micelles
Paclitaxel / pharmacology
Polyethylene Glycols / chemical synthesis
Polyethylene Glycols / chemistry*
Polymers / chemical synthesis
Polymers / chemistry*
Proton Magnetic Resonance Spectroscopy
Urea / chemical synthesis
Urea / chemistry*

Substances

Micelles
Polymers
polyurea
Polyethylene Glycols
Urea
Paclitaxel

Abstract

MeSH terms

Substances

Grants and funding