PEGylated Polyurea Bearing Hindered Urea Bond for Drug Delivery

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...

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Published inMolecules (Basel, Switzerland) Vol. 24; no. 8; p. 1538
Main Authors Chen, Meishan, Feng, Xiangru, Xu, Weiguo, Wang, Yanqiao, Yang, Yanan, Jiang, Zhongyu, Ding, Jianxun
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 18.04.2019
MDPI
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ISSN1420-3049
1420-3049
DOI10.3390/molecules24081538

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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.
AbstractList 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.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.
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.
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.
Author Xu, Weiguo
Wang, Yanqiao
Yang, Yanan
Ding, Jianxun
Jiang, Zhongyu
Chen, Meishan
Feng, Xiangru
AuthorAffiliation 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; xrfeng@ciac.ac.cn (X.F.); wgxu@caic.ac.cn (W.X.); candyqiao77@jlu.edu.cn (Y.W.); jxding@ciac.ac.cn (J.D.)
3 Jilin Biomedical Polymers Engineering Laboratory, 5625 Renmin Street, Changchun 130022, China
AuthorAffiliation_xml – name: 1 Chemical Engineering Institute, Changchun University of Technology, 2055 Yan’an Street, Changchun 130012, China; mschen@ciac.ac.cn
– name: 2 Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun 130022, China; xrfeng@ciac.ac.cn (X.F.); wgxu@caic.ac.cn (W.X.); candyqiao77@jlu.edu.cn (Y.W.); jxding@ciac.ac.cn (J.D.)
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/31003544$$D View this record in MEDLINE/PubMed
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Keywords controlled drug delivery
micelle
amphiphilic copolymer
hydrolyzable polyurea
cancer chemotherapy
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  article-title: Hindered ureas as masked isocyanates: Facile carbamoylation of nucleophiles under neutral conditions
  publication-title: Angew. Chem. Int. Ed.
  doi: 10.1002/anie.200904435
SSID ssj0021415
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Snippet In recent years, polyureas with dynamic hindered urea bonds (HUBs), a class of promising biomedical polymers, have attracted wide attention as a result of...
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StartPage 1538
SubjectTerms amphiphilic copolymer
Animals
cancer chemotherapy
Cancer therapies
Cell Death - drug effects
Cell Line, Tumor
Cell Proliferation - drug effects
controlled drug delivery
Drug Delivery Systems
Female
hydrolyzable polyurea
Mice, Inbred BALB C
micelle
Micelles
Nanoparticles
NMR
Nuclear magnetic resonance
Paclitaxel - pharmacology
Plasmids
Polyethylene Glycols - chemical synthesis
Polyethylene Glycols - chemistry
Polymers - chemical synthesis
Polymers - chemistry
Proton Magnetic Resonance Spectroscopy
Spectrum analysis
Urea - chemical synthesis
Urea - chemistry
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Title PEGylated Polyurea Bearing Hindered Urea Bond for Drug Delivery
URI https://www.ncbi.nlm.nih.gov/pubmed/31003544
https://www.proquest.com/docview/2548967287
https://www.proquest.com/docview/2211947974
https://pubmed.ncbi.nlm.nih.gov/PMC6515048
https://doaj.org/article/35cdb81a1b674d048f316b84a0573b72
Volume 24
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