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Oxidized catechol-derived poly (ethylene glycol) for thiol-specific conjugation
Xu, Longfu1,2; Zhang, Chun1; Wang, Qi1,2; Guo, Fangxia1,2; Li, Zenglan1,2; Liu, Yongdong1; Su, Zhiguo1,3
2017-08-01
发表期刊REACTIVE & FUNCTIONAL POLYMERS
ISSN1381-5148
卷号117页码:97-105
摘要Site-specific PEGylation of clinically used protein via free cysteine residue has been widely applied for a homogeneous product. Herein, we described a new thiol-specific PEGylation strategy based on catechol-derived reactive quinone species. Catechol-derived polyethylene glycol (PEG) was synthesized by coupling linear PEG N-hydroxysuccinimide to dopamine and then oxidized to quinone. PEG-dopaquinone (PEG-DAQ) mostly modifying the free cysteines of two model proteins of truncated flagellin (CBLB502) and recombined human ciliary neurotrophic factor (rhCNTF) evidenced its thiol-specificity. The yield of PEG-DAQ-rhCNTF under neutral pH value was 87.5%, compared with PEG-maleimide of 92.3% and PEG-vinylsulfone of 17.6%, respectively. About 95% reactive capacity for PEG-DAQ was maintained after incubation in aqueous solvent for 96 h, indicating that the reagent was superiorly hydro-stable. Moreover, it was found that quenching the PEGylation reaction by excess cysteine was necessary to obtain more stable conjugate. The resulted PEG-DAQ-rhCNTF remained about 93.5% of the initial products after storage for 14 days. As a comparison, PEG-MAL-rhCNTF was remained to 71.2%. Our results demonstrated that PEG-dopaquinone had properties of high selectivity and reactivity with cysteine thiol, and superior stability for both the reagent itself and its conjugate, showing great promise for developing as an alternative reagent for thiol-selective modification.
关键词Thiol-specific Polyethylene Glycol Pegylation Reagent Catechol-derived Quinone Protein Modification
文章类型Article
WOS标题词Science & Technology ; Physical Sciences ; Technology
DOI10.1016/j.reactfunctpolym.2017.06.005
收录类别SCI
语种英语
关键词[WOS]SITE-SPECIFIC PEGYLATION ; COLONY-STIMULATING FACTOR ; POLY(ETHYLENE GLYCOL) ; POLYETHYLENE-GLYCOL ; THERAPEUTIC PROTEINS ; DOPAMINE ; IMMUNOGENICITY ; STABILITY ; OXIDATION ; HYDROGELS
WOS研究方向Chemistry ; Engineering ; Polymer Science
WOS类目Chemistry, Applied ; Engineering, Chemical ; Polymer Science
项目资助者National Natural Science Foundation of China(21576267) ; Beijing Natural Science Foundation(2162041) ; Major State Basic Research Development Program of China(2013CB733604) ; Open Funding Project of the National Key Laboratory of Biochemical Engineering(2014KF-05)
WOS记录号WOS:000405766000012
引用统计
被引频次:2[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.ipe.ac.cn/handle/122111/22853
专题生化工程国家重点实验室
作者单位1.Chinese Acad Sci, Inst Proc Engn, Natl Key Lab Biochem Engn, Beijing 100190, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
3.Jiangsu Natl Synerget Innovat Ctr Adv Mat SICAM, Nanjing 210023, Jiangsu, Peoples R China
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Xu, Longfu,Zhang, Chun,Wang, Qi,et al. Oxidized catechol-derived poly (ethylene glycol) for thiol-specific conjugation[J]. REACTIVE & FUNCTIONAL POLYMERS,2017,117:97-105.
APA Xu, Longfu.,Zhang, Chun.,Wang, Qi.,Guo, Fangxia.,Li, Zenglan.,...&Su, Zhiguo.(2017).Oxidized catechol-derived poly (ethylene glycol) for thiol-specific conjugation.REACTIVE & FUNCTIONAL POLYMERS,117,97-105.
MLA Xu, Longfu,et al."Oxidized catechol-derived poly (ethylene glycol) for thiol-specific conjugation".REACTIVE & FUNCTIONAL POLYMERS 117(2017):97-105.
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