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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
Source PublicationREACTIVE & FUNCTIONAL POLYMERS
ISSN1381-5148
Volume117Pages:97-105
Abstract

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.

KeywordThiol-specific Polyethylene Glycol Pegylation Reagent Catechol-derived Quinone Protein Modification
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences ; Technology
DOI10.1016/j.reactfunctpolym.2017.06.005
Indexed BySCI
Language英语
WOS KeywordSite-specific Pegylation ; Colony-stimulating Factor ; Poly(Ethylene Glycol) ; Polyethylene-glycol ; Therapeutic Proteins ; Dopamine ; Immunogenicity ; Stability ; Oxidation ; Hydrogels
WOS Research AreaChemistry ; Engineering ; Polymer Science
WOS SubjectChemistry, Applied ; Engineering, Chemical ; Polymer Science
Funding OrganizationNational 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 IDWOS:000405766000012
Citation statistics
Document Type期刊论文
Identifierhttp://ir.ipe.ac.cn/handle/122111/22853
Collection生化工程国家重点实验室
Affiliation1.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
Recommended Citation
GB/T 7714
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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